L-glutamic acid (CHEBI:16015)

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CHEBI:16015 - L-glutamic acid

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ChEBI Name	L-glutamic acid

ChEBI ID	CHEBI:16015

ChEBI ASCII Name	L-glutamic acid

Definition	An optically active form of glutamic acid having L-configuration.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:42825, CHEBI:6224, CHEBI:21304

Supplier Information	ChemicalBook:CB02130578, ChemicalBook:CB4355560, eMolecules:477277, ZINC000001482113

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1.9432 -1.3594 -0.1426 C 0 0 0 0 0 0 0 0 0 0 0 0

0.7780 -0.6985 -0.7012 C 0 0 2 0 0 0 0 0 0 0 0 0

0.1229 0.2856 0.3065 C 0 0 0 0 0 0 0 0 0 0 0 0

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3.0552 -1.2138 -0.6292 O 0 0 0 0 0 0 0 0 0 0 0 0

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-0.1979 -1.7034 -1.1519 N 0 0 0 0 0 0 0 0 0 0 0 0

1.0660 -0.1301 -1.5917 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8694 1.0265 0.6129 H 0 0 0 0 0 0 0 0 0 0 0 0

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2.5490 -2.4603 1.2079 H 0 0 0 0 0 0 0 0 0 0 0 0

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0.2690 -2.3379 -1.8023 H 0 0 0 0 0 0 0 0 0 0 0 0

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reading 19 atoms

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Wikipedia	License
Glutamic acid (symbol Glu or E; known as glutamate in its anionic form) is an α-amino acid that is used by almost all living beings in the biosynthesis of proteins. It is a non-essential nutrient for humans, meaning that the human body can synthesize enough for its use. It is also the most abundant excitatory neurotransmitter in the vertebrate nervous system. It serves as the precursor for the synthesis of the inhibitory gamma-aminobutyric acid (GABA) in GABAergic neurons. Its molecular formula is C5H9NO4. Glutamic acid exists in two optically isomeric forms; the dextrorotatory L-form is usually obtained by hydrolysis of gluten or from the waste waters of beet-sugar manufacture or by fermentation. Its molecular structure could be idealized as HOOC−CH(NH2)−(CH2)2−COOH, with two carboxyl groups −COOH and one amino group −NH2. However, in the solid state and mildly acidic water solutions, the molecule assumes an electrically neutral zwitterion structure −OOC−CH(NH+3)−(CH2)2−COOH. It is encoded by the codons GAA or GAG. The acid can lose one proton from its second carboxyl group to form the conjugate base, the singly-negative anion glutamate −OOC−CH(NH+3)−(CH2)2−COO−. This form of the compound is prevalent in neutral solutions. The glutamate neurotransmitter plays the principal role in neural activation. This anion creates the savory umami flavor of foods and is found in glutamate flavorings such as monosodium glutamate (MSG). In Europe, it is classified as food additive E620. In highly alkaline solutions the doubly negative anion −OOC−CH(NH2)−(CH2)2−COO− prevails. The radical corresponding to glutamate is called glutamyl. The one-letter symbol E for glutamate was assigned as the letter following D for aspartate, as glutamate is larger by one methylene –CH2– group.
Read full article at Wikipedia

Formula

C5H9NO4

Net Charge

Average Mass

147.12930

Monoisotopic Mass

147.05316

InChI

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

InChIKey

WHUUTDBJXJRKMK-VKHMYHEASA-N

SMILES

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

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Chlamydomonas reinhardtii (NCBI:txid3055)	See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. micronutrient Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). ferroptosis inducer Any substance that induces or promotes ferroptosis (a type of programmed cell death dependent on iron and characterized by the accumulation of lipid peroxides) in organisms. neurotransmitter An endogenous compound that is used to transmit information across the synapse between a neuron and another cell. fundamental metabolite Any metabolite produced by all living cells. (via glutamic acid )

Application(s):	nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	L-glutamic acid (CHEBI:16015) has role Escherichia coli metabolite (CHEBI:76971) L-glutamic acid (CHEBI:16015) has role ferroptosis inducer (CHEBI:173085) L-glutamic acid (CHEBI:16015) has role micronutrient (CHEBI:27027) L-glutamic acid (CHEBI:16015) has role mouse metabolite (CHEBI:75771) L-glutamic acid (CHEBI:16015) has role neurotransmitter (CHEBI:25512) L-glutamic acid (CHEBI:16015) has role nutraceutical (CHEBI:50733) L-glutamic acid (CHEBI:16015) is a L-α-amino acid (CHEBI:15705) L-glutamic acid (CHEBI:16015) is a glutamic acid (CHEBI:18237) L-glutamic acid (CHEBI:16015) is a glutamine family amino acid (CHEBI:24318) L-glutamic acid (CHEBI:16015) is a proteinogenic amino acid (CHEBI:83813) L-glutamic acid (CHEBI:16015) is conjugate acid of L-glutamate(1−) (CHEBI:29985) L-glutamic acid (CHEBI:16015) is enantiomer of D-glutamic acid (CHEBI:15966)

Incoming	γ-Glu-Gln (CHEBI:73707) has functional parent L-glutamic acid (CHEBI:16015) γ-Glu-Glu (CHEBI:73705) has functional parent L-glutamic acid (CHEBI:16015) γ-Glu-Met (CHEBI:82965) has functional parent L-glutamic acid (CHEBI:16015) γ-Glu-Tyr (CHEBI:82969) has functional parent L-glutamic acid (CHEBI:16015) 5-L-glutamyl amino acid (CHEBI:15857) has functional parent L-glutamic acid (CHEBI:16015) erythro-4-hydroxy-L-glutamic acid (CHEBI:21285) has functional parent L-glutamic acid (CHEBI:16015) N-acetyl-L-glutamic acid (CHEBI:17533) has functional parent L-glutamic acid (CHEBI:16015) L-γ-glutamyl-L-cysteine (CHEBI:17515) has functional parent L-glutamic acid (CHEBI:16015) L-glutamic acid derivative (CHEBI:83982) has functional parent L-glutamic acid (CHEBI:16015) Ac-Asp-Glu (CHEBI:73688) has functional parent L-glutamic acid (CHEBI:16015) Glu-Ala-Trp (CHEBI:73490) has functional parent L-glutamic acid (CHEBI:16015) Glu-Arg (CHEBI:157844) has functional parent L-glutamic acid (CHEBI:16015) Glu-Arg-Gly (CHEBI:162704) has functional parent L-glutamic acid (CHEBI:16015) Glu-Arg-Gly-Met (CHEBI:191942) has functional parent L-glutamic acid (CHEBI:16015) Glu-Arg-Gly-Met-Thr (CHEBI:191943) has functional parent L-glutamic acid (CHEBI:16015) Glu-Asp (CHEBI:73503) has functional parent L-glutamic acid (CHEBI:16015) Glu-Asp-Arg (CHEBI:156374) has functional parent L-glutamic acid (CHEBI:16015) Glu-Asp-Asp (CHEBI:156328) has functional parent L-glutamic acid (CHEBI:16015) Glu-Asp-Gln-Gln (CHEBI:73465) has functional parent L-glutamic acid (CHEBI:16015) Glu-Asp-Ile (CHEBI:73491) has functional parent L-glutamic acid (CHEBI:16015) Glu-Cys (CHEBI:156047) has functional parent L-glutamic acid (CHEBI:16015) Glu-Cys-Cys (CHEBI:73495) has functional parent L-glutamic acid (CHEBI:16015) Glu-Gln (CHEBI:141435) has functional parent L-glutamic acid (CHEBI:16015) Glu-Glu (CHEBI:5390) has functional parent L-glutamic acid (CHEBI:16015) Glu-Glu-Arg (CHEBI:144557) has functional parent L-glutamic acid (CHEBI:16015) Glu-Glu-Gln (CHEBI:144559) has functional parent L-glutamic acid (CHEBI:16015) Glu-Glu-Gln-Trp (CHEBI:73484) has functional parent L-glutamic acid (CHEBI:16015) Glu-Glu-Glu (CHEBI:73493) has functional parent L-glutamic acid (CHEBI:16015) Glu-Glu-Gly (CHEBI:73494) has functional parent L-glutamic acid (CHEBI:16015) Glu-Glu-Ile (CHEBI:73492) has functional parent L-glutamic acid (CHEBI:16015) Glu-Glu-Leu (CHEBI:156359) has functional parent L-glutamic acid (CHEBI:16015) Glu-Glu-Lys (CHEBI:156360) has functional parent L-glutamic acid (CHEBI:16015) Glu-Gly (CHEBI:73505) has functional parent L-glutamic acid (CHEBI:16015) Glu-Gly-Arg-chloromethylketone (CHEBI:157651) has functional parent L-glutamic acid (CHEBI:16015) Glu-Gly-Phe (CHEBI:140739) has functional parent L-glutamic acid (CHEBI:16015) Glu-Gly-Trp (CHEBI:73496) has functional parent L-glutamic acid (CHEBI:16015) Glu-Ile (CHEBI:141436) has functional parent L-glutamic acid (CHEBI:16015) Glu-Ile-Phe (CHEBI:73497) has functional parent L-glutamic acid (CHEBI:16015) Glu-Ile-Ser (CHEBI:73498) has functional parent L-glutamic acid (CHEBI:16015) Glu-Ile-Val (CHEBI:73499) has functional parent L-glutamic acid (CHEBI:16015) Glu-Leu (CHEBI:73506) has functional parent L-glutamic acid (CHEBI:16015) Glu-Leu-Phe-Ala (CHEBI:73485) has functional parent L-glutamic acid (CHEBI:16015) Glu-Lys (CHEBI:73521) has functional parent L-glutamic acid (CHEBI:16015) Glu-Lys-Trp-Ala (CHEBI:73487) has functional parent L-glutamic acid (CHEBI:16015) Glu-Met (CHEBI:73507) has functional parent L-glutamic acid (CHEBI:16015) Glu-Phe-Gln-Gln (CHEBI:73488) has functional parent L-glutamic acid (CHEBI:16015) Glu-Phe-Val (CHEBI:73501) has functional parent L-glutamic acid (CHEBI:16015) Glu-Pro (CHEBI:73508) has functional parent L-glutamic acid (CHEBI:16015) Glu-Ser (CHEBI:73509) has functional parent L-glutamic acid (CHEBI:16015) Glu-Thr (CHEBI:73510) has functional parent L-glutamic acid (CHEBI:16015) Glu-Thr-Thr-Tyr (CHEBI:73489) has functional parent L-glutamic acid (CHEBI:16015) Glu-Trp (CHEBI:73512) has functional parent L-glutamic acid (CHEBI:16015) Glu-Trp-Asp-Arg (CHEBI:138509) has functional parent L-glutamic acid (CHEBI:16015) Glu-Tyr (CHEBI:73513) has functional parent L-glutamic acid (CHEBI:16015) Glu-Val-Thr-Leu-Tyr peptide residue (CHEBI:85622) has functional parent L-glutamic acid (CHEBI:16015) Glu-Val-Val (CHEBI:73502) has functional parent L-glutamic acid (CHEBI:16015) glutamine hydroxamate (CHEBI:75305) has functional parent L-glutamic acid (CHEBI:16015) Lys-Glu-Glu (CHEBI:144461) has functional parent L-glutamic acid (CHEBI:16015) Lys-Glu-Thr (CHEBI:144459) has functional parent L-glutamic acid (CHEBI:16015) Lys-Tyr-Glu (CHEBI:140742) has functional parent L-glutamic acid (CHEBI:16015) methotrexate (CHEBI:44185) has functional parent L-glutamic acid (CHEBI:16015) methyl-L-glutamic acid (CHEBI:149778) has functional parent L-glutamic acid (CHEBI:16015) norophthalmic acid (CHEBI:143251) has functional parent L-glutamic acid (CHEBI:16015) Pro-Glu-Ile (CHEBI:144613) has functional parent L-glutamic acid (CHEBI:16015) trofinetide (CHEBI:229599) has functional parent L-glutamic acid (CHEBI:16015) L-glutamic acid-d5 (CHEBI:192079) is a L-glutamic acid (CHEBI:16015) L-glutamate(1−) (CHEBI:29985) is conjugate base of L-glutamic acid (CHEBI:16015) D-glutamic acid (CHEBI:15966) is enantiomer of L-glutamic acid (CHEBI:16015) L-α-glutamyl group (CHEBI:46855) is substituent group from L-glutamic acid (CHEBI:16015) L-γ-glutamyl group (CHEBI:32474) is substituent group from L-glutamic acid (CHEBI:16015) L-glutamic acid residue (CHEBI:29972) is substituent group from L-glutamic acid (CHEBI:16015) L-glutamo group (CHEBI:46854) is substituent group from L-glutamic acid (CHEBI:16015) L-glutamoyl group (CHEBI:32475) is substituent group from L-glutamic acid (CHEBI:16015)

IUPAC Names

(2S)-2-aminopentanedioic acid

L-glutamic acid

INNs	Sources
acide glutamique	ChEBI
ácido glutámico	ChEBI
acidum glutamicum	ChEBI
glutamic acid	ChEBI

Synonyms	Sources
(S)-2-aminopentanedioic acid	ChEBI
(S)-glutamic acid	NIST Chemistry WebBook
E	ChEBI
Glu	ChEBI
Glutamate	KEGG COMPOUND
GLUTAMIC ACID	PDBeChem
L-Glu	ChEBI
L-Glutamic acid	KEGG COMPOUND
L-Glutaminic acid	KEGG COMPOUND
L-Glutaminsäure	ChEBI

Manual Xrefs	Databases
1310	DrugCentral
2297	BPDB
C00001358	KNApSAcK
C00025	KEGG COMPOUND
D00007	KEGG DRUG
DB00142	DrugBank
GLT	MetaCyc
GLU_LFOH	PDBeChem
HMDB0000148	HMDB
L-Glutamic_Acid	Wikipedia
LSM-36375	LINCS
View more database links

Registry Numbers	Types	Sources
1723801	Reaxys Registry Number	Reaxys
3502	Gmelin Registry Number	Gmelin
56-86-0	CAS Registry Number	KEGG COMPOUND
56-86-0	CAS Registry Number	ChemIDplus
56-86-0	CAS Registry Number	NIST Chemistry WebBook

Citations

Bordbar A, Mo ML, Nakayasu ES, Schrimpe-Rutledge AC, Kim YM, Metz TO, Jones MB, Frank BC, Smith RD, Peterson SN, Hyduke DR, Adkins JN, Palsson BO (2012)
Model-driven multi-omic data analysis elucidates metabolic immunomodulators of macrophage activation.
Molecular systems biology 8, 558 [PubMed:22735334]
[show Abstract]

Aizawa S, Sakai T, Sakata I (2012)
Glutamine and glutamic acid enhance thyroid-stimulating hormone β subunit mRNA expression in the rat pars tuberalis.
The Journal of endocrinology 212, 383-394 [PubMed:22219301]
[show Abstract]

Stamler J, Brown IJ, Daviglus ML, Chan Q, Kesteloot H, Ueshima H, Zhao L, Elliott P, INTERMAP Research Group (2009)
Glutamic acid, the main dietary amino acid, and blood pressure: the INTERMAP Study (International Collaborative Study of Macronutrients, Micronutrients and Blood Pressure).
Circulation 120, 221-228 [PubMed:19581495]
[show Abstract]

Catarzi D, Colotta V, Varano F (2007)
Competitive AMPA receptor antagonists.
Medicinal research reviews 27, 239-278 [PubMed:16892196]
[show Abstract]

Catarzi D, Colotta V, Varano F (2006)
Competitive Gly/NMDA receptor antagonists.
Current topics in medicinal chemistry 6, 809-821 [PubMed:16719819]
[show Abstract]

Yudkoff M, Daikhin Y, Nissim I, Horyn O, Luhovyy B, Luhovyy B, Lazarow A, Nissim I (2005)
Brain amino acid requirements and toxicity: the example of leucine.
The Journal of nutrition 135, 1531S-8S [PubMed:15930465]
[show Abstract]

Chen X, Li D, Lü J, Fang F (1997)
[Determination of gamma-aminobutyric acid and glutamic acid in human cerebrospinal fluid by high performance liquid chromatography].
Se pu = Chinese journal of chromatography 15, 237-239 [PubMed:15739367]
[show Abstract]

Last Modified

16 April 2024

ChEBI

CHEBI:16015 - L-glutamic acid

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