rac-N-(cyanomethyl)-5,5-difluoro-[4'-(methylthio)-1,1'-biphenyl-2-yl]cyclohexanecarboxamide

ID: ALA201914

Chembl Id: CHEMBL201914

PubChem CID: 11338550

Max Phase: Preclinical

Molecular Formula: C22H22F2N2OS

Molecular Weight: 400.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1ccc(-c2ccccc2C2CCC(F)(F)CC2C(=O)NCC#N)cc1

Standard InChI:  InChI=1S/C22H22F2N2OS/c1-28-16-8-6-15(7-9-16)17-4-2-3-5-18(17)19-10-11-22(23,24)14-20(19)21(27)26-13-12-25/h2-9,19-20H,10-11,13-14H2,1H3,(H,26,27)

Standard InChI Key:  AINATGOAAJKINN-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA201914

   N-(cyanomethyl)-5,5-difluoro-2-[2-(4-methylsulfanylphenyl)phenyl]cyclohexane-1-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: 400.49

Molecular Weight (Monoisotopic): 400.1421

AlogP: 5.23

#Rotatable Bonds: 5

Polar Surface Area: 52.89

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.15

CX Basic pKa: ┄

CX LogP: 4.03

CX LogD: 4.03

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.55

Np Likeness Score: -0.58

References

1. Crane SN, Black WC, Palmer JT, Davis DE, Setti E, Robichaud J, Paquet J, Oballa RM, Bayly CI, McKay DJ, Somoza JR, Chauret N, Seto C, Scheigetz J, Wesolowski G, Massé F, Desmarais S, Ouellet M..  (2006)  Beta-substituted cyclohexanecarboxamide: a nonpeptidic framework for the design of potent inhibitors of cathepsin K.,  49  (3): [PMID:16451072] [10.1021/jm051059p]

2. Robichaud J, Bayly CI, Black WC, Desmarais S, Léger S, Massé F, McKay DJ, Oballa RM, Pâquet J, Percival MD, Truchon JF, Wesolowski G, Crane SN..  (2007)  Beta-substituted cyclohexanecarboxamide cathepsin K inhibitors: modification of the 1,2-disubstituted aromatic core.,  17  (11): [PMID:17408953] [10.1016/j.bmcl.2007.03.028]

3. Robichaud J, Bayly CI, Black WC, Desmarais S, Léger S, Massé F, McKay DJ, Oballa RM, Pâquet J, Percival MD, Truchon JF, Wesolowski G, Crane SN..  (2007)  Beta-substituted cyclohexanecarboxamide cathepsin K inhibitors: modification of the 1,2-disubstituted aromatic core.,  17  (11): [PMID:17408953] [10.1016/j.bmcl.2007.03.028]

Source

Source(1):

• Scientific Literature