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

• ChemBase ID: 2324
• Molecular Formular: C11H18N5O12P3
• Molecular Mass: 505.208203
• Monoisotopic Mass: 505.01648093
• SMILES: Nc1ncnc2c1ncn2[C@@H]1O[C@@H](CO[P@](=O)(O)C[P@@](=O)(O)OP(=O)(O)O)[C@H](O)[C@H]1O
• Canonical SMILES: O[C@H]1[C@H](CO[P@@](=O)(C[P@](=O)(OP(=O)(O)O)O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C11H18N5O12P3/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(27-11)1-26-29(19,20)4-30(21,22)28-31(23,24)25/h2-3,5,7-8,11,17-18H,1,4H2,(H,19,20)(H,21,22)(H2,12,13,14)(H2,23,24,25)/t5-,7-,8+,11+/m0/s1
• InChIKey: CAWZRIXWFRFUQB-WOIOKPISSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[({[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)methyl](hydroxy)phosphoryl}oxy)phosphonic acid
• IUPAC Traditional name: ({[(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}methyl(hydroxy)phosphoryl)oxyphosphonic acid
• Synonyms: Alpha,Beta-Methyleneadenosine-5'-Triphosphate

Database IDs

• PubChem SID: 46507991; 160965776
• PubChem CID: 6323221

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.0142043
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): -10.407348
• LogD (pH = 7.4): -10.861171
• Log P: -7.0924125
• Molar Refractivity: 98.168 cm^3
• Polarizability: 39.627876 Å^3
• Polar Surface Area: 269.9 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.1
• LOG S: -2.07
• Solubility (Water): 4.29e+00 g/l

DETAILS

DrugBank - DB02596

Drug information: experimental