N-(4-(2-amino-5-((3-chlorophenyl)diazenyl)thiazol-4-yl)phenyl)benzamide

ID: ALA2298306

PubChem CID: 136245259

Max Phase: Preclinical

Molecular Formula: C22H16ClN5OS

Molecular Weight: 433.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(-c2ccc(NC(=O)c3ccccc3)cc2)c(/N=N/c2cccc(Cl)c2)s1

Standard InChI:  InChI=1S/C22H16ClN5OS/c23-16-7-4-8-18(13-16)27-28-21-19(26-22(24)30-21)14-9-11-17(12-10-14)25-20(29)15-5-2-1-3-6-15/h1-13H,(H2,24,26)(H,25,29)/b28-27+

Standard InChI Key:  YBRBZAYJLNOMEC-BYYHNAKLSA-N

Molfile:  

     RDKit          2D

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    0.7250  -13.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7238  -14.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4319  -14.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1415  -14.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1387  -13.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4301  -12.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8449  -12.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5541  -13.3633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8418  -12.1401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2603  -12.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9679  -13.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6736  -12.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6714  -12.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9568  -11.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2540  -12.1398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3054  -11.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0950  -11.8285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5390  -11.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0237  -10.5081    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.2613  -10.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3550  -11.0984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5753  -10.3583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -9.5422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9125   -9.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9209   -8.3069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2175   -7.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5054   -8.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5010   -9.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2050   -9.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2249   -7.0752    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  8 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
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 16  2  0
 13 16  1  0
 18 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 26 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2298306

   ---

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: 433.92

Molecular Weight (Monoisotopic): 433.0764

AlogP: 6.71

#Rotatable Bonds: 5

Polar Surface Area: 92.73

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.03

CX LogP: 6.79

CX LogD: 6.79

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.34

Np Likeness Score: -1.54

References

1. Yadlapalli RK, Chourasia OP, Jogi MP, Podile AR, Perali RS.  (2013)  Design, synthesis and in vitro antimicrobial activity of novel phenylbenzamido-aminothiazole-based azasterol mimics,  22  (6): [10.1007/s00044-012-0314-5]

Source

Source(1):

• Scientific Literature