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

ID: ALA2298304

PubChem CID: 136241589

Max Phase: Preclinical

Molecular Formula: C22H16N6O3S

Molecular Weight: 444.48

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H16N6O3S/c23-22-25-19(21(32-22)27-26-17-7-4-8-18(13-17)28(30)31)14-9-11-16(12-10-14)24-20(29)15-5-2-1-3-6-15/h1-13H,(H2,23,25)(H,24,29)/b27-26+

Standard InChI Key:  URJIPUHVTRPGNO-CYYJNZCTSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   31.9763  -13.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9752  -14.2908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6832  -14.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3929  -14.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3901  -13.4676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6815  -13.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0962  -13.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8055  -13.4623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0932  -12.2392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5117  -13.0510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2193  -13.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9250  -13.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9228  -12.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2081  -11.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5054  -12.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5567  -11.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3464  -11.9276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.7904  -11.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2751  -10.6072    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   37.5127  -10.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6064  -11.1975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.8266  -10.4574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.8681   -9.6412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.1639   -9.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1722   -8.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4689   -7.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7567   -8.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7524   -9.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4563   -9.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4743   -7.1717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7703   -6.7567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.1857   -6.7695    0.0000 O   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
 30 31  2  0
 30 32  1  0
 26 30  1  0
M  CHG  2  30   1  32  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2298304

   ---

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: 444.48

Molecular Weight (Monoisotopic): 444.1005

AlogP: 5.97

#Rotatable Bonds: 6

Polar Surface Area: 135.87

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.03

CX LogP: 6.12

CX LogD: 6.12

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.21

Np Likeness Score: -1.59

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