3',5'-Di-tert-butyl-2-methyl-(1,1'-biphenyl)-4-carboxylic acid

ID: ALA4552797

PubChem CID: 155555914

Max Phase: Preclinical

Molecular Formula: C22H28O2

Molecular Weight: 324.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(C(=O)O)ccc1-c1cc(C(C)(C)C)cc(C(C)(C)C)c1

Standard InChI:  InChI=1S/C22H28O2/c1-14-10-15(20(23)24)8-9-19(14)16-11-17(21(2,3)4)13-18(12-16)22(5,6)7/h8-13H,1-7H3,(H,23,24)

Standard InChI Key:  AWKQZMHTVIJZRY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
   41.3493  -26.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3481  -27.5804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0562  -27.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7658  -27.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7630  -26.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0544  -26.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4707  -27.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4706  -28.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1781  -29.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8862  -28.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8823  -27.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1742  -27.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.5951  -29.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.5974  -30.0264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   46.3016  -28.7985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.0520  -25.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7584  -25.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3430  -25.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0441  -24.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6401  -27.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9327  -27.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6395  -28.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9268  -28.3912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7631  -29.2140    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
  2 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
  8 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4552797

   ---

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: 324.46

Molecular Weight (Monoisotopic): 324.2089

AlogP: 5.96

#Rotatable Bonds: 2

Polar Surface Area: 37.30

Molecular Species: ACID

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.07

CX Basic pKa: ┄

CX LogP: 6.88

CX LogD: 3.77

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.74

Np Likeness Score: -0.46

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