N-(4-chlorophenyl)-4-(6-nitro-4-oxo-4H-benzo[e][1,3]thiazin-2-yl)piperazine-1-carbothioamide

ID: ALA3883797

PubChem CID: 134129998

Max Phase: Preclinical

Molecular Formula: C19H16ClN5O3S2

Molecular Weight: 461.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1nc(N2CCN(C(=S)Nc3ccc(Cl)cc3)CC2)sc2ccc([N+](=O)[O-])cc12

Standard InChI:  InChI=1S/C19H16ClN5O3S2/c20-12-1-3-13(4-2-12)21-18(29)23-7-9-24(10-8-23)19-22-17(26)15-11-14(25(27)28)5-6-16(15)30-19/h1-6,11H,7-10H2,(H,21,29)

Standard InChI Key:  VFMXIECOROEWQN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   30.4591   -9.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4580  -10.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1720  -11.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8878  -10.6618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1703   -9.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8880   -9.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5993   -9.4214    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.5990   -8.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8813   -8.1832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.1639   -8.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3138   -8.1828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0280   -8.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7389   -8.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7418   -7.3616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0276   -6.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3104   -7.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4483   -8.1894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.4565   -6.9511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1693   -7.3647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4583   -6.1269    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.8839   -6.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5971   -7.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3112   -6.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3134   -6.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5956   -5.7236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8843   -6.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7421  -11.0776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.7413  -11.9017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0286  -10.6650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.0276   -5.7256    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  6  1  0
  5  1  1  0
  5  6  2  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  8 11  1  0
 10 17  2  0
 14 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 27 28  2  0
 27 29  1  0
  2 27  1  0
 24 30  1  0
M  CHG  2  27   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3883797

   ---

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: 461.96

Molecular Weight (Monoisotopic): 461.0383

AlogP: 3.74

#Rotatable Bonds: 3

Polar Surface Area: 91.61

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.16

CX LogD: 4.16

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.36

Np Likeness Score: -2.37

References

1. Chaudhari K, Surana S, Jain P, Patel HM..  (2016)  Mycobacterium Tuberculosis (MTB) GyrB inhibitors: An attractive approach for developing novel drugs against TB.,  124  [PMID:27569197] [10.1016/j.ejmech.2016.08.034]

2. Dighe SN, Collet TA..  (2020)  Recent advances in DNA gyrase-targeted antimicrobial agents.,  199  [PMID:32460040] [10.1016/j.ejmech.2020.112326]

Source

Source(1):

• Scientific Literature