(S)-2-(Biphenyl-4-yloxy)-3-phenyl-propionic acid

ID: ALA191275

Chembl Id: CHEMBL191275

Cas Number: 862901-87-9

PubChem CID: 11483970

Max Phase: Preclinical

Molecular Formula: C21H18O3

Molecular Weight: 318.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H](Cc1ccccc1)Oc1ccc(-c2ccccc2)cc1

Standard InChI:  InChI=1S/C21H18O3/c22-21(23)20(15-16-7-3-1-4-8-16)24-19-13-11-18(12-14-19)17-9-5-2-6-10-17/h1-14,20H,15H2,(H,22,23)/t20-/m0/s1

Standard InChI Key:  TZTPJJNNACUQQR-FQEVSTJZSA-N

Alternative Forms

1. Parent:

   

   ALA191275

   (2S)-2-(biphenyl-4-yloxy)-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: 318.37

Molecular Weight (Monoisotopic): 318.1256

AlogP: 4.43

#Rotatable Bonds: 6

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: 4.00

CX Basic pKa: ┄

CX LogP: 5.17

CX LogD: 2.01

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.73

Np Likeness Score: -0.06

References

1. Pinelli A, Godio C, Laghezza A, Mitro N, Fracchiolla G, Tortorella V, Lavecchia A, Novellino E, Fruchart JC, Staels B, Crestani M, Loiodice F..  (2005)  Synthesis, biological evaluation, and molecular modeling investigation of new chiral fibrates with PPARalpha and PPARgamma agonist activity.,  48  (17): [PMID:16107150] [10.1021/jm0502844]

2. 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]

3. 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]

4. Laghezza A, Pochetti G, Lavecchia A, Fracchiolla G, Faliti S, Piemontese L, Di Giovanni C, Iacobazzi V, Infantino V, Montanari R, Capelli D, Tortorella P, Loiodice F..  (2013)  New 2-(aryloxy)-3-phenylpropanoic acids as peroxisome proliferator-activated receptor α/γ dual agonists able to upregulate mitochondrial carnitine shuttle system gene expression.,  56  (1): [PMID:23171045] [10.1021/jm301018z]

5. 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]

6. Piemontese L, Fracchiolla G, Carrieri A, Parente M, Laghezza A, Carbonara G, Sblano S, Tauro M, Gilardi F, Tortorella P, Lavecchia A, Crestani M, Desvergne B, Loiodice F..  (2015)  Design, synthesis and biological evaluation of a class of bioisosteric oximes of the novel dual peroxisome proliferator-activated receptor α/γ ligand LT175.,  90  [PMID:25497132] [10.1016/j.ejmech.2014.11.044]

7. Laghezza A, Piemontese L, Cerchia C, Montanari R, Capelli D, Giudici M, Crestani M, Tortorella P, Peiretti F, Pochetti G, Lavecchia A, Loiodice F..  (2018)  Identification of the First PPARα/γ Dual Agonist Able To Bind to Canonical and Alternative Sites of PPARγ and To Inhibit Its Cdk5-Mediated Phosphorylation.,  61  (18): [PMID:30199253] [10.1021/acs.jmedchem.8b00835]

8. Montanari R, Capelli D, Yamamoto K, Awaishima H, Nishikata K, Barendregt A, Heck AJR, Loiodice F, Altieri F, Paiardini A, Grottesi A, Pirone L, Pedone E, Peiretti F, Brunel JM, Itoh T, Pochetti G..  (2020)  Insights into PPARγ Phosphorylation and Its Inhibition Mechanism.,  63  (9): [PMID:32239932] [10.1021/acs.jmedchem.0c00048]

Source

Source(1):

• Scientific Literature