ID: ALA249915

Max Phase: Preclinical

Molecular Formula: C16H17F4N3O3S

Molecular Weight: 407.39

Molecule Type: Small molecule

Representations

Canonical SMILES:  CS(=O)(=O)C[C@H](N[C@@H](c1ccc(F)cc1)C(F)(F)F)C(=O)NC1(C#N)CC1

Standard InChI:  InChI=1S/C16H17F4N3O3S/c1-27(25,26)8-12(14(24)23-15(9-21)6-7-15)22-13(16(18,19)20)10-2-4-11(17)5-3-10/h2-5,12-13,22H,6-8H2,1H3,(H,23,24)/t12-,13-/m0/s1

Standard InChI Key:  HBOZUMOKFHNMQI-STQMWFEESA-N

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

Properties

Molecular Weight: 407.39

Molecular Weight (Monoisotopic): 407.0927

AlogP: 1.60

#Rotatable Bonds: 7

Polar Surface Area: 99.06

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.46

CX Basic pKa: 1.74

CX LogP: 0.71

CX LogD: 0.70

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.67

Np Likeness Score: -1.29

References

1. Gauthier JY, Black WC, Courchesne I, Cromlish W, Desmarais S, Houle R, Lamontagne S, Li CS, Massé F, McKay DJ, Ouellet M, Robichaud J, Truchon JF, Truong VL, Wang Q, Percival MD..  (2007)  The identification of potent, selective, and bioavailable cathepsin S inhibitors.,  17  (17): [PMID:17590332] [10.1016/j.bmcl.2007.06.023]

2. Moss N, Xiong Z, Burke M, Cogan D, Gao DA, Haverty K, Heim-Riether A, Hickey ER, Nagaraja R, Netherton M, O'Shea K, Ramsden P, Schwartz R, Shih DT, Ward Y, Young E, Zhang Q..  (2012)  Exploration of cathepsin S inhibitors characterized by a triazole P1-P2 amide replacement.,  22  (23): [PMID:23084902] [10.1016/j.bmcl.2012.09.054]

Source

Source(1):

• Scientific Literature