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

ID: ALA4572963

PubChem CID: 155563051

Max Phase: Preclinical

Molecular Formula: C20H22O3

Molecular Weight: 310.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)CCCc1ccc(COc2ccc3c(c2)CCC3)cc1

Standard InChI:  InChI=1S/C20H22O3/c21-20(22)6-1-3-15-7-9-16(10-8-15)14-23-19-12-11-17-4-2-5-18(17)13-19/h7-13H,1-6,14H2,(H,21,22)

Standard InChI Key:  FYNUGSMXUABKKL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   18.8240   -5.1493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5337   -4.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5308   -3.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8222   -3.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1160   -4.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1127   -3.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3351   -3.6746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8578   -4.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3404   -4.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2420   -5.1474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9491   -4.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6574   -5.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6541   -5.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3616   -6.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0697   -5.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0657   -5.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3577   -4.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7785   -6.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4851   -5.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1940   -6.3609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9005   -5.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6116   -6.3558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9004   -5.1321    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
 21 22  1  0
 21 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4572963

   ---

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: 310.39

Molecular Weight (Monoisotopic): 310.1569

AlogP: 4.16

#Rotatable Bonds: 7

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: 4.47

CX Basic pKa: ┄

CX LogP: 5.07

CX LogD: 2.24

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.83

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