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

ID: ALA2298307

PubChem CID: 136240240

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/c2ccc(Cl)cc2)s1

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

Standard InChI Key:  GMLVNCISBUSZQU-BYYHNAKLSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    9.4871  -13.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4859  -14.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1940  -14.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9036  -14.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9008  -13.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1922  -13.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6070  -13.0234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3162  -13.4293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6039  -12.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0224  -13.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7301  -13.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4357  -13.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4335  -12.1987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7189  -11.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0161  -12.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0675  -11.6843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8571  -11.8945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3011  -11.2085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7858  -10.5742    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.0235  -10.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1171  -11.1644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3374  -10.4244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3788   -9.6082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6746   -9.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6830   -8.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9796   -7.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2675   -8.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2631   -9.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9671   -9.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5627   -7.9473    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
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2298307

   ---

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: -1.48

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