4-([{6-Phenyl-5-indanyl}oxy]methyl)benzoic acid

ID: ALA4449565

PubChem CID: 155520617

Max Phase: Preclinical

Molecular Formula: C23H20O3

Molecular Weight: 344.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(COc2cc3c(cc2-c2ccccc2)CCC3)cc1

Standard InChI:  InChI=1S/C23H20O3/c24-23(25)18-11-9-16(10-12-18)15-26-22-14-20-8-4-7-19(20)13-21(22)17-5-2-1-3-6-17/h1-3,5-6,9-14H,4,7-8,15H2,(H,24,25)

Standard InChI Key:  IQAYHPJNQXWKTD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    6.0202  -20.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0191  -21.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7271  -22.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4368  -21.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4339  -20.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7253  -20.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1462  -22.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1475  -22.9192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8533  -21.6923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3124  -20.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6048  -20.8758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8970  -20.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9004  -19.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1935  -19.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1952  -20.8761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6076  -19.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3147  -19.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0228  -19.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0250  -18.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3133  -18.0196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6081  -18.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4877  -20.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4845  -19.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6982  -19.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2154  -20.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7034  -20.7296    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 23  2  0
 22 15  2  0
 15 12  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 13 16  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4449565

   ---

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: 344.41

Molecular Weight (Monoisotopic): 344.1412

AlogP: 5.12

#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: 5.85

CX LogD: 2.73

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.70

Np Likeness Score: -0.27

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