(2S)-N-[(1R,2R)-2-(benzyloxy)-1-cyanopropyl]-2-[(3-bromophenyl)formamido]-3-(3-chlorophenyl)propanamide

ID: ALA4744431

PubChem CID: 162647794

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)c1cccc(Br)c1

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

Standard InChI Key:  ZGXKAZRUQQNMKC-AYCKEJKLSA-N

Molfile:  

 
     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
    5.7781  -24.9491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4900  -24.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1977  -24.9491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1977  -25.7704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9095  -24.5364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3294  -26.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0379  -27.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0362  -28.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7438  -28.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4517  -28.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1967  -22.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8997  -21.2730    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.3249  -24.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9125  -26.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0296  -24.1233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0697  -24.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0682  -23.7246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3627  -24.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6571  -24.5426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9506  -24.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9516  -25.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6651  -26.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3686  -25.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6695  -26.9942    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
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 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
 33 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4744431

   ---

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: 11.16

CX Basic pKa: ┄

CX LogP: 5.38

CX LogD: 5.38

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.37

Np Likeness Score: -0.76

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