Aspartic Acid PDF

L-aspartic acid | C4H7NO4 - PubChem
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PubChem CID: 5960
Cite this Record
Chemical Names: L-aspartic acid; aspartic acid; Asparagic acid; L-aspartate; Asparaginic acid;
(2S)-Aspartic acid; More...
Molecular Formula: C4H7NO4
Molecular Weight: 133.10268 g/mol
InChI Key: CKLJMWTZIZZHCS-REOHCLBHSA-N
UNII: 30KYC7MIAI
Create Date: 2004-09-16
One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in
from MeSH [34]
sugar cane and sugar beets. It may be a neurotransmitter.
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Contents
1 2D Structure
2 3D Conformer
3 Identification
4 Chemical and Physical Properties
5 Related Records
6 Chemical Vendors
7 Drug and Medication Information
8 Pharmacology and Biochemistry
9 Use and Manufacturing
10 Safety and Hazards
11 Toxicity
12 Literature
13 Patents
14 Biomolecular Interactions and Pathways
15 Biological Test Results
16 Classification
17 Information Sources
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1 2D Structure
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from PubChem [33]
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2 3D Conformer
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from PubChem [33]
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3 Identification
3.1 Computed Descriptors
3.1.1 IUPAC Name
(2S)-2-aminobutanedioic acid
from PubChem [33]
3.1.2 InChI
InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1
from PubChem [33]
3.1.3 InChI Key

CKLJMWTZIZZHCS-REOHCLBHSA-N
from PubChem [33]
3.1.4 Canonical SMILES

C(C(C(=O)O)N)C(=O)O
from PubChem [33]
3.1.5 Isomeric SMILES

C([C@@H](C(=O)O)N)C(=O)O
from PubChem [33]
3.2 Other Identifiers

3.2.1 CAS
56-84-8
from DrugBank [2] http://www.drugbank.ca/drugs/DB00128
56-84-8
from EPA Chemical Data Report [27] http://www.epa.gov/cdr/
3.2.2 EC Number
200-291-6
from ILO-ICSC [28] http://www.ilo.org/dyn/icsc/showcard.display?p_card_id=1439
200-291-6
from ECHA [29] http://echa.europa.eu/
3.2.3 ICSC Number

1439
3.2.4 RTECS Number

CI9098500
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3.2.5 UNII
30KYC7MIAI
from FDA/SPL Indexing data [32] http://www.fda.gov/ForIndustry/DataStandards/StructuredProductLabeling
/ucm377913.htm
3.2.6 Wikipedia
Aspartic acid
from Wiki [30] http://en.wikipedia.org/wiki/Aspartic_acid
Polyaspartic acid
from Wiki [31] http://en.wikipedia.org/wiki/Polyaspartic_acid
3.3 Synonyms
3.3.1 MeSH Synonyms
1. (+-)-Aspartic Acid
11. Aspartate, Monopotassium
21. Aspartic Acid, Hydrochloride
2. (R,S)-Aspartic Acid
12. Aspartate, Monosodium
22. Aspartic Acid, Magnesium (1:1) Salt, Hydrochlo
3. Ammonium Aspartate
13. Aspartate, Potassium
23. Aspartic Acid, Magnesium (2:1) Salt
4. Aspartate
14. Aspartate, Sodium
24. Aspartic Acid, Magnesium-Potassium (2:1:2) S

25. Aspartic Acid, Monopotassium Salt
5. Aspartate Magnesium Hydrochloride 15. Aspartic Acid

6. Aspartate, Ammonium
16. Aspartic Acid, Ammonium Salt
26. Aspartic Acid, Monosodium Salt
7. Aspartate, Calcium
17. Aspartic Acid, Calcium Salt
27. Aspartic Acid, Potassium Salt
8. Aspartate, Dipotassium
18. Aspartic Acid, Dipotassium Salt 28. Aspartic Acid, Sodium Salt
9. Aspartate, Disodium
19. Aspartic Acid, Disodium Salt
29. Calcium Aspartate
10. Aspartate, Magnesium
20. Aspartic Acid, Hydrobromide
30. Dipotassium Aspartate
from MeSH [34] http://www.ncbi.nlm.nih.gov/mesh/68001224
3.3.2 Depositor-Supplied Synonyms

1. L-aspartic acid
11. (S)-Aspartic acid
21. Acidum asparticum
31. Asparagic acid (VAN)
2. aspartic acid
12. L-Aminosuccinic acid
22. Aspartic acid, L-
32. Acide aspartique [INN-French]
3. Asparagic acid
13. L-Asparagic acid
23. (+)-Aspartic acid
33. Acido aspartico [INN-Spanish]
4. L-aspartate
14. Aspatofort
24. Asparaginsaeure [German] 34. L-(+)-Aspartic acid
5. Asparaginic acid
15. (S)-2-Aminosuccinic acid
25. Aspartate, L-
35. Acido aspartico
6. (2S)-Aspartic acid
16. L-Aspartinsaeure
26. L-2-Aminobutanedioic acid
36. Asparaginic acid (VAN)
7. H-Asp-OH
17. (S)-Aminobutanedioic acid
27. (L)-ASPARTIC ACID
37. Acide aspartique
8. aspartate
18. L-Asparaginsaeure
28. Aminosuccinic acid
38. Butanedioic acid, amino-, (S)-
9. L-Asparaginic acid 19. (2S)-2-aminobutanedioic acid 29. L-Asp

10. 56-84-8
20. L-Asparaginsyra
30. Aspartic acid (VAN)
39. L( )-Aminobernsteinsaeure
40. (L)-Aspartate
from PubChem [33]
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4 Chemical and Physical Properties

4.1 Computed Properties
Molecular Weight
133.10268 g/mol
Molecular Formula
C4H7NO4
XLogP3
-2.8
Hydrogen Bond Donor Count
Hydrogen Bond Acceptor Count
Rotatable Bond Count
Exact Mass
133.037508 g/mol
Monoisotopic Mass
133.037508 g/mol
Topological Polar Surface Area
101 A^2
Heavy Atom Count
Formal Charge
Complexity
133
Isotope Atom Count
Defined Atom Stereocenter Count
Undefined Atom Stereocenter Count
Defined Bond Stereocenter Count
Undefined Bond Stereocenter Count
Covalently-Bonded Unit Count
CACTVS Substructure Key Fingerprint
AAADcYBiOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA
Compound Is Canonicalized
true
from PubChem [33]
4.2 Experimental Properties

4.2.1 Physical Description
PelletsLargeCrystals; DryPowder
COLOURLESS CRYSTALS.
from EPA Chemical Data Report [27] http://www.epa.gov/cdr/

4.2.2 Color
White, crystalline solid
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Ashford, R.D. Ashford's Dictionary of Industrial Chemicals. London, England: Wavelength Publications Ltd., 1994., p. 97
from HSDB [1] http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+@rel+56-84-8

Orthorhombic bisphenoidal leaflets or rods
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station,
NJ: Merck and Co., Inc., 2001., p. 143
4.2.3 Taste
Acidic/neutral
Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers,
1985 to Present., p. VA2: 79 (1985)

Sour
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p.
V2: 559 (1992)
4.2.4 Melting Point

270-271 deg C

270 C
PhysProp

270 C
4.2.5 Solubility
1 g in 222.2 ml water at 20 deg C; 1 g in 149.9 ml water at 30 deg C; more sol in salt soln; sol in acids, alkalies

Insoluble in ethanol, ethyl ether, benzene; soluble in dilute HCl, pyridine
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL
2005, p. 3-30

In water, 5,360 mg/L at 25 deg C
Yalkowsky, S.H., He, Yan., Handbook of Aqueous Solubility Data: An Extensive Compilation of Aqueous Solubility Data for
Organic Compounds Extracted from the AQUASOL dATAbASE. CRC Press LLC, Boca Raton, FL. 2003., p. 105

Water Solubility (5390 mg/L (at 25 C))
YALKOWSKY,SH & DANNENFELSER,RM (1992)
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Solubility in water, g/100ml: 0.45
4.2.6 Density
1.6603 at 13 deg C
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL
2005, p. 3-30

1.7 g/cm3
4.2.7 Vapor Pressure

2.6X10-7 mm Hg at 25 deg C (est)
US EPA; Estimation Program Interface (EPI) Suite. Ver.3.12. Nov 30, 2004. Available from, as of Oct 26, 2006:
http://www.epa.gov/oppt/exposure/pubs/episuitedl.htm
4.2.8 LogP
log Kow = -3.89
Chmelik J et al; Coll Czech Chem Commun 56: 2030-2041 (1991)

-3.89
CHMELIK,J ET AL. (1991)

-3.89
4.2.9 Decomposition
Decomposes at 324C
4.2.10 pKa
2.01 (at 0 C)
KORTUM,G ET AL (1961)
4.2.11 Dissociation Constants

pK1 = 1.92 (COOH); pK2 =3.87 (COOH); pK3 = 9.87 (amine)
Sergeant EP, Dempsey B; Ionisation constants of organic acids in aqueous solution, IUPAC Chemical Data Series No. 2, New
York, NY: Pergamon Press, p. 95 (1979)
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4.2.12 Other Experimental Properties

ASPARTIC ACID HAS RELATIVELY HIGH SOUR, RELATIVELY LOW MSG-LIKE TASTE INTENSITIES /ASPARTIC
ACID/
Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by T.E. Furia and N. Bellanca. 2nd ed.
Cleveland: The Chemical Rubber Co., 1975., p. 824

DECOMPOSES AT 324 DEG C (RAPID HEATING)
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-130

Isoelectric point = 2.98
1985 to Present., p. V2: 62 (1985)

Forms supersaturated soln easily

13C NMR: 479 (Stothers. Carbon-13 NMR Spectroscopy, Academic Press, New York) /DL-Aspartic Acid)
Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL.
1994., p. V1: 230

UV: 1-30 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /dl-Aspartic acid/
1994., p. V1: 230

MASS: 76392 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 290 (National Bureau of Standards EPA-NIH
Mass Spectra Data Base, NSRDS-NBS-63) /DL-Aspartic acid/
1994., p. V1: 320

Specific optical rotation: -2.0 deg at 25 deg C (c=3.93 in 5N HCl) /d-Aspartic acid/

Henry's Law constant = 1.1X10-14 atm-cu m/mol at 25 deg C (est)

Hydroxyl radical reaction rate constant = 4.0X10-11 cm3/molc-sec at 25 deg C (est)
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4.3 Spectral Properties

Specific optical rotation: +25.0 deg (c= 1.97 g in 100 ml 6 N hydrochloric acid) at 20 deg C/D

SPECIFIC OPTICAL ROTATION (WATER): +4.36 DEG @ 20 DEG C/D
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-130

IR: 18085 (Sadtler Research Laboratories IR Grating Collection)
1994., p. v1: 320

MASS: 30615 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)
1994., p. V1: 320

UV: 1-30 (Phillip et al., Organic Electronic Spectral Data, John Wiley & Sons, NY)
1994., p. V1: 320
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5 Related Records
5.1 Related Compounds with Annotation
CLICK TO LOAD...
from PubChem [33]
5.2 Related Compounds

Same Tautomer
52
Same Connectivity
50
Same Stereo
30
Same Isotope
Same Parent, Tautomer
435
Same Parent, Connectivity
433
Same Parent, Stereo
190
Same Parent, Isotope
385
Same Parent, Exact
161
Mixtures, Components, and Neutralized Forms
683
Similar Compounds
367
Similar Conformers
2788
from PubChem [33]
5.3 Related Substances

All
1400
Same
184
Mixture
1216
from PubChem [33]
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5.4 Entrez Crosslinks

PubMed
15439
Protein Structures
72
from PubChem [33]
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6 Chemical Vendors
CLICK TO LOAD...
from PubChem [33]
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7 Drug and Medication Information

7.1 Therapeutic Uses
MEDICATION (VET): TO REDUCE AMMONIA BLOOD LEVELS & SAID TO BE OF VALUE IN OVERCOMING
FATIGUE. ... DOSAGE: GIVEN ORALLY OR AS FEED ADDITIVE AGAINST STRESS INDUCED HIGH BLOOD
AMMONIA LEVELS IN POULTRY & AGAINST AMMONIA INTOXICATED RATS. /ASPARTIC ACID/
Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 28

Parenteral nutrition
1985 to Present., p. VA2 84

/EXPL/: L-aspartate is a glycogenic amino acid, and it can also promote energy production via its metabolism in the
Krebs cycle. These latter activities were the rationale for the claim that supplemental aspartate has an anti-fatigue effect
on skeletal muscle, a claim that was never confirmed. /L-aspartate/
Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ
(2001) p.255

There are claims that L-aspartate is a special type of mineral transporter for cations, such as magnesium, into cells.
Magnesium aspartate has not been found to be more biologically effective when compared with other magnesium salts.
There are also claims that L-aspartate has ergogenic effects, that it enhances performance in both prolonged exercise
and short intensive exercise. It is hypothesized that L-aspartate, especially the potassium magnesium aspartate salt,
spares stores of muscle glycogen and/or promotes a faster rate of glycogen resynthesis during exercise. It has also been
hypothesized that L-aspartate can enhance short intensive exercise by serving as a substrate for energy production in
the Krebs cycle and for stimulating the purine nucleotide cycle. An animal study using injected aspartate failed to find any
evidence of a glycogen-sparing effect or any ergogenic effects whatsoever. A more recent double-blind human study of
male weight trainers similarly found aspartate supplementation to have no effect, and another study of the effect of
aspartate on short intensive exercise again found no effect. /L-aspartate/
(2001) p.254

In 21 patients with ventricular arrhythmias we analysed the effect of an intravenous infusion of potassium-magnesiumaspartate. It could be demonstrated that the frequency of ventricular ectopic beats significantly declined 1 hour after
starting the medication. The maximum effect occurred at the 6th and 7th hour and continued until the 10th hour after
starting the medication. /Potassium magnesium aspartate/ Abstract: PubMed
Kuhn P et al; Wien Med Wochenschr 141 (3): 64-5 (1991)

According to the hypothesis implying that the main reason of physical dependence on opiate is the inhibition of brain
L-asparaginase activity and L-aspartic acid gradually decreases compulsory opiate intake so that physical dependence
disappears by itself, 31 opiate addicts were given 8 g L-aspartic acid for 7 days after withdrawal from opiate and
appearance of abstinence syndrome signs. The attenuations by L-aspartic acid of the abstinence syndrome signs were
statistically compared with those obtained from other 12 opiate addicts received daily 50 mg chlorpromazine + 60 mg
diazepam which have long been used to suppress abstinence syndrome because of their multiple receptor blocking and
sedative effects. The intensity and duration of 13 signs out of 16 ones were found to be significantly more alleviated and
shortened in the addicts treated with L-aspartic acid. Abstract: PubMed
Sener AI et al; Arzneimittelforschung 36 (11): 1684-6 (1986)
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7.2 Drug Warning

Mild gastrointestinal side effects including diarrhea have been reported. /L-aspartate/
(2001) p.255

Because of lack of long-term safety studies, L-aspartate salts should be avoided by children, pregnant women and
lactating women. /L-Aspartate/
(2001) p.255

The effects of oral administration of potassium and magnesium aspartate (K + Mg Asp) on physiologic responses to 90
min of treadmill walking at approximately 62% VO2 max were evaluated in seven healthy males (VO2 max = 59.5 ml X
kg-1 X min-1). A total of 7.2 g of K + Mg Asp were administered to each subject during a 24 h period prior to work and
compared to control and placebo trials. For control, placebo, and K + Mg Asp trials, no significant differences were
observed in resting or exercise values for ventilation (VE), oxygen uptake (VO2), carbon dioxide production (VCO2),
respiratory exchange ratio (RO), heart rate (HR), or blood pressure (BP). In addition, there were no differences between
the three trials for exercise-induced decreases in body weight and increases in rectal temperature, or for pre- and
post-exercise alterations in serum lactic acid, creatine kinase, lactic dehydrogenase, and percentage change in plasma
volume. The findings from this study indicate that oral ingestion of K+ Mg Asp prior to exercise had no effect on
cardiorespiratory, hematologic, and metabolic responses to 90 min of work conducted at approximately 62% VO2 max.
/Potassium magnesium aspartate/ Abstract: PubMed
Hagan RD et al; Int J Sports Med 3 (3): 177-81 (1982)

This study examined the effects of aspartate supplementation (ASP) on plasma ammonia concentrations (NH4+) during
and after a resistance training workout (RTW). Twelve male weight trainers were randomly administered ASP or vitamin
C in a crossover, double blind protocol, each trial separated by 1 wk. ASP and vitamin C were given over a 2 hr period
beginning 5 hr prior to the RTW. The RTW consisted of bench, incline, shoulder, and triceps presses, and biceps curls at
70% of one repetition maximum (1-RM). After the RTW a bench press test (BPT) to failure at 65% of 1-RM was used to
assess performance. (NH4+) was determined preexercise, 20 and 40 min midworkout, immediately postexercise, and 15
min postexercise. Treatment-by-time ANOVAs, paired t tests, and contrast comparisons were used to identify mean
differences. No significant differences were observed between treatments for (NH4+) or BPT. (NH4+) increased
significantly from Pre to immediately postexercise for both the ASP and vitamin C trials. Acute ASP supplementation
does not reduce (NH4+) during and after a high intensity RTW in weight trained subjects. /Potassium magnesium
aspartate/ Abstract: PubMed
Tuttle JL et al; Int J Sport Nutr 5 (2): 102-9 (1995)
7.3 Drug Indication

There is no support for the claim that aspartates are exercise performance enhancers, i.e. ergogenic aids.
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8 Pharmacology and Biochemistry

8.1 Pharmacology
L-aspartate is considered a non-essential amino acid, meaning that, under normal physiological conditions, sufficient
amounts of the amino acid are synthesized in the body to meet the body's requirements. L-aspartate is formed by the
transamination of the Krebs cycle intermediate oxaloacetate. The amino acid serves as a precursor for synthesis of
proteins, oligopeptides, purines, pyrimidines, nucleic acids and L-arginine. L-aspartate is a glycogenic amino acid, and it
can also promote energy production via its metabolism in the Krebs cycle. These latter activities were the rationale for
the claim that supplemental aspartate has an anti-fatigue effect on skeletal muscle, a claim that was never confirmed.
8.2 Absorption, Distribution and Excretion

ASPARTIC ACID PLASMA CONCN WAS ELEVATED 30 MIN AFTER 1 G/KG L-ASPARTATE (ORAL OR IP) TO 15
DAY OLD & ADULT MICE. THEREAFTER, CONCN DECLINED EXPONENTIALLY WITH T/2 OF 0.2 HR IN BOTH.
PLASMA CONCN NOT APPRECIABLY ALTERED BY 10 & 100 MG/KG L-ASPARTATE ORAL OR IP ADMIN.
OPPERMANN ET AL; J ENVIRON PATHOL TOXICOL 2(4) 987 (1979)

Following ingestion, L-aspartate is absorbed from the small intestine by an active transport process. Following
absorption, L-aspartate enters the portal circulation and from there is transported to the liver, where much of it is
metabolized to protein, purines, pyrimidines and L-arginine, and is catabolized as well. L-aspartate is not metabolized in
the liver; it enters the systemic circulation, which distributes it to various tissues of the body. The cations associated with
L-aspartate independently interact with various substances in the body and participate in various physiological
processes. /L-aspartate/
(2001) p.254

... Contents of D- and L-aspartic acids in rats at different stages of growth (from 1 day before birth to 90 days after birth)
were determined. D-Aspartic acid was detected in all the brain tissue samples tested, but at different levels. In the
cerebrum of rats 1 day before birth, D-aspartic acid was found to be at the highest concentration of 81 nmol/g wet tissue.
The level of D-aspartic acid in rat brain falls rapidly after birth, while the L-aspartic acid level increases with age.
Abstract: PubMed
Zhao S et al; J Chromatogr B Biomed Sci Appl 762 (1): 97-101 (2001)

Enzymatic synthesis of 11C-(4)-L-aspartic acid was undertaken using commercially available wheat germ
phosphoenolpyruvate carboxylase. Whole-body distribution of the radioactive compound in rats showed higher
accumulation in the salivary gland, glandular stomach and the pancreas, as well as in the lungs. Within 60 minutes after
intravenous injection of 11C-(4)-L-aspartic acid, about 60% is removed as 11CO2 by expiration, indicating that the
carbon atom at the fourth position of the radioactive compound is easily subjected to decarboxylation. Abstract: PubMed
Nakamura T et al; Radioisotopes 33 (6): 363-9 (1984)

The brain efflux index method has been used to clarify the mechanism of efflux transport of acidic amino acids such as
L-aspartic acid (L-Asp), L-glutamic acid (L-Glu), and D-aspartic acid (D-Asp) across the blood-brain barrier (BBB). About
85% of L-[3H]Asp and 40% of L-(3H)Glu was eliminated from the ipsilateral cerebrum within, respectively, 10 and 20 min
of microinjection into the brain. The efflux rate constant of L-(3H)Asp and L-(3H)Glu was 0.207 and 0.0346 min(-1),
respectively. However, D-(3H)Asp was not eliminated from brain over a 20-min period. The efflux of L-(3H)Asp and
L-(3H)Glu was inhibited in the presence of excess unlabeled L-Asp and L-Glu, whereas D-Asp did not inhibit either form
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of efflux transport. Aspartic acid efflux across the BBB appears to be stereospecific. Using a combination of TLC and the
bioimaging analysis, attempts were made to detect the metabolites of L-(3H)Asp and L-(3H)Glu in the ipsilateral
cerebrum and jugular vein plasma following a microinjection into parietal cortex, area 2. Significant amounts of intact
L-(3H)Asp and L-(3H)Glu were found in all samples examined, including jugular vein plasma, providing direct evidence
that at least a part of the L-Asp and L-Glu in the brain interstitial fluid is transported across the BBB in the intact form. To
compare the transport of acidic amino acids using brain parenchymal cells, brain slice uptake studies were performed.
Although the slice-to-medium ratio of D-(3H)Asp was the highest, followed by L-[3H]Glu and L-[3H]Asp, the initial uptake
rate did not differ for both L-(3H)Asp and D-(3H)Asp, suggesting that the uptake of aspartic acid in brain parenchymal
cells is not stereospecific. These results provide evidence that the BBB may act as an efflux pump for L-Asp and L-Glu to
reduce the brain interstitial fluid concentration and act as a static wall for D-Asp. Abstract: PubMed
Hosoya K et al; J Neurochem 73 (3): 1206-11 (1999)

Absorption
Absorbed from the small intestine by an active transport process
8.3 Metabolism/Metabolites
FOR L-ASPARTIC ACID, OXALOACETIC ACID IS PRODUCT OF OXIDATIVE DEAMINATION OR
TRANSAMINATION; ALPHA-ALANINE IS PRODUCT OF DECARBOXYLATION. /FROM TABLE/

METABOLIC PATHWAYS & PRODUCTS /IN ANIMAL BODY/: ASPARTIC ACID + CARBAMYLPHOSPHATE
/PRODUCE/ PHOSPHORUS + CARBAMYLASPARTIC ACID GIVE PYRIMIDINES; ASPARTIC ACID /PRODUCES/
FUMARIC ACID + NH3; ASPARTIC ACID /PRODUCES/ ASPARTIC SEMIALDEHYDE /PRODUCES/ HOMOSERINE
/PRODUCES/ (I) THREONINE, (II) METHIONINE, OR (III) LYSINE... /FROM TABLE/

METABOLIC PATHWAYS & PRODUCTS /IN ANIMAL BODY/: ASPARTIC ACID GIVES NITROGEN OF PURINE
RING...ASPARTIC ACID + IMP GIVE ADENYLOSUCCINATE GIVES AMP + FUMARATE... /FROM TABLE/

Following ingestion, L-aspartate is absorbed from the small intestine by an active transport process. Following
absorption, L-aspartate enters the portal circulation and from there is transported to the liver, where much of it is
metabolized to protein, purines, pyrimidines and L-arginine, and is catabolized as well. D-aspartate is not metabolized in
the liver; it enters the systemic circulation, which distributes it to various tissues of the body. The cations associated with
L-aspartate independently interact with various substances in the body and participate in various physiological
processes. /L-aspartate; D-aspartate/
(2001) p.254
8.4 Mechanism of Action

There are also claims that L-aspartate has ergogenic effects, that it enhances performance in both prolonged exercise
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and short intensive exercise. It is hypothesized that L-aspartate, especially the potassium magnesium aspartate salt,
spares stores of muscle glycogen and/or promotes a faster rate of glycogen resynthesis during exercise. It has also been
hypothesized that L-aspartate can enhance short intensive exercise by serving as a substrate for energy production in
the Krebs cycle and for stimulating the purine nucleotide cycle.
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9 Use and Manufacturing

9.1 Methods of Manufacturing
Hydrolysis of asparagine, reaction of ammonia with diethyl fumarate
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p.
100

L-Aspartic acid is industrially manufactured by an enzymatic process in which aspartase (l-aspartate ammonia lyase, EC
4.3.1.1) catalyzes the addition of ammonia to fumaric acid. Advantages of the enzymatic production method are higher
product concentration and productivity and the formation of fewer byproducts. Thus, l-aspartic acid can be easily
separated from the reaction mixture by crystallization.
Ullmann's Encyclopedia of Industrial Chemistry. 6th ed.Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co.
2003 to Present, p. V2 470 (2003)

In 1973, an immobilized cell system based on Escherichia coli cells entrapped in polyacrylamide gel lattice was
introduced for large-scale production.
Ullmann's Encyclopedia of Industrial Chemistry. 6th ed.Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co.
2003 to Present, p. V2 470 (2003)
9.2 Formulations/Preparations
(VET) COMMERCIALLY AVAILABLE AS MIXT OF POTASSIUM & MAGNESIUM ASPARTATES= SPARTASE.
/ASPARTIC ACID/

AVAILABLE COMMERCIALLY AS D(-)-, L(+)-, & DL-ASPARTIC ACID. /ASPARTIC ACID/
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p.
100

150 G ASPARTIC ACID WAS POLYMERIZED IN PRESENCE OF H3PO4 TO GIVE 150 G
POLY(DEHYDROASPARTIC ACID) WHICH WAS TREATED WITH MORPHOLINE. POLYMER WAS INCORPORATED
INTO AN ANIONIC SHAMPOO WITH 4% CONCN.
JACQUET ET AL; POLY(ASPARTIC ACID AMIDES) USEFUL IN COSMETIC PREPN; FR DEMANDE PATENT 2424292
11/23/79 (OREAL SA)

USP and FCC grades; 99% min grade
Kuney, J.H., J.M. Mullican (eds.). Chemcyclopedia. Washington, DC: American Chemical Society, 1994., p. 258
9.3 U.S. Production

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or
imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update
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Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program on (L)-Aspartic Acid
(56-84-8). Available from, as of November 16, 2006: http://www.epa.gov/hpv/pubs/general/opptsrch.htm

(1992) No data
United States International Trade Commission. Synthetic Organic Chemicals - United States Production and Sales, 1992. USITC
Publication 2720, Feb. 1994 Washington, D.C.: United States Trade Commission, 1994., p. 3-139

World market for L-aspartic acid in 1982: 450 tonnes; in 1984: 250 tonnes
1985 to Present., p. VA2 90

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.
Year
Production Range (pounds)
1986
10,000 - 500,000
1990
No Reports
1994
>10 million - 50 million
1998
10,000 - 500,000
2002
No Reports
US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002
Inventory Update Rule (IUR). L-Aspartic acid (56-84-8). Available from, as of November 7, 2006: http://www.epa.gov/oppt/iur
/tools/data/2002-vol.html
9.4 Analytic Laboratory Methods

MANOMETRIC DETERMINATION OF L-ASPARTIC ACID, IN PROTEINS.
Bergmeyer, H.W. (ed.). Methods of Enzymatic Analysis. 2nd English ed. New York City: Academic Press, 1974., p. 1662

AMINO ACID ANALYZER, GLC.
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing
Co., 1975., p. 633

AOAC method 960.47, Amino Acids in Vitamin Preparations; microbiological method using basal media /Amino acids/
Association of Official Analytical Chemists. Official Methods of Analysis. 15th ed. and Supplements. Washington, DC:
Association of Analytical Chemists, 1990, p. 1087

The following methods have been developed for the analysis of free amino acids in blood, food, and feedstocks: (1)
Protein hydrolysis, (2) Chromatographic methods that include high performance liquid chromatography (HPLC), gas
chromatography (GC) and thin-layer chromatography (TLC), (3) Colorimetric and Fluorimetric Analysis, (4) Spectrometric
Analysis, and (5) Enzymatic Determination and Microbial Assay /Amino acids/
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p.
V2 531-4
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Analyte: L-aspartic acid; matrix: chemical identification; procedure: infrared absorption spectrophotometry with
comparison to standards
U.S. Pharmacopeia. The United States Pharmacopeia, USP 29/The National Formulary, NF 24; Rockville, MD: U.S.
Pharmacopeial Convention, Inc., p196 (2006)

Analyte: L-aspartic acid; matrix: chemical purity; procedure: dissolution in water; addition of bromothymol blue indicator;
titration with sodium hydroxide until color changes from yellow to blue
U.S. Pharmacopeia. The United States Pharmacopeia, USP 29/The National Formulary, NF 24; Rockville, MD: U.S.
Pharmacopeial Convention, Inc., p196 (2006)

Analyte: aspartic acid; matrix: tissue (oocyte); procedure: high-performance liquid chromatography with ultraviolet
detection at 254 nm
O'Connor CM; Mol Reprod Dev 39: 392-396 (1994). As cited in: Lunn G; HPLC Methods for Pharmaceutical Analysis. Volumes
2-4. New York, NY: John Wiley & Sons, 2000, p.300

Analyte: aspartic acid; matrix: tissue (nervous system); procedure: high-performance liquid chromatography with
fluorescence detection; limit of detection: <1 pmole
Okuma E, Abe H; J Chromatogr B 660: 243-250 (1994). As cited in: Lunn G; HPLC Methods for Pharmaceutical Analysis.
Volumes 2-4. New York, NY: John Wiley & Sons, 2000, p.301

Analyte: aspartic acid; matrix: urine; procedure: high-performance liquid chromatography with ultraviolet detection at 254
nm; limit of detection: 250 pmole
Lippincott S et al; Bone 10: 265-268 (1989). As cited in: Lunn G; HPLC Methods for Pharmaceutical Analysis. Volumes 2-4. New
York, NY: John Wiley & Sons, 2000, p.302

Analyte: aspartic acid; matrix: urine; procedure: high-performance liquid chromatography with fluorescence detection;
limit of detection: 50-500 fmole
Carducci C et al; J Chromatogr A 729: 173-180 (1996). As cited in: Lunn G; HPLC Methods for Pharmaceutical Analysis.

Analyte: aspartic acid; matrix: food (potato tuber); procedure: high-performance liquid chromatography with fluorescence
detection; limit of quantitation: 20 pmole
Bartok T et al; J Liq Chromatogr 17: 4391-4403 (1994). As cited in: Lunn G; HPLC Methods for Pharmaceutical Analysis.

Analyte: aspartic acid; matrix: food (yogurt); procedure: high-performance liquid chromatography with ultraviolet
detection;
Bruckner H et al; J Chromatogr 476: 73-82 (1989). As cited in: Lunn G; HPLC Methods for Pharmaceutical Analysis. Volumes

Analyte: aspartic acid; matrix: blood (plasma); procedure: high-performance liquid chromatography with fluorescence
detection; limit of quantitation: 31 microM
Uhe AM et al; J Chromatogr 564: 81-91 (1991). As cited in: Lunn G; HPLC Methods for Pharmaceutical Analysis. Volumes 2-4.
New York, NY: John Wiley & Sons, 2000, p.214

Analyte: aspartic acid; matrix: blood (plasma), food (cheese, meat, sausage, fish), plant material, tissue; procedure:
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reversed-phase high-performance liquid chromatography with ultraviolet detection at 436 nm; limit of detection: 0.12-0.52
pmole
Krause L et al; J Chromatogr A 715: 67-79 (1995). As cited in: Lunn G; HPLC Methods for Pharmaceutical Analysis. Volumes

Analyte: aspartic acid; matrix: blood (plasma), protein; procedure: high-performance liquid chromatography with
fluorescence detection and ultraviolet detection at 263 nm; limit of detection: 50 fmole
Haynes PA et al; J Chromatogr 588: 107-114 (1991). As cited in: Lunn G; HPLC Methods for Pharmaceutical Analysis. Volumes

Analyte: aspartic acid; matrix: blood (serum), urine; procedure: high-performance liquid chromatography with
electrochemical detection
Sherwood RA et al; J Chromatogr 528: 293-303 (1990). As cited in: Lunn G; HPLC Methods for Pharmaceutical Analysis.

Analyte: aspartic acid; matrix: food (cheese); procedure: high-performance liquid chromatography with ultraviolet
detection at 214 nm
Roturier JM et al; J Chromatogr A 696: 209-217 (1995). As cited in: Lunn G; HPLC Methods for Pharmaceutical Analysis.

Analyte: aspartic acid; matrix: amniotic fluid, blood (plasma), cerebrospinal fluid, urine; procedure: high-performance
liquid chromatography with ultraviolet detection at 254 nm
Davey JR, Ersser RS; J Chromatogr 528: 9-23 (1990). As cited in: Lunn G; HPLC Methods for Pharmaceutical Analysis.

Analyte: aspartic acid; matrix: beverage (wine); procedure: high-performance liquid chromatography with fluorescence
detection; limit of detection: 2 microM
Kato M et al; Biomed Chromatogr 9: 193-194 (1995). As cited in: Lunn G; HPLC Methods for Pharmaceutical Analysis. Volumes
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10 Safety and Hazards

10.1 Hazards Identification
10.1.1 GHS Classification
10.1.2 Fire Hazard

Combustible.
10.1.3 Explosion Hazard

Finely dispersed particles form explosive mixtures in air.
10.1.4 Inhalation Hazard

Cough. Sore throat.
10.1.5 Eye Hazard

Redness. Pain.
10.1.6 Ingestion Hazard

Burning sensation in the throat and chest.
10.2 Safety and Hazard Properties

10.2.1 Physical Danger
Dust explosion possible if in powder or granular form, mixed with air. If dry, it can be charged electrostatically by swirling,
pneumatic transport, pouring, etc.
10.2.2 Chemical Danger

Decomposes on burning. This produces toxic gases including nitrogen oxides. Reacts violently with oxidants.
10.2.3 Occupational Exposure Limits
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TLV (NOT-ESTABLISHED):.
10.2.4 Inhalation Risk

Evaporation at 20C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached
quickly when dispersed, especially if powdered.
10.2.5 Effects of Short Term Exposure

The substance is irritating to the eyes and respiratory tract.
10.3 First Aid Measures

10.3.1 Fire First Aid
In case of fire in the surroundings, use appropriate extinguishing media.
10.3.2 Inhalation First Aid

Fresh air, rest. Refer for medical attention.
10.3.3 Skin First Aid

Remove contaminated clothes. Rinse and then wash skin with water and soap.
10.3.4 Eye First Aid

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical
attention.
10.3.5 Ingestion First Aid

Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink.
10.4 Accidental Release Measures

10.4.1 Spillage Disposal
Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Wash away remainder
with plenty of water. Personal protection: particulate filter respirator adapted to the airborne concentration of the
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substance.
10.4.2 Disposal Methods

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to
significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with
environmental regulatory agencies for guidance on acceptable disposal practices.
10.5 Handling and Storage

10.5.1 Safety Storage
Separated from strong oxidants.
10.6 Exposure Control and Personal Protection

10.6.1 Fire Prevention
NO open flames.
10.6.2 Explosion Prevention

Prevent build-up of electrostatic charges (e.g., by grounding). Closed system, ventilation, explosion-proof electrical
equipment and lighting. Prevent deposition of dust.
10.6.3 Exposure Prevention

PREVENT DISPERSION OF DUST! from ILO-ICSC [28] http://www.ilo.org/dyn/icsc/showcard.display?p_card_id=1439
10.6.4 Inhalation Prevention

Use local exhaust or breathing protection.
10.6.5 Skin Prevention

Protective gloves.
10.6.6 Eye Prevention

Wear safety spectacles.
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10.6.7 Ingestion Prevention

Do not eat, drink, or smoke during work.
10.7 Transport Information

10.7.1 Packaging and Labelling
10.7.2 EC Classification
10.7.3 UN Classification
10.8 Regulatory Information

10.8.1 FDA Requirements
L-Aspartic acid is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity
of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical,
nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food
grade and is prepared and handled as a food ingredient.
21 CFR 172.320; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from,
as of August 30, 2006: http://www.gpoaccess.gov/ecfr
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11 Toxicity
11.1 Toxicological Information
11.1.1 Exposure Routes
The substance can be absorbed into the body by ingestion.
11.1.2 Interactions
ASPARTIC ACID PREVENTED TO SOME EXTENT THE APPEARANCE OF SYMPTOMS OF PHYSICAL MORPHINE
DEPENDENCE IN BALB/C MICE.
EROGLU L, H KOYUNCUOGLU; POL J PHARMACOL PHARM 31(2) 83 (1979)

The effects of amino acids on the embryotoxicity and placental transfer of nickel chloride, day 10 rat embryos were
cultured in rat serum medium containing nickel chloride or NiCl2-63 (0.34 or 0.68 uM NiCl with or without L-histidine (2
uM), L-aspartic acid, glycine (2 or 8 uM) or L-cysteine (2 uM). After 26 hr, conceptuses were assessed for survival,
growth and development and malformations. The nickel-63 contents of embryos and yolk sacs and the extent of
Nickel-63 binding to the proteins of the culture medium were also determined. Nickel chloride alone did not affect the
embryonic development at 0.34 uM and caused growth retardation and brain and caudal abnormalities at 0.68 uM.
Coincubation of L-histidine, L-cysteine, or L-aspartic acid 0.68 uM Ni reduced the growth retardation and the incidence
and/or severity of brain defects caused by nickel chloride and decreased the concentrations of nickel-63 in the yolk sacs
compared to 0.68 uM nickel-63 alone. In the presence of L-histidine, L-cysteine or L-aspartic acid there was a shift of
nickel-63 binding from the high molecular weight proteins of the culture medium to the low molecular weight fraction.
Abstract: PubMed
Saillenfait AM et al; Toxicol Appl Pharmacol 123 (2): 299-308 (1993)

The effect of oral D-aspartic acid and/or L-aspartic acid (aspartic acid) on the body weight of rats was studied. Rats given
the D- or D- plus L-isomers showed a greater decrease in weight and in protein, triglyceride and glycogen than did rats
given the L-isomer alone. The results were discussed with reference to amino acid antagonism of opioids.
Koyuncuoglu H et al; Arzneim. Forsch 32 (7): 738-741 (1982)
11.1.3 Toxicity Summary

Toxicity
Mild gastrointestinal side effects including diarrhea. LD50 (rat) > 5,000 mg/kg.
11.1.4 Antidote and Emergency Treatment

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if
necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by
nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and
treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with
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water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse
mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and
does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier
Mosby, St. Louis, MO 2005, p. 160

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is
unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques
with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering
a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as
necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated
Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously.
Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to
assist eye irrigation ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier
Mosby, St. Louis, MO 2005, p. 160-1
11.1.5 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Neurotoxicity/ The effect of L-aspartic acid, L-asparagine and/or L-asparaginase were
compared with those of imipramine on immobility, number of defecations, increase of nociceptive threshold, and
hypothermia, induced by forced swimming in rats. L-Aspartic acid was found to be as effective as imipramine in reducing
the effects of forced swimming, presumable by normalizing the decreased level of endogenous L-aspartic acid, due to
the inhibition of L-asparaginase activity and/or by stimulating the inhibited enzyme. The other treatments antagonized the
immobility, but not the increased number of defecations. All compounds abolished the elevation of nociceptive threshold
and hypothermia. Abstract: PubMed
Koyuncuoglu H et al; Experientia 38 (1): 117-8 (1982)

/OTHER TOXICITY INFORMATION/ Aspartate ... when administered to young rodents in large dosage alters the ERG
/electroretinogram/ and causes wide spread histologically demonstrable injury to the retina. In amphibians, aspartate
interferes with protein synthesis by the retina, and suppresses electrical activity of the retina, though leaving the
response of photoreceptors unaffected.
Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 121

/OTHER TOXICITY INFORMATION/ EXCESSIVE LEVELS PARENTERALLY PRODUCE VOMITING.

/OTHER TOXICITY INFORMATION/ Taste aversions to either monosodium glutamate, L-aspartic acid or N-methylD-aspartate were produced by injecting rats with LiCl after they had ingested one of these stimuli. Subsequently, rats
were tested to determine whether they would ingest any of the above compounds. The results clearly show that a
conditioned aversion to monosodium glutamate generalized to L-aspartic acid in a dose-dependent manner. Conversely,
rats conditioned to avoid L-aspartic acid also avoided monosodium glutamate. Conditioned aversions to monosodium
glutamate or L-aspartic acid generalized to sucrose when amiloride was included in all solutions. Importantly, aversions
to monosodium glutamate or L-aspartic acid did not generalize to N-methyl-D-aspartate, NaCl or KCl, and aversions to
N-methyl-D-aspartate did not generalize to monosodium glutamate, L-aspartic acid, sucrose or KCl. These data indicate
that rats perceive monosodium glutamate and L-aspartic acid as similar tastes, whereas N-methyl-D-aspartate, NaCl and
KCl elicit other tastes. The results do not support a dominant role for the N-methyl-D-aspartate subtype of glutamate
receptors in taste transduction for MSG (i.e. umami) in rats. Abstract: PubMed
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Stapleton JR et al; Chem. Senses 24: 449-457 (1999)
11.2 Ecological Information

11.2.1 Environmental Fate/Exposure Summary
L-Aspartic acid's production and use as a roborant and as a raw material in the synthesis of peptide drugs and, as the
DL-aspartic acid mixture, used in biological and clinical studies, preparation of culture media, an organic intermediate, an
ingredient of aspartame, detergents, fungicides, germicides, and in metal complexation may result in its release to the
environment through various waste streams. In addition, L-aspartic acid, as the DL-aspartic acid mixture, is a naturallyoccurring non-essential amino acid and is found in both plants and animals. If released to air, an estimated vapor
pressure of 2.6X10-7 mm Hg at 25 deg C indicates L-aspartic acid will exist in both the vapor and particulate phases in
the atmosphere. Vapor-phase L-aspartic acid will be degraded in the atmosphere by reaction with photochemicallyproduced hydroxyl radicals; the half-life for this reaction in air is estimated to be 10 hours. Particulate-phase L-aspartic
acid will be removed from the atmosphere by wet or dry deposition. L-Aspartic acid does not contain chromophores that
absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight. If
released to soil, L-aspartic acid is expected to have very high mobility based upon an estimated Koc of 39. The pKa
values for L-aspartic acid are 1.92 (COOH), 3.87 (COOH), and 9.87 (amine), indicating that this compound will exist as a
zwitterion in the environment. Volatilization from moist soil surfaces and from water surfaces is not expected to be an
important fate process because ionic compounds do not volatilize. L-Aspartic acid is not expected to volatilize from dry
soil surfaces based upon its vapor pressure. Based on results from several screening tests, L-aspartic acid is expected
to readily biodegrade under both aerobic and anaerobic conditions in soil and water environments. If released into water,
L-aspartic acid is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. An
estimated BCF of 0.7 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected
to be an important environmental fate process since this compound lacks functional groups that hydrolyze under
environmental conditions. Occupational exposure to L-aspartic acid may occur through inhalation of dust and dermal
contact with this compound at workplaces where L-aspartic acid is produced or used. L-Aspartic acid is a non-essential
amino acid which is naturally produced by both plants and animals. In addition, L-aspartic acid is ubiquitous in the diet of
the general public through the ingestion of both plants and meats. Intake of L-aspartic acid may be increased by the
additional use of nutritional supplements containing this compound by some individuals. (SRC)
11.2.2 Natural Occurring Sources

Aspartic acid, as the DL mixture, is a naturally-occurring non-essential amino acid(1).
(1) Lewis RJ Sr; Hawley's Condensed Chemical Dictionary, 14th ed. John Wiley & Sons, Inc.: New York, NY, p. 95 (2001)
11.2.3 Artificial Sources

L-Aspartic acid's production and use as a roborant (1), a raw material in the synthesis of peptide drugs(2), and, as the
DL-aspartic acid mixture, used in biological and clinical studies, preparation of culture media, an organic intermediate, an
ingredient of aspartame, detergents, fungicides, germicides, and in metal complexation(3) may result in its release to the
environment through various waste streams(SRC).
(1) O'Neil MJ et al; The Merck Index. 13th ed., Merck & Co., Inc.: Whitehouse Station, NJ p. 143 (2001) (2) Ashford RD;
Ashford's Dictionary of Industrial Chemicals, Wavelength Publications Ltd: London, England p. 97 (1994) (3) Lewis RJ Sr;
Hawley's Condensed Chemical Dictionary, 14th ed. John Wiley & Sons, Inc.: New York, NY, p. 95 (2001)
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11.2.4 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 39(SRC), determined from a
water solubility of 5,360 mg/L at 25 deg C(2) and a regression-derived equation(3), indicates that L-aspartic acid is
expected to have very high mobility in soil(SRC). L-Aspartic acid has pKa values of 1.92, 3.87, and 9.87 at 25 deg C(4)
indicating that L-aspartic acid will exist as a zwitterion in the environment. Volatilization of L-aspartic acid from moist soil
surfaces is not expected to be an important fate process(SRC) since ionic compounds do not volatilize. L-Aspartic acid is
not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.6X10-7 mm Hg at 25
deg C(SRC), determined from a fragment constant method(5). Based on results from several screening tests, L-aspartic
acid is expected to readily biodegrade under both aerobic (6-10) and anaerobic(11) conditions(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) Yalkowsky SH, He Y; Handbook of Aqueous Solubility Data. CRC Press LLC,
Boca Raton, FL, p. 105 (2003) (3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer
Chem Soc pp. 4-9 (1990) (4) Sergeant EP, Dempsey B; Ionisation constants of organic acids in aqueous solution, IUPAC
Chemical Data Series No. 2, New York, NY: Pergamon Press, p. 95 (1979) (5) Lyman WJ; p. 31 in Environmental Exposure
From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985) (6) Babeu L et al.; J Indust Microb 2: 107-15
(1987) (7) Takemoto S et al.; Suishitsu Odaku Kenkyu 4: 80-90 (1981) (8) Heukelekian H, Rand MC; J Water Pollut Contr Assoc,
27: 1040-53 (1955) (9) Helfgott TB et al; An Index of Refractory Organics, EPA-600/2-77-174. Ada, OK: U.S. EPA (1977) (10)
Malaney GW, Gerhold RM; J Water Pollut Control Fed, 41: R18-R33 (1969) (11) Stuckey DC, McCarty PL; Water Res 18:
1343-53 (1984)

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 39(SRC), determined from a water
solubility of 5,360 mg/L at 25 deg C(2) and a regression-derived equation(3), indicates that L-aspartic acid is not
expected to adsorb to suspended solids and sediment(SRC). Measured pKa values of 1.92, 3.87, and 9.87 at 25 deg
C(4) indicate that L-aspartic acid will exist as a zwitterion in the environment. Volatilization from water surfaces is not
expected because ionic compounds do not volatilize. According to a classification scheme(5), an estimated BCF of
0.7(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in
aquatic organisms is low(SRC). The biodegradation of L-aspartic acid is expected to occur readily based on results from
both screening and grab sample tests. Relative rates of total utilization of 2.7, 1.5, and 0.10%/hr were measured over a
4-hour period in three samples of seawater(6). In aerobic screening tests, 38.7 to 80.5% BODT was reached in 5 days
using a sewage inoculum(7-9) while in an anaerobic screening test, 79% biodegradation was reported in 35 days(10).
(1) Swann RL et al; Res Rev 85: 17-28 (1983) (2) Yalkowsky SH, He Y; Handbook of Aqueous Solubility Data. CRC Press LLC,
Boca Raton, FL, p. 105 (2003) (3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer
Chem Soc pp. 4-9, 5-5 (1990) (4) Sergeant EP, Dempsey B; Ionisation constants of organic acids in aqueous solution, IUPAC
Chemical Data Series No. 2, New York, NY: Pergamon Press, p. 95 (1979) (5) Franke C et al; Chemosphere 29: 1501-14 (1994)
(6) Billen G et al; Estuarine Coastal Mar Sci 11:279-294 (1980) (7) Babeu L et al; J Indust Microb 2: 107-15 (1987) (8) Takemoto
S et al; Suishitsu Odaku Kenkyu 4: 80-90 (1981) (9) Heukelekian H, Rand MC; J Water Pollut Contr Assoc, 27: 1040-53 (1955)
(10) Stuckey DC, McCarty PL; Water Res 18: 1343-53 (1984)

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the
atmosphere(1), L-aspartic acid, which has an estimated vapor pressure of 2.6X10-7 mm Hg at 25 deg C(SRC),
determined from a fragment constant method(2), is expected to exist in both the vapor and particulate phases in the
ambient atmosphere. Vapor-phase L-aspartic acid is degraded in the atmosphere by reaction with photochemicallyproduced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 10 hours(SRC), calculated from its
rate constant of 4.0x10-11 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation
method(3). Particulate-phase L-aspartic acid may be removed from the air by wet or dry deposition(SRC). L-Aspartic
acid does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be
susceptible to direct photolysis by sunlight(4).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988) (2) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I,
Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985) (3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993) (4)
Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 8-12 (1990)
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11.2.5 Biodegredation
AEROBIC: The biodegradation of L-aspartic acid was measured in several BOD5 tests. After 5 days, 48.5%(1) 38.7(2)
and 80.5%(3) of the theoretical BOD was reached using a sewage inoculum. L-Aspartic acid was degraded by 81%
BODT after 30 days using a sewage inoculum(4). In a second Warburg test using an activated sludge inoculum, 8.9,
16.2, and 28.8% BODT was reached after 0.25, 0.5, and 1 day, respectively(5). DL-Aspartic acid was rapidly degraded
by 98 to >99% in a laboratory-scale activated sludge unit at initial concentrations of 599, 1198, 2396, and 4792 mg/L and
average detention times of 20.5, 29, 42, and 85 hours, respectively(6). Samples of marine water from the Scheldt
estuary, the Belgian coastal zone of the North Sea, and the English Channel were incubated with 14C-labeled
DL-aspartic acid and relative rates of total utilization (incorporation plus respiration) of 2.7, 1.5, and 0.10%/hr,
respectively, were measured over a 4-hour period(7). Based on these data, L-aspartic acid is expected to biodegrade
rapidly.
(1) Babeu L et al; J Indust Microb 2: 107-15 (1987) (2) Takemoto S et al; Suishitsu Odaku Kenkyu 4: 80-90 (1981) (3)
Heukelekian H, Rand MC; J Water Pollut Contr Assoc, 27: 1040-53 (1955) (4) Helfgott TB et al; An Index of Refractory Organics,
EPA-600/2-77-174. Ada, OK: U.S. EPA (1977) (5) Malaney GW, Gerhold RM; J Water Pollut Control Fed, 41: R18-R33 (1969)
(6) Chudoba J et al; Sb VYS Sk Chem - Technol Praze, Technol Vody, 13: 45-63 (1968) (7) Billen G et al; Estuarine Coastal Mar
Sci 11: 279-294 (1980)

ANAEROBIC: The biodegradability of L-aspartic acid at 2 g/L was measured in the Biochemical Methane Potential assay
and incubated anaerobically at 35 and 55 deg C. After 35 and 78 days, 79 and 73% bioconversion to methane was
reported(1). The fermentation of L-aspartic acid proceeded through acetate and propionate(1).
(1) Stuckey DC, McCarty PL; Water Res 18: 1343-53 (1984)
11.2.6 Abiotic Degredation

The rate constant for the vapor-phase reaction of L-aspartic acid with photochemically-produced hydroxyl radicals has
been estimated as 4.0X10-11 cu cm/molecule-sec at 25 deg C(SRC) using a structure estimation method(1). This
corresponds to an atmospheric half-life of about 10 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals
per cu cm(1). L-Aspartic acid is not expected to undergo hydrolysis in the environment due to the lack of functional
groups that hydrolyze under environmental conditions(2). L-Aspartic acid does not contain chromophores that absorb at
wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(2). Measured pKa
values of 1.92 (COOH), 3.87 (COOH), and 9.87 (amine) at 25 deg C(3) indicate that L-aspartic acid will exist as a
zwitterion in the environment.
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993) (2) Lyman WJ et al; Handbook of Chemical Property Estimation
Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 8-12 (1990) (3) Sergeant EP, Dempsey B; Ionisation constants of
organic acids in aqueous solution, IUPAC Chemical Data Series No. 2, New York, NY: Pergamon Press, p. 95 (1979)

The chlorination of aspartic acid at 10 mg/L by sodium hypochlorite produced 2.7 ug/L dichloroacetonitrile following a
60-minute incubation(1). Abstract: PubMed
(1) Ueno H et al; Chemosphere 33: 1425-33 (1996)
11.2.7 Bioconcentration
An estimated BCF of 0.7 was calculated in fish for L-aspartic acid(SRC), using a water solubility of 5,360 mg/L(1) and a
regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for
bioconcentration in aquatic organisms is low(SRC).
(1) Yalkowsky SH, He Y; Handbook of Aqueous Solubility Data. CRC Press LLC, Boca Raton, FL, p. 105 (2003) (2) Lyman WJ et
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al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 5-5 (1990) (3) Franke C et al;
Chemosphere 29: 1501-14 (1994)
11.2.8 Soil Adsorption/Mobility

The Koc of L-aspartic acid is estimated as 39(SRC), using a water solubility of 5,360 mg/L(1) and a regression-derived
equation(2). According to a classification scheme(3), this estimated Koc value suggests that L-aspartic acid is expected
to have very high mobility in soil. However, L-aspartic acid has pKa values of 1.92, 3.87, and 9.87(5), indicating that this
compound will exist as a zwitterion in the environment. In H(Al) montmorillonite, aspartic acid showed an L-2 type
adsorption isotherm with an initial preferential sorption when compared with the solvent or other solutes followed by a
decrease in sorption as more solute was sorbed(4).
(1) Yalkowsky SH, He Y; Handbook of Aqueous Solubility Data. CRC Press LLC, Boca Raton, FL, p. 105 (2003) (2) Lyman WJ et
al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990) (3) Swann RL et al;
Res Rev 85: 17-28 (1983) (4) Weber JB, Miller CT; in Reactions and Movement of Organic Chemicals in Soils, SSSA Special
Publication No. 22, p. 305-33 (1989) (5) Sergeant EP, Dempsey B; Ionisation constants of organic acids in aqueous solution,
IUPAC Chemical Data Series No. 2, New York, NY: Pergamon Press, p. 95 (1979)
11.2.9 Volatilization from Water/Soil

Measured pKa values of 1.92, 3.87, and 9.87 at 25 deg C(1) indicate that L-aspartic acid will exist as a zwitterion in the
environment. Volatilization from moist soil surfaces and water surfaces will not occur as ionic compounds do not
volatilize. L-Aspartic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor
pressure of 2.6X10-7 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2).
(1) Sergeant EP, Dempsey B; Ionisation constants of organic acids in aqueous solution, IUPAC Chemical Data Series No. 2,
New York, NY: Pergamon Press, p. 95 (1979) (2) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB,
Blau GE, eds, Boca Raton, FL: CRC Press (1985)
11.2.10 Water Concentrations

SURFACE WATER: Water samples collected on June 3, 1986 from the lower Tama River, Japan, a highly eutrophic
urban river, contained aspartic acid at concentrations of 0.66 to 1.09 umol/L(1).
(1) Ochiai M et al; Mar Chem 25: 265-78 (1988)

SEAWATER: Concentrations of DL-aspartic acid were measured at 3 marine locations representing an estuarine, a
coastal and an open sea environment during 1977-1978(1). DL-Aspartic acid concentrations ranged from 0.010 to 0.033
umol/L in water from the Scheldt estuary, from 0.019-0.031 umol/L in water collected from the Belgian coastal zone of
the North Sea, and from 0.010 to 0.10 umol/L in water collected from the English Channel(1).
(1) Billen G et al; Estuarine Coastal Mar Sci 11:279-294 (1980)

RAIN/SNOW/FOG: Aspartic acid was measured in 30 of 73 precipitation samples (range of <2 nM to 339 nM) collected
from Charlottesville, VA, a small non-industrial town, from April, 1988 to April, 1989(1).
(1) Gorzelska K et al; Atmos Environ Part A 26: 1005-18 (1992)
11.2.11 Sediment/Soil Concentrations
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SOIL: Aspartic acid was not detectable in soil samples collected from 3 depths at a landfill in Spain containing urban
wastes (detection limit not provided although measurements for other amino acids were provided in units of nmol/g)(1).
(1) Gonzalez-Vila FJ et al; Chemosphere 31: 2817-25 (1995)

SEDIMENT: A Fanning Island (Central Pacific Ocean)lagoon carbonate mud sediment contained aspartic acid at
concentrations of 10.68, 8.40, 4.14, 3.10, 2.60, 4.11 and 3.38 umol/g in grain size fractions of <2, 2-6, 6-10, 10-20,
20-40, 63-125, 125-250 microns, respectively(1).
(1) Muller PJ, Suess E; Geochim Casmochim Acta 41: 941-9 (1977)
11.2.12 Fish/Seafood Concentrations

Aspartic acid was measured in soft tissues of zebra mussels from Oneida Lake, NY collected in October and November
of 1991 and clams (from previously published data, source not reported) at concentrations of 7.51 and 6.77 g/100 g dry
weight, respectively(1).
(1) Secor CL et al; Chemosphere 26: 1559-75 (1993)
11.2.13 Probable Routes of Human Exposure

NIOSH (NOES Survey 1981-1983) has statistically estimated that 9,033 workers (6,545 of these are female) are
potentially exposed to L-aspartic acid in the US(1). Occupational exposure to L-aspartic acid may occur through
inhalation of dust and dermal contact with this compound at workplaces where L-aspartic acid is produced or
used(SRC). L-Aspartic acid is a non-essential amino acid which is naturally produced by both plants and animals. In
addition, L-aspartic acid is ubiquitous in the diet of the general public through the ingestion of both plants and meats.
Intake of L-aspartic acid may be increased by the additional use of nutritional supplements containing this compound by
some individuals(SRC).
(1) NIOSH; NOES. National Occupational Exposure Survey conducted from 1981-1983. Estimated numbers of employees
potentially exposed to specific agents by 2-digit standard industrial classification (SIC). Available at http://www.cdc.gov/noes/ as
of Oct 24, 2006.
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12 Literature
12.1 Depositor Provided PubMed Citations
Depositor Provided PubMed Citation Count (15439)
from PubChem [33]
12.2 NLM Curated PubMed Citations

CLICK TO LOAD...
from PubChem [33]
12.3 Synthesis References

Synthesis Reference
Nguyen-Cong Duc, "Method of making L-aspartic acid from fumaric acid." U.S. Patent US3933586, issued August, 1965.
09/04/15 10:41
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13 Patents
13.1 Depositor-Supplied Patent Identifiers
CLICK TO LOAD...
from PubChem [33]
09/04/15 10:41
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14 Biomolecular Interactions and Pathways

14.1 Protein Bound 3-D Structures
CLICK TO LOAD...
from PubChem [33]
14.2 Biosystems and Pathways

CLICK TO LOAD...
from PubChem [33]
14.3 DrugBank Interactions

1 of 24 DrugBank Interactions
Target
Ribonuclease pancreatic
General Function
Involved in nucleic acid binding
Specific Function
Endonuclease that catalyzes the cleavage of RNA on the 3' side of pyrimidine
nucleotides. Acts on single stranded and double stranded RNA
Gene Name
RNASE1
GenBank Gene
D26129
References
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN,
Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
Pubmed
from DrugBank [3] http://www.drugbank.ca/drugs/DB00128#targets
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Target
Lysozyme C
General Function
Involved in retina homeostasis
Specific Function
Lysozymes have primarily a bacteriolytic function; those in tissues and body fluids
are associated with the monocyte-macrophage system and enhance the activity of
immunoagents.
Gene Name
LYZ
References
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN,
Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
Pubmed
Target
Calcium-binding mitochondrial carrier protein Aralar2
General Function
Involved in amino acid transport activity
Specific Function
Calcium-dependent mitochondrial aspartate and glutamate carrier. May have a

function in the urea cycle
Gene Name
SLC25A13
GenBank Gene
AJ496569
GenBank Protein
22002963
1. Contreras L, Gomez-Puertas P, Iijima M, Kobayashi K, Saheki T, Satrustegui J:
Ca2+ Activation kinetics of the two aspartate-glutamate mitochondrial carriers,
aralar and citrin: role in the heart malate-aspartate NADH shuttle. J Biol Chem.
2007 Mar 9;282(10):7098-106. Epub 2007 Jan 9. Pubmed
References
2. Saheki T, Iijima M, Li MX, Kobayashi K, Horiuchi M, Ushikai M, Okumura F,

Meng XJ, Inoue I, Tajima A, Moriyama M, Eto K, Kadowaki T, Sinasac DS, Tsui
LC, Tsuji M, Okano A, Kobayashi T: Citrin/mitochondrial glycerol-3-phosphate
dehydrogenase double knock-out mice recapitulate features of human citrin
deficiency. J Biol Chem. 2007 Aug 24;282(34):25041-52. Epub 2007 Jun 25.
Pubmed
3. Satrustegui J, Pardo B, Del Arco A: Mitochondrial transporters as novel targets
for intracellular calcium signaling. Physiol Rev. 2007 Jan;87(1):29-67. Pubmed
4. Ikeda S: [Adult-onset citrullinemia] Brain Nerve. 2007 Jan;59(1):59-66. Pubmed
5. Ikeda S: [Adult-onset citrullinemia] No To Shinkei. 2007 Jan;59(1):59-66.
Pubmed
Target
Aspartate aminotransferase, cytoplasmic
General Function
Amino acid transport and metabolism
Gene Name
GOT1
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GenBank Gene
M37400
GenBank Protein
179067
1. Tordjman J, Leroyer S, Chauvet G, Quette J, Chauvet C, Tomkiewicz C,
Chapron C, Barouki R, Forest C, Aggerbeck M, Antoine B: Cytosolic aspartate
aminotransferase, a new partner in adipocyte glyceroneogenesis and an
atypical target of thiazolidinedione. J Biol Chem. 2007 Aug
10;282(32):23591-602. Epub 2007 Jun 1. Pubmed
2. Girgin S, Gedik E, Tacyildiz IH, Akgun Y, Bac B, Uysal E: Factors affecting
morbidity and mortality in gangrenous cholecystitis. Acta Chir Belg. 2006
Sep-Oct;106(5):545-9. Pubmed
References
3. Guidetti P, Amori L, Sapko MT, Okuno E, Schwarcz R: Mitochondrial aspartate

aminotransferase: a third kynurenate-producing enzyme in the mammalian
brain. J Neurochem. 2007 Jul;102(1):103-11. Epub 2007 Apr 17. Pubmed
4. Wu ZM, Wen T, Tan YF, Liu Y, Ren F, Wu H: Effects of salvianolic acid a on
oxidative stress and liver injury induced by carbon tetrachloride in rats. Basic
Clin Pharmacol Toxicol. 2007 Feb;100(2):115-20. Pubmed
5. Zappacosta B, Manni A, Persichilli S, Boari A, Scribano D, Minucci A, Raffaelli
L, Giardina B, De Sole P: Salivary thiols and enzyme markers of cell damage in
periodontal disease. Clin Biochem. 2007 Jun;40(9-10):661-5. Epub 2007 Jan
26. Pubmed
Target
General Function
Specific Function

Gene Name
SLC25A13
GenBank Gene
AJ496569
GenBank Protein
22002963
1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there?
Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number
of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
References
3. Lu YB, Kobayashi K, Ushikai M, Tabata A, Iijima M, Li MX, Lei L, Kawabe K,

Taura S, Yang Y, Liu TT, Chiang SH, Hsiao KJ, Lau YL, Tsui LC, Lee DH,
Saheki T: Frequency and distribution in East Asia of 12 mutations identified in
the SLC25A13 gene of Japanese patients with citrin deficiency. J Hum Genet.
2005;50(7):338-46. Epub 2005 Jul 30. Pubmed
4. Moriyama M, Li MX, Kobayashi K, Sinasac DS, Kannan Y, Iijima M, Horiuchi M,
Tsui LC, Tanaka M, Nakamura Y, Saheki T: Pyruvate ameliorates the defect in
ureogenesis from ammonia in citrin-deficient mice. J Hepatol. 2006
May;44(5):930-8. Epub 2005 Nov 8. Pubmed
5. Begum L, Jalil MA, Kobayashi K, Iijima M, Li MX, Yasuda T, Horiuchi M, del
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Arco A, Satrustegui J, Saheki T: Expression of three mitochondrial solute
carriers, citrin, aralar1 and ornithine transporter, in relation to urea cycle in
mice. Biochim Biophys Acta. 2002 Apr 12;1574(3):283-92. Pubmed
Target
Aspartoacylase
General Function
Specific Function
Catalyzes the deacetylation of N-acetylaspartic acid (NAA) to produce acetate and

L-aspartate. NAA occurs in high concentration in brain and its hydrolysis NAA plays
a significant part in the maintenance of intact white matter. In other tissues it act as
a scavenger of NAA from body fluids
Gene Name
ASPA
GenBank Gene
S67156
GenBank Protein
455834
1. Wang J, Matalon R, Bhatia G, Wu G, Li H, Liu T, Lu ZH, Ledeen RW: Bimodal
occurrence of aspartoacylase in myelin and cytosol of brain. J Neurochem.
2007 Apr;101(2):448-57. Epub 2007 Jan 24. Pubmed
2. Bitto E, Bingman CA, Wesenberg GE, McCoy JG, Phillips GN Jr: Structure of
aspartoacylase, the brain enzyme impaired in Canavan disease. Proc Natl
Acad Sci U S A. 2007 Jan 9;104(2):456-61. Epub 2006 Dec 28. Pubmed
References
3. Janson CG, McPhee SW, Francis J, Shera D, Assadi M, Freese A, Hurh P,

Haselgrove J, Wang DJ, Bilaniuk L, Leone P: Natural history of Canavan
disease revealed by proton magnetic resonance spectroscopy (1H-MRS) and
diffusion-weighted MRI. Neuropediatrics. 2006 Aug;37(4):209-21. Pubmed
4. Srikanth SG, Chandrashekar HS, Nagarajan K, Jayakumar PN: Restricted
diffusion in Canavan disease. Childs Nerv Syst. 2007 Apr;23(4):465-8. Epub
2007 Jan 12. Pubmed
5. Moffett JR, Ross B, Arun P, Madhavarao CN, Namboodiri AM:
N-Acetylaspartate in the CNS: from neurodiagnostics to neurobiology. Prog
Neurobiol. 2007 Feb;81(2):89-131. Epub 2007 Jan 5. Pubmed
Target
Asparagine synthetase [glutamine-hydrolyzing]
General Function
Gene Name
ASNS
GenBank Gene
M27396
GenBank Protein
179100
References
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Target
Argininosuccinate synthase
General Function
Nucleotide transport and metabolism
Gene Name
ASS1
GenBank Gene
X01630
GenBank Protein
28872
References
3. Flam BR, Eichler DC, Solomonson LP: Endothelial nitric oxide production is
tightly coupled to the citrulline-NO cycle. Nitric Oxide. 2007
Nov-Dec;17(3-4):115-21. Epub 2007 Aug 3. Pubmed
4. Ben-Yoseph Y, Mitchell DA: Detection of kinetically abnormal argininosuccinate
synthase in neonatal citrullinemia by conversion of citrulline to arginine in intact
fibroblasts. Clin Chim Acta. 1989 Aug 15;183(2):125-33. Pubmed
5. Shen LJ, Beloussow K, Shen WC: Accessibility of endothelial and inducible
nitric oxide synthase to the intracellular citrulline-arginine regeneration pathway.
Biochem Pharmacol. 2005 Jan 1;69(1):97-104. Pubmed
Target
Aminoacylase-1
General Function
Specific Function
Involved in the hydrolysis of N-acylated or N-acetylated amino acids (except

L-aspartate)
Gene Name
ACY1
GenBank Gene
L07548
GenBank Protein
178071
References
3. Mitta M, Ohnogi H, Yamamoto A, Kato I, Sakiyama F, Tsunasawa S: The
primary structure of porcine aminoacylase 1 deduced from cDNA sequence. J
Biochem (Tokyo). 1992 Dec;112(6):737-42. Pubmed
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Target
Aspartate aminotransferase, mitochondrial
General Function
Gene Name
GOT2
GenBank Gene
M22632
GenBank Protein
179104
3. Collier RH, Kohlhaw G: Nonidentity of the aspartate and the aromatic
aminotransferase components of transaminase A in Escherichia coli. J
Bacteriol. 1972 Oct;112(1):365-71. Pubmed
References
4. Grell EH: Genetic analysis of aspartate aminotransferase isozymes from

hybrids between Drosophila melanogaster and Drosophila simulans and
mutagen-induced isozyme variants. Genetics. 1976 Aug;83(4):753-64. Pubmed
5. Recasens M, Mandel P: Similarities between cysteinesulphinate transaminase
and aspartate aminotransferase. Ciba Found Symp. 1979;(72):259-70. Pubmed
6. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov
IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan
1;28(1):235-42. Pubmed
Target
Aspartate--tRNA ligase, cytoplasmic
General Function
Translation, ribosomal structure and biogenesis
Gene Name
DARS
GenBank Gene
J05032
GenBank Protein
179102
References
3. Eiler S, Dock-Bregeon A, Moulinier L, Thierry JC, Moras D: Synthesis of

aspartyl-tRNA(Asp) in Escherichia coli--a snapshot of the second step. EMBO
J. 1999 Nov 15;18(22):6532-41. Pubmed
4. Fender A, Sauter C, Messmer M, Putz J, Giege R, Florentz C, Sissler M: Loss
of a primordial identity element for a mammalian mitochondrial aminoacylation
system. J Biol Chem. 2006 Jun 9;281(23):15980-6. Epub 2006 Apr 5. Pubmed
5. Cavarelli J, Eriani G, Rees B, Ruff M, Boeglin M, Mitschler A, Martin F, Gangloff
J, Thierry JC, Moras D: The active site of yeast aspartyl-tRNA synthetase:
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structural and functional aspects of the aminoacylation reaction. EMBO J. 1994
Jan 15;13(2):327-37. Pubmed
Target
General Function
Specific Function

Gene Name
SLC25A12
GenBank Gene
Y14494
GenBank Protein
3559910
1. Correia C, Coutinho AM, Diogo L, Grazina M, Marques C, Miguel T, Ataide A,
Almeida J, Borges L, Oliveira C, Oliveira G, Vicente AM: Brief report: High
frequency of biochemical markers for mitochondrial dysfunction in autism: no
association with the mitochondrial aspartate/glutamate carrier SLC25A12 gene.
J Autism Dev Disord. 2006 Nov;36(8):1137-40. Pubmed
References
2. Contreras L, Gomez-Puertas P, Iijima M, Kobayashi K, Saheki T, Satrustegui J:

Ca2+ Activation kinetics of the two aspartate-glutamate mitochondrial carriers,
aralar and citrin: role in the heart malate-aspartate NADH shuttle. J Biol Chem.
2007 Mar 9;282(10):7098-106. Epub 2007 Jan 9. Pubmed
3. Satrustegui J, Contreras L, Ramos M, Marmol P, Del Arco A, Saheki T, Pardo
B: Role of aralar, the mitochondrial transporter of aspartate-glutamate, in brain
N-acetylaspartate formation and Ca(2+) signaling in neuronal mitochondria. J
Neurosci Res. 2007 May 11;. Pubmed
4. Satrustegui J, Pardo B, Del Arco A: Mitochondrial transporters as novel targets
for intracellular calcium signaling. Physiol Rev. 2007 Jan;87(1):29-67. Pubmed
Target
Aspartyl/asparaginyl beta-hydroxylase
General Function
Posttranslational modification, protein turnover, chaperones
Specific Function
Specifically hydroxylates an Asp or Asn residue in certain epidermal growth

factor-like (EGF) domains of a number of proteins
Gene Name
ASPH
GenBank Gene
U03109
GenBank Protein
458032
References
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3. Whiteman P, Marks C, Freese E: The sodium effect of Bacillus subtilis growth
on aspartate. J Gen Microbiol. 1980 Aug;119(2):493-504. Pubmed
4. Iijima T, Diesterhaft MD, Freese E: Sodium effect of growth on aspartate and
genetic analysis of a Bacillus subtilis mutant with high aspartase activity. J
Bacteriol. 1977 Mar;129(3):1440-7. Pubmed
Target
Multifunctional protein ADE2
General Function
Specific Function
ATP + 5-amino-1-(5-phospho-D- ribosyl)imidazole-4-carboxylate + L-aspartate =

ADP + phosphate + (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4carboxamido)succinate
Gene Name
PAICS
GenBank Gene
X53793
GenBank Protein
28384
References
Target
CAD protein
General Function
Specific Function
This protein is a "fusion" protein encoding four enzymatic activities of the pyrimidine
pathway (GATase, CPSase, ATCase and DHOase)
Gene Name
CAD
GenBank Gene
D78586
GenBank Protein
1228049
References
Target
Adenylosuccinate synthetase isozyme 2
General Function
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Specific Function
Plays an important role in the de novo pathway of purine nucleotide biosynthesis
Gene Name
ADSS
GenBank Gene
X66503
GenBank Protein
415849
References
3. Raman J, Mehrotra S, Anand RP, Balaram H: Unique kinetic mechanism of

Plasmodium falciparum adenylosuccinate synthetase. Mol Biochem Parasitol.
2004 Nov;138(1):1-8. Pubmed
4. Mehrotra S, Balaram H: Kinetic Characterization of Adenylosuccinate
Synthetase from the Thermophilic Archaea Methanocaldococcus jannaschii.
Biochemistry. 2007 Oct 11;. Pubmed
5. Datta SK, Guicherit OM, Kellems RE: Adenylosuccinate synthetase: a dominant
amplifiable genetic marker in mammalian cells. Somat Cell Mol Genet. 1994
Sep;20(5):381-9. Pubmed
Target
Excitatory amino acid transporter 3
General Function
Energy production and conversion
Specific Function
Transports L-glutamate and also L- and D-aspartate. Essential for terminating the
postsynaptic action of glutamate by rapidly removing released glutamate from the
synaptic cleft. Acts as a symport by cotransporting sodium. Negatively regulated by
ARL6IP5
Gene Name
SLC1A1
GenBank Gene
U08989
GenBank Protein
507898
1. Tao Z, Grewer C: Cooperation of the conserved aspartate 439 and bound
amino acid substrate is important for high-affinity Na+ binding to the glutamate
transporter EAAC1. J Gen Physiol. 2007 Apr;129(4):331-44. Pubmed
2. Teichman S, Kanner BI: Aspartate-444 is essential for productive substrate
interactions in a neuronal glutamate transporter. J Gen Physiol. 2007
Jun;129(6):527-39. Pubmed
References
3. Tai YH, Wang YH, Tsai RY, Wang JJ, Tao PL, Liu TM, Wang YC, Wong CS:
Amitriptyline preserves morphine's antinociceptive effect by regulating the
glutamate transporter GLAST and GLT-1 trafficking and excitatory amino acids
concentration in morphine-tolerant rats. Pain. 2007 Jun;129(3):343-54. Epub
2007 Mar 7. Pubmed
4. Ozawa S: [Role of glutamate transporters in excitatory synapses in cerebellar
Purkinje cells] Brain Nerve. 2007 Jul;59(7):669-76. Pubmed
09/04/15 10:41
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Target
Aspartate aminotransferase
General Function
Specific Function
L-aspartate + 2-oxoglutarate = oxaloacetate + L-glutamate
Gene Name
GIG18
GenBank Gene
AY513279
GenBank Protein
46981967
References
Target
Argininosuccinate synthetase, isoform CRA_a
General Function
Gene Name
ASS1
GenBank Gene
AL354898
GenBank Protein
55958410
References
3. Flam BR, Eichler DC, Solomonson LP: Endothelial nitric oxide production is
tightly coupled to the citrulline-NO cycle. Nitric Oxide. 2007
Nov-Dec;17(3-4):115-21. Epub 2007 Aug 3. Pubmed
4. Ben-Yoseph Y, Mitchell DA: Detection of kinetically abnormal argininosuccinate
synthase in neonatal citrullinemia by conversion of citrulline to arginine in intact
fibroblasts. Clin Chim Acta. 1989 Aug 15;183(2):125-33. Pubmed
5. Shen LJ, Beloussow K, Shen WC: Accessibility of endothelial and inducible
nitric oxide synthase to the intracellular citrulline-arginine regeneration pathway.
Biochem Pharmacol. 2005 Jan 1;69(1):97-104. Pubmed
Target
Aspartate--tRNA ligase, mitochondrial
General Function
Translation, ribosomal structure and biogenesis
Specific Function
ATP + L-aspartate + tRNA(Asp) = AMP + diphosphate + L-aspartyl-tRNA(Asp)
Gene Name
DARS2
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GenBank Gene
AL109921
GenBank Protein
56203852
References
3. Eiler S, Dock-Bregeon A, Moulinier L, Thierry JC, Moras D: Synthesis of

aspartyl-tRNA(Asp) in Escherichia coli--a snapshot of the second step. EMBO
J. 1999 Nov 15;18(22):6532-41. Pubmed
4. Fender A, Sauter C, Messmer M, Putz J, Giege R, Florentz C, Sissler M: Loss
of a primordial identity element for a mammalian mitochondrial aminoacylation
system. J Biol Chem. 2006 Jun 9;281(23):15980-6. Epub 2006 Apr 5. Pubmed
5. Cavarelli J, Eriani G, Rees B, Ruff M, Boeglin M, Mitschler A, Martin F, Gangloff
J, Thierry JC, Moras D: The active site of yeast aspartyl-tRNA synthetase:
structural and functional aspects of the aminoacylation reaction. EMBO J. 1994
Jan 15;13(2):327-37. Pubmed
Target
Isoaspartyl peptidase/L-asparaginase
General Function
Gene Name
ASRGL1
GenBank Gene
BC021295
GenBank Protein
127798426
References
Target
Adenylosuccinate synthetase isozyme 1
General Function
Specific Function
Plays an important role in the de novo pathway of purine nucleotide biosynthesis
Gene Name
ADSSL1
GenBank Gene
AY037159
GenBank Protein
21303413
References
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Target
Aspartoacylase-2
General Function
Specific Function
N-acyl-L-aspartate + H(2)O = a carboxylate + L-aspartate
Gene Name
ACY3
GenBank Gene
AY040761
GenBank Protein
21654856
References
Transporter
Monocarboxylate transporter 10
Action
inhibitor
General Function
Carbohydrate transport and metabolism
Specific Function
Sodium-independent transporter that mediates the update of aromatic acid. Can

function as a net efflux pathway for aromatic amino acids in the basosolateral
epithelial cells (By similarity)
Gene Name
SLC16A10
GenBank Gene
AB057445
GenBank Protein
18640047
References
Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression

cloning of a Na+-independent aromatic amino acid transporter with structural
similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May
18;276(20):17221-8. Epub 2001 Feb 20. Pubmed
from DrugBank [26] http://www.drugbank.ca/drugs/DB00128#transporters
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15 Biological Test Results

15.1 BioAssay Results
CLICK TO LOAD...
from PubChem [33]
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16 Classification
16.1 Ontologies
16.1.1 MeSH Tree
CLICK TO LOAD...
from MeSH [35] http://www.nlm.nih.gov/mesh/meshhome.html
16.1.2 ChEBI Ontology

CLICK TO LOAD...
from ChEBI [36] http://www.ebi.ac.uk/chebi/userManualForward.do#ChEBI%20Ontology
16.1.3 KEGG: Metabolite

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from KEGG [37] http://www.genome.jp/dbget-bin/www_bget?brite:br08001
16.1.4 KEGG: JP15

CLICK TO LOAD...
16.1.5 KEGG: Risk Category of Japanese OTC Drugs

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16.1.6 KEGG: Additive

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16.1.7 WIPO IPC

CLICK TO LOAD...
from WIPO [40] http://www.wipo.int/classifications/ipc/
16.1.8 WHO ATC Classification System

CLICK TO LOAD...
from WHO ATC Code [42] http://www.whocc.no/atc/
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16.2 Substance Categorization Classification

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from PubChem [33]
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17 Information Sources
1. (L)-ASPARTIC ACID from HSDB 1430 http://toxnet.nlm.nih.gov/cgi-bin/sis/search
/r?dbs+hsdb:@term+@rn+@rel+56-84-8
2. L-Aspartic Acid from DrugBank DB00128 http://www.drugbank.ca/drugs/DB00128
One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially
in sugar cane and sugar beets. It may be a neurotransmitter. [PubChem]
3. DrugBank DB00128 interaction #1 http://www.drugbank.ca/drugs/DB00128#targets
26. DrugBank DB00128 interaction #24 http://www.drugbank.ca/drugs/DB00128#transporters
27. L-Aspartic acid from EPA Chemical Data Report 56-84-8 http://www.epa.gov/cdr/
28. L-ASPARTIC ACID from ILO-ICSC 1439 http://www.ilo.org/dyn/icsc/showcard.display?p_card_id=1439
Peer-Review Status: 10.09.2002 Validated
29. ECHA 200-291-6 http://echa.europa.eu/
30. Wiki 218 http://en.wikipedia.org/wiki/Aspartic_acid
31. Wiki 10943 http://en.wikipedia.org/wiki/Polyaspartic_acid
32. FDA/SPL Indexing data 30KYC7MIAI http://www.fda.gov/ForIndustry/DataStandards/StructuredProductLabeling
/ucm377913.htm
33. PubChem http://pubchem.ncbi.nlm.nih.gov
Data deposited in or computed by PubChem
34. Aspartic Acid from MeSH 68001224 http://www.ncbi.nlm.nih.gov/mesh/68001224
35. MeSH Tree from MeSH DescTree http://www.nlm.nih.gov/mesh/meshhome.html
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MeSH (Medical Subject Headings) is the NLM controlled vocabulary thesaurus used for indexing articles for
PubMed.
36. ChEBI Ontology from ChEBI OBO http://www.ebi.ac.uk/chebi/userManualForward.do#ChEBI%20Ontology
The ChEBI Ontology is a structured classification of the entities contained within ChEBI.
37. Metabolite from KEGG br08001 http://www.genome.jp/dbget-bin/www_bget?brite:br08001
Compounds with biological roles
38. JP15 from KEGG br08311 http://www.genome.jp/dbget-bin/www_bget?brite:br08311
Drugs listed in the Japanese Pharmacopoeia
39. KEGG br08312 http://www.genome.jp/dbget-bin/www_bget?brite:br08312
Risk category of Japanese OTC drugs
40. International Patent Classification 2015 from WIPO IPC http://www.wipo.int/classifications/ipc/
The World Intellectual Property Organization (WIPO) International Patent Classification (IPC) provides for a
hierarchical system of language independent symbols for the classification of patents and utility models according to
the different areas of technology to which they pertain.
41. Additive from KEGG br08316 http://www.genome.jp/dbget-bin/www_bget?brite:br08316
Pharmaceutical additives
42. ATC Code from WHO ATC Code ATCTree http://www.whocc.no/atc/
In the World Health Organization (WHO) Anatomical Therapeutic Chemical (ATC) classification system, the active
substances are divided into different groups according to the organ or system on which they act and their
therapeutic, pharmacological and chemical properties.
09/04/15 10:41

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L-aspartic acid | C4H7NO4 - PubChem

U.S. National Library of Medicine

National Center for Biotechnology Information

PubChem CID: 5960

Cite this Record

L-aspartic acid | C4H7NO4 - PubChem

L-aspartic acid | C4H7NO4 - PubChem

from PubChem [33]

L-aspartic acid | C4H7NO4 - PubChem

L-aspartic acid | C4H7NO4 - PubChem

from PubChem [33]

from PubChem [33]

3.1.3 InChI Key

from PubChem [33]

3.1.4 Canonical SMILES

from PubChem [33]

3.1.5 Isomeric SMILES

from PubChem [33]

3.2 Other Identifiers

from DrugBank [2] http://www.drugbank.ca/drugs/DB00128

from EPA Chemical Data Report [27] http://www.epa.gov/cdr/

from ILO-ICSC [28] http://www.ilo.org/dyn/icsc/showcard.display?p_card_id=1439

from ECHA [29] http://echa.europa.eu/

3.2.3 ICSC Number

from ILO-ICSC [28] http://www.ilo.org/dyn/icsc/showcard.display?p_card_id=1439

3.2.4 RTECS Number

from ILO-ICSC [28] http://www.ilo.org/dyn/icsc/showcard.display?p_card_id=1439

L-aspartic acid | C4H7NO4 - PubChem

from Wiki [30] http://en.wikipedia.org/wiki/Aspartic_acid

from Wiki [31] http://en.wikipedia.org/wiki/Polyaspartic_acid

11. Aspartate, Monopotassium

21. Aspartic Acid, Hydrochloride

12. Aspartate, Monosodium

22. Aspartic Acid, Magnesium (1:1) Salt, Hydrochlo

13. Aspartate, Potassium

23. Aspartic Acid, Magnesium (2:1) Salt

14. Aspartate, Sodium

24. Aspartic Acid, Magnesium-Potassium (2:1:2) S

5. Aspartate Magnesium Hydrochloride 15. Aspartic Acid

16. Aspartic Acid, Ammonium Salt

26. Aspartic Acid, Monosodium Salt

17. Aspartic Acid, Calcium Salt

27. Aspartic Acid, Potassium Salt

19. Aspartic Acid, Disodium Salt

29. Calcium Aspartate

10. Aspartate, Magnesium

20. Aspartic Acid, Hydrobromide

30. Dipotassium Aspartate

from MeSH [34] http://www.ncbi.nlm.nih.gov/mesh/68001224

3.3.2 Depositor-Supplied Synonyms

11. (S)-Aspartic acid

21. Acidum asparticum

31. Asparagic acid (VAN)

12. L-Aminosuccinic acid

22. Aspartic acid, L-

32. Acide aspartique [INN-French]

13. L-Asparagic acid

23. (+)-Aspartic acid

33. Acido aspartico [INN-Spanish]

24. Asparaginsaeure [German] 34. L-(+)-Aspartic acid

15. (S)-2-Aminosuccinic acid

35. Acido aspartico