(S)-2-(4-benzylphenoxy)-3-phenylpropanoic acid

ID: ALA489074

Chembl Id: CHEMBL489074

PubChem CID: 44241499

Max Phase: Preclinical

Molecular Formula: C22H20O3

Molecular Weight: 332.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H](Cc1ccccc1)Oc1ccc(Cc2ccccc2)cc1

Standard InChI:  InChI=1S/C22H20O3/c23-22(24)21(16-18-9-5-2-6-10-18)25-20-13-11-19(12-14-20)15-17-7-3-1-4-8-17/h1-14,21H,15-16H2,(H,23,24)/t21-/m0/s1

Standard InChI Key:  YVAQXSJDDQRTTP-NRFANRHFSA-N

Alternative Forms

1. Parent:

   

   ALA489074

   (2S)-2-(4-benzylphenoxy)-3-phenylpropanoic acid

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: 332.40

Molecular Weight (Monoisotopic): 332.1412

AlogP: 4.35

#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: 3.86

CX Basic pKa: ┄

CX LogP: 5.61

CX LogD: 2.38

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.70

Np Likeness Score: 0.02

References

1. Montanari R, Saccoccia F, Scotti E, Crestani M, Godio C, Gilardi F, Loiodice F, Fracchiolla G, Laghezza A, Tortorella P, Lavecchia A, Novellino E, Mazza F, Aschi M, Pochetti G..  (2008)  Crystal structure of the peroxisome proliferator-activated receptor gamma (PPARgamma) ligand binding domain complexed with a novel partial agonist: a new region of the hydrophobic pocket could be exploited for drug design.,  51  (24): [PMID:19053776] [10.1021/jm800733h]

2. Fracchiolla G, Laghezza A, Piemontese L, Tortorella P, Mazza F, Montanari R, Pochetti G, Lavecchia A, Novellino E, Pierno S, Conte Camerino D, Loiodice F..  (2009)  New 2-aryloxy-3-phenyl-propanoic acids as peroxisome proliferator-activated receptors alpha/gamma dual agonists with improved potency and reduced adverse effects on skeletal muscle function.,  52  (20): [PMID:19775169] [10.1021/jm900941b]

3. Carrieri A, Giudici M, Parente M, De Rosas M, Piemontese L, Fracchiolla G, Laghezza A, Tortorella P, Carbonara G, Lavecchia A, Gilardi F, Crestani M, Loiodice F..  (2013)  Molecular determinants for nuclear receptors selectivity: chemometric analysis, dockings and site-directed mutagenesis of dual peroxisome proliferator-activated receptors α/γ agonists.,  63  [PMID:23502212] [10.1016/j.ejmech.2013.02.015]

Source

Source(1):

• Scientific Literature