orotic acid (CHEBI:16742)

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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:CB3364529, ChemicalBook:CB34796861, eMolecules:29538748, eMolecules:490388, Selleckchem:Chloramphenicol(Chloromycetin), ZINC000000113382

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Wikipedia	License
Chloramphenicol is an antibiotic useful for the treatment of a number of bacterial infections. This includes use as an eye ointment to treat conjunctivitis. By mouth or by injection into a vein, it is used to treat meningitis, plague, cholera, and typhoid fever. Its use by mouth or by injection is only recommended when safer antibiotics cannot be used. Monitoring both blood levels of the medication and blood cell levels every two days is recommended during treatment. Common side effects include bone marrow suppression, nausea, and diarrhea. The bone marrow suppression may result in death. To reduce the risk of side effects treatment duration should be as short as possible. People with liver or kidney problems may need lower doses. In young infants, a condition known as gray baby syndrome may occur which results in a swollen stomach and low blood pressure. Its use near the end of pregnancy and during breastfeeding is typically not recommended. Chloramphenicol is a broad-spectrum antibiotic that typically stops bacterial growth by stopping the production of proteins. Chloramphenicol was discovered after being isolated from Streptomyces venezuelae in 1947. Its chemical structure was identified and it was first synthesized in 1949. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.
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Formulae

C5H4N2O4
C5H4N2O4

Net Charge

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).

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

Last Modified

16 July 2020