3-(4-aminophenylthio)-8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-carbonitrile

ID: ALA1672082

Chembl Id: CHEMBL1672082

Cas Number: 1265829-41-1

PubChem CID: 51003123

Max Phase: Preclinical

Molecular Formula: C21H11N3OS

Molecular Weight: 353.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CC1=C2C(=NC1=O)c1cccc3c(Sc4ccc(N)cc4)ccc2c13

Standard InChI:  InChI=1S/C21H11N3OS/c22-10-16-19-14-8-9-17(26-12-6-4-11(23)5-7-12)13-2-1-3-15(18(13)14)20(19)24-21(16)25/h1-9H,23H2

Standard InChI Key:  FNSJVQXUTIKAPS-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1672082

   3-(4-aminophenylthio)-8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-carbonitrile

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: 353.41

Molecular Weight (Monoisotopic): 353.0623

AlogP: 4.19

#Rotatable Bonds: 2

Polar Surface Area: 79.24

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.85

CX LogP: 3.34

CX LogD: 3.34

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.70

Np Likeness Score: -0.76

References

1. Zhang Z, Wu G, Xie F, Song T, Chang X..  (2011)  3-Thiomorpholin-8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-carbonitrile (S1) based molecules as potent, dual inhibitors of B-cell lymphoma 2 (Bcl-2) and myeloid cell leukemia sequence 1 (Mcl-1): structure-based design and structure-activity relationship studies.,  54  (4): [PMID:21235240] [10.1021/jm101181u]

2. Song T, Li X, Chang X, Liang X, Zhao Y, Wu G, Xie S, Su P, Wu Z, Feng Y, Zhang Z..  (2013)  3-Thiomorpholin-8-oxo-8H-acenaphtho [1,2-b] pyrrole-9-carbonitrile (S1) derivatives as pan-Bcl-2-inhibitors of Bcl-2, Bcl-xL and Mcl-1.,  21  (1): [PMID:23206987] [10.1016/j.bmc.2012.11.008]

Source

Source(1):

• Scientific Literature