3''-tert-butyl-4''-diethylamino-4'-(4-hydroxybutoxy)-[1,1';3',1'']terphenyl-4-carboxylic acid

ID: ALA3960035

PubChem CID: 11554936

Max Phase: Preclinical

Molecular Formula: C31H39NO4

Molecular Weight: 489.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)c1ccc(-c2cc(-c3ccc(C(=O)O)cc3)ccc2OCCCCO)cc1C(C)(C)C

Standard InChI:  InChI=1S/C31H39NO4/c1-6-32(7-2)28-16-14-25(21-27(28)31(3,4)5)26-20-24(15-17-29(26)36-19-9-8-18-33)22-10-12-23(13-11-22)30(34)35/h10-17,20-21,33H,6-9,18-19H2,1-5H3,(H,34,35)

Standard InChI Key:  MFJSSFBKCJUROC-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3960035

   3''-Tert-butyl-4''-diethylamino-4'-(4-hydroxybutoxy)-[1,1';3',1'']terphenyl-4-carboxylic 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: 489.66

Molecular Weight (Monoisotopic): 489.2879

AlogP: 7.01

#Rotatable Bonds: 11

Polar Surface Area: 70.00

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.05

CX Basic pKa: 5.37

CX LogP: 5.59

CX LogD: 3.93

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.28

Np Likeness Score: -0.33

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