5-Ethyl-4-[6-methyl-6-(1H-tetrazol-5-yl)-heptyloxy]-3'-trifluoromethyl-biphenyl-2-ol

ID: ALA167580

PubChem CID: 10600128

Max Phase: Preclinical

Molecular Formula: C24H29F3N4O2

Molecular Weight: 462.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1cc(-c2cccc(C(F)(F)F)c2)c(O)cc1OCCCCCC(C)(C)c1nn[nH]n1

Standard InChI:  InChI=1S/C24H29F3N4O2/c1-4-16-14-19(17-9-8-10-18(13-17)24(25,26)27)20(32)15-21(16)33-12-7-5-6-11-23(2,3)22-28-30-31-29-22/h8-10,13-15,32H,4-7,11-12H2,1-3H3,(H,28,29,30,31)

Standard InChI Key:  GBQJYQUQMXHDLH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    9.5167   -3.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5667   -3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2125   -2.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1167   -3.4667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6292   -2.6250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667   -2.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667   -3.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -2.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -2.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -3.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875   -3.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375   -2.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0500   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.9167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -2.4167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.2000   -3.2625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792   -1.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -3.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542   -1.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292   -1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875   -4.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -3.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7417   -4.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3417   -4.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4500   -3.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9667   -3.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4875   -3.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -4.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  2  0
  3  1  1  0
  4  1  1  0
  5  3  2  0
  6 12  1  0
  7  9  2  0
  8 10  2  0
  9 14  1  0
 10 13  1  0
 11  7  1  0
 12 15  2  0
 13 21  1  0
 14 13  2  0
 15 11  1  0
 16  2  1  0
 17  6  1  0
 18  6  1  0
 19  6  1  0
 20  8  1  0
 21 29  1  0
 22 11  2  0
 23 24  2  0
 24 22  1  0
 25 14  1  0
 26 16  1  0
 27 16  1  0
 28 16  1  0
 29 31  1  0
 30 26  1  0
 31 32  1  0
 32 30  1  0
 33 25  1  0
  5  2  1  0
  8  7  1  0
 12 23  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA167580

   Sodium;4-ethyl-5-[6-methyl-6-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)heptoxy]-2-[3-(trifluoromethyl)phenyl]phenol

2. Parent:

   

   ALA167580

   4-ethyl-5-[6-methyl-6-(2H-tetrazol-5-yl)heptoxy]-2-[3-(trifluoromethyl)phenyl]phenol

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: 462.52

Molecular Weight (Monoisotopic): 462.2243

AlogP: 6.07

#Rotatable Bonds: 10

Polar Surface Area: 83.92

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.78

CX Basic pKa: ┄

CX LogP: 7.63

CX LogD: 6.33

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.36

Np Likeness Score: -0.59

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]

2. Wikel JH, Sofia MJ, Saussy DL, Bemis KG.  (1994)  QSAR Study of ortho-phenylphenol leukotriene B4 receptor antagonists,  4  (6): [10.1016/S0960-894X(01)80850-7]

Source

Source(1):

• Scientific Literature