biphenyl-4-carboxylic acid [2-(1H-indol-3-yl)-ethyl]-methyl-amide

ID: ALA213805

Chembl Id: CHEMBL213805

Cas Number: 883561-04-4

PubChem CID: 11610059

Max Phase: Preclinical

Molecular Formula: C24H22N2O

Molecular Weight: 354.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(CCc1c[nH]c2ccccc12)C(=O)c1ccc(-c2ccccc2)cc1

Standard InChI:  InChI=1S/C24H22N2O/c1-26(16-15-21-17-25-23-10-6-5-9-22(21)23)24(27)20-13-11-19(12-14-20)18-7-3-2-4-8-18/h2-14,17,25H,15-16H2,1H3

Standard InChI Key:  CPKLVRIYXBROSG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA213805

   N-(2-(1H-indol-3-yl)ethyl)-N-methyl-[1,1'-biphenyl]-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: 354.45

Molecular Weight (Monoisotopic): 354.1732

AlogP: 5.15

#Rotatable Bonds: 5

Polar Surface Area: 36.10

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa:

CX LogP: 5.03

CX LogD: 5.03

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.53

Np Likeness Score: -0.75

References

1. Mahale S, Aubry C, James Wilson A, Jenkins PR, Maréchal JD, Sutcliffe MJ, Chaudhuri B..  (2006)  CA224, a non-planar analogue of fascaplysin, inhibits Cdk4 but not Cdk2 and arrests cells at G0/G1 inhibiting pRB phosphorylation.,  16  (16): [PMID:16750360] [10.1016/j.bmcl.2006.05.065]

2. Jenkins PR, Wilson J, Emmerson D, Garcia MD, Smith MR, Gray SJ, Britton RG, Mahale S, Chaudhuri B..  (2008)  Design, synthesis and biological evaluation of new tryptamine and tetrahydro-beta-carboline-based selective inhibitors of CDK4.,  16  (16): [PMID:18650093] [10.1016/j.bmc.2008.07.002]

3. Mahale S, Bharate SB, Manda S, Joshi P, Bharate SS, Jenkins PR, Vishwakarma RA, Chaudhuri B..  (2014)  Biphenyl-4-carboxylic acid [2-(1H-indol-3-yl)-ethyl]-methylamide (CA224), a nonplanar analogue of fascaplysin, inhibits Cdk4 and tubulin polymerization: evaluation of in vitro and in vivo anticancer activity.,  57  (22): [PMID:25368960] [10.1021/jm5014743]

Source

Source(1):

• Scientific Literature