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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (92)transporters (2) Show 94 proteins XML

enzymes (92)transporters (2) Show 94 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2025-05-29 18:10:03 UTC

HMDB ID

HMDB0000148

Secondary Accession Numbers

HMDB00148

Metabolite Identification

Common Name

Glutamic acid

Description

Glutamic acid (Glu), also known as L-glutamic acid or as glutamate, the name of its anion, is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (-NH2) and carboxyl (-COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-glutamic acid is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Glutamic acid is found in all organisms ranging from bacteria to plants to animals. It is classified as an acidic, charged (at physiological pH), aliphatic amino acid. In humans it is a non-essential amino acid and can be synthesized via alanine or aspartic acid via alpha-ketoglutarate and the action of various transaminases. Glutamate also plays an important role in the body's disposal of excess or waste nitrogen. Glutamate undergoes deamination, an oxidative reaction catalysed by glutamate dehydrogenase leading to alpha-ketoglutarate. In many respects glutamate is a key molecule in cellular metabolism. 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 (http://en.wikipedia.org/wiki/Glutamic_acid). Glutamate was discovered in 1866 when it was extracted from wheat gluten (from where it got its name. Glutamate has an important role as a food additive and food flavoring agent. In 1908, Japanese researcher Kikunae Ikeda identified brown crystals left behind after the evaporation of a large amount of kombu broth (a Japanese soup) as glutamic acid. These crystals, when tasted, reproduced a salty, savory flavor detected in many foods, most especially in seaweed. Professor Ikeda termed this flavor umami. He then patented a method of mass-producing a crystalline salt of glutamic acid, monosodium glutamate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

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 Weight

147.1293

Monoisotopic Molecular Weight

147.053157781

IUPAC Name

(2S)-2-aminopentanedioic acid

Traditional Name

L-glutamic acid

CAS Registry Number

56-86-0

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 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	8.57 mg/mL	Not Available
LogP	-3.69	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	125.64	30932474
[M-H]-	McLean	125.839	30932474
[M+H]+	Baker	134.586	30932474
[M-H]-	Not Available	125.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000075

Predicted Molecular 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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	130.757	31661259
DarkChem	[M-H]-	125.077	31661259
AllCCS	[M+H]+	133.83	32859911
AllCCS	[M-H]-	126.642	32859911
DeepCCS	[M+H]+	127.758	30932474
DeepCCS	[M-H]-	123.923	30932474
DeepCCS	[M-2H]-	161.438	30932474
DeepCCS	[M+Na]+	136.847	30932474
AllCCS	[M+H]+	133.8	32859911
AllCCS	[M+H-H2O]+	129.8	32859911
AllCCS	[M+NH4]+	137.6	32859911
AllCCS	[M+Na]+	138.6	32859911
AllCCS	[M-H]-	126.6	32859911
AllCCS	[M+Na-2H]-	128.8	32859911
AllCCS	[M+HCOO]-	131.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.0 minutes	32390414
Predicted by Siyang on May 30, 2022	9.2343 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.62 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	400.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	484.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	318.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	40.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	195.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	67.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	287.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	220.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	836.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	584.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	39.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	677.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	198.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	277.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	725.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	480.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	478.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Glutamic acid	N[C@@H](CCC(O)=O)C(O)=O	2199.6	Standard polar	33892256
L-Glutamic acid	N[C@@H](CCC(O)=O)C(O)=O	1237.6	Standard non polar	33892256
L-Glutamic acid	N[C@@H](CCC(O)=O)C(O)=O	1815.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Glutamic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@H](N)C(=O)O	1507.5	Semi standard non polar	33892256
L-Glutamic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)O	1472.0	Semi standard non polar	33892256
L-Glutamic acid,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)O	1533.4	Semi standard non polar	33892256
L-Glutamic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@H](N)C(=O)O[Si](C)(C)C	1518.9	Semi standard non polar	33892256
L-Glutamic acid,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O	1617.6	Semi standard non polar	33892256
L-Glutamic acid,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C	1589.3	Semi standard non polar	33892256
L-Glutamic acid,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C	1729.5	Semi standard non polar	33892256
L-Glutamic acid,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1625.8	Semi standard non polar	33892256
L-Glutamic acid,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1664.7	Standard non polar	33892256
L-Glutamic acid,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1807.9	Standard polar	33892256
L-Glutamic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1779.5	Semi standard non polar	33892256
L-Glutamic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1718.7	Standard non polar	33892256
L-Glutamic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1969.6	Standard polar	33892256
L-Glutamic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1765.0	Semi standard non polar	33892256
L-Glutamic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1708.5	Standard non polar	33892256
L-Glutamic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1949.2	Standard polar	33892256
L-Glutamic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1804.2	Semi standard non polar	33892256
L-Glutamic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1776.6	Standard non polar	33892256
L-Glutamic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1746.4	Standard polar	33892256
L-Glutamic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](N)C(=O)O	1765.9	Semi standard non polar	33892256
L-Glutamic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCC(=O)O	1743.3	Semi standard non polar	33892256
L-Glutamic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)O	1797.0	Semi standard non polar	33892256
L-Glutamic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C	1982.4	Semi standard non polar	33892256
L-Glutamic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2094.9	Semi standard non polar	33892256
L-Glutamic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2043.8	Semi standard non polar	33892256
L-Glutamic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2168.8	Semi standard non polar	33892256
L-Glutamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2272.6	Semi standard non polar	33892256
L-Glutamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2259.4	Standard non polar	33892256
L-Glutamic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2195.4	Standard polar	33892256
L-Glutamic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2433.4	Semi standard non polar	33892256
L-Glutamic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2321.6	Standard non polar	33892256
L-Glutamic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2263.8	Standard polar	33892256
L-Glutamic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2427.8	Semi standard non polar	33892256
L-Glutamic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2289.5	Standard non polar	33892256
L-Glutamic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2256.1	Standard polar	33892256
L-Glutamic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2668.5	Semi standard non polar	33892256
L-Glutamic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2533.6	Standard non polar	33892256
L-Glutamic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2243.6	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Mitochondria
Lysosome
Endoplasmic reticulum

Biospecimen Locations

Blood
Cellular Cytoplasm
Cerebrospinal Fluid (CSF)
Feces
Saliva
Sweat
Urine

Tissue Locations

Adipose Tissue
Adrenal Medulla
Epidermis
Fibroblasts
Intestine
Kidney
Neuron
Pancreas
Placenta
Platelet
Prostate
Skeletal Muscle
Spleen

Pathways

Name	SMPDB/PathBank	KEGG
Alanine, aspartate and glutamate metabolism	Not Available
Histidine metabolism
Malate-Aspartate Shuttle		Not Available
Nitrogen metabolism	Not Available
Cysteine Metabolism

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	24.0 (9.0-39.0) uM	Adult (>18 years old)	Both	Normal	12297216	details
Blood	Detected and Quantified	65.0 +/- 35.0 uM	Newborn (0-30 days old)	Not Specified	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	35.0 +/- 14.0 uM	Children (1-13 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	37.0 +/- 14.0 uM	Children (1-13 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	60.0 +/- 16.0 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	46.0 +/- 13.0 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	33.0 +/- 12.0 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	145.0 +/- 6.0 uM	Adult (>18 years old)	Male	Normal	16789974	details
Blood	Detected and Quantified	97.4 +/- 13.2 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	15-80 uM	Newborn (0-30 days old)	Both	Normal	BC Children's Hos...	details
Blood	Detected and Quantified	10-80 uM	Infant (1 - 3 months old)	Both	Normal	BC Children's Hos...	details
Blood	Detected and Quantified	8-80 uM	Children (3 months - 6 years old)	Both	Normal	BC Children's Hos...	details
Blood	Detected and Quantified	8-80 uM	Children (6 - 18 years old)	Both	Normal	BC Children's Hos...	details
Blood	Detected and Quantified	33.5 +/- 3.20 uM	Adult (>18 years old)	Both	Normal	25004141	details
Blood	Detected and Quantified	65.19 +/- 48.71 uM	Adult (>18 years old)	Both	Normal	24713860	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22024767	details
Blood	Detected and Quantified	46.2 +/- 21.4 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	20.00-110.0 uM	Adult (>18 years old)	Both	Normal	The Metabolo...	details
Blood	Detected and Quantified	90 +/- 65 uM	Infant (0-1 year old)	Both	Normal	7623444	details
Blood	Detected and Quantified	176.9(140.6-218.8) uM	Children (1-13 uears old)	Both	Normal	27294788	details
Blood	Detected and Quantified	114.1 (75.2-203.1) uM	Infant (0-1 year old)	Not Specified	Normal	894411	details
Blood	Detected and Quantified	2-118 uM	Infant (0-1 year old)	Not Specified	Normal	24341803	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	71.36 ± 20.73 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	88.79 ± 36.74 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	146.6 ± 39.76 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	56.33 ± 21.94 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	68.91 ± 20.16 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	158.79 ± 64.68 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	32.93 ± 15.76 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	35.39 ± 21.53 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	135.89 ± 48.02 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Cellular Cytoplasm	Detected and Quantified	1400 (1200-1600) uM	Adult (>18 years old)	Both	Normal	8579834	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.8 +/- 0.7 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.62 (0.18-1.15) uM	Adult (>18 years old)	Both	Normal	9004939	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.34 +/- 0.14 uM	Adult (>18 years old)	Not Specified	Normal	2453224	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	32.6 +/- 6.9 uM	Adult (>18 years old)	Not Specified	Normal	15911239	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	40 +/- 52 uM	Adult (>18 years old)	Both	Normal	18502700	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.44 +/- 0.29 uM	Adult (>18 years old)	Both	Normal	7595563	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0-15 uM	Children (0 - 10 years old)	Both	Normal	BC Children's Hos...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0-15 uM	Adolescent (>11 years old)	Both	Normal	BC Children's Hos...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.143-0.298 uM	Children (1-13 years old)	Not Specified	Normal	8916158	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	7.0 +/- 4.9 uM	Infant (0-1 year old)	Not Specified	Normal	894411	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0 uM	Children (1-13 years old)	Not Specified	Normal	24341803	details
Feces	Detected and Quantified	484.608 +/- 314.757 nmol/g wet feces	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21330412	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	22944170	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23940645	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Both	Normal	25486321	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17269711	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	24130822	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25598765	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27065191	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27107423	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Normal	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	27622378	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	Christopher ...	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28842642	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28587349	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	28701177	details
Saliva	Detected and Quantified	>10 uM	Adult (>18 years old)	Both	Normal	12097436	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20300169	details
Saliva	Detected and Quantified	13.6 +/- 2.4 uM	Adult (>18 years old)	Male	Normal	21164041	details
Saliva	Detected and Quantified	13.3 +/- 6.0 uM	Adult (>18 years old)	Male	Normal	21164041	details
Saliva	Detected and Quantified	12.6 +/- 6.5 uM	Adult (>18 years old)	Male	Normal	21164041	details
Saliva	Detected and Quantified	11.6 +/- 6.9 uM	Adult (>18 years old)	Male	Normal	21164041	details
Sweat	Detected and Quantified	< 10 uM	Adult (60 years old)	Male	Normal	22194922	details
Sweat	Detected and Quantified	< 10 uM	Adult (40 years old)	Male	Normal	22194922	details
Sweat	Detected but not Quantified	Not Quantified	Adult	Both	Normal	26755145	details
Urine	Detected and Quantified	1.711 (0.329-3.092) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Not Available	details
Urine	Detected and Quantified	37.78 (8.89-66.67) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected and Quantified	6.87 +/- 3.51 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2026685	details
Urine	Detected and Quantified	1.38 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details
Urine	Detected and Quantified	<4.76-217.61 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	David F. Putnam C...	details
Urine	Detected and Quantified	6.4 (0.6-17.5) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	8.5 (3.3-18.4) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	16939360	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	16939360	details
Urine	Detected and Quantified	10.0 +/- 3.7 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Tanaka, T. and Na...	details
Urine	Detected and Quantified	13.3351 +/- 13.4213 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	30.83 +/- 23.237 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0 - 29.96 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	2.04 - 29.06 umol/mmol creatinine	Infant (1 - 6 months old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 17.98 umol/mmol creatinine	Infant (6 months - <1 year old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 17.98 umol/mmol creatinine	Children (1 - 2 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 9.95 umol/mmol creatinine	Children (2 - 4 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 9.04 umol/mmol creatinine	Children (4 - 13 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 11.98 umol/mmol creatinine	Adolescent (13 - 21 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	0 - 11.98 umol/mmol creatinine	Adult (>21 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	1.2-2.3 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	1.1-1.7 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22024767	details
Urine	Detected and Quantified	<11 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	24341803	details
Urine	Detected and Quantified	23.86 +/- 46.36 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	19468821	details
Urine	Detected and Quantified	32.67 +/- 44.09 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	19468821	details
Urine	Detected and Quantified	34.94 +/- 56.53 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	19468821	details
Urine	Detected and Quantified	1.96-35.26 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	14.25 +/- 10.09 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	11.51 +/- 6.97 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected and Quantified	<27.48 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	1.36-14.48 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	<8.60 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	<4.41 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	<7.013 umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	<3.85 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	6.31 (4.56-16.08) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	29.8 (27.6-32.0) uM	Adult (>18 years old)	Both	Epilepsy	14992292	details
Blood	Detected and Quantified	97.5 (60-241) uM	Children (1-13 years old)	Male	Lipoyltransferase 1 Deficiency	24341803	details
Blood	Detected and Quantified	48.4 (24.8-87.2) uM	Infant (0-1 year old)	Male	Dicarboxylic Aminoaciduria	894411	details
Blood	Detected and Quantified	251.7(156.9-334.7) uM	Children (1-13 uears old)	Both	Environmental enteric dysfunction	27294788	details
Blood	Detected and Quantified	64-173 uM	Infant (0-1 year old)	Male	N-Acetylglutamate synthetase deficiency	7623444	details
Blood	Detected and Quantified	109-296 uM	Newborn (0-30 days old)	Male	N-Acetylglutamate synthetase deficiency	7623444	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22024767	details
Blood	Detected and Quantified	77.93 +/- 39.86 uM	Adult (>18 years old)	Both	Schizophrenia	24713860	details
Blood	Detected and Quantified	71.3 +/- 12.3 uM	Adult (>18 years old)	Both	Schizophrenia	25004141	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	superficial gastric cancer	21443661	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	gastric cancer	21443661	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	oesophago-gastric cancer	23896378	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Pancreatic Cancer	25429707	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Blood	Detected and Quantified	32.7 +/- 18.0 uM	Adult (>18 years old)	Male	Schizophrenia	2480613	details
Blood	Detected and Quantified	34.7 +/- 26.0 uM	Adult (>18 years old)	Both	Schizophrenia	2480613	details
Blood	Detected and Quantified	33.18 +/- 11.26 uM	Elderly (>65 years old)	Both	Alzheimer's disease	17031479	details
Blood	Detected and Quantified	56.6 (44.6-68.6) uM	Adult (>18 years old)	Both	Epilepsy	14992292	details
Blood	Detected and Quantified	39.7 (36.5-42.9) uM	Children (1-13 years old)	Both	Epilepsy	14992292	details
Blood	Detected and Quantified	172.0 +/- 6.0 uM	Adult (>18 years old)	Both	Heart failure	16789974	details
Blood	Detected and Quantified	72 +/- 36.9 uM	Adult (>18 years old)	Both	Heart Transplant	21359215	details
Cellular Cytoplasm	Detected and Quantified	2500 (2100-2900) uM	Adult (>18 years old)	Both	Anoxia	8579834	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.213-0.539 uM	Children (1-13 years old)	Female	Rett syndrome	8916158	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	26.8 +/- 5.9 uM	Children (1-13 years old)	Not Specified	Leukemia	15911239	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	23.6 +/- 8.5 uM	Children (1-13 years old)	Not Specified	Leukemia	15911239	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.252-0.332 uM	Adolescent (13-18 years old)	Female	Rett syndrome	8916158	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	7.5 uM	Infant (0-1 year old)	Male	Dicarboxylic Aminoaciduria	894411	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0 uM	Children (1-13 years old)	Male	Lipoyltransferase 1 Deficiency	24341803	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.32 +/- 0.09 uM	Adult (>18 years old)	Both	Schizophrenia	7595563	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	obese	26505825	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Both	Sepsis	28701177	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	28587349	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Myalgic encephalomyelitis/chronic fatigue syndrome	Christopher ...	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	symptomatic uncomplicated diverticular disease	27622378	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	asymptomatic diverticulosis	27622378	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Unclassified IBD	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Ulcerative colitis	27609529	details
Feces	Detected but not Quantified	Not Quantified	Children (6 - 18 years old)	Not Specified	Crohns disease	27609529	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27107423	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	25598765	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohns disease	25598765	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Autism	24130822	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	23940645	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Irritable bowel syndrome	21330412	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cryptosporidium infection	22944170	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	23940645	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	28842642	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohn disease	28842642	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Pancreatic cancer	20300169	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Oral cancer	20300169	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Periodontal diseases	20300169	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Breast cancer	20300169	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22024767	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	oesophago-gastric cancer	23896378	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details
Urine	Detected and Quantified	0.0064 umol/mmol creatinine	Adult (>18 years old)	Both	ADPKD	21389975	details
Urine	Detected and Quantified	21.741 +/- 15.628 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	2 umol/mmol creatinine	Children (1-13 years old)	Male	Lipoyltransferase 1 Deficiency	24341803	details
Urine	Detected and Quantified	20.6656 +/- 23.9161 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details
Urine	Detected and Quantified	11.2759 +/- 6.8729 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Epilepsy
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. [PubMed:14992292 ]
Schizophrenia
Alfredsson G, Wiesel FA: Monoamine metabolites and amino acids in serum from schizophrenic patients before and during sulpiride treatment. Psychopharmacology (Berl). 1989;99(3):322-7. [PubMed:2480613 ] Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. [PubMed:7595563 ] Fukushima T, Iizuka H, Yokota A, Suzuki T, Ohno C, Kono Y, Nishikiori M, Seki A, Ichiba H, Watanabe Y, Hongo S, Utsunomiya M, Nakatani M, Sadamoto K, Yoshio T: Quantitative analyses of schizophrenia-associated metabolites in serum: serum D-lactate levels are negatively correlated with gamma-glutamylcysteine in medicated schizophrenia patients. PLoS One. 2014 Jul 8;9(7):e101652. doi: 10.1371/journal.pone.0101652. eCollection 2014. [PubMed:25004141 ] Koike S, Bundo M, Iwamoto K, Suga M, Kuwabara H, Ohashi Y, Shinoda K, Takano Y, Iwashiro N, Satomura Y, Nagai T, Natsubori T, Tada M, Yamasue H, Kasai K: A snapshot of plasma metabolites in first-episode schizophrenia: a capillary electrophoresis time-of-flight mass spectrometry study. Transl Psychiatry. 2014 Apr 8;4:e379. doi: 10.1038/tp.2014.19. [PubMed:24713860 ] Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
Alzheimer's disease
Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. [PubMed:17031479 ]
Heart failure
Norrelund H, Wiggers H, Halbirk M, Frystyk J, Flyvbjerg A, Botker HE, Schmitz O, Jorgensen JO, Christiansen JS, Moller N: Abnormalities of whole body protein turnover, muscle metabolism and levels of metabolic hormones in patients with chronic heart failure. J Intern Med. 2006 Jul;260(1):11-21. [PubMed:16789974 ]
Lipoyltransferase 1 Deficiency
Soreze Y, Boutron A, Habarou F, Barnerias C, Nonnenmacher L, Delpech H, Mamoune A, Chretien D, Hubert L, Bole-Feysot C, Nitschke P, Correia I, Sardet C, Boddaert N, Hamel Y, Delahodde A, Ottolenghi C, de Lonlay P: Mutations in human lipoyltransferase gene LIPT1 cause a Leigh disease with secondary deficiency for pyruvate and alpha-ketoglutarate dehydrogenase. Orphanet J Rare Dis. 2013 Dec 17;8:192. doi: 10.1186/1750-1172-8-192. [PubMed:24341803 ]
Dicarboxylic aminoaciduria
Melancon SB, Dallaire L, Lemieux B, Robitaille P, Potier M: Dicarboxylic aminoaciduria: an inborn error of amino acid conservation. J Pediatr. 1977 Sep;91(3):422-7. [PubMed:894411 ]
N-acetylglutamate synthetase deficiency
Guffon N, Vianey-Saban C, Bourgeois J, Rabier D, Colombo JP, Guibaud P: A new neonatal case of N-acetylglutamate synthase deficiency treated by carbamylglutamate. J Inherit Metab Dis. 1995;18(1):61-5. [PubMed:7623444 ]
Stomach cancer
Yu L, Aa J, Xu J, Sun M, Qian S, Cheng L, Yang S, Shi R: Metabolomic phenotype of gastric cancer and precancerous stages based on gas chromatography time-of-flight mass spectrometry. J Gastroenterol Hepatol. 2011 Aug;26(8):1290-7. doi: 10.1111/j.1440-1746.2011.06724.x. [PubMed:21443661 ]
Anoxia
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. [PubMed:8579834 ]
Leukemia
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. [PubMed:15911239 ]
Rett syndrome
Lappalainen R, Riikonen RS: High levels of cerebrospinal fluid glutamate in Rett syndrome. Pediatr Neurol. 1996 Oct;15(3):213-6. [PubMed:8916158 ]
Sepsis
Stewart CJ, Embleton ND, Marrs ECL, Smith DP, Fofanova T, Nelson A, Skeath T, Perry JD, Petrosino JF, Berrington JE, Cummings SP: Longitudinal development of the gut microbiome and metabolome in preterm neonates with late onset sepsis and healthy controls. Microbiome. 2017 Jul 12;5(1):75. doi: 10.1186/s40168-017-0295-1. [PubMed:28701177 ]
Diverticular disease
Tursi A, Mastromarino P, Capobianco D, Elisei W, Miccheli A, Capuani G, Tomassini A, Campagna G, Picchio M, Giorgetti G, Fabiocchi F, Brandimarte G: Assessment of Fecal Microbiota and Fecal Metabolome in Symptomatic Uncomplicated Diverticular Disease of the Colon. J Clin Gastroenterol. 2016 Oct;50 Suppl 1:S9-S12. doi: 10.1097/MCG.0000000000000626. [PubMed:27622378 ]
Obesity
Haro C, Montes-Borrego M, Rangel-Zuniga OA, Alcala-Diaz JF, Gomez-Delgado F, Perez-Martinez P, Delgado-Lista J, Quintana-Navarro GM, Tinahones FJ, Landa BB, Lopez-Miranda J, Camargo A, Perez-Jimenez F: Two Healthy Diets Modulate Gut Microbial Community Improving Insulin Sensitivity in a Human Obese Population. J Clin Endocrinol Metab. 2016 Jan;101(1):233-42. doi: 10.1210/jc.2015-3351. Epub 2015 Oct 27. [PubMed:26505825 ]
Ulcerative colitis
Bjerrum JT, Wang Y, Hao F, Coskun M, Ludwig C, Gunther U, Nielsen OH: Metabonomics of human fecal extracts characterize ulcerative colitis, Crohn's disease and healthy individuals. Metabolomics. 2015;11:122-133. Epub 2014 Jun 1. [PubMed:25598765 ] Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ] Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Crohn's disease
Bjerrum JT, Wang Y, Hao F, Coskun M, Ludwig C, Gunther U, Nielsen OH: Metabonomics of human fecal extracts characterize ulcerative colitis, Crohn's disease and healthy individuals. Metabolomics. 2015;11:122-133. Epub 2014 Jun 1. [PubMed:25598765 ] Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ] Azario I, Pievani A, Del Priore F, Antolini L, Santi L, Corsi A, Cardinale L, Sawamoto K, Kubaski F, Gentner B, Bernardo ME, Valsecchi MG, Riminucci M, Tomatsu S, Aiuti A, Biondi A, Serafini M: Neonatal umbilical cord blood transplantation halts skeletal disease progression in the murine model of MPS-I. Sci Rep. 2017 Aug 25;7(1):9473. doi: 10.1038/s41598-017-09958-9. [PubMed:28842642 ]
Autism
De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Colorectal cancer
Weir TL, Manter DK, Sheflin AM, Barnett BA, Heuberger AL, Ryan EP: Stool microbiome and metabolome differences between colorectal cancer patients and healthy adults. PLoS One. 2013 Aug 6;8(8):e70803. doi: 10.1371/journal.pone.0070803. Print 2013. [PubMed:23940645 ] Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ] Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Lin Y, Ma C, Liu C, Wang Z, Yang J, Liu X, Shen Z, Wu R: NMR-based fecal metabolomics fingerprinting as predictors of earlier diagnosis in patients with colorectal cancer. Oncotarget. 2016 May 17;7(20):29454-64. doi: 10.18632/oncotarget.8762. [PubMed:27107423 ] Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Wang X, Wang J, Rao B, Deng L: Gut flora profiling and fecal metabolite composition of colorectal cancer patients and healthy individuals. Exp Ther Med. 2017 Jun;13(6):2848-2854. doi: 10.3892/etm.2017.4367. Epub 2017 Apr 20. [PubMed:28587349 ]
Irritable bowel syndrome
Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ]
Periodontal disease
Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Pancreatic cancer
Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ] Xie G, Lu L, Qiu Y, Ni Q, Zhang W, Gao YT, Risch HA, Yu H, Jia W: Plasma metabolite biomarkers for the detection of pancreatic cancer. J Proteome Res. 2015 Feb 6;14(2):1195-202. doi: 10.1021/pr501135f. Epub 2014 Dec 8. [PubMed:25429707 ]
Perillyl alcohol administration for cancer treatment
Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Autosomal dominant polycystic kidney disease
Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]

Associated OMIM IDs

181500 (Schizophrenia)
104300 (Alzheimer's disease)
137215 (Stomach cancer)
608300 (N-acetylglutamate synthetase deficiency)
222730 (Dicarboxylic aminoaciduria)
616299 (Lipoyltransferase 1 Deficiency)
312750 (Rett syndrome)
114500 (Colorectal cancer)
209850 (Autism)
266600 (Crohn's disease)
601665 (Obesity)
260350 (Pancreatic cancer)
170650 (Periodontal disease)
601313 (Autosomal dominant polycystic kidney disease)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB00142

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012535

KNApSAcK ID

C00001358

Chemspider ID

Not Available

KEGG Compound ID

C00025

BioCyc ID

GLT

BiGG ID

Not Available

Wikipedia Link

L-Glutamic_Acid

METLIN ID

Not Available

PubChem Compound

33032

PDB ID

Not Available

ChEBI ID

16015

Food Biomarker Ontology

Not Available

VMH ID

GLU_L

MarkerDB ID

MDB00000070

Good Scents ID

rw1025121

References

Synthesis Reference

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. [PubMed:15592994 ]
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. [PubMed:19212411 ]
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. [PubMed:12097436 ]
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. [PubMed:8579834 ]
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. [PubMed:6696735 ]
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. [PubMed:15911239 ]
Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [PubMed:12297216 ]
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. [PubMed:14992292 ]
Mross K, Maessen P, van der Vijgh WJ, Gall H, Boven E, Pinedo HM: Pharmacokinetics and metabolism of epidoxorubicin and doxorubicin in humans. J Clin Oncol. 1988 Mar;6(3):517-26. [PubMed:3162516 ]
Noorlander CW, de Graan PN, Nikkels PG, Schrama LH, Visser GH: Distribution of glutamate transporters in the human placenta. Placenta. 2004 Jul;25(6):489-95. [PubMed:15135231 ]
Grasselli G, Vigano L, Capri G, Locatelli A, Tarenzi E, Spreafico C, Bertuzzi A, Giani A, Materazzo C, Cresta S, Perotti A, Valagussa P, Gianni L: Clinical and pharmacologic study of the epirubicin and paclitaxel combination in women with metastatic breast cancer. J Clin Oncol. 2001 Apr 15;19(8):2222-31. [PubMed:11304775 ]
Frayn KN, Khan K, Coppack SW, Elia M: Amino acid metabolism in human subcutaneous adipose tissue in vivo. Clin Sci (Lond). 1991 May;80(5):471-4. [PubMed:1851687 ]
Alfredsson G, Wiesel FA, Tylec A: Relationships between glutamate and monoamine metabolites in cerebrospinal fluid and serum in healthy volunteers. Biol Psychiatry. 1988 Apr 1;23(7):689-97. [PubMed:2453224 ]
Zoia C, Cogliati T, Tagliabue E, Cavaletti G, Sala G, Galimberti G, Rivolta I, Rossi V, Frattola L, Ferrarese C: Glutamate transporters in platelets: EAAT1 decrease in aging and in Alzheimer's disease. Neurobiol Aging. 2004 Feb;25(2):149-57. [PubMed:14749132 ]
Rizzo V, Anesi A, Montalbetti L, Bellantoni G, Trotti R, Melzi d'Eril GV: Reference values of neuroactive amino acids in the cerebrospinal fluid by high-performance liquid chromatography with electrochemical and fluorescence detection. J Chromatogr A. 1996 Apr 5;729(1-2):181-8. [PubMed:9004939 ]
Agnati LF, Ferre S, Lluis C, Franco R, Fuxe K: Molecular mechanisms and therapeutical implications of intramembrane receptor/receptor interactions among heptahelical receptors with examples from the striatopallidal GABA neurons. Pharmacol Rev. 2003 Sep;55(3):509-50. Epub 2003 Jul 17. [PubMed:12869660 ]
Rutten EP, Engelen MP, Wouters EF, Schols AM, Deutz NE: Metabolic effects of glutamine and glutamate ingestion in healthy subjects and in persons with chronic obstructive pulmonary disease. Am J Clin Nutr. 2006 Jan;83(1):115-23. [PubMed:16400059 ]
Agarwal A, Tripathi LM, Pandey VC: Status of ammonia, glutamate, lactate and pyruvate during Plasmodium yoelii infection and pyrimethamine treatment in mice. J Commun Dis. 1997 Sep;29(3):235-41. [PubMed:9465528 ]
Heuschen UA, Allemeyer EH, Hinz U, Langer K, Heuschen G, Decker-Baumann C, Herfarth C, Stern J: Glutamine distribution in patients with ulcerative colitis and in patients with familial adenomatous polyposis coli before and after restorative proctocolectomy. Int J Colorectal Dis. 2002 Jul;17(4):245-52. Epub 2001 Dec 18. [PubMed:12073073 ]
Olson RC: A proposed role for nerve growth factor in the etiology of multiple sclerosis. Med Hypotheses. 1998 Dec;51(6):493-8. [PubMed:10052870 ]
Nakamura K, Matsumura K, Kobayashi S, Kaneko T: Sympathetic premotor neurons mediating thermoregulatory functions. Neurosci Res. 2005 Jan;51(1):1-8. [PubMed:15596234 ]
Corrie JE, DeSantis A, Katayama Y, Khodakhah K, Messenger JB, Ogden DC, Trentham DR: Postsynaptic activation at the squid giant synapse by photolytic release of L-glutamate from a 'caged' L-glutamate. J Physiol. 1993 Jun;465:1-8. [PubMed:7901400 ]
Reeds PJ, Burrin DG, Stoll B, Jahoor F: Intestinal glutamate metabolism. J Nutr. 2000 Apr;130(4S Suppl):978S-82S. [PubMed:10736365 ]
Smith QR: Transport of glutamate and other amino acids at the blood-brain barrier. J Nutr. 2000 Apr;130(4S Suppl):1016S-22S. [PubMed:10736373 ]
Okumoto S, Looger LL, Micheva KD, Reimer RJ, Smith SJ, Frommer WB: Detection of glutamate release from neurons by genetically encoded surface-displayed FRET nanosensors. Proc Natl Acad Sci U S A. 2005 Jun 14;102(24):8740-5. Epub 2005 Jun 6. [PubMed:15939876 ]
Augustin H, Grosjean Y, Chen K, Sheng Q, Featherstone DE: Nonvesicular release of glutamate by glial xCT transporters suppresses glutamate receptor clustering in vivo. J Neurosci. 2007 Jan 3;27(1):111-23. [PubMed:17202478 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 94 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Irreversible conversion of delta-1-pyrroline-5-carboxylate (P5C), derived either from proline or ornithine, to glutamate. This is a necessary step in the pathway interconnecting the urea and tricarboxylic acid cycles. The preferred substrate is glutamic gamma-semialdehyde, other substrates include succinic, glutaric and adipic semialdehydes.
Gene Name:: ALDH4A1
Uniprot ID:: P30038
Molecular weight:: 55117.24

Reactions

1-Pyrroline-5-carboxylic acid + NAD(P)(+) + Water → Glutamic acid + NAD(P)H	details
L-Glutamic gamma-semialdehyde + NAD + Water → Glutamic acid + NADH + Hydrogen Ion	details
1-Pyrroline-5-carboxylic acid + NAD + Water → Glutamic acid + NADH + Hydrogen Ion	details
1-Pyrroline-5-carboxylic acid + NADP + Water → Glutamic acid + NADPH + Hydrogen Ion	details

Enzyme Details

2. Glutathione reductase, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Maintains high levels of reduced glutathione in the cytosol.
Gene Name:: GSR
Uniprot ID:: P00390
Molecular weight:: 56256.565

Enzyme Details

3. Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2

General function:: Involved in metabolic process
Specific function:: Controls the flux of glucose into the hexosamine pathway. Most likely involved in regulating the availability of precursors for N- and O-linked glycosylation of proteins.
Gene Name:: GFPT2
Uniprot ID:: O94808
Molecular weight:: 76929.885

Reactions

Glutamine + Fructose 6-phosphate → Glutamic acid + Glucosamine 6-phosphate	details

Enzyme Details

4. Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 1

General function:: Involved in metabolic process
Specific function:: Controls the flux of glucose into the hexosamine pathway. Most likely involved in regulating the availability of precursors for N- and O-linked glycosylation of proteins.
Gene Name:: GFPT1
Uniprot ID:: Q06210
Molecular weight:: 78805.81

Reactions

Glutamine + Fructose 6-phosphate → Glutamic acid + Glucosamine 6-phosphate	details

Enzyme Details

5. 4-aminobutyrate aminotransferase, mitochondrial

General function:: Involved in 4-aminobutyrate transaminase activity
Specific function:: Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine.
Gene Name:: ABAT
Uniprot ID:: P80404
Molecular weight:: 56438.405

Reactions

gamma-Aminobutyric acid + Oxoglutaric acid → Succinic acid semialdehyde + Glutamic acid	details
(S)-beta-Aminoisobutyric acid + Oxoglutaric acid → 2-Methyl-3-oxopropanoic acid + Glutamic acid	details
beta-Alanine + Oxoglutaric acid → Malonic semialdehyde + Glutamic acid	details
(S)-beta-Aminoisobutyric acid + Oxoglutaric acid → (S)-Methylmalonic acid semialdehyde + Glutamic acid	details

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Imai H, Okuno T, Wu JY, Lee TJ: GABAergic innervation in cerebral blood vessels: an immunohistochemical demonstration of L-glutamic acid decarboxylase and GABA transaminase. J Cereb Blood Flow Metab. 1991 Jan;11(1):129-34. [PubMed:1983997 ]
Happola O, Paivarinta H, Soinila S, Wu JY, Panula P: Localization of L-glutamate decarboxylase and GABA transaminase immunoreactivity in the sympathetic ganglia of the rat. Neuroscience. 1987 Apr;21(1):271-81. [PubMed:3299141 ]
Far SR, Millimoria FR: Levels of glutamic acid decarboxylase (GAD), gamma amino butyric acid transaminase (GABA-T), glutamic acid dehydrogenase (GLDH) and proteins in cerebrospinal fluid of certain neurological disorders. Indian J Med Sci. 1996 Apr;50(4):99-102. [PubMed:8979623 ]

Enzyme Details

6. Tyrosine aminotransferase

General function:: Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:: Transaminase involved in tyrosine breakdown. Converts tyrosine to p-hydroxyphenylpyruvate. Can catalyze the reverse reaction, using glutamic acid, with 2-oxoglutarate as cosubstrate (in vitro). Has much lower affinity and transaminase activity towards phenylalanine.
Gene Name:: TAT
Uniprot ID:: P17735
Molecular weight:: 50398.895

Reactions

L-Tyrosine + Oxoglutaric acid → 4-Hydroxyphenylpyruvic acid + Glutamic acid	details
Phenylalanine + Oxoglutaric acid → Phenylpyruvic acid + Glutamic acid	details
2-Oxo-4-methylthiobutanoic acid + Glutamic acid → Methionine + Oxoglutaric acid	details

References

Ozturk M, Chiu CY, Akdeniz N, Jenq SF, Chang SC, Hsa CY, Jap TS: Two novel mutations in the MEN1 gene in subjects with multiple endocrine neoplasia-1. J Endocrinol Invest. 2006 Jun;29(6):523-7. [PubMed:16840830 ]

Enzyme Details

7. Aspartate aminotransferase, cytoplasmic

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Plays a key role in amino acid metabolism (By similarity).
Gene Name:: GOT1
Uniprot ID:: P17174
Molecular weight:: 46247.14

Reactions

L-Aspartic acid + Oxoglutaric acid → Oxalacetic acid + Glutamic acid	details
Phenylalanine + Oxoglutaric acid → Phenylpyruvic acid + Glutamic acid	details
L-Tyrosine + Oxoglutaric acid → 4-Hydroxyphenylpyruvic acid + Glutamic acid	details
Cysteic acid + Oxoglutaric acid → 3-Sulfopyruvic acid + Glutamic acid	details
3-Sulfinoalanine + Oxoglutaric acid → 3-Sulfinylpyruvic acid + Glutamic acid	details
4-Hydroxy-L-glutamic acid + Oxoglutaric acid → D-4-Hydroxy-2-oxoglutarate + Glutamic acid	details

References

Yudkoff M, Daikhin Y, Melo TM, Nissim I, Sonnewald U, Nissim I: The ketogenic diet and brain metabolism of amino acids: relationship to the anticonvulsant effect. Annu Rev Nutr. 2007;27:415-30. [PubMed:17444813 ]

Enzyme Details

8. Aspartate aminotransferase, mitochondrial

General function:: Involved in transferase activity, transferring nitrogenous groups
Specific function:: Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:: GOT2
Uniprot ID:: P00505
Molecular weight:: 47517.285

Reactions

L-Aspartic acid + Oxoglutaric acid → Oxalacetic acid + Glutamic acid	details
Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glutamic acid	details
Phenylalanine + Oxoglutaric acid → Phenylpyruvic acid + Glutamic acid	details
L-Tyrosine + Oxoglutaric acid → 4-Hydroxyphenylpyruvic acid + Glutamic acid	details
Cysteic acid + Oxoglutaric acid → 3-Sulfopyruvic acid + Glutamic acid	details
3-Sulfinoalanine + Oxoglutaric acid → 3-Sulfinylpyruvic acid + Glutamic acid	details
4-Hydroxy-L-glutamic acid + Oxoglutaric acid → D-4-Hydroxy-2-oxoglutarate + Glutamic acid	details

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Recasens M, Mandel P: Similarities between cysteinesulphinate transaminase and aspartate aminotransferase. Ciba Found Symp. 1979;(72):259-70. [PubMed:261660 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

9. Branched-chain-amino-acid aminotransferase, cytosolic

General function:: Involved in catalytic activity
Specific function:: Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine.
Gene Name:: BCAT1
Uniprot ID:: P54687
Molecular weight:: 38644.77

Reactions

Leucine + Oxoglutaric acid → Ketoleucine + Glutamic acid	details
Isoleucine + Oxoglutaric acid → 3-Methyl-2-oxovaleric acid + Glutamic acid	details
L-Valine + Oxoglutaric acid → alpha-Ketoisovaleric acid + Glutamic acid	details

References

Smirnov SV, Samsonova NN, Novikova AE, Matrosov NG, Rushkevich NY, Kodera T, Ogawa J, Yamanaka H, Shimizu S: A novel strategy for enzymatic synthesis of 4-hydroxyisoleucine: identification of an enzyme possessing HMKP (4-hydroxy-3-methyl-2-keto-pentanoate) aldolase activity. FEMS Microbiol Lett. 2007 Aug;273(1):70-7. Epub 2007 Jun 6. [PubMed:17559390 ]

Enzyme Details

10. Amidophosphoribosyltransferase

General function:: Involved in amidophosphoribosyltransferase activity
Specific function:: Not Available
Gene Name:: PPAT
Uniprot ID:: Q06203
Molecular weight:: 57398.52

Reactions

5-Phosphoribosylamine + Pyrophosphate + Glutamic acid → Glutamine + Phosphoribosyl pyrophosphate + Water	details

Transporters

Enzyme Details

1. Monocarboxylate transporter 1

General function:: Involved in transmembrane transport
Specific function:: Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
Gene Name:: SLC16A1
Uniprot ID:: P53985
Molecular weight:: 53957.7

References

Tamai I, Sai Y, Ono A, Kido Y, Yabuuchi H, Takanaga H, Satoh E, Ogihara T, Amano O, Izeki S, Tsuji A: Immunohistochemical and functional characterization of pH-dependent intestinal absorption of weak organic acids by the monocarboxylic acid transporter MCT1. J Pharm Pharmacol. 1999 Oct;51(10):1113-21. [PubMed:10579682 ]

Enzyme Details

2. Monocarboxylate transporter 10

General function:: Involved in transmembrane transport
Specific function:: Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells
Gene Name:: SLC16A10
Uniprot ID:: Q8TF71
Molecular weight:: 55492.1

References

Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508 ]
Kim DK, Kanai Y, Matsuo H, Kim JY, Chairoungdua A, Kobayashi Y, Enomoto A, Cha SH, Goya T, Endou H: The human T-type amino acid transporter-1: characterization, gene organization, and chromosomal location. Genomics. 2002 Jan;79(1):95-103. [PubMed:11827462 ]

Only showing the first 10 proteins. There are 94 proteins in total.

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Showing metabocard for Glutamic acid (HMDB0000148)

MOL for HMDB0000148 (Glutamic acid)

3D MOL for HMDB0000148 (Glutamic acid)

3D SDF for HMDB0000148 (Glutamic acid)

3D-SDF for HMDB0000148 (Glutamic acid)

PDB for HMDB0000148 (Glutamic acid)

3D PDB for HMDB0000148 (Glutamic acid)

SMILES for HMDB0000148 (Glutamic acid)

INCHI for HMDB0000148 (Glutamic acid)

Structure for HMDB0000148 (Glutamic acid)

3D Structure for HMDB0000148 (Glutamic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

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Derivatized

Enzymes

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