1-[(2R,3R,4R,5S)-5-({[(S)-({[(2S,3S,4R,5R)-5-(6-amino-8-bromo-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1$l^{5}-pyridin-1-ylium

• ChemBase ID: 3594
• Molecular Formular: C21H27BrN7O17P3
• Molecular Mass: 822.301063
• Monoisotopic Mass: 820.98596433
• SMILES: NC(=O)c1ccc[n+](c1)[C@@H]1O[C@@H](COP(=O)([O-])O[P@](=O)(O)OC[C@@H]2O[C@H]([C@H](OP(=O)(O)O)[C@H]2O)n2c(Br)nc3c2ncnc3N)[C@H](O)[C@H]1O
• Canonical SMILES: O[C@@H]1[C@@H](O)[C@@H](O[C@H]1[n+]1cccc(c1)C(=O)N)COP(=O)(O[P@@](=O)(OC[C@@H]1O[C@H]([C@@H]([C@H]1O)OP(=O)(O)O)n1c(Br)nc2c1ncnc2N)O)[O-]
• InChI: InChI=1S/C21H27BrN7O17P3/c22-21-27-11-16(23)25-7-26-18(11)29(21)20-15(45-47(34,35)36)13(31)10(44-20)6-42-49(39,40)46-48(37,38)41-5-9-12(30)14(32)19(43-9)28-3-1-2-8(4-28)17(24)33/h1-4,7,9-10,12-15,19-20,30-32H,5-6H2,(H7-,23,24,25,26,33,34,35,36,37,38,39,40)/t9-,10-,12-,13-,14+,15+,19+,20+/m0/s1
• InChIKey: MDKMTCCUJSRQGW-ZDYBBARQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4R,5S)-5-({[(S)-({[(2S,3S,4R,5R)-5-(6-amino-8-bromo-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1$l^{5}-pyridin-1-ylium
• IUPAC Traditional name: 1-[(2R,3R,4R,5S)-5-({[(S)-([(2S,3S,4R,5R)-5-(6-amino-8-bromopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl phosphonato)]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1$l^{5}-pyridin-1-ylium
• Synonyms: Nicotinamide 8-Bromo-Adenine Dinucleotide Phosphate

Database IDs

• PubChem SID: 46506551; 160967032
• PubChem CID: 46936845

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.651389
• H Acceptors: 17
• H Donor: 8
• LogD (pH = 5.5): -12.685275
• LogD (pH = 7.4): -14.456213
• Log P: -9.351633
• Molar Refractivity: 159.3729 cm^3
• Polarizability: 63.979534 Å^3
• Polar Surface Area: 367.62 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.4
• LOG S: -2.31
• Solubility (Water): 4.28e+00 g/l

DETAILS

DrugBank - DB03962

Drug information: experimental