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Showing Compound D-Glutamic acid (FDB023148)

Record Information
Version1.0
Creation date2011-09-21 00:25:22 UTC
Update date2026-10-16 00:56:35 UTC
Primary IDFDB023148
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameD-Glutamic acid
DescriptionThere are two forms of glutamic acid found in nature: L-glutamic acid and D-glutamic acid. D-glutamic acid, is not endogenously produced in higher mammals. It is found naturally primarily in the cell walls of certain bacteria. D-glutamate is also present in certain foods e.g., soybeans and also arises from the turnover of the intestinal tract microflora, whose cell walls contain significant D-glutamate. Unlike other D-amino acids, D-glutamate is not oxidized by the D-amino acid oxidases, and therefore this detoxification pathway is not available for handling D-glutamate. Likewise, D-glutamic acid, when ingested, largely escapes most deamination reactions (unlike the L-counterpart). Free D-glutamate is found in mammalian tissue at surprisingly high levels, with D-glutamate accounting for 9% of the total glutamate present in liver. D-glutamate is the most potent natural inhibitor of glutathione synthesis identified to date and this may account for its localization to the liver, since circulating D-glutamate may alter redox stabiity (PMID 11158923). Certain eels are known to use D-glutamic acid as a phermone for chemical communication. [HMDB]
CAS Number6893-26-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(R)-2-Aminopentanedioic acidChEBI
D-2-Aminoglutaric acidChEBI
D-Glutaminic acidChEBI
D-GlutaminsaeureChEBI
DGLChEBI
Glutamic acid D-formChEBI
(R)-2-AminopentanedioateGenerator
D-2-AminoglutarateGenerator
D-GlutaminateGenerator
Glutamate D-formGenerator
D-GlutamateGenerator
(2R)-2-AminopentanedioateHMDB
(2R)-2-Aminopentanedioic acidHMDB
D-2-AminopentanedioateHMDB
D-2-Aminopentanedioic acidHMDB
delta-2-AminoglutarateHMDB
delta-2-Aminoglutaric acidHMDB
delta-2-AminopentanedioateHMDB
delta-2-Aminopentanedioic acidHMDB
delta-GlutamateHMDB
delta-Glutamic acidHMDB
delta-GlutaminateHMDB
delta-Glutaminic acidHMDB
delta-GlutaminsaeureHMDB
GlutamateHMDB
Lopac-g-2128HMDB
Lopac-gamma-2128HMDB
R-(-)-GlutamateHMDB
R-(-)-Glutamic acidHMDB
Tocris-0217HMDB
Glutamic acid, (D)-isomerHMDB
L Glutamic acidHMDB
L-GlutamateHMDB
L-Glutamic acidHMDB
D GlutamateHMDB
Glutamate, potassiumHMDB
L-Glutamate, aluminumHMDB
Aluminum L glutamateHMDB
Glutamic acidHMDB
L GlutamateHMDB
Aluminum L-glutamateHMDB
Potassium glutamateHMDB
(2R)-2-aminopentanedioatehmdb
(2R)-2-aminopentanedioic acidhmdb
(R)-2-aminopentanedioatehmdb
(R)-2-aminopentanedioic acidhmdb
D-Glutamic acidhmdb
glutamic acid D-formhmdb
Lopac-G-2128hmdb
Predicted Properties
PropertyValueSource
Water Solubility80.6 g/LALOGPS
logP-3.5ALOGPS
logP-3.2ChemAxon
logS-0.26ALOGPS
pKa (Strongest Acidic)1.88ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.29 m³·mol⁻¹ChemAxon
Polarizability13.19 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H9NO4
IUPAC name(2R)-2-aminopentanedioic acid
InChI IdentifierInChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m1/s1
InChI KeyWHUUTDBJXJRKMK-GSVOUGTGSA-N
Isomeric SMILESN[C@H](CCC(O)=O)C(O)=O
Average Molecular Weight147.1293
Monoisotopic Molecular Weight147.053157781
Classification
Description Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic 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 ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • Alpha-amino acid
  • D-alpha-amino acid
  • Amino fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • 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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSD-Glutamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0k9x-9300000000-a43e0122a45b9abf09d6Spectrum
Predicted GC-MSD-Glutamic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9240000000-53c8c708191dfcd550d0Spectrum
Predicted GC-MSD-Glutamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-Glutamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-ad4a2989e599a67182c02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-c449cfd2231fe941d44f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-1900000000-f71458032a132069f94f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-7900000000-810570c8cfcea8da64f52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-d5167570d11d77fd541e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0900000000-c7d42b011a328bb7991d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9300000000-9fd882f84339f600b5eb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-407a30a35de9c1cceb3a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-8610ea89d52ef116caf52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-331b7ed6ea33880c306e2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3900000000-58248bb2a0c7ddc905cf2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zgi-9600000000-076b628a6858a60a475f2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-bd3823a5fab8a2d9b62c2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-11233b5887638266e5122015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fba-4900000000-1e8ea62e3fbd8467396f2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9100000000-6c956e122b59de69a4722015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-4900000000-c467fa409affedc9ab852021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-ddda6500978ea1670dcf2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-4c6639c8639f077b57a02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-4900000000-503f6a47bc72662de09c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ugi-3900000000-ec06b29308ff068bf7a22021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-e06c31345e8a86e71de12021-09-24View Spectrum
NMRNot Available
ChemSpider ID21814
ChEMBL IDCHEMBL76232
KEGG Compound IDC00217
Pubchem Compound ID23327
Pubchem Substance IDNot Available
ChEBI ID15966
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03339
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00019577
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDGL
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference

3 unique sources. Numbers in the composition tables above point here.