2-{3-[3-(5-Ethyl-4'-fluoro-2-hydroxy-biphenyl-4-yloxy)-propoxy]-2-propyl-benzyl}-benzoic acid

ID: ALA138954

PubChem CID: 10745069

Max Phase: Preclinical

Molecular Formula: C34H35FO5

Molecular Weight: 542.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1c(Cc2ccccc2C(=O)O)cccc1OCCCOc1cc(O)c(-c2ccc(F)cc2)cc1CC

Standard InChI:  InChI=1S/C34H35FO5/c1-3-9-28-25(20-26-10-5-6-12-29(26)34(37)38)11-7-13-32(28)39-18-8-19-40-33-22-31(36)30(21-23(33)4-2)24-14-16-27(35)17-15-24/h5-7,10-17,21-22,36H,3-4,8-9,18-20H2,1-2H3,(H,37,38)

Standard InChI Key:  RNMNAOKPFGPBSK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 40 43  0  0  0  0  0  0  0  0999 V2000
    1.3375   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -4.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3375   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6542   -6.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9417   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5125   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6542   -5.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2250   -5.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -5.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8000   -5.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167   -4.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9375   -7.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0792   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167   -3.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0500   -3.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3667   -7.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125   -3.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917   -5.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083   -4.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5250   -2.9292    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.3625   -5.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167   -4.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -5.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9417   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8000   -6.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7917   -4.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3667   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -6.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0750   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6417   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167   -7.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7750   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6542   -4.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3667   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167   -7.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  2  0
  5  8  1  0
  6  9  1  0
  7 12  1  0
  8  6  1  0
  9  7  1  0
 10 11  2  0
 11  3  1  0
 12 15  2  0
 13  1  1  0
 14  5  2  0
 15 25  1  0
 16 13  1  0
 17 13  2  0
 18  2  1  0
 19  5  1  0
 20 22  2  0
 21 10  1  0
 22 17  1  0
 23 16  2  0
 24 20  1  0
 25 35  1  0
 26 30  1  0
 27 34  1  0
 28  6  2  0
 29 12  1  0
 30 33  2  0
 31  8  2  0
 32 11  1  0
 33 15  1  0
 34 21  1  0
 35 27  1  0
 36 29  1  0
 37 32  1  0
 38 28  1  0
 39 38  2  0
 40 36  1  0
 23 20  1  0
 10  4  1  0
  7 26  2  0
 31 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA138954

   2-[[3-[3-[2-Ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]propoxy]-2-propylphenyl]methyl]benzoic acid

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: 542.65

Molecular Weight (Monoisotopic): 542.2469

AlogP: 7.85

#Rotatable Bonds: 13

Polar Surface Area: 75.99

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.83

CX Basic pKa: ┄

CX LogP: 9.12

CX LogD: 5.86

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.17

Np Likeness Score: -0.16

References

1. Sawyer JS, Bach NJ, Baker SR, Baldwin RF, Borromeo PS, Cockerham SL, Fleisch JH, Floreancig P, Froelich LL, Jackson WT..  (1995)  Synthetic and structure/activity studies on acid-substituted 2-arylphenols: discovery of 2-[2-propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5- hydroxyphenoxy]-propoxy]phenoxy]benzoic acid, a high-affinity leukotriene B4 receptor antagonist.,  38  (22): [PMID:7473568] [10.1021/jm00022a006]

Source

Source(1):

• Scientific Literature