{[(2S,3R,4R,5R)-5-(2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 2055
• Molecular Formular: C10H13N4O9P
• Molecular Mass: 364.205381
• Monoisotopic Mass: 364.04201465
• SMILES: O[C@H]1[C@H](COP(=O)(O)O)O[C@H]([C@@H]1O)n1cnc2c1[nH]c(=O)[nH]c2=O
• Canonical SMILES: O=c1[nH]c(=O)c2c([nH]1)n(cn2)[C@@H]1O[C@H]([C@@H]([C@H]1O)O)COP(=O)(O)O
• InChI: InChI=1S/C10H13N4O9P/c15-5-3(1-22-24(19,20)21)23-9(6(5)16)14-2-11-4-7(14)12-10(18)13-8(4)17/h2-3,5-6,9,15-16H,1H2,(H2,19,20,21)(H2,12,13,17,18)/t3-,5-,6+,9+/m0/s1
• InChIKey: DCTLYFZHFGENCW-BZKDHIKHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,4R,5R)-5-(2,6-dioxo-2,3,6,9-tetrahydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2S,3R,4R,5R)-5-(2,6-dioxo-1,3-dihydropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
• Synonyms: 5--Monophosphate-9-Beta-D-Ribofuranosyl Xanthine

Database IDs

• PubChem SID: 160965509; 46504859
• PubChem CID: 46936344; 6328706

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.2561243
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -4.3716793
• LogD (pH = 7.4): -5.4704556
• Log P: -2.1784012
• Molar Refractivity: 73.0814 cm^3
• Polarizability: 28.369602 Å^3
• Polar Surface Area: 192.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.22
• LOG S: -2.35
• Solubility (Water): 1.80e+00 g/l

DETAILS

DrugBank - DB02309

Drug information: experimental