4-([{(5-tert-Butyl-1,1'-biphenyl)-2-yl}oxy]methyl)benzoic acid

ID: ALA4445748

PubChem CID: 155517898

Max Phase: Preclinical

Molecular Formula: C24H24O3

Molecular Weight: 360.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(OCc2ccc(C(=O)O)cc2)c(-c2ccccc2)c1

Standard InChI:  InChI=1S/C24H24O3/c1-24(2,3)20-13-14-22(21(15-20)18-7-5-4-6-8-18)27-16-17-9-11-19(12-10-17)23(25)26/h4-15H,16H2,1-3H3,(H,25,26)

Standard InChI Key:  DSMPSZKEDOMDHY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   16.2846   -4.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2835   -5.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9915   -5.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7012   -5.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6984   -4.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9897   -3.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4106   -5.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4119   -6.3691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1177   -5.1422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5768   -3.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8692   -4.3256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1614   -3.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1648   -3.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4579   -2.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7493   -3.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7521   -3.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4597   -4.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0409   -2.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0396   -1.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3339   -3.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3292   -2.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8720   -2.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5791   -3.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2872   -2.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2895   -1.8794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5777   -1.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8725   -1.8781    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  1  0
  7  9  2  0
  4  7  1  0
  1 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 13 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4445748

   ---

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: 360.45

Molecular Weight (Monoisotopic): 360.1725

AlogP: 5.93

#Rotatable Bonds: 5

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: 4.06

CX Basic pKa: ┄

CX LogP: 6.39

CX LogD: 3.27

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: -0.52

References

1. Heitel P, Gellrich L, Kalinowsky L, Heering J, Kaiser A, Ohrndorf J, Proschak E, Merk D..  (2019)  Computer-Assisted Discovery and Structural Optimization of a Novel Retinoid X Receptor Agonist Chemotype.,  10  (2): [PMID:30783504] [10.1021/acsmedchemlett.8b00551]

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