GLUTAMIC ACID HYDROCHLORIDE (CHEM005858)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:07:16 UTC
Update Date2016-11-09 01:09:37 UTC
Accession NumberCHEM005858
Identification
Common NameGLUTAMIC ACID HYDROCHLORIDE
ClassSmall Molecule
DescriptionGlutamic acid is the most common excitatory neurotransmitter in the central nervous system.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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
Chemical FormulaC5H9NO4
Average Molecular Mass147.129 g/mol
Monoisotopic Mass147.053 g/mol
CAS Registry Number138-15-8
IUPAC Name(2R)-2-aminopentanedioic acid
Traditional NameD-glutamic acid
SMILESN[C@H](CCC(O)=O)C(O)=O
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k9x-9300000000-a43e0122a45b9abf09d6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9240000000-53c8c708191dfcd550d0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-ad4a2989e599a67182c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-c449cfd2231fe941d44fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-1900000000-f71458032a132069f94fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-7900000000-810570c8cfcea8da64f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-d5167570d11d77fd541eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0900000000-c7d42b011a328bb7991dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9300000000-9fd882f84339f600b5ebSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-407a30a35de9c1cceb3aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-9000000000-8610ea89d52ef116caf5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-331b7ed6ea33880c306eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3900000000-58248bb2a0c7ddc905cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zgi-9600000000-076b628a6858a60a475fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-bd3823a5fab8a2d9b62cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-11233b5887638266e512Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fba-4900000000-1e8ea62e3fbd8467396fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9100000000-6c956e122b59de69a472Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-4900000000-c467fa409affedc9ab85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9100000000-ddda6500978ea1670dcfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-4c6639c8639f077b57a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-4900000000-503f6a47bc72662de09cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ugi-3900000000-ec06b29308ff068bf7a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-e06c31345e8a86e71de1Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB02517
HMDB IDHMDB0003339
FooDB IDFDB023148
Phenol Explorer IDNot Available
KNApSAcK IDC00019577
BiGG IDNot Available
BioCyc IDD-GLT
METLIN ID6895
PDB IDNot Available
Wikipedia LinkGlutamic acid
Chemspider ID21814
ChEBI ID15966
PubChem Compound ID23327
Kegg Compound IDC00217
YMDB IDNot Available
ECMDB IDECMDB03339
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Ozaki, Akio; Yagasaki, Makoto; Takada, Hideyoshi; Hashimoto, Yukio. Manufacture of D-glutamic acid with Lactobacillus. Jpn. Kokai Tokkyo Koho (1990), 4 pp.
2. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
3. Ozaki, Akio; Yagasaki, Makoto; Takada, Hideyoshi; Hashimoto, Yukio. Manufacture of D-glutamic acid with Lactobacillus. Jpn. Kokai Tokkyo Koho (1990), 4 pp.
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6. Danke NA, Koelle DM, Yee C, Beheray S, Kwok WW: Autoreactive T cells in healthy individuals. J Immunol. 2004 May 15;172(10):5967-72.
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8. Nagai A, Suzuki Y, Baek SY, Lee KS, Lee MC, McLarnon JG, Kim SU: Generation and characterization of human hybrid neurons produced between embryonic CNS neurons and neuroblastoma cells. Neurobiol Dis. 2002 Oct;11(1):184-98.
9. Persson H, Pelto-Huikko M, Metsis M, Soder O, Brene S, Skog S, Hokfelt T, Ritzen EM: Expression of the neurotransmitter-synthesizing enzyme glutamic acid decarboxylase in male germ cells. Mol Cell Biol. 1990 Sep;10(9):4701-11.
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12. Mally MI, Cirulli V, Hayek A, Otonkoski T: ICA69 is expressed equally in the human endocrine and exocrine pancreas. Diabetologia. 1996 Apr;39(4):474-80.
13. Maechler P, Gjinovci A, Wollheim CB: Implication of glutamate in the kinetics of insulin secretion in rat and mouse perfused pancreas. Diabetes. 2002 Feb;51 Suppl 1:S99-102.
14. Ahlman B, Andersson K, Leijonmarck CE, Ljungqvist O, Hedenborg L, Wernerman J: Short-term starvation alters the free amino acid content of the human intestinal mucosa. Clin Sci (Lond). 1994 Jun;86(6):653-62.
15. Nielsen C, Hansen D, Husby S, Jacobsen BB, Lillevang ST: No allelic variation in genes with high gliadin homology in patients with celiac disease and type 1 diabetes. Immunogenetics. 2004 Aug;56(5):375-8. Epub 2004 Aug 7.
16. Luo J, Kaplitt MG, Fitzsimons HL, Zuzga DS, Liu Y, Oshinsky ML, During MJ: Subthalamic GAD gene therapy in a Parkinson's disease rat model. Science. 2002 Oct 11;298(5592):425-9.
17. Meyer W, Poehling HM, Neurand K: Intraepidermal distribution of free amino acids in porcine skin. J Dermatol Sci. 1991 Sep;2(5):383-92.
18. Cuervo JH, Rodriguez B, Houghten RA: The Magainins: sequence factors relevant to increased antimicrobial activity and decreased hemolytic activity. Pept Res. 1988 Nov-Dec;1(2):81-6.
19. Roll U, Scheeser J, Standl E, Ziegler AG: Alterations of lymphocyte subsets in children of diabetic mothers. Diabetologia. 1994 Nov;37(11):1132-41.
20. Bill JR, Mack DG, Falta MT, Maier LA, Sullivan AK, Joslin FG, Martin AK, Freed BM, Kotzin BL, Fontenot AP: Beryllium presentation to CD4+ T cells is dependent on a single amino acid residue of the MHC class II beta-chain. J Immunol. 2005 Nov 15;175(10):7029-37.
21. Raj D, Langford M, Krueger S, Shelton M, Welbourne T: Regulatory responses to an oral D-glutamate load: formation of D-pyrrolidone carboxylic acid in humans. Am J Physiol Endocrinol Metab. 2001 Feb;280(2):E214-20.
22. Zareian M, Ebrahimpour A, Bakar FA, Mohamed AK, Forghani B, Ab-Kadir MS, Saari N: A glutamic acid-producing lactic acid bacteria isolated from Malaysian fermented foods. Int J Mol Sci. 2012;13(5):5482-97. doi: 10.3390/ijms13055482. Epub 2012 May 7.