4-(2',4'-difluoro-5'-(methylsulfonyl)biphenyl-3-yl)-3-methyl-8-(trifluoromethyl)quinoline

ID: ALA1097159

PubChem CID: 46887890

Max Phase: Preclinical

Molecular Formula: C24H16F5NO2S

Molecular Weight: 477.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cnc2c(C(F)(F)F)cccc2c1-c1cccc(-c2cc(S(C)(=O)=O)c(F)cc2F)c1

Standard InChI:  InChI=1S/C24H16F5NO2S/c1-13-12-30-23-16(7-4-8-18(23)24(27,28)29)22(13)15-6-3-5-14(9-15)17-10-21(33(2,31)32)20(26)11-19(17)25/h3-12H,1-2H3

Standard InChI Key:  GKRQECRQGLCHTJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -5.4514  -11.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4526  -11.9982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7378  -12.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7396  -10.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0242  -11.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0234  -11.9940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3081  -12.4050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5931  -11.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5979  -11.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3138  -10.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3187   -9.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6048   -9.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6088   -8.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3260   -8.2837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0406   -8.7044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0331   -9.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8952   -8.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1784   -8.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4664   -8.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4700   -7.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1915   -7.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9005   -7.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7359  -13.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4494  -13.6502    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0204  -13.6469    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7417  -14.0583    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1983   -6.2185    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4873   -5.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0000   -6.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6167   -5.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859  -10.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2419   -7.0318    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1753   -9.5148    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 16 11  1  0
 10 11  1  0
  7  8  2  0
  5  4  2  0
 17 18  2  0
  8  9  1  0
 18 19  1  0
  4  1  1  0
 19 20  2  0
  9 10  2  0
 20 21  1  0
 10  5  1  0
 21 22  2  0
 22 17  1  0
 13 17  1  0
  3 23  1  0
  2  3  1  0
 23 24  1  0
 11 12  2  0
 23 25  1  0
  5  6  1  0
 23 26  1  0
 12 13  1  0
 21 27  1  0
  3  6  2  0
 27 28  1  0
 13 14  2  0
 27 29  2  0
  6  7  1  0
 27 30  2  0
 14 15  1  0
  9 31  1  0
  1  2  2  0
 20 32  1  0
 15 16  2  0
 18 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1097159

   4-(2'',4''-Difluoro-5''-(methylsulfonyl)biphenyl-3-yl)-3-methyl-8-(trifluoromethyl)quinoline

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: 477.45

Molecular Weight (Monoisotopic): 477.0822

AlogP: 6.58

#Rotatable Bonds: 3

Polar Surface Area: 47.03

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.56

CX LogP: 5.94

CX LogD: 5.94

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.25

Np Likeness Score: -1.03

References

1. Ullrich JW, Morris R, Bernotas RC, Travins JM, Jetter J, Unwalla R, Quinet E, Nambi P, Feingold I, Huselton C, Enroth C, Wilhelmsson A, Goos-Nilsson A, Wrobel J..  (2010)  Synthesis of 4-(3-biaryl)quinoline sulfones as potent liver X receptor agonists.,  20  (9): [PMID:20382019] [10.1016/j.bmcl.2010.03.031]

Source

Source(1):

• Scientific Literature