[({[(2S,3R,4R,5R)-5-(6-amino-8-bromo-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid

• ChemBase ID: 4122
• Molecular Formular: C10H14BrN5O10P2
• Molecular Mass: 506.097182
• Monoisotopic Mass: 504.93992693
• SMILES: Nc1ncnc2c1nc(Br)n2[C@@H]1O[C@@H](CO[P@@](=O)(O)OP(=O)(O)O)[C@H](O)[C@H]1O
• Canonical SMILES: O[C@H]1[C@H](CO[P@](=O)(OP(=O)(O)O)O)O[C@H]([C@@H]1O)n1c(Br)nc2c1ncnc2N
• InChI: InChI=1S/C10H14BrN5O10P2/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(18)5(17)3(25-9)1-24-28(22,23)26-27(19,20)21/h2-3,5-6,9,17-18H,1H2,(H,22,23)(H2,12,13,14)(H2,19,20,21)/t3-,5-,6+,9+/m0/s1
• InChIKey: KVVVTFSHHQCHNZ-BZKDHIKHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [({[(2S,3R,4R,5R)-5-(6-amino-8-bromo-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
• IUPAC Traditional name: {[(2S,3R,4R,5R)-5-(6-amino-8-bromopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
• Synonyms: 8-Bromoadenosine-5'-Diphosphate

Database IDs

• PubChem SID: 160967554; 46508153
• PubChem CID: 46937008

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.7894467
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -5.998627
• LogD (pH = 7.4): -6.6164746
• Log P: -3.7147975
• Molar Refractivity: 92.5662 cm^3
• Polarizability: 37.08909 Å^3
• Polar Surface Area: 232.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.04
• LOG S: -2.26
• Solubility (Water): 2.76e+00 g/l

DETAILS

DrugBank - DB04554

Drug information: experimental