N-((S)-1-(((1R,2R)-2-(benzyloxy)-1-cyanopropyl)amino)-3-(3-chlorophenyl)-1-oxopropan-2-yl)-4-bromobenzamide

ID: ALA4757831

PubChem CID: 162656116

Max Phase: Preclinical

Molecular Formula: C27H25BrClN3O3

Molecular Weight: 554.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@@H](OCc1ccccc1)[C@@H](C#N)NC(=O)[C@H](Cc1cccc(Cl)c1)NC(=O)c1ccc(Br)cc1

Standard InChI:  InChI=1S/C27H25BrClN3O3/c1-18(35-17-19-6-3-2-4-7-19)25(16-30)32-27(34)24(15-20-8-5-9-23(29)14-20)31-26(33)21-10-12-22(28)13-11-21/h2-14,18,24-25H,15,17H2,1H3,(H,31,33)(H,32,34)/t18-,24+,25-/m1/s1

Standard InChI Key:  KNHLEJQNWOTWPT-AYCKEJKLSA-N

Molfile:  

 
     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
   31.7549  -15.5885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.4667  -15.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1744  -15.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1744  -16.4099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8863  -15.1758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5947  -15.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5962  -16.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3047  -16.8076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.3062  -17.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0146  -18.0321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0129  -18.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7206  -19.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4285  -18.8474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4244  -18.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7162  -17.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4678  -14.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1760  -13.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8813  -14.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5890  -13.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5905  -13.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8783  -12.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1735  -13.1390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8765  -11.9124    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   35.3017  -15.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8893  -16.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0064  -14.7627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.0464  -15.1812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0449  -14.3641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3395  -15.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6338  -15.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9274  -15.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9284  -16.4093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6419  -16.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3454  -16.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2220  -16.8201    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  2 16  1  1
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 21 23  1  0
  6 24  1  6
  7 25  1  6
 24 26  3  0
  1 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
 32 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4757831

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 554.87

Molecular Weight (Monoisotopic): 553.0768

AlogP: 5.06

#Rotatable Bonds: 10

Polar Surface Area: 91.22

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.15

CX Basic pKa: ┄

CX LogP: 5.38

CX LogD: 5.38

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.37

Np Likeness Score: -0.70

References

1. Cianni L,Rocho FDR,Bonatto V,Martins FCP,Lameira J,Leitão A,Montanari CA,Shamim A.  (2021)  Design, synthesis and stepwise optimization of nitrile-based inhibitors of cathepsins B and L.,  29  [PMID:33254069] [10.1016/j.bmc.2020.115827]

Source

Source(1):

• Scientific Literature