2-{4-[(2S,3S,4R,5R)-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: 154229
• Molecular Formular: C24H27N9O6
• Molecular Mass: 537.52788
• Monoisotopic Mass: 537.20842963
• SMILES: c1cc2c(c(c1)NC(=O)CN1CCN(CC1)C(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc3c1ncnc3N)O)O)CNC2=O
• 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+/m0/s1
• InChIKey: DDFLFKTXUWPNMV-UAKAABGRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{4-[(2S,3S,4R,5R)-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-[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolane-2-carbonyl]piperazin-1-yl}-N-(1-oxo-2,3-dihydroisoindol-4-yl)acetamide
• Synonyms: EB-47

Database IDs

• MDL Number: MFCD06411565
• PubChem SID: 162248368
• PubChem CID: 9871899

CALCULATED PROPERTIES

• Acid pKa: 12.245025
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -2.74283
• LogD (pH = 7.4): -2.5481398
• 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

PROPERTIES

Physical Property

• Solubility: H2O: soluble10 mg/mL
• Apperance: solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C24H29N9O6Cl2

DETAILS

Sigma Aldrich - E8405

Biochem/physiol Actions
Potent inhibitor of poly (ADP-ribose) polymerase (PARP).