CHEBI:27248 - urocanic acid

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ChEBI Name urocanic acid
ChEBI ID CHEBI:27248
Definition An α,β-unsaturated monocarboxylic acid that is prop-2-enoic acid substituted by a 1H-imidazol-4-yl group at position 3. It is a metabolite of hidtidine.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C6H6N2O2
Net Charge 0
Average Mass 138.12412
Monoisotopic Mass 138.043
InChI InChI=1S/C6H6N2O2/c9-6(10)2-1-5-3-7-4-8-5/h1-4H,(H,7,8)(H,9,10)
InChIKey LOIYMIARKYCTBW-UHFFFAOYSA-N
SMILES [H]C(=C([H])c1c[nH]cn1)C(O)=O
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) See: PubMed
Roles Classification
Chemical Role(s): chromophore
The part (atom or group of atoms) of a molecular entity in which the electronic transition responsible for a given spectral band is approximately localized.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
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ChEBI Ontology
Outgoing urocanic acid (CHEBI:27248) has role chromophore (CHEBI:23240)
urocanic acid (CHEBI:27248) has role human metabolite (CHEBI:77746)
urocanic acid (CHEBI:27248) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
urocanic acid (CHEBI:27248) is a imidazoles (CHEBI:24780)
urocanic acid (CHEBI:27248) is conjugate acid of urocanate (CHEBI:27247)
Incoming cis-urocanic acid (CHEBI:30818) is a urocanic acid (CHEBI:27248)
trans-urocanic acid (CHEBI:30817) is a urocanic acid (CHEBI:27248)
urocanate (CHEBI:27247) is conjugate base of urocanic acid (CHEBI:27248)
IUPAC Name
3-(1H-imidazol-4-yl)prop-2-enoic acid
Synonyms Sources
3-(1H-imidazol-4-yl)-2-propenoic acid ChemIDplus
3-imidazol-4-ylacrylic acid ChemIDplus
Manual Xrefs Databases
ECMDB21396 ECMDB
HMDB0000301 HMDB
URO PDBeChem
UROCANATE MetaCyc
Urocanic_acid Wikipedia
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Registry Numbers Types Sources
104-98-3 CAS Registry Number ChemIDplus
8128219 Beilstein Registry Number Beilstein
8128219 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11669511 PubMed citation Europe PMC
24397532 PubMed citation Europe PMC
24627570 PubMed citation Europe PMC
Last Modified
09 February 2017