N-(5-Nitrothiazol-2-yl)-2-(trifluoromethoxy)benzamide

ID: ALA4097372

PubChem CID: 137658973

Max Phase: Preclinical

Molecular Formula: C11H6F3N3O4S

Molecular Weight: 333.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ncc([N+](=O)[O-])s1)c1ccccc1OC(F)(F)F

Standard InChI:  InChI=1S/C11H6F3N3O4S/c12-11(13,14)21-7-4-2-1-3-6(7)9(18)16-10-15-5-8(22-10)17(19)20/h1-5H,(H,15,16,18)

Standard InChI Key:  AOBXGXBHBCYFNI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    3.4366  -22.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354  -23.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1435  -23.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8531  -23.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8503  -22.4939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417  -22.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5565  -22.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2657  -22.4886    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5534  -21.2654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9719  -22.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7190  -22.4057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2635  -21.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8522  -21.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0536  -21.2631    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1836  -20.3388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7007  -19.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9960  -20.2502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1392  -21.2714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4303  -20.8650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4279  -20.0478    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7238  -21.2757    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7198  -20.4545    0.0000 F   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  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  1  0
 15 16  2  0
 15 17  1  0
 13 15  1  0
  6 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
M  CHG  2  15   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4097372

   ---

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: 333.25

Molecular Weight (Monoisotopic): 333.0031

AlogP: 3.20

#Rotatable Bonds: 4

Polar Surface Area: 94.36

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.66

CX Basic pKa: ┄

CX LogP: 3.95

CX LogD: 3.95

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.68

Np Likeness Score: -2.18

References

1. Buchieri MV, Cimino M, Rebollo-Ramirez S, Beauvineau C, Cascioferro A, Favre-Rochex S, Helynck O, Naud-Martin D, Larrouy-Maumus G, Munier-Lehmann H, Gicquel B..  (2017)  Nitazoxanide Analogs Require Nitroreduction for Antimicrobial Activity in Mycobacterium smegmatis.,  60  (17): [PMID:28846409] [10.1021/acs.jmedchem.7b00726]

Source

Source(1):

• Scientific Literature