2-((4-Methoxybenzyl)carbamoyl)-7-nitro-5-(trifluoromethyl)benzo[d]thiazole 3-oxide

ID: ALA4777898

PubChem CID: 162644229

Max Phase: Preclinical

Molecular Formula: C17H12F3N3O5S

Molecular Weight: 427.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(CNC(=O)c2sc3c([N+](=O)[O-])cc(C(F)(F)F)cc3[n+]2[O-])cc1

Standard InChI:  InChI=1S/C17H12F3N3O5S/c1-28-11-4-2-9(3-5-11)8-21-15(24)16-22(25)12-6-10(17(18,19)20)7-13(23(26)27)14(12)29-16/h2-7H,8H2,1H3,(H,21,24)

Standard InChI Key:  NGRFUVBHTJBECA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    8.0646   -8.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2470   -8.2210    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.9607   -9.7235    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.4425   -9.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9681   -8.4012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1887   -8.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1857   -9.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4731   -9.8687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7676   -9.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7705   -8.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4831   -8.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4701  -10.6859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1757  -11.1006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7575  -11.0925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2596   -9.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6743   -8.3619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6662   -9.7800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4915   -8.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9021   -7.6634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4997   -6.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9103   -6.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7274   -6.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1340   -6.9609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7193   -7.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1422   -5.5469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9593   -5.5540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2253   -7.6262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0714   -7.4091    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  4  8  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
  8  9  2  0
 11  2  1  0
 13 14  2  0
 13 15  1  0
  9 13  1  0
 16 17  1  0
 16 18  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
 26 27  1  0
 23 26  1  0
 17 19  1  0
  5 16  1  0
  6 28  1  0
  2 29  1  0
M  CHG  4   6   1  13   1  15  -1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4777898

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 427.36

Molecular Weight (Monoisotopic): 427.0450

AlogP: 3.40

#Rotatable Bonds: 5

Polar Surface Area: 108.41

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.11

CX Basic pKa: ┄

CX LogP: 3.28

CX LogD: 3.28

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.29

Np Likeness Score: -1.04

References

1. Liu, Rui, Markley, Lowell, Miller, Patricia A., Franzblau, Scott, Shetye, Gauri, Ma, Rui, Savkova, Karin, Mikusova, Katarina, Lee, Bei Shi, Pethe, Kevin, Moraski, Garrett C., Miller, Marvin J..  (2021)  Hydride-induced Meisenheimer complex formation reflects activity of nitro aromatic anti-tuberculosis compounds,  12  (1): [PMID:34046598] [10.1039/d0md00390e]

Source

Source(1):

• Scientific Literature