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

• ChemBase ID: 3985
• Molecular Formular: C10H17N6O12P3
• Molecular Mass: 506.196263
• Monoisotopic Mass: 506.0117299
• SMILES: Nc1ncnc2c1ncn2[C@@H]1O[C@@H](CO[P@@](=O)(O)O[P@](=O)(O)NP(=O)(O)O)[C@H](O)[C@H]1O
• Canonical SMILES: O[C@H]1[C@H](CO[P@](=O)(O[P@@](=O)(NP(=O)(O)O)O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C10H17N6O12P3/c11-8-5-9(13-2-12-8)16(3-14-5)10-7(18)6(17)4(27-10)1-26-31(24,25)28-30(22,23)15-29(19,20)21/h2-4,6-7,10,17-18H,1H2,(H,24,25)(H2,11,12,13)(H4,15,19,20,21,22,23)/t4-,6-,7+,10+/m0/s1
• InChIKey: PVKSNHVPLWYQGJ-FCIPNVEPSA-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)oxy](hydroxy)phosphoryl}amino)phosphonic acid
• IUPAC Traditional name: ({[(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)aminophosphonic acid
• Synonyms: Phosphoaminophosphonic Acid-Adenylate Ester

Database IDs

• PubChem SID: 46507028; 160967420
• PubChem CID: 44462678

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.34270534
• H Acceptors: 14
• H Donor: 8
• LogD (pH = 5.5): -10.606115
• LogD (pH = 7.4): -12.588192
• Log P: -7.64975
• Molar Refractivity: 97.7641 cm^3
• Polarizability: 39.179405 Å^3
• Polar Surface Area: 281.93 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.99
• LOG S: -2.08
• Solubility (Water): 4.17e+00 g/l

DETAILS

DrugBank - DB04395

• Drug Groups: experimental
• Description: 5'-Adenylic acid, monoanhydride with imidodiphosphoric acid. An analog of ATP, in which the oxygen atom bridging the beta to the gamma phosphate is replaced by a nitrogen atom. It is a potent competitive inhibitor of soluble and membrane-bound mitochondrial ATPase and also inhibits ATP-dependent reactions of oxidative phosphorylation. [PubChem]