N-((1S,2R)-2-((4-bromo-2-(methylcarbamoyl)-6-nitrophenyl)amino)cyclohexyl)-1-naphthamide

ID: ALA5278228

Max Phase: Preclinical

Molecular Formula: C25H25BrN4O4

Molecular Weight: 525.40

Names and Identifiers

Canonical SMILES:  CNC(=O)c1cc(Br)cc([N+](=O)[O-])c1N[C@@H]1CCCC[C@@H]1NC(=O)c1cccc2ccccc12

Standard InChI:  InChI=1S/C25H25BrN4O4/c1-27-24(31)19-13-16(26)14-22(30(33)34)23(19)28-20-11-4-5-12-21(20)29-25(32)18-10-6-8-15-7-2-3-9-17(15)18/h2-3,6-10,13-14,20-21,28H,4-5,11-12H2,1H3,(H,27,31)(H,29,32)/t20-,21+/m1/s1

Standard InChI Key:  BGDFZXDFZMAZSX-RTWAWAEBSA-N

Molfile:  

 
     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   -3.5721    2.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8575    3.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1456    2.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1456    2.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8558    1.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4278    1.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7162    2.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7180    2.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4329    3.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278    0.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132    0.4139    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132   -0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013   -0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013   -1.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7132   -2.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7160   -0.4112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4306   -0.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1454   -0.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8575   -0.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8575   -1.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1472   -2.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4306   -1.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7160   -2.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7160   -2.8903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013   -3.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092   -2.0651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5721   -2.0614    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1454    0.4137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8600    0.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4308    0.8263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1425    0.4139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  3 10  1  0
  7 11  1  0
 11 12  1  0
 13 12  1  6
 14 13  1  0
 15 14  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
 13 18  1  0
 14 19  1  6
 19 20  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
 24 23  1  0
 25 24  2  0
 20 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  2  0
 23 30  1  0
 31 21  1  0
 31 32  1  0
 31 33  2  0
 11 34  2  0
M  CHG  2  31   1  32  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5278228

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 525.40

Molecular Weight (Monoisotopic): 524.1059

AlogP: 5.02

#Rotatable Bonds: 6

Polar Surface Area: 113.37

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.26

CX Basic pKa: ┄

CX LogP: 5.16

CX LogD: 5.16

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.31

Np Likeness Score: -1.00

References

1. Chen R, Gao Y, Liu H, Li H, Chen W, Ma J..  (2023)  Advances in research on 3C-like protease (3CL^pro) inhibitors against SARS-CoV-2 since 2020.,  14  (1): [PMID:36760740] [10.1039/d2md00344a]

Source

Source(1):

• Scientific Literature