Orotidine 5'-monophosphate

Orotidine 5'-monophosphate

Names
IUPAC name 3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-​(phosphonooxymethyl)oxolan-2-yl]​-2,6-dioxo-pyrimidine-4-carboxylic acid
Other names Orotidylic acid, OMP
Identifiers
CAS Number	2149-82-8
ChemSpider	141140
Jmol interactive 3D	Image
MeSH	Orotidine+5'-monophosphate
PubChem	160617
InChI InChI=1S/C10H13N2O11P/c13-5-1-3(9(16)17)12(10(18)11-5)8-7(15)6(14)4(23-8)2-22-24(19,20)21/h1,4,6-8,14-15H,2H2,(H,16,17)(H,11,13,18)(H2,19,20,21)/t4-,6-,7-,8-/m1/s1 Key: KYOBSHFOBAOFBF-XVFCMESISA-N InChI=1/C10H13N2O11P/c13-5-1-3(9(16)17)12(10(18)11-5)8-7(15)6(14)4(23-8)2-22-24(19,20)21/h1,4,6-8,14-15H,2H2,(H,16,17)(H,11,13,18)(H2,19,20,21)/t4-,6-,7-,8-/m1/s1 Key: KYOBSHFOBAOFBF-XVFCMESIBC
SMILES c1c(n(c(=O)nc1O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)C(=O)O
Properties
Chemical formula	C10H13N2O11P
Molar mass	368.191 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Orotidine 5'-monophosphate (OMP), also known as orotidylic acid, is a pyrimidine nucleotide which is the last intermediate in the biosynthesis of uridine monophosphate. OMP is formed from orotate and phosphoribosyl pyrophosphate by the enzyme Orotate phosphoribosyltransferase

In humans, the enzyme UMP synthase converts OMP into uridine 5'- monophosphate. If UMP synthase is defective, orotic aciduria can result.