N-acetyl-L-glutamic acid (CHEBI:17533)

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CHEBI:17533 - N-acetyl-L-glutamic acid

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ChEBI Name	N-acetyl-L-glutamic acid

ChEBI ID	CHEBI:17533

ChEBI ASCII Name	N-acetyl-L-glutamic acid

Definition	An N-acyl-L-amino acid that is L-glutamic acid in which one of the amine hydrogens is substituted by an acetyl group.

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

Secondary ChEBI IDs	CHEBI:21552, CHEBI:44335, CHEBI:7150

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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24 23 0 0 1 0 999 V2000

-0.9555 0.8704 1.3233 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.1845 -0.4044 0.4662 C 0 0 0 0 0 0 0 0 0 0 0 0

0.1198 -1.0996 -0.0196 C 0 0 2 0 0 0 0 0 0 0 0 0

0.9159 -0.1982 -0.7412 N 0 0 0 0 0 0 0 0 0 0 0 0

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Wikipedia	License
N-Acetylglutamic acid (also referred to as N-acetylglutamate, abbreviated NAG, chemical formula C7H11NO5) is biosynthesized from glutamate and acetylornithine by ornithine acetyltransferase, and from glutamic acid and acetyl-CoA by the enzyme N-acetylglutamate synthase. The reverse reaction, hydrolysis of the acetyl group, is catalyzed by a specific hydrolase. It is the first intermediate involved in the biosynthesis of arginine in prokaryotes and simple eukaryotes and a regulator in the process known as the urea cycle that converts toxic ammonia to urea for excretion from the body in vertebrates.
Read full article at Wikipedia

Formula

C7H11NO5

Net Charge

Average Mass

189.16598

Monoisotopic Mass

189.06372

InChI

InChI=1S/C7H11NO5/c1-4(9)8-5(7(12)13)2-3-6(10)11/h5H,2-3H2,1H3,(H,8,9)(H,10,11)(H,12,13)/t5-/m0/s1

InChIKey

RFMMMVDNIPUKGG-YFKPBYRVSA-N

SMILES

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

Metabolite of Species	Details
Rattus norvegicus (NCBI:txid10116)	See: MetaboLights Study
Vitis vinifera (NCBI:txid29760)	See: DOI
Saccharomyces cerevisiae (NCBI:txid4932)	See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	Source: yeast.sf.net See: PubMed
Saccharomyces cerevisiae (NCBI:txid4932)	See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	See: DOI

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

Biological Role(s):	Saccharomyces cerevisiae metabolite Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ). human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	N-acetyl-L-glutamic acid (CHEBI:17533) has functional parent L-glutamic acid (CHEBI:16015) N-acetyl-L-glutamic acid (CHEBI:17533) has role Saccharomyces cerevisiae metabolite (CHEBI:75772) N-acetyl-L-glutamic acid (CHEBI:17533) has role human metabolite (CHEBI:77746) N-acetyl-L-glutamic acid (CHEBI:17533) is a N-acetyl-L-amino acid (CHEBI:21545) N-acetyl-L-glutamic acid (CHEBI:17533) is a N-acyl-L-glutamic acid (CHEBI:21650) N-acetyl-L-glutamic acid (CHEBI:17533) is conjugate acid of N-acetyl-L-glutamate(1−) (CHEBI:21549)

Incoming	N-acetyl-L-glutamate(1−) (CHEBI:21549) is conjugate base of N-acetyl-L-glutamic acid (CHEBI:17533)

IUPAC Names

(2S)-2-acetamidopentanedioic acid

N-acetyl-L-glutamic acid

Synonyms	Sources
(S)-2-(acetylamino)pentanedioic acid	ChEBI
Ac-Glu-OH	HMDB
Acetyl-L-glutamic acid	HMDB
acetylglutamic acid	ChEBI
Acetylglutamic acid	ChEBI
L-N-acetylglutamic acid	ChemIDplus
N-Ac-Glu-OH	HMDB
N-ACETYL-L-GLUTAMATE	PDBeChem
N-Acetyl-L-glutamic acid	KEGG COMPOUND
N-acetyl-L-glutamic acid	PDBeChem
N-Acetylglutamic acid	HMDB

Manual Xrefs	Databases
C00624	KEGG COMPOUND
DB04075	DrugBank
HMDB0001138	HMDB
N-Acetylglutamic_acid	Wikipedia
NLG	PDBeChem
View more database links

Registry Numbers	Types	Sources
1188-37-0	CAS Registry Number	KEGG COMPOUND
1188-37-0	CAS Registry Number	ChemIDplus
1727473	Reaxys Registry Number	Reaxys

Citations	Types	Sources
115331	PubMed citation	Europe PMC
17190852	PubMed citation	Europe PMC
17439666	PubMed citation	Europe PMC
5924663	PubMed citation	Europe PMC
6035272	PubMed citation	Europe PMC
9037750	PubMed citation	Europe PMC

Last Modified

12 February 2016

CHEBI:17533 - N-acetyl-L-glutamic acid

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