Orotidine 5'-monophosphate

Orotidine 5'-monophosphate (OMP), also known as orotidylic acid, is a pyrimidine nucleotide[1] which is the last intermediate in the biosynthesis of uridine monophosphate.[2] OMP is formed from orotate and phosphoribosyl pyrophosphate by the enzyme orotate phosphoribosyltransferase.

Orotidine 5'-monophosphate
Names
IUPAC name
2,6-Dioxo-3-(5-O-phosphono-β-D-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
Systematic IUPAC name
3-{(2R,3R,4S,5R)-3,4-Dihydroxy-6-[(phosphonooxy)methyl]oxolan-2-yl}-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
Other names
Orotidylic acid,
OMP
Identifiers
3D model (JSmol)
ChemSpider
MeSH Orotidine+5'-monophosphate
UNII
  • 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 ☒N
    Key: KYOBSHFOBAOFBF-XVFCMESISA-N ☒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
  • 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
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

In humans, the enzyme UMP synthase converts OMP into uridine 5'- monophosphate.[2] If UMP synthase is defective, orotic aciduria can result.[2]

References
  1. PubChem. "Orotidine-5'-monophosphate". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-01-26.
  2. "UMPS uridine monophosphate synthetase [Homo sapiens (human)] - Gene - NCBI". www.ncbi.nlm.nih.gov. Retrieved 2023-01-26.
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