tert-Butyl-(E)-(4-((2-(3-(trifluoromethyl)phenyl)vinyl)sulfonamido)phenyl)carbamate

ID: ALA4568723

PubChem CID: 155560539

Max Phase: Preclinical

Molecular Formula: C20H21F3N2O4S

Molecular Weight: 442.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)Nc1ccc(NS(=O)(=O)/C=C/c2cccc(C(F)(F)F)c2)cc1

Standard InChI:  InChI=1S/C20H21F3N2O4S/c1-19(2,3)29-18(26)24-16-7-9-17(10-8-16)25-30(27,28)12-11-14-5-4-6-15(13-14)20(21,22)23/h4-13,25H,1-3H3,(H,24,26)/b12-11+

Standard InChI Key:  DAQWMJUFAGPCST-VAWYXSNFSA-N

Molfile:  

 
     RDKit          2D

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    7.4538   -9.0799    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8622   -8.3675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194   -9.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9183  -10.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6263  -10.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3360  -10.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3332   -9.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6246   -9.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0393   -9.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7486   -9.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1640   -9.4866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2116   -9.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2114   -8.2752    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5040   -9.5012    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011   -8.6837    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.8702   -9.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5752   -9.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2810   -9.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.5644   -7.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8616   -8.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9842   -7.8427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6939   -8.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3996   -7.8358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6979   -9.0650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1093   -8.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8150   -7.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1133   -9.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8138   -8.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
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  6  7  2  0
  7  8  1  0
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  2 12  1  0
  4 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 12 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
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 22 17  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4568723

   ---

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: 442.46

Molecular Weight (Monoisotopic): 442.1174

AlogP: 5.47

#Rotatable Bonds: 5

Polar Surface Area: 84.50

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.04

CX Basic pKa: ┄

CX LogP: 4.47

CX LogD: 4.47

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.64

Np Likeness Score: -1.43

References

1. Sabbah M, Mendes V, Vistal RG, Dias DMG, Záhorszká M, Mikušová K, Korduláková J, Coyne AG, Blundell TL, Abell C..  (2020)  Fragment-Based Design of Mycobacterium tuberculosis InhA Inhibitors.,  63  (9): [PMID:32240584] [10.1021/acs.jmedchem.0c00007]

Source

Source(1):

• Scientific Literature