N-{4-[3,5-Bis(trifluoromethyl)phenoxy]phenyl}-2-chloro-6-fluorobenzamide

ID: ALA4475557

PubChem CID: 2741936

Max Phase: Preclinical

Molecular Formula: C21H11ClF7NO2

Molecular Weight: 477.76

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(Oc2cc(C(F)(F)F)cc(C(F)(F)F)c2)cc1)c1c(F)cccc1Cl

Standard InChI:  InChI=1S/C21H11ClF7NO2/c22-16-2-1-3-17(23)18(16)19(31)30-13-4-6-14(7-5-13)32-15-9-11(20(24,25)26)8-12(10-15)21(27,28)29/h1-10H,(H,30,31)

Standard InChI Key:  ZBTXLIOBUPNJDF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   27.2342   -3.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2330   -4.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9411   -5.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6507   -4.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6479   -3.8594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9393   -3.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3541   -3.4482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0633   -3.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0631   -4.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7715   -5.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4786   -4.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4729   -3.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7639   -3.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1884   -5.0685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8940   -4.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6038   -5.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8898   -3.8391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6053   -5.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3143   -6.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0208   -5.8709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0140   -5.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3045   -4.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2972   -3.8311    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.9409   -5.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2331   -6.3172    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.6485   -6.3175    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.9331   -6.7233    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.5264   -3.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5262   -2.6374    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.8187   -3.8634    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.8158   -3.0459    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.8989   -6.2892    0.0000 Cl  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
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 16  1  0
 22 23  1  0
  3 24  1  0
 24 25  1  0
 24 26  1  0
 24 27  1  0
  1 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
 18 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475557

   N-[4-[3,5-bis(trifluoromethyl)phenoxy]phenyl]-2-chloro-6-fluorobenzamide

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: 477.76

Molecular Weight (Monoisotopic): 477.0367

AlogP: 7.56

#Rotatable Bonds: 4

Polar Surface Area: 38.33

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.98

CX Basic pKa: ┄

CX LogP: 7.07

CX LogD: 7.07

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.39

Np Likeness Score: -1.48

References

1. Padilla-Salinas R, Anderson R, Sakaniwa K, Zhang S, Nordeen P, Lu C, Shimizu T, Yin H..  (2019)  Discovery of Novel Small Molecule Dual Inhibitors Targeting Toll-Like Receptors 7 and 8.,  62  (22): [PMID:31687820] [10.1021/acs.jmedchem.9b01201]

Source

Source(1):

• Scientific Literature