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

ID: ALA4519831

PubChem CID: 22688013

Max Phase: Preclinical

Molecular Formula: C18H18O3

Molecular Weight: 282.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)Cc1ccc(COc2ccc3c(c2)CCC3)cc1

Standard InChI:  InChI=1S/C18H18O3/c19-18(20)10-13-4-6-14(7-5-13)12-21-17-9-8-15-2-1-3-16(15)11-17/h4-9,11H,1-3,10,12H2,(H,19,20)

Standard InChI Key:  FKDVOUNKBZEBLY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    6.2112  -16.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9209  -16.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9180  -15.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2094  -15.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5032  -16.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4999  -15.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7223  -15.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2450  -16.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7276  -16.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6292  -16.9636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3363  -16.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0446  -16.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0413  -17.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7488  -18.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4568  -17.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4529  -16.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7448  -16.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1657  -18.1812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8723  -17.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5834  -18.1760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8721  -16.9523    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
 19 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4519831

   2-[4-(2,3-dihydro-1H-inden-5-yloxymethyl)phenyl]acetic 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: 282.34

Molecular Weight (Monoisotopic): 282.1256

AlogP: 3.38

#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: 3.97

CX Basic pKa: ┄

CX LogP: 4.19

CX LogD: 1.01

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.91

Np Likeness Score: -0.39

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