{[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-{[(2R,3R,4R,5R,6R)-3-hydroxy-6-(hydroxymethyl)-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid

• ChemBase ID: 125632
• Molecular Formular: C16H26N5O18P3
• Molecular Mass: 669.321623
• Monoisotopic Mass: 669.04856891
• SMILES: O=P(O)(O)O[C@@H]1[C@H](O[C@H]2O[C@@H]([C@@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H]2O)CO)[C@H](O[C@H]1n1c2ncnc(N)c2nc1)CO
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)OP(=O)(O)O)OP(=O)(O)O)OP(=O)(O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C16H26N5O18P3/c17-13-7-14(19-3-18-13)21(4-20-7)15-12(39-42(31,32)33)9(5(1-22)34-15)36-16-8(24)11(38-41(28,29)30)10(6(2-23)35-16)37-40(25,26)27/h3-6,8-12,15-16,22-24H,1-2H2,(H2,17,18,19)(H2,25,26,27)(H2,28,29,30)(H2,31,32,33)/t5-,6-,8-,9-,10-,11-,12-,15-,16-/m1/s1
• InChIKey: RENVITLQVBEFDT-MZQFDOALSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-{[(2R,3R,4R,5R,6R)-3-hydroxy-6-(hydroxymethyl)-4,5-bis(phosphonooxy)oxan-2-yl]oxy}-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: adenophostin
• Synonyms: Adenophostin

Database IDs

• CAS Number: 149091-92-9
• PubChem SID: 162219982
• PubChem CID: 123695
• CHEMBL: 204385
• Chemspider ID: 110268
• Wikipedia Title: Adenophostin

CALCULATED PROPERTIES

• Acid pKa: 0.16148931
• H Acceptors: 19
• H Donor: 10
• LogD (pH = 5.5): -12.095838
• LogD (pH = 7.4): -16.152056
• Log P: -6.49518
• Molar Refractivity: 128.2276 cm^3
• Polarizability: 52.1355 Å^3
• Polar Surface Area: 358.28 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false