(R)-2-((S)-1-(4-bromophenyl)-2,2,2-trifluoroethylamino)-N-(1-cyanocyclopropyl)-3-(methylsulfonyl)propanamide

ID: ALA400387

PubChem CID: 23648277

Max Phase: Preclinical

Molecular Formula: C16H17BrF3N3O3S

Molecular Weight: 468.30

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H17BrF3N3O3S/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:  QHDGGHMKRWZOAZ-STQMWFEESA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
   15.7323  -21.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3219  -21.0054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9111  -21.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6079  -21.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6067  -21.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3221  -22.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0390  -21.8530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0362  -21.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3203  -20.6113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8915  -22.2633    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.7497  -20.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4661  -21.0172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7465  -19.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7401  -18.9534    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.5715  -19.7756    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.9216  -19.7870    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.1796  -20.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8920  -21.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1765  -19.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8858  -19.3619    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.5964  -18.9409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3051  -20.0700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4712  -18.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8951  -21.8368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6054  -20.5945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0350  -20.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7479  -20.1722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0
 13 14  1  0
  1  3  1  0
 13 15  1  0
  7  8  1  0
 13 16  1  0
 12 17  1  0
  8  9  2  0
 17 18  1  0
  9  4  1  0
 17 19  1  1
  4  5  2  0
 19 20  1  0
  5 10  1  0
 20 21  1  0
  2  1  1  0
 20 22  2  0
  8 11  1  0
 20 23  2  0
  5  6  1  0
 18 24  2  0
 11 12  1  0
 18 25  1  0
 25  2  1  0
  3  2  1  0
  2 26  1  0
 11 13  1  1
 26 27  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA400387

   Trifluoroethylamine inhibitor, 2

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: 468.30

Molecular Weight (Monoisotopic): 467.0126

AlogP: 2.23

#Rotatable Bonds: 7

Polar Surface Area: 99.06

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.48

CX Basic pKa: 1.81

CX LogP: 1.33

CX LogD: 1.33

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: -1.18

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. Méthot N, Rubin J, Guay D, Beaulieu C, Ethier D, Reddy TJ, Riendeau D, Percival MD..  (2007)  Inhibition of the activation of multiple serine proteases with a cathepsin C inhibitor requires sustained exposure to prevent pro-enzyme processing.,  282  (29): [PMID:17535802] [10.1074/jbc.m702615200]

Source

Source(1):

• Scientific Literature