Orotidine 5'-monophosphate - Misplaced Pages

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-oxolan-2-yl}-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
Other names Orotidylic acid, OMP
Identifiers
CAS Number	2149-82-8
3D model (JSmol)	Interactive image
ChemSpider	141140
MeSH	Orotidine+5'-monophosphate
PubChem CID	160617
UNII	H0ARN8U4Y9
CompTox Dashboard (EPA)	DTXSID40944090
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/s1Key: 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/s1Key: KYOBSHFOBAOFBF-XVFCMESIBC
SMILES c1c(n(c(=O)nc1O)2(((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 , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

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.

References

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

anabolism

R5P→IMP:	Ribose 5-phosphate (R5P) Phosphoribosyl pyrophosphate (PRPP) Phosphoribosylamine (PRA) Glycineamide ribonucleotide (GAR) Phosphoribosyl-N-formylglycineamide (FGAR) 5′-Phosphoribosylformylglycinamidine (FGAM) 5-Aminoimidazole ribotide (AIR) 5′-Phosphoribosyl-4-carboxy-5-aminoimidazole (CAIR) Phosphoribosylaminoimidazolesuccinocarboxamide (SAICAR) AICA ribonucleotide (AICAR) 5-Formamidoimidazole-4-carboxamide ribotide (FAICAR)
IMP→AMP:	Adenylosuccinate
IMP→GMP:	Xanthosine monophosphate

catabolism

anabolism

catabolism

uracil:	β-Alanine Dihydrouracil 3-Ureidopropionic acid
thymine:	3-Aminoisobutyric acid Dihydrothymine β-Ureidoisobutyric acid

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