2-{4-[(2R,3R,4S,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolane-2-carbonyl]piperazin-1-yl}-N-(1-oxo-2,3-dihydro-1H-isoindol-4-yl)acetamide

• ChemBase ID: 167939
• Molecular Formular: C24H27N9O6
• Molecular Mass: 537.52788
• Monoisotopic Mass: 537.20842963
• SMILES: n1([C@H]2O[C@H]([C@@H]([C@@H]2O)O)C(=O)N2CCN(CC(=O)Nc3c4c(C(=O)NC4)ccc3)CC2)c2c(nc1)c(ncn2)N
• Canonical SMILES: O=C(Nc1cccc2c1CNC2=O)CN1CCN(CC1)C(=O)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C24H27N9O6/c25-20-16-21(28-10-27-20)33(11-29-16)24-18(36)17(35)19(39-24)23(38)32-6-4-31(5-7-32)9-15(34)30-14-3-1-2-12-13(14)8-26-22(12)37/h1-3,10-11,17-19,24,35-36H,4-9H2,(H,26,37)(H,30,34)(H2,25,27,28)/t17-,18+,19-,24+/m1/s1
• InChIKey: DDFLFKTXUWPNMV-LFALDJFMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{4-[(2R,3R,4S,5S)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolane-2-carbonyl]piperazin-1-yl}-N-(1-oxo-2,3-dihydro-1H-isoindol-4-yl)acetamide
• IUPAC Traditional name: 2-{4-[(2R,3R,4S,5S)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolane-2-carbonyl]piperazin-1-yl}-N-(1-oxo-2,3-dihydroisoindol-4-yl)acetamide
• Synonyms: 5'-Deoxy-5'-[4-[2-[(2,3-dihydro-1-oxo-1H-isoindol-4-yl)amino]-2-oxoethyl]-1-piperazinyl]-5'-oxoadenosine Dihydrochloride; 4-[1-(6-Amino-9H-purin-9-yl)-1-deoxy-β-D-ribofuranuronoyl]-N-(2,3-dihydro-1-oxo-1H-isoindol-4-yl)-1-piperazineacetamide Dihydrochloride; EB 47

Database IDs

• CAS Number: 366454-36-6
• PubChem SID: 162262072
• PubChem CID: 53229989

CALCULATED PROPERTIES

• Acid pKa: 12.250541
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -2.74283
• LogD (pH = 7.4): -2.5481396
• Log P: -2.5453315
• Molar Refractivity: 137.6203 cm^3
• Polarizability: 51.730507 Å^3
• Polar Surface Area: 201.06 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E320300

EB 47 is a potent inhibitor of poly(ADP-ribose) polymerase-1 (PARP-1). Poly(ADP-ribose) polymerases (PARPs) play a major role in cellular survival and maintenance of energy stores after genotoxic insult.

REFERENCES

• Jagtap, et al.: Bioorg. Med. Chem. Lett., 14, 81 (2004)
• Gaymes, et al.: Haematologica, 94, 638 (2004)
• Ferraris, et al.: J. Med. Chem. 53, 4561 (2004)