ContaminantDB: L-Glutamic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (76)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:16:44 UTC

Update Date

2026-05-14 16:24:14 UTC

Accession Number

CHEM003256

Identification

Common Name

L-Glutamic acid

Class

Small Molecule

Description

Glutamic acid (Glu), also referred to as glutamate (the anion), is one of the 20 proteinogenic amino acids. It is not among the essential amino acids. Glutamate is a key molecule in cellular metabolism. In humans, dietary proteins are broken down by digestion into amino acids, which serves as metabolic fuel or other functional roles in the body. Glutamate is the most abundant fast excitatory neurotransmitter in the mammalian nervous system. At chemical synapses, glutamate is stored in vesicles. Nerve impulses trigger release of glutamate from the pre-synaptic cell. In the opposing post-synaptic cell, glutamate receptors, such as the NMDA receptor, bind glutamate and are activated. Because of its role in synaptic plasticity, it is believed that glutamic acid is involved in cognitive functions like learning and memory in the brain. Glutamate transporters are found in neuronal and glial membranes. They rapidly remove glutamate from the extracellular space. In brain injury or disease, they can work in reverse and excess glutamate can accumulate outside cells. This process causes calcium ions to enter cells via NMDA receptor channels, leading to neuronal damage and eventual cell death, and is called excitotoxicity. The mechanisms of cell death include: * Damage to mitochondria from excessively high intracellular Ca2+. * Glu/Ca2+-mediated promotion of transcription factors for pro-apoptotic genes, or downregulation of transcription factors for anti-apoptotic genes. Excitotoxicity due to glutamate occurs as part of the ischemic cascade and is associated with stroke and diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. glutamic acid has been implicated in epileptic seizures. Microinjection of glutamic acid into neurons produces spontaneous depolarization around one second apart, and this firing pattern is similar to what is known as paroxysmal depolarizing shift in epileptic attacks. This change in the resting membrane potential at seizure foci could cause spontaneous opening of voltage activated calcium channels, leading to glutamic acid release and further depolarization.

Contaminant Sources

EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
HPV EPA Chemicals
OECD HPV Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Animal Toxin
Dietary Supplement
Drug
Food Toxin
Household Toxin
Metabolite
Micronutrient
Natural Compound
Non-Essential Amino Acid
Nutraceutical
Organic Compound
Supplement

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(S)-2-Aminopentanedioic acid	ChEBI
(S)-Glutamic acid	ChEBI
Acide glutamique	ChEBI
Acido glutamico	ChEBI
Acidum glutamicum	ChEBI
E	ChEBI
Glu	ChEBI
Glutamate	ChEBI
GLUTAMIC ACID	ChEBI
L-Glu	ChEBI
L-Glutaminic acid	ChEBI
L-Glutaminsaeure	ChEBI
(S)-2-Aminopentanedioate	Generator
(S)-Glutamate	Generator
L-Glutaminate	Generator
L-Glutamate	Generator
D-Glutamate	MeSH
L Glutamate	MeSH
L Glutamic acid	MeSH
Aluminum L glutamate	MeSH
Aluminum L-glutamate	MeSH
Potassium glutamate	MeSH
D Glutamate	MeSH
Glutamate, potassium	MeSH
Glutamic acid, (D)-isomer	MeSH
L-Glutamate, aluminum	MeSH
(2S)-2-Aminopentanedioate	HMDB
(2S)-2-Aminopentanedioic acid	HMDB
(S)-(+)-Glutamate	HMDB
(S)-(+)-Glutamic acid	HMDB
1-amino-Propane-1,3-dicarboxylate	HMDB
1-amino-Propane-1,3-dicarboxylic acid	HMDB
1-Aminopropane-1,3-dicarboxylate	HMDB
1-Aminopropane-1,3-dicarboxylic acid	HMDB
2-Aminoglutarate	HMDB
2-Aminoglutaric acid	HMDB
2-Aminopentanedioate	HMDB
2-Aminopentanedioic acid	HMDB
a-Aminoglutarate	HMDB
a-Aminoglutaric acid	HMDB
a-Glutamate	HMDB
a-Glutamic acid	HMDB
Aciglut	HMDB
alpha-Aminoglutarate	HMDB
alpha-Aminoglutaric acid	HMDB
alpha-Glutamate	HMDB
alpha-Glutamic acid	HMDB
Aminoglutarate	HMDB
Aminoglutaric acid	HMDB
Glt	HMDB
Glusate	HMDB
Glut	HMDB
Glutacid	HMDB
Glutamicol	HMDB
Glutamidex	HMDB
Glutaminate	HMDB
Glutaminic acid	HMDB
Glutaminol	HMDB
Glutaton	HMDB
L-(+)-Glutamate	HMDB
L-(+)-Glutamic acid	HMDB
L-a-Aminoglutarate	HMDB
L-a-Aminoglutaric acid	HMDB
L-alpha-Aminoglutarate	HMDB
L-alpha-Aminoglutaric acid	HMDB
2-Acetamido-2-deoxy-D-glucose	HMDB
D-GlcNAc	HMDB
N-Acetyl-D-glucosamine	HMDB
N-Acetylchitosamine	HMDB
N Acetyl D glucosamine	HMDB
2 Acetamido 2 deoxy D glucose	HMDB
2 Acetamido 2 deoxyglucose	HMDB
2-Acetamido-2-deoxyglucose	HMDB
Acetylglucosamine	HMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholan-24-oylglycine	HMDB
N-[(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxy-24-oxocholan-24-yl]glycine	HMDB
N-Choloylglycine	HMDB
3a,7a,12a-Trihydroxy-5b-cholan-24-oylglycine	HMDB
3Α,7α,12α-trihydroxy-5β-cholan-24-oylglycine	HMDB
N-[(3a,5b,7a,12a)-3,7,12-Trihydroxy-24-oxocholan-24-yl]glycine	HMDB
N-[(3Α,5β,7α,12α)-3,7,12-trihydroxy-24-oxocholan-24-yl]glycine	HMDB
Glycocholate	HMDB
Glycine cholate	HMDB
Glycocholic acid, sodium salt	HMDB
Cholylglycine	HMDB
Glycocholate sodium	HMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholanic acid-24-glycine	HMDB
3alpha,7alpha,12alpha-Trihydroxy-N-(carboxymethyl)-5beta-cholan-24-amide	HMDB
3Α,7α,12α-trihydroxy-5β-cholanic acid-24-glycine	HMDB
3Α,7α,12α-trihydroxy-N-(carboxymethyl)-5β-cholan-24-amide	HMDB
Glycoreductodehydrocholic acid	HMDB
Glycylcholate	HMDB
Glycylcholic acid	HMDB
N-(Carboxymethyl)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholan-24-amide	HMDB
N-(Carboxymethyl)-3α,7α,12α-trihydroxy-5β-cholan-24-amide	HMDB
N-Choloyl-glycine	HMDB
3-Hydroxy-1,3,5(10)-estratrien-17-one	HMDB
Follicular hormone	HMDB
Folliculin	HMDB
Oestrone	HMDB
(+)-Estrone	HMDB
1,3,5(10)-Estratrien-3-ol-17-one	HMDB
3-Hydroxy-17-keto-estra-1,3,5-triene	HMDB
3-Hydroxyestra-1,3,5(10)-trien-17-one	HMDB
3-Hydroxyestra-1,3,5(10)-triene-17-one	HMDB
3-Hydroxyoestra-1,3,5(10)-trien-17-one	HMDB
D1,3,5(10)-Estratrien-3-ol-17-one	HMDB
Estrone, (+-)-isomer	HMDB
Hyrex brand OF estrone	HMDB
Estrone, (9 beta)-isomer	HMDB
Estrovarin	HMDB
Kestrone	HMDB
Wehgen	HMDB
Estrone, (8 alpha)-isomer	HMDB
Hauck brand OF estrone	HMDB
Unigen	HMDB
Vortech brand OF estrone	HMDB
alpha,beta-Hydroxypropionic acid	HMDB
D-GroA	HMDB
R-Glyceric acid	HMDB
Glycerate	HMDB
(R)-Glycerate	HMDB
a,b-Hydroxypropionate	HMDB
a,b-Hydroxypropionic acid	HMDB
alpha,beta-Hydroxypropionate	HMDB
Α,β-hydroxypropionate	HMDB
Α,β-hydroxypropionic acid	HMDB
R-Glycerate	HMDB
(R)-Glyceric acid	HMDB
D-Glycerate	HMDB
D-Glyceric acid	HMDB
(2R)-2,3-Dihydroxypropanoic acid	HMDB
(R)-2,3-Dihydroxypropanoic acid	HMDB
D-2,3-Dihydroxypropanoic acid	HMDB
1-Amino-2-hydroxyethane	HMDB
2-Amino-1-ethanol	HMDB
2-Amino-ethanol	HMDB
2-Aminoethan-1-ol	HMDB
2-Aminoethyl alcohol	HMDB
2-Hydroxyethylamine	HMDB
Aethanolamin	HMDB
Aminoethanol	HMDB
beta-Aminoethanol	HMDB
beta-Aminoethyl alcohol	HMDB
beta-Ethanolamine	HMDB
beta-Hydroxyethylamine	HMDB
Colamine	HMDB
ETA	HMDB
Glycinol	HMDB
Hea	HMDB
MEA	HMDB
MONOETHANOLAMINE	HMDB
b-Aminoethanol	HMDB
Β-aminoethanol	HMDB
b-Aminoethyl alcohol	HMDB
Β-aminoethyl alcohol	HMDB
b-Ethanolamine	HMDB
Β-ethanolamine	HMDB
b-Hydroxyethylamine	HMDB
Β-hydroxyethylamine	HMDB
2-Aminoethanol	HMDB
2-Ethanolamine	HMDB
2-Hydroxyethanamine	HMDB
Envision conditioner PDD 9020	HMDB
Ethylolamine	HMDB
H-Glycinol	HMDB
Monoaethanolamin	HMDB
Olamine	HMDB
2 Aminoethanol	HMDB
(3R,4S,5R)-5-[(1R)-1-Carboxy-2,2-difluoro-1-(phosphonooxy)ethoxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylate	HMDB
(1S)-2-[(3-O-b-D-Glucopyranosyl-b-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoate	HMDB
(1S)-2-[(3-O-b-D-Glucopyranosyl-b-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoic acid	HMDB
(1S)-2-[(3-O-beta-D-Glucopyranosyl-beta-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoic acid	HMDB
(1S)-2-[(3-O-Β-D-glucopyranosyl-β-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoate	HMDB
(1S)-2-[(3-O-Β-D-glucopyranosyl-β-D-galactopyranosyl)oxy]-1-{[(9E)-octadec-9-enoyloxy]methyl}ethyl (10E)-nonadec-10-enoic acid	HMDB

Chemical Formula

C₅H₉NO₄

Average Molecular Mass

147.129 g/mol

Monoisotopic Mass

147.053 g/mol

CAS Registry Number

56-86-0

IUPAC Name

(2S)-2-aminopentanedioic acid

Traditional Name

L-glutamic acid

SMILES

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

InChI Identifier

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

InChI Key

WHUUTDBJXJRKMK-VKHMYHEASA-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
Alpha-amino acid
L-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 Framework

Aliphatic acyclic compounds

External Descriptors

proteinogenic amino acid (CHEBI:16015 )
L-alpha-amino acid (CHEBI:16015 )
glutamic acid (CHEBI:16015 )
glutamine family amino acid (CHEBI:16015 )
Common amino acids (C00025 )
Amino acids (C00025 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Endoplasmic reticulum
Extracellular
Lysosome
Membrane
Mitochondria

Biofluid Locations

Not Available

Tissue Locations

Adipose Tissue
Adrenal Medulla
Epidermis
Fibroblasts
Intestine
Kidney
Muscle
Myelin
Nerve Cells
Neuron
Pancreas
Placenta
Platelet
Prostate
Skeletal Muscle
Spleen
Stratum Corneum

Pathways

Name	SMPDB Link	KEGG Link
Alanine Metabolism	SMP00055	map00250
Amino Sugar Metabolism	SMP00045	map00520
Ammonia Recycling	SMP00009	map00910
Arginine and Proline Metabolism	SMP00020	map00330
Cysteine Metabolism	SMP00013	map00270
Folate Metabolism	SMP00053	map00670
Glucose-Alanine Cycle	SMP00127	Not Available
Glutamate Metabolism	SMP00072	map00250
Glutathione Metabolism	SMP00015	map00480
Glycine and Serine Metabolism	SMP00004	map00260
Histidine Metabolism	SMP00044	map00340
Malate-Aspartate Shuttle	SMP00129	Not Available
Transcription/Translation	SMP00019	Not Available
Urea Cycle	SMP00059	Not Available
Argininosuccinic Aciduria	SMP00003	Not Available

Applications

nutraceutical

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	224 dec°C
Boiling Point	Not Available
Solubility	8570 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	80.6 g/L	ALOGPS
logP	-3.5	ALOGPS
logP	-3.2	ChemAxon
logS	-0.26	ALOGPS
pKa (Strongest Acidic)	1.88	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.62 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.29 m³·mol⁻¹	ChemAxon
Polarizability	13.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-0002-2950000000-2d6edc93ec5f8dee2223	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-002b-0940000000-4e285988bc537825d94d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00dj-9630000000-1ecc76aab86283892139	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-8910000000-00f65ced0c55aa4ad169	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0032-3980000000-3069de5b6c49e4176968	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-0790000000-79d3e289c22cb183faa1	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-2950000000-2d6edc93ec5f8dee2223	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-002b-0940000000-4e285988bc537825d94d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-QQ (Non-derivatized)	splash10-00ea-6932100000-30d3f5dcc198a5971e96	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dj-9630000000-1ecc76aab86283892139	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-8910000000-00f65ced0c55aa4ad169	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0032-3980000000-3069de5b6c49e4176968	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0znc-9300000000-f88e86b78a4cee99a2d4	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-8290000000-f99e03763f636e557887	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-003r-6900000000-95b0a084dc076f9c7b91	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-c37d4c80a14ec029ef63	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a59-9000000000-6f1888aa71bcb0adf76c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004j-0900000000-5fa8a338dcd2f2a6bdd2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0900000000-16763200aa07f7629ad4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-03di-3900000000-d9cfc5187aa799f6f978	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0a4i-0900000000-10ee9a593e13550bec1c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0900000000-4d045a3c1fc6e56f801b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-001i-9000000000-c3c7f8f3754109a0c25b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-004i-0900000000-48bfae26c69408b7f0ae	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0900000000-82c2a681e7522a7bb1d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0002-0905010000-af1c9ec4d0062fa6960e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-01q9-9700000000-2b967b896a6e48914512	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-1434321646181ea894a0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0900000000-11fadb2530828eedad8a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-006t-0941100000-07d051890cb1d9e5c856	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-9200000000-f8619d11f1f54d836bb1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-0900000000-ea2dd00e79ef06e8dc04	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00di-0900000000-3e239d4014c95a2ef873	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-b548959edce39d319cf4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0900000000-40d901f655797db2cd0f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0udi-1900000000-f997527a39900ac431c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0udi-7900000000-60816f0601a4e6d25ffb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0007-9000000000-6ee821f657c604d1afca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-000t-0900000000-7c02624abe56da9247a2	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Absorbed from the lumen of the small intestine into the enterocytes.Absorption is efficient and occurs by an active transport mechanism.

Mechanism of Toxicity

Glutamate activates both ionotropic and metabotropic glutamate receptors. The ionotropic ones being non-NMDA (AMPA and kainate) and NMDA receptors. Free glutamic acid cannot cross the blood-brain barrier in appreciable quantities; instead it is converted into L-glutamine, which the brain uses for fuel and protein synthesis. It is conjectured that glutamate is involved in cognitive functions like learning and memory in the brain, though excessive amounts may cause neuronal damage associated in diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. Also, the drug phencyclidine (more commonly known as PCP) antagonizes glutamate at the NMDA receptor, causing behavior reminiscent of schizophrenia. Glutamate in action is extremely difficult to study due to its transient nature.

Metabolism

Hepatic

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Considered to be nature's "Brain food" by improving mental capacities; helps speed the healing of ulcers; gives a "lift" from fatigue; helps control alcoholism, schizophrenia and the craving for sugar.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00142

HMDB ID

HMDB0000148

FooDB ID

FDB012535

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001358

BiGG ID

Not Available

BioCyc ID

GLT

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

L-Glutamic_Acid

Chemspider ID

Not Available

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Nobuharu Tujimoto, Yoshimi Kikuchi, Osamu Kurahashi, Yoshiko Kawahara, “Mutant Escherichia coli capable of enhanced L-glutamic acid production.” U.S. Patent US5393671, issued August, 1960.

MSDS

Link

General References

1. Horner, L.; Gross, A. Tertiary phosphines. IV. Use of phosphine imines in causing the introduction of primary amino groups. Liebigs Ann. Chem. (1955), 591 117-34.

2. Molinari F, Raas-Rothschild A, Rio M, Fiermonte G, Encha-Razavi F, Palmieri L, Palmieri F, Ben-Neriah Z, Kadhom N, Vekemans M, Attie-Bitach T, Munnich A, Rustin P, Colleaux L: Impaired mitochondrial glutamate transport in autosomal recessive neonatal myoclonic epilepsy. Am J Hum Genet. 2005 Feb;76(2):334-9. Epub 2004 Dec 8.

3. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.

4. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7.

5. Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36.

6. Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75.

7. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14.

8. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6.

9. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24.