4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2,6-dipropylphenoxy)butanoic acid

ID: ALA3590141

PubChem CID: 122181380

Max Phase: Preclinical

Molecular Formula: C19H24F6O4

Molecular Weight: 430.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1cc(C(O)(C(F)(F)F)C(F)(F)F)cc(CCC)c1OCCCC(=O)O

Standard InChI:  InChI=1S/C19H24F6O4/c1-3-6-12-10-14(17(28,18(20,21)22)19(23,24)25)11-13(7-4-2)16(12)29-9-5-8-15(26)27/h10-11,28H,3-9H2,1-2H3,(H,26,27)

Standard InChI Key:  JOLUEAVJLHHISJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5988   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5983   -3.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5992   -0.3004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9383   -1.3508    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8994    0.4492    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9383   -0.1510    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6370   -3.6021    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.5587   -3.6005    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.5974   -4.2012    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6331   -3.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3063    4.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8003    1.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8024    2.6887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8387    0.8872    0.0000 O   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
  1  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
  8 11  1  0
  8 12  1  0
  8 13  1  0
  9 14  1  0
  9 15  1  0
  9 16  1  0
  5 17  1  0
 17 18  1  0
 18 19  1  0
  3 20  1  0
 20 21  1  0
 21 22  1  0
  4 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3590141

   ---

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: 430.39

Molecular Weight (Monoisotopic): 430.1579

AlogP: 5.15

#Rotatable Bonds: 10

Polar Surface Area: 66.76

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.22

CX Basic pKa: ┄

CX LogP: 5.75

CX LogD: 2.46

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.40

Np Likeness Score: -0.02

References

1. Koura M, Matsuda T, Okuda A, Watanabe Y, Yamaguchi Y, Kurobuchi S, Matsumoto Y, Shibuya K..  (2015)  Design, synthesis and pharmacology of 1,1-bistrifluoromethylcarbinol derivatives as liver X receptor β-selective agonists.,  25  (13): [PMID:25998501] [10.1016/j.bmcl.2015.04.080]

Source

Source(1):

• Scientific Literature