CHEBI:27487 - 3-(imidazol-5-yl)lactic acid

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ChEBI Name 3-(imidazol-5-yl)lactic acid
ChEBI ID CHEBI:27487
Definition A 2-hydroxy monocarboxylic acid that is lactic acid in which one of the methyl hydrogens has been replaced by an imidazol-5-yl group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:1119, CHEBI:24774, CHEBI:5873
Supplier Information
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Formula C6H8N2O3
Net Charge 0
Average Mass 156.140
Monoisotopic Mass 156.053
InChI InChI=1S/C6H8N2O3/c9-5(6(10)11)1-4-2-7-3-8-4/h2-3,5,9H,1H2,(H,7,8)(H,10,11)
InChIKey ACZFBYCNAVEFLC-UHFFFAOYSA-N
SMILES C=1N=CNC1CC(C(=O)O)O
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): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 3-(imidazol-5-yl)lactic acid (CHEBI:27487) has functional parent 2-hydroxypropanoic acid (CHEBI:78320)
3-(imidazol-5-yl)lactic acid (CHEBI:27487) has role Escherichia coli metabolite (CHEBI:76971)
3-(imidazol-5-yl)lactic acid (CHEBI:27487) has role human metabolite (CHEBI:77746)
3-(imidazol-5-yl)lactic acid (CHEBI:27487) has role metabolite (CHEBI:25212)
3-(imidazol-5-yl)lactic acid (CHEBI:27487) is a 2-hydroxy monocarboxylic acid (CHEBI:49302)
3-(imidazol-5-yl)lactic acid (CHEBI:27487) is a imidazoles (CHEBI:24780)
3-(imidazol-5-yl)lactic acid (CHEBI:27487) is conjugate acid of 3-(imidazol-5-yl)lactate (CHEBI:24773)
Incoming (S)-3-(imidazol-5-yl)lactic acid (CHEBI:16373) is a 3-(imidazol-5-yl)lactic acid (CHEBI:27487)
3-(imidazol-5-yl)lactate (CHEBI:24773) is conjugate base of 3-(imidazol-5-yl)lactic acid (CHEBI:27487)
IUPAC Name
2-hydroxy-3-(1H-imidazol-5-yl)propanoic acid
Synonyms Sources
2-Hydroxy-3-(1H-imidazol-5-yl)-propanoic acid KEGG COMPOUND
2-Hydroxy-3-[4-imidazolyl]-propanoate KEGG COMPOUND
α-hydroxy-1H-imidazolepropanoic acid ChemIDplus
Imidazole lactate KEGG COMPOUND
Imidazole lactic acid KEGG COMPOUND
Manual Xref Database
C05568 KEGG COMPOUND
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Registry Numbers Types Sources
30581-88-5 CAS Registry Number ChemIDplus
464711 Gmelin Registry Number Gmelin
7795 Reaxys Registry Number Reaxys
7795 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
13220477 PubMed citation Europe PMC
22770225 PubMed citation Europe PMC
6017775 PubMed citation Europe PMC
6333900 PubMed citation Europe PMC
Last Modified
08 February 2017
General Comment
2014-01-23 Biochem. Biophys. Res. Commun.(1966), 25(3), 335-339.