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

• ChemBase ID: 2666
• Molecular Formular: C10H13N2O11P
• Molecular Mass: 368.190781
• Monoisotopic Mass: 368.02569588
• SMILES: O[C@@H]1[C@@H](O)[C@@H](O[C@H]1COP(=O)(O)O)n1c(=O)[nH]c(=O)cc1C(=O)O
• Canonical SMILES: O[C@@H]1[C@@H](O)[C@@H](O[C@H]1n1c(=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)/t4-,6-,7+,8+/m0/s1
• InChIKey: KYOBSHFOBAOFBF-ZAKLUEHWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2R,3R,4R,5S)-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'-monophosphate
• Synonyms: Orotidine-5'-Monophosphate

Database IDs

• PubChem SID: 46507709; 160966115
• PubChem CID: 46936537

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -1.67
• LOG S: -1.63
• Solubility (Water): 8.61e+00 g/l

DETAILS

DrugBank - DB02957

Drug information: experimental