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

ID: ALA3954703

PubChem CID: 11663505

Max Phase: Preclinical

Molecular Formula: C33H40N2O3

Molecular Weight: 512.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(C(C)=O)c1ccc(-c2cc(-c3ccc(C(=O)O)cc3)ccc2CCCNC2CC2)cc1C(C)(C)C

Standard InChI:  InChI=1S/C33H40N2O3/c1-6-35(22(2)36)31-18-15-27(21-30(31)33(3,4)5)29-20-26(23-9-12-25(13-10-23)32(37)38)14-11-24(29)8-7-19-34-28-16-17-28/h9-15,18,20-21,28,34H,6-8,16-17,19H2,1-5H3,(H,37,38)

Standard InChI Key:  FPOHPLBFFPXIPO-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3954703

   4-[3-[4-[Acetyl(ethyl)amino]-3-tert-butylphenyl]-4-[3-(cyclopropylamino)propyl]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: 512.69

Molecular Weight (Monoisotopic): 512.3039

AlogP: 7.07

#Rotatable Bonds: 10

Polar Surface Area: 69.64

Molecular Species: ZWITTERION

HBA: 3

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.07

CX Basic pKa: 10.00

CX LogP: 4.21

CX LogD: 4.21

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.29

Np Likeness Score: -0.33

References

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

2. 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]

3. 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]

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

5. 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]

6. 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]

7. 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(1):

• Patent Bioactivity Data