3''-tert-butyl-4'-(2-hydroxyethoxy)-4''-(2-oxopyrrolidin-1-yl)-[1,1';3',1'']terphenyl-4-caboxylic acid

ID: ALA3910072

Chembl Id: CHEMBL3910072

PubChem CID: 11634244

Max Phase: Preclinical

Molecular Formula: C29H31NO5

Molecular Weight: 473.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(-c2cc(-c3ccc(C(=O)O)cc3)ccc2OCCO)ccc1N1CCCC1=O

Standard InChI:  InChI=1S/C29H31NO5/c1-29(2,3)24-18-22(10-12-25(24)30-14-4-5-27(30)32)23-17-21(11-13-26(23)35-16-15-31)19-6-8-20(9-7-19)28(33)34/h6-13,17-18,31H,4-5,14-16H2,1-3H3,(H,33,34)

Standard InChI Key:  KJXUVPHGZBSVDB-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3910072

   4-[3-[3-Tert-butyl-4-(2-oxopyrrolidin-1-yl)phenyl]-4-(2-hydroxyethoxy)phenyl]benzoic 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: 473.57

Molecular Weight (Monoisotopic): 473.2202

AlogP: 5.51

#Rotatable Bonds: 7

Polar Surface Area: 87.07

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.08

CX Basic pKa: ┄

CX LogP: 4.95

CX LogD: 1.84

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.47

Np Likeness Score: -0.36

References

1.  (2008)  Novel ligands that modulate RAR receptors and pharmaceutical/cosmetic compositions comprised thereof, 

2. Thoreau E, Arlabosse JM, Bouix-Peter C, Chambon S, Chantalat L, Daver S, Dumais L, Duvert G, Feret A, Ouvry G, Pascau J, Raffin C, Rodeville N, Soulet C, Tabet S, Talano S, Portal T..  (2018)  Structure-based design of Trifarotene (CD5789), a potent and selective RARγ agonist for the treatment of acne.,  28  (10): [PMID:29706423] [10.1016/j.bmcl.2018.04.036]

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data