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

• ChemBase ID: 3036
• Molecular Formular: C10H13BrN5O7P
• Molecular Mass: 426.117281
• Monoisotopic Mass: 424.97359641
• SMILES: Nc1ncnc2c1nc(Br)n2[C@@H]1O[C@@H](COP(=O)(O)O)[C@H](O)[C@H]1O
• Canonical SMILES: O[C@@H]1[C@@H](O)[C@@H](O[C@H]1n1c(Br)nc2c1ncnc2N)COP(=O)(O)O
• InChI: InChI=1S/C10H13BrN5O7P/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(18)5(17)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,17-18H,1H2,(H2,12,13,14)(H2,19,20,21)/t3-,5-,6+,9+/m0/s1
• InChIKey: DNPIJKNXFSPNNY-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}phosphonic acid
• IUPAC Traditional name: [(2S,3R,4R,5R)-5-(6-amino-8-bromopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
• Synonyms: 8-Bromo-Adenosine-5'-Monophosphate

Database IDs

• PubChem SID: 46506327; 160966483
• PubChem CID: 46936648

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.3506385
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -3.603713
• LogD (pH = 7.4): -4.6811476
• Log P: -3.7312248
• Molar Refractivity: 81.6933 cm^3
• Polarizability: 32.28468 Å^3
• Polar Surface Area: 186.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.46
• LOG S: -2.12
• Solubility (Water): 3.26e+00 g/l

DETAILS

DrugBank - DB03349

Drug information: experimental