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

ID: ALA3883383

PubChem CID: 134131268

Max Phase: Preclinical

Molecular Formula: C20H19N5O3S2

Molecular Weight: 441.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(NC(=S)N2CCN(c3nc(=O)c4cc([N+](=O)[O-])ccc4s3)CC2)cc1

Standard InChI:  InChI=1S/C20H19N5O3S2/c1-13-2-4-14(5-3-13)21-19(29)23-8-10-24(11-9-23)20-22-18(26)16-12-15(25(27)28)6-7-17(16)30-20/h2-7,12H,8-11H2,1H3,(H,21,29)

Standard InChI Key:  OZIGHEHIXXYXHF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   30.7098  -15.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7085  -16.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4227  -16.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1384  -16.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4209  -15.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1386  -15.5462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8499  -15.1326    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.8497  -14.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1319  -13.8944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4144  -14.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5644  -13.8939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.2787  -14.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9897  -13.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9926  -13.0728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.2782  -12.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5610  -13.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6989  -13.9007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.7072  -12.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4201  -13.0759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.7090  -11.8381    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   37.1347  -12.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8479  -13.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5621  -12.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5643  -11.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8463  -11.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1352  -11.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9926  -16.7889    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9919  -17.6131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2791  -16.3762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.2783  -11.4367    0.0000 C   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
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  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:

   

   ALA3883383

   ---

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: 441.54

Molecular Weight (Monoisotopic): 441.0929

AlogP: 3.39

#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: 4.07

CX LogD: 4.07

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: -2.28

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