Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:35:56 UTC
Update Date2024-04-30 19:31:54 UTC
Metabolite IDMMDBc0000352
Metabolite Identification
Common Name4,5-Dihydroorotic acid
Description4,5-Dihydroorotic acid, also known as dihydroorotate or hydroorotate is a pyrimidinemonocarboxylic acid that results from the base-catalysed cyclisation of N-alpha-carbethoxyasparagine. It is classified as a secondary amide, a monocarboxylic acid, a pyrimidinemonocarboxylic acid and a N-acylurea. 4,5-Dihydroorotic acid is a derivative of orotic acid which serves as an intermediate in pyrimidine biosynthesis. 4,5-Dihydroorotic acid exists in all living species, ranging from bacteria to plants to humans. 4,5-Dihydroorotic acid is synthesized by the enzyme known as Dihydroorotase (EC 3.5.2.3) which converts carbamoyl aspartic acid into 4,5-dihydroorotic acid as part of the de novo pyrimidine biosynthesis pathway (PMID: 13163076 ). 4,5-Dihydroorotic acid is also a substrate for the enzyme known as dihydroorotate dehydrogenase (DHODH). In mammalian species, DHODH catalyzes the fourth step in the de novo pyrimidine biosynthesis pathway, which involves the ubiquinone-mediated oxidation of dihydroorotate to orotate and the reduction of flavin mononucleotide (FMN) to dihydroflavin mononucleotide (FMNH2). Inhibition of DHODH activity with teriflunomide (an immunomodulatory drug) or expression with RNA interference results in reduced ROS generation and consequent apoptosis of transformed skin and prostate epithelial cells. Mutations in the DHOD gene have been shown to cause Miller syndrome, also known as Genee-Wiedemann syndrome, Wildervanck-Smith syndrome or post-axial acrofacial dystosis (PMID: 19915526 ).
Structure
Synonyms
ValueSource
5,6-Dihydro-orotic acidChEBI
DL-Dihydroortotic acidChEBI
Hydroorotic acidChEBI
5,6-Dihydro-orotateGenerator
DL-DihydroortotateGenerator
HydroorotateGenerator
4,5-DihydroorotateGenerator
4,5-Dihydroorotic acid, (D)-isomerMeSH
4,5-Dihydroorotic acid, (DL)-isomerMeSH
4,5-Dihydroorotic acid, (L)-isomerMeSH
5,6-DihydroorotateMeSH
L-DihydroorotateMeSH
DihydroorotateMeSH
(+)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylateHMDB
(+)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylic acidHMDB
(R)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylateHMDB
(R)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylic acidHMDB
(S)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylateHMDB
(S)-2,6-dioxo-hexahydro-Pyrimidine-4-carboxylic acidHMDB
2,6-dioxo-hexahydro-Pyrimidine-4-carboxylateHMDB
2,6-dioxo-hexahydro-Pyrimidine-4-carboxylic acidHMDB
L-HydroorotateHMDB
L-Hydroorotic acidHMDB
R,S-HydroorotateHMDB
Molecular FormulaC5H6N2O4
Average Mass158.1121
Monoisotopic Mass158.03275669
IUPAC Name2,6-dioxo-1,3-diazinane-4-carboxylic acid
Traditional Namedihydroorotic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1CC(=O)NC(=O)N1
InChI Identifier
InChI=1S/C5H6N2O4/c8-3-1-2(4(9)10)6-5(11)7-3/h2H,1H2,(H,9,10)(H2,6,7,8,11)
InChI KeyUFIVEPVSAGBUSI-UHFFFAOYSA-N