3-(2-(2-chloro-4-nitrophenyl)hydrazono)-N-(3-chlorophenyl)-6-oxocyclohexa-1,4-dienecarboxamide

ID: ALA5283839

Max Phase: Preclinical

Molecular Formula: C19H12Cl2N4O4

Molecular Weight: 431.24

Names and Identifiers

Canonical SMILES:  O=C1C=C/C(=N\Nc2ccc([N+](=O)[O-])cc2Cl)C=C1C(=O)Nc1cccc(Cl)c1

Standard InChI:  InChI=1S/C19H12Cl2N4O4/c20-11-2-1-3-12(8-11)22-19(27)15-9-13(4-7-18(15)26)23-24-17-6-5-14(25(28)29)10-16(17)21/h1-10,24H,(H,22,27)/b23-13+

Standard InChI Key:  IRUCTMUVKDPOSM-YDZHTSKRSA-N

Molfile:  

 
     RDKit          2D

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   -4.6229   -0.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9095   -1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2024   -0.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2024    0.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9113    0.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4908    0.6161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792    0.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0676    0.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0676    1.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3560    1.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3555    1.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3555    0.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3560    0.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0672    0.2053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7787    0.6161    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4904    0.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2021    0.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112    0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9112   -0.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2039   -1.0263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4904   -0.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228   -1.0270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3345   -0.6162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228   -1.8487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2021    1.4376    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792    1.8487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7792   -0.6163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3345    0.6157    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  1  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
 10  9  1  0
 11 10  1  0
 12 11  2  0
 13 12  1  0
 14 13  1  0
  9 14  2  0
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 18 17  2  0
 19 18  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 17 22  1  0
 23 20  1  0
 23 24  2  0
 23 25  1  0
 18 26  1  0
 10 27  2  0
  8 28  2  0
  1 29  1  0
M  CHG  2  23   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5283839

   ---

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: 431.24

Molecular Weight (Monoisotopic): 430.0236

AlogP: 4.37

#Rotatable Bonds: 5

Polar Surface Area: 113.70

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.10

CX Basic pKa: 3.53

CX LogP: 5.31

CX LogD: 5.31

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.32

Np Likeness Score: -1.49

References

1. Voss S, Nitsche C..  (2021)  Targeting the protease of West Nile virus.,  12  (8.0): [PMID:34458734] [10.1039/D1MD00080B]

Source

Source(1):

• Scientific Literature