4-((4-isopropylphenoxy)methyl)benzoic acid

ID: ALA4553859

Cas Number: 149288-64-2

PubChem CID: 843040

Max Phase: Preclinical

Molecular Formula: C17H18O3

Molecular Weight: 270.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)c1ccc(OCc2ccc(C(=O)O)cc2)cc1

Standard InChI:  InChI=1S/C17H18O3/c1-12(2)14-7-9-16(10-8-14)20-11-13-3-5-15(6-4-13)17(18)19/h3-10,12H,11H2,1-2H3,(H,18,19)

Standard InChI Key:  AJPPQRKAQFRNEF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   17.2545   -4.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2534   -5.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9614   -5.8675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6711   -5.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6683   -4.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9596   -4.2301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3805   -5.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3818   -6.6827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0876   -5.4558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5467   -4.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8391   -4.6393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1313   -4.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1347   -3.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4278   -3.0047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7192   -3.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7220   -4.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4296   -4.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0108   -3.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0095   -2.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3038   -3.4158    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
M  END

Alternative Forms

1. Parent:

   

   ALA4553859

   4-[(4-Isopropylphenoxy)methyl]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: 270.33

Molecular Weight (Monoisotopic): 270.1256

AlogP: 4.09

#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: 4.44

CX LogD: 1.32

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.89

Np Likeness Score: -0.47

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