3-(4-((2,3-dihydro-1H-inden-5-yloxy)methyl)phenyl)propanoic acid

ID: ALA4513928

PubChem CID: 155539095

Max Phase: Preclinical

Molecular Formula: C19H20O3

Molecular Weight: 296.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)CCc1ccc(COc2ccc3c(c2)CCC3)cc1

Standard InChI:  InChI=1S/C19H20O3/c20-19(21)11-8-14-4-6-15(7-5-14)13-22-18-10-9-16-2-1-3-17(16)12-18/h4-7,9-10,12H,1-3,8,11,13H2,(H,20,21)

Standard InChI Key:  MJXUNTFOTRPPSB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    6.4299  -22.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1396  -22.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1368  -21.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4282  -20.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7219  -22.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7186  -21.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9410  -20.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4637  -21.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9464  -22.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8480  -22.4694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5550  -22.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2634  -22.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2600  -23.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9675  -23.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6756  -23.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6717  -22.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9636  -22.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3845  -23.6870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0910  -23.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7999  -23.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5064  -23.2722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8023  -24.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  2 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
 19 20  1  0
 20 21  1  0
 20 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4513928

   ---

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: 296.37

Molecular Weight (Monoisotopic): 296.1412

AlogP: 3.77

#Rotatable Bonds: 6

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: 4.25

CX Basic pKa: ┄

CX LogP: 4.63

CX LogD: 1.63

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.88

Np Likeness Score: -0.23

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