3-((4-((4-methoxybenzyl)oxy)benzyl)amino)benzoic acid

ID: ALA4237449

Chembl Id: CHEMBL4237449

PubChem CID: 139501186

Max Phase: Preclinical

Molecular Formula: C22H21NO4

Molecular Weight: 363.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(COc2ccc(CNc3cccc(C(=O)O)c3)cc2)cc1

Standard InChI:  InChI=1S/C22H21NO4/c1-26-20-9-7-17(8-10-20)15-27-21-11-5-16(6-12-21)14-23-19-4-2-3-18(13-19)22(24)25/h2-13,23H,14-15H2,1H3,(H,24,25)

Standard InChI Key:  OEODGXYWIGASDE-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA4237449

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Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 363.41

Molecular Weight (Monoisotopic): 363.1471

AlogP: 4.58

#Rotatable Bonds: 8

Polar Surface Area: 67.79

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.82

CX Basic pKa: 3.38

CX LogP: 4.03

CX LogD: 1.65

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: -0.77

References

1. Dou XZ, Nath D, Shin Y, Ma JX, Duerfeldt AS..  (2018)  Structure-guided evolution of a 2-phenyl-4-carboxyquinoline chemotype into PPARα selective agonists: New leads for oculovascular conditions.,  28  (16): [PMID:29628329] [10.1016/j.bmcl.2018.03.010]

2. Dou X, Nath D, Shin H, Nurmemmedov E, Bourne PC, Ma JX, Duerfeldt AS..  (2020)  Evolution of a 4-Benzyloxy-benzylamino Chemotype to Provide Efficacious, Potent, and Isoform Selective PPARα Agonists as Leads for Retinal Disorders.,  63  (6): [PMID:32096640] [10.1021/acs.jmedchem.9b01189]

Source

Source(1):

• Scientific Literature