2-((2,3-dihydro-1H-inden-5-yloxy)methyl)benzoic acid

ID: ALA4473128

PubChem CID: 22686157

Max Phase: Preclinical

Molecular Formula: C17H16O3

Molecular Weight: 268.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccccc1COc1ccc2c(c1)CCC2

Standard InChI:  InChI=1S/C17H16O3/c18-17(19)16-7-2-1-4-14(16)11-20-15-9-8-12-5-3-6-13(12)10-15/h1-2,4,7-10H,3,5-6,11H2,(H,18,19)

Standard InChI Key:  CPEIKVFFPXMHQI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    7.1440  -11.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8536  -11.4838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8508  -10.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1422  -10.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4359  -11.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4326  -10.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6550  -10.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1777  -11.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6604  -11.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5620  -11.8913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2690  -11.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9774  -11.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9740  -12.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6816  -13.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3896  -12.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3857  -11.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6776  -11.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6719  -10.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3768  -10.2434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9614  -10.2529    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
 18 19  1  0
 18 20  2  0
 17 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4473128

   2-(2,3-dihydro-1H-inden-5-yloxymethyl)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: 268.31

Molecular Weight (Monoisotopic): 268.1099

AlogP: 3.45

#Rotatable Bonds: 4

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: 3.71

CX Basic pKa: ┄

CX LogP: 4.21

CX LogD: 0.90

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.92

Np Likeness Score: -0.60

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