3-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid

• ChemBase ID: 128745
• Molecular Formular: C10H13N2O11P
• Molecular Mass: 368.190781
• Monoisotopic Mass: 368.02569588
• SMILES: c1c(n(c(=O)[nH]c1=O)C1C(C(C(O1)COP(=O)(O)O)O)O)C(=O)O
• Canonical SMILES: OC1C(O)C(OC1n1c(=O)[nH]c(=O)cc1C(=O)O)COP(=O)(O)O
• 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)
• InChIKey: KYOBSHFOBAOFBF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
• IUPAC Traditional name: orotidine-5'-phosphate
• Synonyms: Orotidylic acid; OMP; Orotidine 5'-monophosphate

Database IDs

• CAS Number: 2149-82-8
• PubChem SID: 162223051
• PubChem CID: 968
• MeSH Name: Orotidine+5'-monophosphate
• Wikipedia Title: Orotidine_5'-monophosphate

CALCULATED PROPERTIES

• Acid pKa: 1.2130129
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -7.9186134
• LogD (pH = 7.4): -9.835156
• Log P: -2.9111817
• Molar Refractivity: 70.7438 cm^3
• Polarizability: 28.087341 Å^3
• Polar Surface Area: 203.16 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false