{[(2R,3S,4S,5R)-5-(4-amino-5-bromo-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 4408
• Molecular Formular: C9H13BrN3O8P
• Molecular Mass: 402.092581
• Monoisotopic Mass: 400.96236302
• SMILES: Nc1nc(=O)n(cc1Br)[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@@H]1O
• Canonical SMILES: O[C@H]1[C@H](O)[C@H](O[C@H]1n1cc(Br)c(nc1=O)N)COP(=O)(O)O
• InChI: InChI=1S/C9H13BrN3O8P/c10-3-1-13(9(16)12-7(3)11)8-6(15)5(14)4(21-8)2-20-22(17,18)19/h1,4-6,8,14-15H,2H2,(H2,11,12,16)(H2,17,18,19)/t4-,5-,6+,8-/m1/s1
• InChIKey: KOHPTSGPCYTYFB-MNCSTQPFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,4S,5R)-5-(4-amino-5-bromo-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: CB2
• Synonyms: CB2; Phosphoric Acid Mono-[5-(4-Amino-5-Bromo-2-Oxo-2H-Pyrimidin-1-Yl)-3,4-Dihydroxy-Tetrahydro-Furan-2-Ylmethyl] Ester; 5-bromo-cytidinemonophosphate

Database IDs

• PubChem SID: 46505049; 160967840
• PubChem CID: 23644074

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.2256521
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -4.537114
• LogD (pH = 7.4): -5.625424
• Log P: -2.0955896
• Molar Refractivity: 73.027 cm^3
• Polarizability: 29.152063 Å^3
• Polar Surface Area: 175.14 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.37
• LOG S: -1.5
• Solubility (Water): 1.27e+01 g/l

DETAILS

DrugBank - DB05248

Drug information: experimental