N-[(2E)-3-[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]prop-2-en-1-yl]-2,3-dihydroxy-5-nitrobenzamide

• ChemBase ID: 3544
• Molecular Formular: C19H19N7O8
• Molecular Mass: 473.39626
• Monoisotopic Mass: 473.1295106
• SMILES: Nc1ncnc2c1ncn2[C@@H]1O[C@@H](/C=C/CNC(=O)c2cc(cc(O)c2O)[N+](=O)[O-])[C@H](O)[C@H]1O
• Canonical SMILES: O[C@H]1[C@H](/C=C/CNC(=O)c2cc(cc(c2O)O)[N+](=O)[O-])O[C@H]([C@@H]1O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C19H19N7O8/c20-16-12-17(23-6-22-16)25(7-24-12)19-15(30)14(29)11(34-19)2-1-3-21-18(31)9-4-8(26(32)33)5-10(27)13(9)28/h1-2,4-7,11,14-15,19,27-30H,3H2,(H,21,31)(H2,20,22,23)/b2-1+/t11-,14-,15+,19+/m0/s1
• InChIKey: UHHBFOLQOQSPLU-PINBASSTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2E)-3-[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]prop-2-en-1-yl]-2,3-dihydroxy-5-nitrobenzamide
• IUPAC Traditional name: N-[(2E)-3-[(2S,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]prop-2-en-1-yl]-2,3-dihydroxy-5-nitrobenzamide
• Synonyms: N-{3-[5-(6-Amino-Purin-9-Yl)-3,4-Dihydroxy-Tetrahydro-Furan-2-Yl]-Allyl}-2,3-Dihydroxy-5-Nitro-Benzamide

Database IDs

• PubChem SID: 46504513; 160966983
• PubChem CID: 70789234

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.0843253
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -0.2707287
• LogD (pH = 7.4): -1.3126717
• Log P: -0.34730032
• Molar Refractivity: 116.5725 cm^3
• Polarizability: 43.010513 Å^3
• Polar Surface Area: 234.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 1.98
• LOG S: -2.68
• Solubility (Water): 9.97e-01 g/l

DETAILS

DrugBank - DB03907

Drug information: experimental