CHEBI:16742 - orotic acid

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ChEBI Name orotic acid
ChEBI ID CHEBI:16742
Definition A pyrimidinemonocarboxylic acid that is uracil bearing a carboxy substituent at position C-6.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44781, CHEBI:7787, CHEBI:25720
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Formulae C5H4N2O4
C5H4N2O4
Net Charge 0
Average Mass 156.09630
Monoisotopic Mass 156.017
InChI InChI=1S/C5H4N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h1H,(H,9,10)(H2,6,7,8,11)
InChIKey PXQPEWDEAKTCGB-UHFFFAOYSA-N
SMILES OC(=O)c1cc(=O)[nH]c(=O)[nH]1
Metabolite of Species Details
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:562) See: PubMed
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.
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing orotic acid (CHEBI:16742) has functional parent uracil (CHEBI:17568)
orotic acid (CHEBI:16742) has role Escherichia coli metabolite (CHEBI:76971)
orotic acid (CHEBI:16742) has role metabolite (CHEBI:25212)
orotic acid (CHEBI:16742) has role mouse metabolite (CHEBI:75771)
orotic acid (CHEBI:16742) is a pyrimidinemonocarboxylic acid (CHEBI:26447)
orotic acid (CHEBI:16742) is conjugate acid of orotate (CHEBI:30839)
Incoming dihydroorotic acid (CHEBI:30865) has functional parent orotic acid (CHEBI:16742)
orotate (CHEBI:30839) is conjugate base of orotic acid (CHEBI:16742)
IUPAC Name
2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
Synonyms Sources
Orotic acid KEGG COMPOUND
OROTIC ACID PDBeChem
Orotsäure ChEBI
Uracil-6-carboxylic acid KEGG COMPOUND
Database Links Databases
C00019689 KNApSAcK
C00295 KEGG COMPOUND
D00055 KEGG DRUG
DB02262 DrugBank
HMDB00226 HMDB
ORO PDBeChem
OROTATE MetaCyc
Orotic_acid Wikipedia
View more database links
Registry Numbers Types Sources
101990 Gmelin Registry Number Gmelin
383901 Reaxys Registry Number Reaxys
383901 Beilstein Registry Number Beilstein
65-86-1 CAS Registry Number KEGG COMPOUND
65-86-1 CAS Registry Number NIST Chemistry WebBook
65-86-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11059538 PubMed citation CiteXplore
22019295 PubMed citation CiteXplore
22285839 PubMed citation CiteXplore
22307261 PubMed citation CiteXplore
22371390 PubMed citation CiteXplore
22634191 PubMed citation CiteXplore
22707164 PubMed citation CiteXplore
22770225 PubMed citation CiteXplore
22863860 PubMed citation CiteXplore
7264771 PubMed citation CiteXplore
Last Modified
27 January 2016