4-(4'-methoxy-3'-(methylsulfonyl)biphenyl-3-yl)-3-methyl-8-(trifluoromethyl)quinoline

ID: ALA1099133

PubChem CID: 46887888

Max Phase: Preclinical

Molecular Formula: C25H20F3NO3S

Molecular Weight: 471.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2cccc(-c3c(C)cnc4c(C(F)(F)F)cccc34)c2)cc1S(C)(=O)=O

Standard InChI:  InChI=1S/C25H20F3NO3S/c1-15-14-29-24-19(8-5-9-20(24)25(26,27)28)23(15)18-7-4-6-16(12-18)17-10-11-21(32-2)22(13-17)33(3,30)31/h4-14H,1-3H3

Standard InChI Key:  MKHOYUJKXDXRQG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.2986   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2974   -2.6023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0122   -3.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0104   -1.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7258   -1.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7266   -2.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4419   -3.0091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1569   -2.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1521   -1.7644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4362   -1.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4313   -0.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1452   -0.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4240    1.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7169   -0.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2836    1.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2800    1.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5585    2.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8495    1.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0141   -3.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3006   -4.2544    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.7296   -4.2510    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -4.6625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.5517    3.1774    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.2627    3.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7500    2.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1333    3.8958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8641   -1.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9919    2.3640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7089    1.9559    0.0000 C   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
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 13 17  1  0
  3 23  1  0
  2  3  1  0
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 11 12  2  0
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  5  6  1  0
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  3  6  2  0
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 13 14  2  0
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  9 31  1  0
  1  2  2  0
 20 32  1  0
 15 16  2  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1099133

   4-(4''-Methoxy-3''-(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: 471.50

Molecular Weight (Monoisotopic): 471.1116

AlogP: 6.31

#Rotatable Bonds: 4

Polar Surface Area: 56.26

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.57

CX LogP: 5.50

CX LogD: 5.50

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.35

Np Likeness Score: -0.94

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