7-Nitro-2-((4-(4-(4-(trifluoromethoxy)phenyl)piperidin-1-yl)benzyl)carbamoyl)-5-(trifluoromethyl)benzo[d]thiazole 3-oxide

ID: ALA4749710

PubChem CID: 162651870

Max Phase: Preclinical

Molecular Formula: C28H22F6N4O5S

Molecular Weight: 640.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NCc1ccc(N2CCC(c3ccc(OC(F)(F)F)cc3)CC2)cc1)c1sc2c([N+](=O)[O-])cc(C(F)(F)F)cc2[n+]1[O-]

Standard InChI:  InChI=1S/C28H22F6N4O5S/c29-27(30,31)19-13-22-24(23(14-19)38(41)42)44-26(37(22)40)25(39)35-15-16-1-5-20(6-2-16)36-11-9-18(10-12-36)17-3-7-21(8-4-17)43-28(32,33)34/h1-8,13-14,18H,9-12,15H2,(H,35,39)

Standard InChI Key:  RRBNTQLTDSTYKP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 44 48  0  0  0  0  0  0  0  0999 V2000
   17.3880   -3.9209    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.6823   -3.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6813   -4.3278    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.9556  -11.2013    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.3683  -10.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5507  -10.4910    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.2716  -11.9725    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.7501  -11.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2725  -10.6501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4959  -10.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4978  -11.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7897  -12.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0797  -11.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0777  -10.9060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7858  -10.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5673  -11.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9783  -10.6002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9776  -12.0184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7955  -10.6023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2024   -9.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7920   -9.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1989   -8.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0161   -8.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4264   -9.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0195   -9.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4230   -7.7661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0168   -7.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4237   -6.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2409   -6.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6512   -7.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2402   -7.7641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6478   -5.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2374   -4.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6443   -4.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4615   -4.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8718   -4.9321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4649   -5.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8684   -3.5180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7917  -12.9473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0836  -13.3576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4977  -13.3583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5211   -9.8764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3711   -9.6819    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.0925   -2.8074    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  7 11  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
 11 12  2  0
 14  5  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
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 26 31  1  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 32 37  2  0
 38  2  1  0
 35 38  1  0
 29 32  1  0
 23 26  1  0
 17 19  1  0
  8 16  1  0
 39 40  2  0
 39 41  1  0
 12 39  1  0
  9 42  1  0
  5 43  1  0
  2 44  1  0
M  CHG  4   9   1  39   1  41  -1  42  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4749710

   ---

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: 640.56

Molecular Weight (Monoisotopic): 640.1215

AlogP: 6.67

#Rotatable Bonds: 7

Polar Surface Area: 111.65

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.15

CX Basic pKa: 5.38

CX LogP: 7.25

CX LogD: 7.24

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.08

Np Likeness Score: -1.11

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