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

ID: ALA3884935

PubChem CID: 134131596

Max Phase: Preclinical

Molecular Formula: C19H17N5O3S2

Molecular Weight: 427.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1nc(N2CCN(C(=S)Nc3ccccc3)CC2)sc2ccc([N+](=O)[O-])cc12

Standard InChI:  InChI=1S/C19H17N5O3S2/c25-17-15-12-14(24(26)27)6-7-16(15)29-19(21-17)23-10-8-22(9-11-23)18(28)20-13-4-2-1-3-5-13/h1-7,12H,8-11H2,(H,20,28)

Standard InChI Key:  UTLILQNOKQDLCD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   30.0778   -4.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0767   -5.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7847   -5.9418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4944   -5.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7829   -4.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4946   -4.7124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1998   -4.3024    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.1996   -3.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4880   -3.0747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.7765   -3.4864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9083   -3.0742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6165   -3.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3214   -3.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3243   -2.2600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.6161   -1.8504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9050   -2.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0670   -3.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0329   -1.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7397   -2.2631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.0347   -1.0358    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.4483   -1.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1554   -2.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8635   -1.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8657   -1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1539   -0.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4487   -1.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3667   -5.9446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3661   -6.7618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6594   -5.5354    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  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
M  CHG  2  27   1  29  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3884935

   ---

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: 427.51

Molecular Weight (Monoisotopic): 427.0773

AlogP: 3.08

#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: 3.56

CX LogD: 3.56

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.39

Np Likeness Score: -2.26

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