(R)-3-(4-bromophenylsulfonyl)-N-(1-cyanocyclopropyl)-2-((S)-2,2,2-trifluoro-1-phenylethylamino)propanamide

ID: ALA250720

PubChem CID: 23648290

Max Phase: Preclinical

Molecular Formula: C21H19BrF3N3O3S

Molecular Weight: 530.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CC1(NC(=O)[C@H](CS(=O)(=O)c2ccc(Br)cc2)N[C@@H](c2ccccc2)C(F)(F)F)CC1

Standard InChI:  InChI=1S/C21H19BrF3N3O3S/c22-15-6-8-16(9-7-15)32(30,31)12-17(19(29)28-20(13-26)10-11-20)27-18(21(23,24)25)14-4-2-1-3-5-14/h1-9,17-18,27H,10-12H2,(H,28,29)/t17-,18-/m0/s1

Standard InChI Key:  GLDNCRGNTMYXND-ROUUACIJSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  1  0  0  0  0  0999 V2000
    1.3356  -14.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8092  -13.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5260  -14.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9082  -13.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9169  -14.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2023  -14.6701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4831  -14.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4777  -13.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1918  -13.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7657  -13.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0481  -13.4327    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3358  -13.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190  -13.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0958  -13.0240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190  -14.2651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3412  -12.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8729  -12.1822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3358  -12.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7657  -12.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7657  -11.3705    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9355  -12.1957    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5860  -12.1957    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184  -11.7869    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0976  -11.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2020  -12.5053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0272  -11.0732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8081  -11.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5238  -11.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250  -10.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8045  -10.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0918  -10.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2394  -10.1382    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14  2  1  0
  2 16  1  0
 16 17  3  0
 12 18  1  1
 10 19  1  1
 19 20  1  0
 19 21  1  0
 19 22  1  0
 18 23  1  0
 23 24  1  0
 23 25  2  0
 23 26  2  0
 24 27  2  0
  2  1  1  0
 27 28  1  0
  3  2  1  0
 28 29  2  0
  1  3  1  0
 29 30  1  0
  4  5  2  0
 30 31  2  0
 31 24  1  0
  5  6  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA250720

   Trifluoroethylamine inhibitor, 20

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: 530.37

Molecular Weight (Monoisotopic): 529.0283

AlogP: 3.66

#Rotatable Bonds: 8

Polar Surface Area: 99.06

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.51

CX Basic pKa: 1.82

CX LogP: 3.45

CX LogD: 3.45

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.54

Np Likeness Score: -1.27

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]

Source

Source(1):

• Scientific Literature