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

ID: ALA4554527

PubChem CID: 155556139

Max Phase: Preclinical

Molecular Formula: C21H18O3

Molecular Weight: 318.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(OCc2ccc(C(=O)O)cc2)c(-c2ccccc2)c1

Standard InChI:  InChI=1S/C21H18O3/c1-15-7-12-20(19(13-15)17-5-3-2-4-6-17)24-14-16-8-10-18(11-9-16)21(22)23/h2-13H,14H2,1H3,(H,22,23)

Standard InChI Key:  CZJISVOVARFHLM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   16.2557   -9.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2546  -10.6794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9626  -11.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6723  -10.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6695   -9.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9608   -9.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3817  -11.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3830  -11.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0888  -10.6768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5479   -9.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8403   -9.8603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1325   -9.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1360   -8.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4290   -8.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7204   -8.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7232   -9.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4308   -9.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8431   -8.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5502   -8.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2583   -8.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2606   -7.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5488   -7.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8436   -7.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0120   -8.2270    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
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 13 18  1  0
 15 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4554527

   ---

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: 318.37

Molecular Weight (Monoisotopic): 318.1256

AlogP: 4.94

#Rotatable Bonds: 5

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: 5.36

CX LogD: 2.24

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: -0.49

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