N-(cyanomethyl)-3-(3,5-dimethylphenyl)-2-(2,2-diphenylacetamido)propanamide

ID: ALA477531

PubChem CID: 11761693

Max Phase: Preclinical

Molecular Formula: C27H27N3O2

Molecular Weight: 425.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C)cc(CC(NC(=O)C(c2ccccc2)c2ccccc2)C(=O)NCC#N)c1

Standard InChI:  InChI=1S/C27H27N3O2/c1-19-15-20(2)17-21(16-19)18-24(26(31)29-14-13-28)30-27(32)25(22-9-5-3-6-10-22)23-11-7-4-8-12-23/h3-12,15-17,24-25H,14,18H2,1-2H3,(H,29,31)(H,30,32)

Standard InChI Key:  UHSPVUASELRRIQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -4.8431    0.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8443    0.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1294   -0.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4130    0.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4159    0.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1312    1.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6979   -0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6966   -1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4117   -1.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4108   -2.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6951   -2.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9789   -2.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834   -1.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9841    0.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2689   -0.3318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9854    0.9046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5551    0.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1600   -0.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5564    0.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1574    1.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8722    0.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855    1.3200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5847    2.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8645    2.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1541    2.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3004    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8603    3.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1613   -1.1546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8738    0.0840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5889   -0.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3028    0.0863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0125    0.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
 14 16  2  0
  7  8  1  0
 15 17  1  0
 17 18  1  0
  8  9  2  0
 17 19  1  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 20 21  2  0
  2  3  1  0
 21 22  1  0
 10 11  2  0
 22 23  2  0
  5  6  2  0
 23 24  1  0
 11 12  1  0
 24 25  2  0
 25 20  1  0
  6  1  1  0
 22 26  1  0
 12 13  2  0
 24 27  1  0
 13  8  1  0
 18 28  2  0
  1  2  2  0
 18 29  1  0
  7 14  1  0
 29 30  1  0
  4  7  1  0
 30 31  1  0
 14 15  1  0
 31 32  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA477531

   N-(cyanomethyl)-3-(3,5-dimethylphenyl)-2-(2,2-diphenylacetamido)propanamide

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: 425.53

Molecular Weight (Monoisotopic): 425.2103

AlogP: 3.80

#Rotatable Bonds: 8

Polar Surface Area: 81.99

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.10

CX Basic pKa: ┄

CX LogP: 4.39

CX LogD: 4.39

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.54

Np Likeness Score: -0.60

References

1. 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