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

ID: ALA201782

Chembl Id: CHEMBL201782

PubChem CID: 11574887

Max Phase: Preclinical

Molecular Formula: C22H22F2N2OS

Molecular Weight: 400.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1ccc(-c2ccccc2[C@@H]2CCC(F)(F)C[C@H]2C(=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)/t19-,20+/m0/s1

Standard InChI Key:  AINATGOAAJKINN-VQTJNVASSA-N

Alternative Forms

1. Parent:

   

   ALA201782

   Cyclohexanecarboxamide derivative, (-)-34a

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, Black WC, Thérien M, Paquet J, Oballa RM, Bayly CI, McKay DJ, Wang Q, Isabel E, Léger S, Mellon C, Kimmel DB, Wesolowski G, Percival MD, Massé F, Desmarais S, Falgueyret JP, Crane SN..  (2008)  Identification of a nonbasic, nitrile-containing cathepsin K inhibitor (MK-1256) that is efficacious in a monkey model of osteoporosis.,  51  (20): [PMID:18811135] [10.1021/jm800610j]

Source

Source(1):

• Scientific Literature