{[(2R,3R,4S,5S)-4-(acetyloxy)-3,5-dihydroxyoxolan-2-yl]methoxy}[({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid

• ChemBase ID: 3154
• Molecular Formular: C17H25N5O15P2
• Molecular Mass: 601.352422
• Monoisotopic Mass: 601.08223839
• SMILES: CC(=O)O[C@@H]1[C@@H](O)O[C@H](CO[P@@](=O)(O)O[P@](=O)(O)OC[C@@H]2O[C@H]([C@H](O)[C@H]2O)n2cnc3c2ncnc3N)[C@H]1O
• Canonical SMILES: CC(=O)O[C@@H]1[C@@H](O)O[C@@H]([C@H]1O)CO[P@](=O)(O[P@@](=O)(OC[C@@H]1O[C@H]([C@@H]([C@H]1O)O)n1cnc2c1ncnc2N)O)O
• InChI: InChI=1S/C17H25N5O15P2/c1-6(23)34-13-11(25)8(36-17(13)27)3-33-39(30,31)37-38(28,29)32-2-7-10(24)12(26)16(35-7)22-5-21-9-14(18)19-4-20-15(9)22/h4-5,7-8,10-13,16-17,24-27H,2-3H2,1H3,(H,28,29)(H,30,31)(H2,18,19,20)/t7-,8+,10-,11+,12+,13-,16+,17-/m0/s1
• InChIKey: BFNOPXRXIQJDHO-BVNNLCGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3R,4S,5S)-4-(acetyloxy)-3,5-dihydroxyoxolan-2-yl]methoxy}[({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphinic acid
• IUPAC Traditional name: [(2R,3R,4S,5S)-4-(acetyloxy)-3,5-dihydroxyoxolan-2-yl]methoxy({[(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)phosphinic acid
• Synonyms: 2'-O-Acetyl Adenosine-5-Diphosphoribose

Database IDs

• PubChem SID: 160966598; 46505222
• PubChem CID: 46936692

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.7855422
• H Acceptors: 15
• H Donor: 7
• LogD (pH = 5.5): -8.030994
• LogD (pH = 7.4): -8.347386
• Log P: -6.241814
• Molar Refractivity: 120.2748 cm^3
• Polarizability: 49.152504 Å^3
• Polar Surface Area: 297.59 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.67
• LOG S: -2.23
• Solubility (Water): 3.54e+00 g/l

DETAILS

DrugBank - DB03478

Drug information: experimental