5-(3,5-Di-tert-butylphenyl)pyridine-2-carboxylic acid

ID: ALA4574947

PubChem CID: 155560966

Max Phase: Preclinical

Molecular Formula: C20H25NO2

Molecular Weight: 311.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1cc(-c2ccc(C(=O)O)nc2)cc(C(C)(C)C)c1

Standard InChI:  InChI=1S/C20H25NO2/c1-19(2,3)15-9-14(10-16(11-15)20(4,5)6)13-7-8-17(18(22)23)21-12-13/h7-12H,1-6H3,(H,22,23)

Standard InChI Key:  QTIUJAHQUZABFP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   32.2653  -27.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2641  -27.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9722  -28.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6818  -27.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6790  -27.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9704  -26.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3867  -28.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3866  -29.0939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0941  -29.5013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.8022  -29.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7982  -28.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0902  -27.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5111  -29.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5134  -30.3153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2176  -29.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.9679  -25.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6744  -25.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2590  -25.4173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9600  -25.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5561  -28.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8487  -27.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5554  -29.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8428  -28.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  4  7  1  0
 10 13  1  0
 13 14  2  0
 13 15  1  0
  6 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  2 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4574947

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 311.43

Molecular Weight (Monoisotopic): 311.1885

AlogP: 5.04

#Rotatable Bonds: 2

Polar Surface Area: 50.19

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.06

CX Basic pKa: 5.30

CX LogP: 4.20

CX LogD: 2.35

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.84

Np Likeness Score: -0.60

References

1. Pollinger J, Schierle S, Gellrich L, Ohrndorf J, Kaiser A, Heitel P, Chaikuad A, Knapp S, Merk D..  (2019)  A Novel Biphenyl-based Chemotype of Retinoid X Receptor Ligands Enables Subtype and Heterodimer Preferences.,  10  (9): [PMID:31531208] [10.1021/acsmedchemlett.9b00306]

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]

Source

Source(1):

• Scientific Literature