(1R/S,2R/S)-N-(cyanomethyl)-2-({[4-(methylsulfinyl)phenyl]-sulfonyl}methyl)-cyclohexanecarboxamide

ID: ALA427377

Chembl Id: CHEMBL427377

PubChem CID: 44406953

Max Phase: Preclinical

Molecular Formula: C17H22N2O4S2

Molecular Weight: 382.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[S+]([O-])c1ccc(S(=O)(=O)C[C@@H]2CCCC[C@H]2C(=O)NCC#N)cc1

Standard InChI:  InChI=1S/C17H22N2O4S2/c1-24(21)14-6-8-15(9-7-14)25(22,23)12-13-4-2-3-5-16(13)17(20)19-11-10-18/h6-9,13,16H,2-5,11-12H2,1H3,(H,19,20)/t13-,16+,24?/m0/s1

Standard InChI Key:  NSMIEPGLWQXDAC-KUESFKKXSA-N

Alternative Forms

1. Parent:

   

   ALA427377

   (1R,2R)-N-(cyanomethyl)-2-[(4-methylsulfinylphenyl)sulfonylmethyl]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: 382.51

Molecular Weight (Monoisotopic): 382.1021

AlogP: 1.64

#Rotatable Bonds: 6

Polar Surface Area: 110.09

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.34

CX Basic pKa: ┄

CX LogP: -0.01

CX LogD: -0.01

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.59

Np Likeness Score: -0.82

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]

Source

Source(1):

• Scientific Literature