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
3D model (Jmol)	Interactive image
ChemSpider	141140
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).
Y verify (what is ^YN ?)
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.

Anabolism

R5P→IMP:	R5P PRPP PRA GAR FGAR FGAM AIR CAIR SAICAR AICAR FAICAR

IMP→AMP:	Adenylosuccinate

IMP→GMP:	Xanthosine monophosphate

Catabolism

Anabolism

Catabolism

uracil:	Dihydrouracil 3-Ureidopropionic acid β-Alanine

thymine:	Dihydrothymine β-Ureidoisobutyric acid 3-Aminoisobutyric acid

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