2-(3-methyl-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-8-nitro-6-(trifluoromethyl)-4H-benzo[e][1,3]thiazin-4-one

ID: ALA5208588

PubChem CID: 168295240

Max Phase: Preclinical

Molecular Formula: C15H11F3N6O3S

Molecular Weight: 412.35

Names and Identifiers

Canonical SMILES:  Cc1nnc2n1CCN(c1nc(=O)c3cc(C(F)(F)F)cc([N+](=O)[O-])c3s1)C2

Standard InChI:  InChI=1S/C15H11F3N6O3S/c1-7-20-21-11-6-22(2-3-23(7)11)14-19-13(25)9-4-8(15(16,17)18)5-10(24(26)27)12(9)28-14/h4-5H,2-3,6H2,1H3

Standard InChI Key:  CVUPJRFXCUZFKX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    1.7851    1.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0695    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0695    0.1723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7831   -0.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4914    0.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4914    0.9939    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3623   -0.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3501    0.1758    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0559   -0.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0559   -1.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3480   -1.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3623   -1.0575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3480   -2.2836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7658   -1.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4747   -1.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4747   -0.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7658    0.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7658    0.9935    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4732    1.4020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0584    1.4020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1814   -1.4688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1801   -2.2858    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8890   -1.0603    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8890   -1.8773    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0998    1.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9569    2.2026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7695    2.2858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890    1.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  3  4  1  0
  5  4  1  0
  1  6  1  0
  6  5  1  0
  3  7  1  0
  8  7  1  0
  8  9  1  0
 10  9  2  0
 11 10  1  0
  7 12  2  0
 12 11  1  0
 11 13  2  0
 14 10  1  0
 15 14  2  0
 16 15  1  0
 17 16  2  0
 17  9  1  0
 18 17  1  0
 18 19  2  0
 18 20  1  0
 21 15  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
  6 25  1  0
  1 26  2  0
 26 27  1  0
 27 25  2  0
 25 28  1  0
M  CHG  2  18   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5208588

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 412.35

Molecular Weight (Monoisotopic): 412.0565

AlogP: 2.50

#Rotatable Bonds: 2

Polar Surface Area: 107.05

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.32

CX LogP: 1.46

CX LogD: 1.46

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: -1.93

References

1. Schieferdecker S, Bernal FA, Wojtas KP, Keiff F, Li Y, Dahse HM, Kloss F..  (2022)  Development of Predictive Classification Models for Whole Cell Antimycobacterial Activity of Benzothiazinones.,  65  (9.0): [PMID:35502994] [10.1021/acs.jmedchem.2c00098]

Source

Source(1):

• Scientific Literature