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

ID: ALA3953756

PubChem CID: 11504066

Max Phase: Preclinical

Molecular Formula: C31H37NO4

Molecular Weight: 487.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(-c2cc(-c3ccc(C(=O)O)cc3)ccc2OCCCCO)ccc1N1CCCC1

Standard InChI:  InChI=1S/C31H37NO4/c1-31(2,3)27-21-25(12-14-28(27)32-16-4-5-17-32)26-20-24(13-15-29(26)36-19-7-6-18-33)22-8-10-23(11-9-22)30(34)35/h8-15,20-21,33H,4-7,16-19H2,1-3H3,(H,34,35)

Standard InChI Key:  RNSFAMNEIAFEFD-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3953756

   4-[3-(3-Tert-butyl-4-pyrrolidin-1-ylphenyl)-4-(4-hydroxybutoxy)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: 487.64

Molecular Weight (Monoisotopic): 487.2723

AlogP: 6.77

#Rotatable Bonds: 9

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: 3.97

CX Basic pKa: 4.75

CX LogP: 5.73

CX LogD: 3.61

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.33

Np Likeness Score: -0.30

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]

3. Zhang, L L and 7 more authors.  1996-07-05  Discovery of novel retinoic acid receptor agonists having potent antiproliferative activity in cervical cancer cells.  [PMID:8709094]

4. Canan Koch, S S SS and 6 more authors.  1999-02-25  Synthesis of retinoid X receptor-specific ligands that are potent inducers of adipogenesis in 3T3-L1 cells.  [PMID:10052980]

5. Haffner, Curt D CD and 13 more authors.  2004-04-08  Structure-based design of potent retinoid X receptor alpha agonists.  [PMID:15056000]

6. Patch, Raymond J RJ and 16 more authors.  2011-02-10  Identification of diaryl ether-based ligands for estrogen-related receptor α as potential antidiabetic agents.  [PMID:21218783]

7. Gege, Christian C, Schlüter, Thomas T and Hoffmann, Thomas T.  2014-11-15  Identification of the first inverse agonist of retinoid-related orphan receptor (ROR) with dual selectivity for RORβ and RORγt.  [PMID:25305688]

8. Haffez, Hesham and 7 more authors.  2018-05-01  Probing biological activity through structural modelling of ligand-receptor interactions of 2,4-disubstituted thiazole retinoids.  [PMID:29439915]

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data