3'-tert-Butyl-(1,1'-biphenyl)-4-carboxylic acid

ID: ALA4552520

Cas Number: 5728-34-7

PubChem CID: 59205486

Max Phase: Preclinical

Molecular Formula: C17H18O2

Molecular Weight: 254.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cccc(-c2ccc(C(=O)O)cc2)c1

Standard InChI:  InChI=1S/C17H18O2/c1-17(2,3)15-6-4-5-14(11-15)12-7-9-13(10-8-12)16(18)19/h4-11H,1-3H3,(H,18,19)

Standard InChI Key:  JIHQMQMGCUONBM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   40.3175   -3.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3163   -3.9768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0244   -4.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7340   -3.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7312   -3.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0226   -2.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4389   -4.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4388   -5.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1463   -5.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8544   -5.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8505   -4.3776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1424   -3.9739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5633   -5.6056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5656   -6.4228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.2698   -5.1949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.0202   -1.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7266   -1.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3112   -1.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0123   -1.1102    0.0000 C   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
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  4  7  1  0
 10 13  1  0
 13 14  2  0
 13 15  1  0
  6 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4552520

   3'-(1,1-Dimethylethyl)[1,1'-biphenyl]-4-carboxylic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 254.33

Molecular Weight (Monoisotopic): 254.1307

AlogP: 4.35

#Rotatable Bonds: 2

Polar Surface Area: 37.30

Molecular Species: ACID

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.07

CX Basic pKa: ┄

CX LogP: 4.82

CX LogD: 1.71

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.86

Np Likeness Score: -0.64

References

1. Pollinger J, Schierle S, Gellrich L, Ohrndorf J, Kaiser A, Heitel P, Chaikuad A, Knapp S, Merk D..  (2019)  A Novel Biphenyl-based Chemotype of Retinoid X Receptor Ligands Enables Subtype and Heterodimer Preferences.,  10  (9): [PMID:31531208] [10.1021/acsmedchemlett.9b00306]

2. Zhang, L L and 7 more authors.  1996-07-05  Discovery of novel retinoic acid receptor agonists having potent antiproliferative activity in cervical cancer cells.  [PMID:8709094]

3. Canan Koch, S S SS and 6 more authors.  1999-02-25  Synthesis of retinoid X receptor-specific ligands that are potent inducers of adipogenesis in 3T3-L1 cells.  [PMID:10052980]

Source

Source(1):

• Scientific Literature