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Details

Stereochemistry ABSOLUTE
Molecular Formula C5H9NO4
Molecular Weight 147.1295
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLUTAMIC ACID

SMILES

C(CC(=O)O)[C@@]([H])(C(=O)O)N

InChI

InChIKey=WHUUTDBJXJRKMK-VKHMYHEASA-N
InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/11724641

Glutamic acid is a non-essential aminoacid used in biosynthesis of proteins. Besides being a building block of proteins, glutamic acid plays a principal role in neural activation. Glutamate is also responsible for the umami (savory) flavor of certain foods. In medicine, glutamate is used as a metabolic supplemnet in patients undergoing coronary surgery.

Originator

Curator's Comment:: Glutamic acid was discovered in 1866 by the German chemist Karl Heinrich Ritthausen who treated wheat gluten (for which it was named) with sulfuric acid.

Approval Year

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Conversion of the ion selectivity of the 5-HT(3a) receptor from cationic to anionic reveals a conserved feature of the ligand-gated ion channel superfamily.
2001 Apr 6
Cooperative helix stabilization by complex Arg-Glu salt bridges.
2001 Aug 1
Calcium channels triggering transmitter release in the rat medial superior olive.
2001 Dec
Block by gabapentin of the facilitation of glutamate release from rat trigeminal nucleus following activation of protein kinase C or adenylyl cyclase.
2001 Sep
Distinct signal transduction pathways for GABA-induced GABA(A) receptor down-regulation and uncoupling in neuronal culture: a role for voltage-gated calcium channels.
2001 Sep
Interaction between vanilloid and glutamate receptors in the central modulation of nociception.
2002 Mar 29
Protective effect of dopamine D2 agonists in cortical neurons via the phosphatidylinositol 3 kinase cascade.
2002 Nov 1
Effects of ammonia on high affinity glutamate uptake and glutamate transporter EAAT3 expression in cultured rat cerebellar granule cells.
2003 Jul
Cellular and molecular mechanisms in environmental and occupational inhalation toxicology.
2004
Linkage and association of the mitochondrial aspartate/glutamate carrier SLC25A12 gene with autism.
2004 Apr
Expression of connexin36 in cone pedicles and OFF-cone bipolar cells of the mouse retina.
2004 Mar 31
Protein S100B release from rat brain slices during and after ischemia: comparison with lactate dehydrogenase leakage.
2005 Dec
Nonsense-mediated mRNA decay mutation in Aspergillus nidulans.
2006 Nov
The drugs don't work-or do they? Pharmacological and transgenic studies of the contribution of NMDA and GluR-A-containing AMPA receptors to hippocampal-dependent memory.
2006 Nov
Sequential emergence and clinical implications of viral mutants with K70E and K65R mutation in reverse transcriptase during prolonged tenofovir monotherapy in rhesus macaques with chronic RT-SHIV infection.
2007 Apr 6
Felbamate but not phenytoin or gabapentin reduces glutamate release by blocking presynaptic NMDA receptors in the entorhinal cortex.
2007 Dec
Comprehensive gene expression analysis in bipolar disorder.
2007 Dec
Alanine aminotransferase catalyses the breakdown of alanine after hypoxia in Arabidopsis thaliana.
2007 Mar
[Selective disturbance of associative memory reactivation by serotonin or NMDA glutamate receptor antagonists in snail].
2007 Oct
Neuroprotective effects of cannabidiol in endotoxin-induced uveitis: critical role of p38 MAPK activation.
2008
Rapid synapse-specific regulation of hypothalamic magnocellular neurons by glucocorticoids.
2008
(-)-Epigallocatechin gallate induces Nrf2-mediated antioxidant enzyme expression via activation of PI3K and ERK in human mammary epithelial cells.
2008 Aug 15
Neurochemical diversity of afferent neurons that transduce sensory signals from dog ventricular myocardium.
2008 Aug 18
EndoS from Streptococcus pyogenes is hydrolyzed by the cysteine proteinase SpeB and requires glutamic acid 235 and tryptophans for IgG glycan-hydrolyzing activity.
2008 Jan 8
Calculation of the isoelectric point of tryptic peptides in the pH 3.5-4.5 range based on adjacent amino acid effects.
2008 Jul
Genetics of Meesmann corneal dystrophy: a novel mutation in the keratin 3 gene in an asymptomatic family suggests genotype-phenotype correlation.
2008 Sep 15
[Epileptic seizures in critically ill patients].
2009
Molecular and functional characterization of a c-type lysozyme from the Asian corn borer, Ostrinia furnacalis.
2009
Reversible phosphorylation as a molecular switch to regulate plasma membrane targeting of acylated SH4 domain proteins.
2009 Aug
Biochemical evidence for the tyrosine involvement in cationic intermediate stabilization in mouse beta-carotene 15, 15'-monooxygenase.
2009 Dec 14
Excitatory neurotransmitters in brain regions in interictal migraine patients.
2009 Jun 30
Full domain closure of the ligand-binding core of the ionotropic glutamate receptor iGluR5 induced by the high affinity agonist dysiherbaine and the functional antagonist 8,9-dideoxyneodysiherbaine.
2009 May 22
An evaluation of minimal cellular functions to sustain a bacterial cell.
2009 Nov 28
Association and expression studies of glutamate-cysteine ligase modifier (GCLM) and schizophrenia in the Chinese Han population.
2009 Oct
Neurotoxicity of perfluorooctane sulfonate (PFOS) in rats and mice after single oral exposure.
2009 Oct
Differential distribution of aggrecan isoforms in perineuronal nets of the human cerebral cortex.
2009 Sep
Muscle differentiation in a colonial ascidian: organisation, gene expression and evolutionary considerations.
2009 Sep 8
The functional organisation of glia in the adult brain of Drosophila and other insects.
2010 Apr
Synaptic localization and activity of ADAM10 regulate excitatory synapses through N-cadherin cleavage.
2010 Dec 1
A biologically plausible model of time-scale invariant interval timing.
2010 Feb
On the structure of the proton-binding site in the F(o) rotor of chloroplast ATP synthases.
2010 Jan 8
Effect of estrogen on mitochondrial function and intracellular stress markers in rat liver and kidney following trauma-hemorrhagic shock and prolonged hypotension.
2010 Jul-Aug
Entamoeba histolytica Phosphoserine aminotransferase (EhPSAT): insights into the structure-function relationship.
2010 Mar 3
Cholinergic modulation of fast inhibitory and excitatory transmission to pedunculopontine thalamic projecting neurons.
2010 May
Molecular and cellular mechanisms of excitotoxic neuronal death.
2010 Nov
Characterization of JG024, a pseudomonas aeruginosa PB1-like broad host range phage under simulated infection conditions.
2010 Nov 26
Metabotropic glutamate receptors 1 and 5 differentially regulate bulbar dopaminergic cell function.
2010 Oct 1
Gabapentin suppresses cortical spreading depression susceptibility.
2010 Sep
Patents

Sample Use Guides

As a dietary supplement for taste improvement, glutamate is administered orally with food. Glutamate is administered intravenously in patients undergoing coronary artery bypass surgery.
Route of Administration: Other
In Vitro Use Guide
To study binding of glutamate to AMPA and Kainate ion channels, [3H]APMA and [3H]kainic acid were used as a radioligands.
Name Type Language
GLUTAMIC ACID
EP   INCI   INN   MI   USAN   USP-RS   VANDF   WHO-DD  
INCI   USAN   INN  
Official Name English
L-2-AMINO-PENTANEDIOIC ACID
Common Name English
L-GLUTAMIC ACID [JAN]
Common Name English
GLUTAMIC ACID [VANDF]
Common Name English
GLUTAMIC ACID [EP MONOGRAPH]
Common Name English
GLUTAMIC ACID [USP-RS]
Common Name English
GLUTAMIC ACID [INCI]
Common Name English
L-GLUTAMIC ACID [FHFI]
Common Name English
GLUTAMIC ACID [MI]
Common Name English
LYSINE ACETATE IMPURITY B [EP]
Common Name English
NSC-143503
Code English
L-(+)-GLUTAMIC ACID
Systematic Name English
GLUTAMIDEX
Common Name English
(S)-2-AMINO-1,5-PENTANEDIOIC ACID
Systematic Name English
L-GLUTAMIC ACID
FCC   FHFI   JAN  
Systematic Name English
(S)-2-AMINOPENTANEDIOIC ACID
Systematic Name English
INS NO.620
Code English
FEMA NO. 3285
Code English
2-AMINOPENTANEDIOIC ACID
Systematic Name English
GLUTAMIC ACID [USAN]
Common Name English
E 620
Code English
GLUTAMIC ACID [WHO-DD]
Common Name English
E-620
Code English
(S)-(+)-GLUTAMIC ACID
Systematic Name English
GLUTAMIC ACID, L-
Common Name English
INS-620
Code English
L-GLUTAMIC ACID [FCC]
Common Name English
L-ALPHA-AMINOGLUTARIC ACID
Common Name English
GLUTAMIC ACID [INN]
Common Name English
Classification Tree Code System Code
JECFA EVALUATION INS-620
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
CODEX ALIMENTARIUS (GSFA) INS-620
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
EPA PESTICIDE CODE 374350
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
NCI_THESAURUS C68442
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
CFR 21 CFR 310.532
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
NCI_THESAURUS C29596
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
CFR 21 CFR 172.320
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
DSLD 2305 (Number of products:567)
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
WHO-ATC A09AB01
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL575060
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY
EVMPD
SUB11991MIG
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY
HSDB
490
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY
CAS
6899-05-4
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
ALTERNATIVE
DRUG BANK
DB00142
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY
MESH
D018698
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY
JECFA MONOGRAPH
INS-620
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY
WIKIPEDIA
GLUTAMIC ACID
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY
PUBCHEM
33032
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY
MERCK INDEX
M5775
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
200-293-7
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY
DRUG CENTRAL
1310
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY
NCI_THESAURUS
C1115
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY
EVMPD
SUB35454
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY
FDA UNII
3KX376GY7L
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY
RXCUI
25916
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY RxNorm
CAS
56-86-0
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY
EPA CompTox
56-86-0
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY
USP_CATALOG
1294976
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY USP-RS
INN
66
Created by admin on Fri Jun 25 21:11:01 UTC 2021 , Edited by admin on Fri Jun 25 21:11:01 UTC 2021
PRIMARY