N-(3-chloro-4-(4-(trifluoromethylthio)phenylamino)phenyl)-2-hydroxy-5-nitrobenzamide

ID: ALA2046986

PubChem CID: 70688324

Max Phase: Preclinical

Molecular Formula: C20H13ClF3N3O4S

Molecular Weight: 483.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(Nc2ccc(SC(F)(F)F)cc2)c(Cl)c1)c1cc([N+](=O)[O-])ccc1O

Standard InChI:  InChI=1S/C20H13ClF3N3O4S/c21-16-9-12(26-19(29)15-10-13(27(30)31)4-8-18(15)28)3-7-17(16)25-11-1-5-14(6-2-11)32-20(22,23)24/h1-10,25,28H,(H,26,29)

Standard InChI Key:  DUYAYHZGZDKOEM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   15.0236    1.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0224    0.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7372    0.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4537    0.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4508    1.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7354    2.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1637    2.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1688    0.4284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8797    1.6757    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1606    2.9105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5927    2.0909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3107    1.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0231    2.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0205    2.9160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2994    3.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5899    2.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7389    1.6800    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.7328    3.3321    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4494    2.9233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4514    2.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1672    1.6860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8805    2.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8736    2.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1573    3.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3106    2.0748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5962    1.6622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3104    2.8998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5976    1.6943    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.6029    0.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3200    0.4614    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.8911    0.4522    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.5958    0.0458    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  2  0
 16 11  1  0
  4  8  1  0
 13 17  1  0
 14 18  1  0
  7  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
  7 10  2  0
 20 21  1  0
  2  3  1  0
 21 22  2  0
  9 11  1  0
 22 23  1  0
  5  6  2  0
 23 24  2  0
 24 19  1  0
 11 12  2  0
  6  1  1  0
 12 13  1  0
 25 26  2  0
 25 27  1  0
  1 25  1  0
  1  2  2  0
 22 28  1  0
 13 14  2  0
 28 29  1  0
  5  7  1  0
 29 30  1  0
 14 15  1  0
 29 31  1  0
  3  4  2  0
 29 32  1  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2046986

   N-[3-chloro-4-[4-(trifluoromethylsulfanyl)anilino]phenyl]-2-hydroxy-5-nitrobenzamide

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: 483.86

Molecular Weight (Monoisotopic): 483.0267

AlogP: 6.56

#Rotatable Bonds: 6

Polar Surface Area: 104.50

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.58

CX Basic pKa: ┄

CX LogP: 6.71

CX LogD: 5.09

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.21

Np Likeness Score: -1.80

References

1. Natesan S, Wang T, Lukacova V, Bartus V, Khandelwal A, Subramaniam R, Balaz S..  (2012)  Cellular quantitative structure-activity relationship (Cell-QSAR): conceptual dissection of receptor binding and intracellular disposition in antifilarial activities of Selwood antimycins.,  55  (8): [PMID:22468611] [10.1021/jm201371y]

Source

Source(1):

• Scientific Literature