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

ID: ALA1097140

PubChem CID: 46887924

Max Phase: Preclinical

Molecular Formula: C23H14F5NO2S

Molecular Weight: 463.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)c1cc(-c2cccc(-c3ccnc4c(C(F)(F)F)cccc34)c2)c(F)cc1F

Standard InChI:  InChI=1S/C23H14F5NO2S/c1-32(30,31)21-11-17(19(24)12-20(21)25)14-5-2-4-13(10-14)15-8-9-29-22-16(15)6-3-7-18(22)23(26,27)28/h2-12H,1H3

Standard InChI Key:  UWFHFVAFWATDDO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   12.0444  -10.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0432  -11.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7581  -11.5735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7563   -9.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4716  -10.3297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4724  -11.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1877  -11.5675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9027  -11.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8980  -10.3227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1821   -9.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1772   -9.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8911   -8.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8871   -7.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1699   -7.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4552   -7.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4628   -8.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6006   -7.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3174   -7.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0294   -7.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0259   -6.6112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3044   -6.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5953   -6.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7600  -12.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0465  -12.8127    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.4754  -12.8094    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.7542  -13.2208    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.2975   -5.3810    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.0085   -4.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4958   -5.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8792   -4.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7378   -6.1943    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.3205   -8.6773    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  2  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
 20 31  1  0
  1  2  2  0
 18 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1097140

   4-(2'',4''-Difluoro-5''-(methylsulfonyl)biphenyl-3-yl)-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: 463.43

Molecular Weight (Monoisotopic): 463.0665

AlogP: 6.27

#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: 3.15

CX LogP: 5.43

CX LogD: 5.43

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.27

Np Likeness Score: -1.04

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