2-{[1-(4-Methylbenzyl)piperidin-4-yl]methyl}-3-oxo-2,3-dihydro-1H-isoindole-4-carboxamide

ID: ALA3605984

Chembl Id: CHEMBL3605984

PubChem CID: 50943478

Max Phase: Preclinical

Molecular Formula: C23H27N3O2

Molecular Weight: 377.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(CN2CCC(CN3Cc4cccc(C(N)=O)c4C3=O)CC2)cc1

Standard InChI:  InChI=1S/C23H27N3O2/c1-16-5-7-17(8-6-16)13-25-11-9-18(10-12-25)14-26-15-19-3-2-4-20(22(24)27)21(19)23(26)28/h2-8,18H,9-15H2,1H3,(H2,24,27)

Standard InChI Key:  BIQGCSULLOYSIK-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3605984

   2-[[1-[(4-methylphenyl)methyl]piperidin-4-yl]methyl]-3-oxo-1H-isoindole-4-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 377.49

Molecular Weight (Monoisotopic): 377.2103

AlogP: 2.96

#Rotatable Bonds: 5

Polar Surface Area: 66.64

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.25

CX Basic pKa: 8.86

CX LogP: 2.60

CX LogD: 1.13

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.87

Np Likeness Score: -1.00

References

1. Papeo G, Posteri H, Borghi D, Busel AA, Caprera F, Casale E, Ciomei M, Cirla A, Corti E, D'Anello M, Fasolini M, Forte B, Galvani A, Isacchi A, Khvat A, Krasavin MY, Lupi R, Orsini P, Perego R, Pesenti E, Pezzetta D, Rainoldi S, Riccardi-Sirtori F, Scolaro A, Sola F, Zuccotto F, Felder ER, Donati D, Montagnoli A..  (2015)  Discovery of 2-[1-(4,4-Difluorocyclohexyl)piperidin-4-yl]-6-fluoro-3-oxo-2,3-dihydro-1H-isoindole-4-carboxamide (NMS-P118): A Potent, Orally Available, and Highly Selective PARP-1 Inhibitor for Cancer Therapy.,  58  (17): [PMID:26222319] [10.1021/acs.jmedchem.5b00680]

2.  (2014)  3-oxo-2,3-dihydro-1H-isoindole-4-carboxamides as PARP inhibitors, 

Source

Source(2):

• Scientific Literature
• BindingDB Database