4'-[(5-Methylhexyl)oxy][1,1'-biphenyl]-4-carboxylic acid

ID: ALA469281

PubChem CID: 15951927

Max Phase: Preclinical

Molecular Formula: C20H24O3

Molecular Weight: 312.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CCCCOc1ccc(-c2ccc(C(=O)O)cc2)cc1

Standard InChI:  InChI=1S/C20H24O3/c1-15(2)5-3-4-14-23-19-12-10-17(11-13-19)16-6-8-18(9-7-16)20(21)22/h6-13,15H,3-5,14H2,1-2H3,(H,21,22)

Standard InChI Key:  KAMPGBXWQOLHJJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   16.8791   -4.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5935   -5.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3066   -4.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3094   -3.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6012   -3.4516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8839   -3.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1618   -5.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4494   -4.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7322   -5.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7273   -5.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4418   -6.3286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1590   -5.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0266   -3.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0315   -2.6321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7411   -3.8703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0101   -6.3213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2977   -5.9099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5805   -6.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8702   -5.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1529   -6.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4386   -5.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4414   -5.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7213   -6.3030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
  1  7  1  0
 13 14  2  0
 13 15  1  0
  4 13  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 16 17  1  0
 10 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA469281

   4'-(5-Methyl-hexyloxy)-biphenyl-4-carboxylic 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: 312.41

Molecular Weight (Monoisotopic): 312.1725

AlogP: 5.26

#Rotatable Bonds: 8

Polar Surface Area: 46.53

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.08

CX Basic pKa: ┄

CX LogP: 5.62

CX LogD: 2.51

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.68

Np Likeness Score: -0.12

References

1. Lund BW, Knapp AE, Piu F, Gauthier NK, Begtrup M, Hacksell U, Olsson R..  (2009)  Design, synthesis, and structure-activity analysis of isoform-selective retinoic acid receptor beta ligands.,  52  (6): [PMID:19239230] [10.1021/jm801532e]

Source

Source(1):

• Scientific Literature