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L-Aspartic acid (FDB012567)

Record Information
Version1.0
Creation date2010-04-08 22:10:14 UTC
Update date2020-09-17 15:31:47 UTC
Primary IDFDB012567
Secondary Accession Numbers
  • FDB030958
Chemical Information
FooDB NameL-Aspartic acid
DescriptionAspartic acid (Asp, D), also known as aspartate, the name of its anion, is one of the 20 natural proteinogenic amino acids which are the building blocks of proteins. As its name indicates, aspartic acid is the carboxylic acid analog of asparagine. As a neurotransmitter, aspartic acid may provide resistance to fatigue and thus lead to endurance, although the evidence to support this idea is not strong. Aspartic acid is a nonessential amino acid, since it can be made from glutamic acid by enzymes using vitamin B6. The amino acid has important roles in the urea cycle and DNA metabolism. Aspartic acid is a major excitatory neurotransmitter, which is sometimes found to be increased in epileptic and stroke patients. It is decreased in depressed patients and in patients with brain atrophy. Aspartic acid supplements are being evaluated. Five grams can raise blood levels. Magnesium and zinc may be natural inhibitors of some of the actions of aspartic acid. Aspartic acid, with the amino acid phenylalanine, is a part of the natural sweetener, aspartame. This sweetener is an advance in artificial sweeteners and is probably safe in normal doses to all except phenylketonurics. The jury is still out on the long-term effects it has on many brain neurohormones. Aspartic acid may be a significant immunostimulant of the thymus and can protect against some of the damaging effects of radiation. Many claims have been made for the special value of administering aspartic acid in the form of potassium and magnesium salts. Since aspartic acid is relatively nontoxic, studies are now in progress to elucidate its pharmacological and therapeutic roles.
CAS Number56-84-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility142 g/LALOGPS
logP-3.5ALOGPS
logP-3.5ChemAxon
logS0.03ALOGPS
pKa (Strongest Acidic)1.7ChemAxon
pKa (Strongest Basic)9.61ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.53 m³·mol⁻¹ChemAxon
Polarizability11.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H7NO4
IUPAC name(2S)-2-aminobutanedioic acid
InChI IdentifierInChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1
InChI KeyCKLJMWTZIZZHCS-REOHCLBHSA-N
Isomeric SMILESN[C@@H](CC(O)=O)C(O)=O
Average Molecular Weight133.1027
Monoisotopic Molecular Weight133.037507717
Classification
Description Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAspartic acid and derivatives
Alternative Parents
Substituents
  • Aspartic acid or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 36.10%; H 5.30%; N 10.52%; O 48.08%DFC
Melting PointMp 269-271° dec.DFC
Boiling PointNot Available
Experimental Water Solubility5.36 mg/mL at 25 oCYALKOWSKY,SH & HE,Y (2003)
Experimental logP-3.89CHMELIK,J ET AL. (1991)
Experimental pKapKa3 9.82-0 (25°,1-COOH)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +25.4 (c, 1 in 5M HCl)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSL-Aspartic acid, 3 TMS, GC-MS Spectrumsplash10-0f89-0960000000-5a6a6cb21e9fc0875f84Spectrum
GC-MSL-Aspartic acid, 3 TMS, GC-MS Spectrumsplash10-0f89-0950000000-51399a8446c394459765Spectrum
GC-MSL-Aspartic acid, 3 TMS, GC-MS Spectrumsplash10-0f89-0950000000-f07e7f52b3c31fd119f5Spectrum
GC-MSL-Aspartic acid, 3 TMS, GC-MS Spectrumsplash10-0f89-0950000000-9e175dfa17a8b17a72d2Spectrum
GC-MSL-Aspartic acid, non-derivatized, GC-MS Spectrumsplash10-0f89-0950000000-f4475587d5a3b20bfc58Spectrum
GC-MSL-Aspartic acid, 3 TMS, GC-MS Spectrumsplash10-00di-9430000000-0cac9a97e698db1672b5Spectrum
GC-MSL-Aspartic acid, 2 TMS, GC-MS Spectrumsplash10-03yi-1900000000-ea61b8526ee02ae79b66Spectrum
GC-MSL-Aspartic acid, 3 TMS, GC-MS Spectrumsplash10-0f89-1890000000-7da576c8129142b71a1bSpectrum
GC-MSL-Aspartic acid, 4 TMS, GC-MS Spectrumsplash10-0pb9-0981000000-ad23d55e348f55115f00Spectrum
GC-MSL-Aspartic acid, non-derivatized, GC-MS Spectrumsplash10-001i-0590000000-13cc5a7841854e97f68bSpectrum
GC-MSL-Aspartic acid, non-derivatized, GC-MS Spectrumsplash10-0f89-0960000000-5a6a6cb21e9fc0875f84Spectrum
GC-MSL-Aspartic acid, non-derivatized, GC-MS Spectrumsplash10-0f89-0950000000-51399a8446c394459765Spectrum
GC-MSL-Aspartic acid, non-derivatized, GC-MS Spectrumsplash10-0f89-0950000000-f07e7f52b3c31fd119f5Spectrum
GC-MSL-Aspartic acid, non-derivatized, GC-MS Spectrumsplash10-0f89-0950000000-9e175dfa17a8b17a72d2Spectrum
GC-MSL-Aspartic acid, non-derivatized, GC-MS Spectrumsplash10-0f89-0950000000-f4475587d5a3b20bfc58Spectrum
GC-MSL-Aspartic acid, non-derivatized, GC-MS Spectrumsplash10-0g4i-6946100000-0ae49e3be0f2f1f92065Spectrum
GC-MSL-Aspartic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9430000000-0cac9a97e698db1672b5Spectrum
GC-MSL-Aspartic acid, non-derivatized, GC-MS Spectrumsplash10-03yi-1900000000-ea61b8526ee02ae79b66Spectrum
GC-MSL-Aspartic acid, non-derivatized, GC-MS Spectrumsplash10-0f89-1890000000-7da576c8129142b71a1bSpectrum
GC-MSL-Aspartic acid, non-derivatized, GC-MS Spectrumsplash10-0pb9-0981000000-ad23d55e348f55115f00Spectrum
Predicted GC-MSL-Aspartic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000f-9100000000-b7db3377089f4c95001bSpectrum
Predicted GC-MSL-Aspartic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01w4-9610000000-0f1463c6395830708e12Spectrum
Predicted GC-MSL-Aspartic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Aspartic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Aspartic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0079-9300000000-92f9914d94078d96f5cf2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-c467d10f2b7e21ed17342012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00dl-9000000000-87f0c58226f5a2f3ac8a2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-fde7ef1951fddff4b8172012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uk9-8900000000-2d7e5609618437e592722012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-4b43567f4a446aed08282012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-4900000000-45382d9abd25be948e5b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-3f39a9b758e282358ac02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-3900000000-44d361ad09ff9a30dd142012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-18e1dba62e6b803e17b82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0930000000-d97f9518a2d516d830c52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-02ai-0962100000-909bb894b2c1318afee42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-9000000000-f2059dd438fcf62f62e12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03dr-7900000000-8b7b89ed34530e3310242012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-0190000000-58a78949f4b93de22aab2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0921000000-214b6b969fdc4216ca712012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03dr-6900000000-4918748927dd097d28792012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-88dc2f1093f261e762012012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0290000000-a8856f56645a2961baac2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-8cf9870557ca9adc33742012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9400000000-81b2804a712625a2d9c42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-9bf77ba12ad952f84ac02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-9000000000-e08bfb96c5fd8c9b9db72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-876e30f6c9ed061091fe2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00dl-9000000000-6c0d44d4e3853e5701a32012-08-31View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Spectrum
ChemSpider ID5745
ChEMBL IDCHEMBL274323
KEGG Compound IDC00049
Pubchem Compound ID5960
Pubchem Substance IDNot Available
ChEBI ID17053
Phenol-Explorer IDNot Available
DrugBank IDDB00128
HMDB IDHMDB00191
CRC / DFC (Dictionary of Food Compounds) IDHJB19-Y:HJB17-W
EAFUS ID264
Dr. Duke IDASPARAGINIC-ACID|ASPARAGIC-ACID|ASPARTIC-ACID|L-ASPARTIC-ACID
BIGG ID33663
KNApSAcK IDC00001342
HET IDASP
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1037291
SuperScent IDNot Available
Wikipedia IDAspartic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti morphinicDUKE
neuroexcitantDUKE
roborantDUKE
neurotransmitter25512 An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.CHEBI
Enzymes
NameGene NameUniProt ID
Aspartate aminotransferase, cytoplasmicGOT1P17174
Aspartate aminotransferase, mitochondrialGOT2P00505
Asparagine synthetase [glutamine-hydrolyzing]ASNSP08243
Isoaspartyl peptidase/L-asparaginaseASRGL1Q7L266
60 kDa lysophospholipaseASPGQ86U10
Lysozyme CLYZP61626
Putative aspartate aminotransferase, cytoplasmic 2GOT1L1Q8NHS2
Glutamate decarboxylase 2GAD2Q05329
Glutamate decarboxylase 1GAD1Q99259
Argininosuccinate synthaseASS1P00966
AspartoacylaseASPAP45381
Aspartoacylase-2ACY3Q96HD9
Ribonuclease pancreaticRNASE1P07998
Aspartate aminotransferaseGIG18Q2TU84
Aspartate--tRNA ligase, cytoplasmicDARSP14868
Multifunctional protein ADE2PAICSP22234
N(4)-(beta-N-acetylglucosaminyl)-L-asparaginaseAGAP20933
Aspartate--tRNA ligase, mitochondrialDARS2Q6PI48
Pathways
NameSMPDB LinkKEGG Link
Ammonia RecyclingSMP00009 map00910
Arginine and Proline MetabolismSMP00020 map00330
Aspartate MetabolismSMP00067 map00250
Beta-Alanine MetabolismSMP00007 map00410
Malate-Aspartate ShuttleSMP00129 Not Available
Transcription/TranslationSMP00019 Not Available
Urea CycleSMP00059 map00330
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).