4-([{4-tert-Butyl-2-chloro}phenoxy]methyl)benzoic acid

ID: ALA4514278

PubChem CID: 155539294

Max Phase: Preclinical

Molecular Formula: C18H19ClO3

Molecular Weight: 318.80

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H19ClO3/c1-18(2,3)14-8-9-16(15(19)10-14)22-11-12-4-6-13(7-5-12)17(20)21/h4-10H,11H2,1-3H3,(H,20,21)

Standard InChI Key:  FFQIAIOKDXEIME-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   15.9792  -20.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9781  -21.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6861  -21.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3958  -21.4139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3929  -20.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6843  -20.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1052  -21.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1065  -22.6386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8123  -21.4117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2714  -20.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5638  -20.5952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8560  -20.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8594  -19.3690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1525  -18.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4439  -19.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4467  -20.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1542  -20.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7355  -18.9619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7342  -18.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0284  -19.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0238  -18.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5680  -18.9619    0.0000 Cl  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
 13 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4514278

   ---

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: 318.80

Molecular Weight (Monoisotopic): 318.1023

AlogP: 4.91

#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: 5.35

CX LogD: 2.22

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.87

Np Likeness Score: -0.89

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