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
Supplier Information ChemicalBook:CB34796962, ChemicalBook:CB5691265, eMolecules:816071, eMolecules:530220, Selleckchem:Orotic-acid(6-Carboxyuracil), ZINC000001408068
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Orotic acid () is a pyrimidinedione and a carboxylic acid. Historically, it was believed to be part of the vitamin B complex and was called vitamin B13, but it is now known that it is not a vitamin. The compound is synthesized in the body via a mitochondrial enzyme, dihydroorotate dehydrogenase or a cytoplasmic enzyme of pyrimidine synthesis pathway. It is sometimes used as a mineral carrier in some dietary supplements (to increase their bioavailability), most commonly for lithium orotate.
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Formulae C5H4N2O4
C5H4N2O4
Net Charge 0
Average Mass 156.09630
Monoisotopic Mass 156.01711
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:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) 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 N-[(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)carbonyl]-β-alanine (CHEBI:156205) has functional parent orotic acid (CHEBI:16742)
dihydroorotic acid (CHEBI:30865) has functional parent orotic acid (CHEBI:16742)
methyl N-[(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)carbonyl]-β-alaninate (CHEBI:156206) 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
Manual Xrefs Databases
3402 DrugCentral
C00019689 KNApSAcK
C00295 KEGG COMPOUND
D00055 KEGG DRUG
DB02262 DrugBank
HMDB0000226 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
65-86-1 CAS Registry Number KEGG COMPOUND
65-86-1 CAS Registry Number ChemIDplus
65-86-1 CAS Registry Number NIST Chemistry WebBook
Citations
Khajehsharifi H, Tavallali H, Shekoohi M, Sadeghi M (2013)
Spectrophotometric simultaneous determination of orotic acid, creatinine and uric acid by orthogonal signal correction-partial least squares in spiked real samples.
Drug testing and analysis 5, 353-360 [PubMed:22371390]
[show Abstract]
Gerhardt V, Tutughamiarso M, Bolte M (2012)
Conformational studies of hydantoin-5-acetic acid and orotic acid.
Acta crystallographica. Section C, Crystal structure communications 68, o92-8 [PubMed:22307261]
[show Abstract]
Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)
Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer.
Analytical chemistry 84, 6429-6437 [PubMed:22770225]
[show Abstract]
Niu H, Chen Y, Xie J, Chen X, Bai J, Wu J, Liu D, Ying H (2012)
Ion-exclusion chromatography determination of organic acid in uridine 5'-monophosphate fermentation broth.
Journal of chromatographic science 50, 709-713 [PubMed:22634191]
[show Abstract]
D'Apolito O, Garofalo D, la Marca G, Dello Russo A, Corso G (2012)
Reference intervals for orotic acid in urine, plasma and dried blood spot using hydrophilic interaction liquid chromatography-tandem mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 883-884, 155-160 [PubMed:22019295]
[show Abstract]
Fryčák P, Jirkovský J, Ranc V, Bednář P, Havlíček V, Lemr K (2012)
Secondary processes in atmospheric pressure chemical ionization-ion trap mass spectrometry: a case study of orotic acid.
Journal of mass spectrometry : JMS 47, 720-726 [PubMed:22707164]
[show Abstract]
Pôrto LC, de Castro CH, Savergnini SS, Santos SH, Ferreira AV, Cordeiro LM, Sobrinho DB, Santos RA, de Almeida AP, Botion LM (2012)
Improvement of the energy supply and contractile function in normal and ischemic rat hearts by dietary orotic acid.
Life sciences 90, 476-483 [PubMed:22285839]
[show Abstract]
Jung EJ, Lee KY, Lee BH (2012)
Proliferating effect of orotic acid through mTORC1 activation mediated by negative regulation of AMPK in SK-Hep1 hepatocellular carcinoma cells.
The Journal of toxicological sciences 37, 813-821 [PubMed:22863860]
[show Abstract]
Asai M, Sumi S, Kidouchi K, Imaeda H, Togari H, Wada Y (2000)
Urinary pyrimidine analysis in healthy newborns, infants, children, adults and patients with congenital metabolic diseases.
Pediatrics international : official journal of the Japan Pediatric Society 42, 499-503 [PubMed:11059538]
[show Abstract]
Gargallo J, Zimmerman D (1981)
Effect of casein and starch infusion in the large intestine on nitrogen metabolism of growing swine.
The Journal of nutrition 111, 1390-1396 [PubMed:7264771]
[show Abstract]
Last Modified
16 July 2020