3'-(Propan-2-yloxy)-(1,1'-biphenyl)-4-carboxylic acid

ID: ALA4560357

PubChem CID: 80198302

Max Phase: Preclinical

Molecular Formula: C16H16O3

Molecular Weight: 256.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)Oc1cccc(-c2ccc(C(=O)O)cc2)c1

Standard InChI:  InChI=1S/C16H16O3/c1-11(2)19-15-5-3-4-14(10-15)12-6-8-13(9-7-12)16(17)18/h3-11H,1-2H3,(H,17,18)

Standard InChI Key:  DLWPTKJYKHDBTL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   22.7148  -10.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7137  -11.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4217  -12.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1314  -11.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1286  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4200  -10.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8362  -12.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8362  -12.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5437  -13.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2518  -12.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2478  -12.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5398  -11.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9606  -13.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9630  -14.0911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6672  -12.8633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4175   -9.5996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1240   -9.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1216   -8.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8329   -9.5954    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
 17 18  1  0
 17 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4560357

   4-(3-Propan-2-yloxyphenyl)benzoic 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: 256.30

Molecular Weight (Monoisotopic): 256.1099

AlogP: 3.84

#Rotatable Bonds: 4

Polar Surface Area: 46.53

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.06

CX Basic pKa: ┄

CX LogP: 3.89

CX LogD: 0.77

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.90

Np Likeness Score: -0.71

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