(2,4-dihydroxyphenyl)(2-(trifluoromethyl)-3,4-dihydroquinolin-1(2H)-yl)methanone

ID: ALA3718579

PubChem CID: 117970935

Max Phase: Preclinical

Molecular Formula: C17H14F3NO3

Molecular Weight: 337.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(O)cc1O)N1c2ccccc2CCC1C(F)(F)F

Standard InChI:  InChI=1S/C17H14F3NO3/c18-17(19,20)15-8-5-10-3-1-2-4-13(10)21(15)16(24)12-7-6-11(22)9-14(12)23/h1-4,6-7,9,15,22-23H,5,8H2

Standard InChI Key:  OAODSMWKFRASCR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -2.5954   -5.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2959   -6.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0027   -5.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0018   -3.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2978   -3.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5964   -3.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0423   -5.8514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6342   -5.8545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2995   -2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3402   -3.5957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8926   -1.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8934   -2.6991    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9317   -0.8987    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9322   -2.0986    0.0000 F   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
  3  7  1  0
  1  8  1  0
  4  9  1  0
  9 17  1  0
  9 10  2  0
 15 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 16  1  0
 15 16  2  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3718579

   (2,4-dihydroxyphenyl)-[2-(trifluoromethyl)-3,4-dihydro-2H-quinolin-1-yl]methanone

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: 337.30

Molecular Weight (Monoisotopic): 337.0926

AlogP: 3.62

#Rotatable Bonds: 1

Polar Surface Area: 60.77

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.82

CX Basic pKa: ┄

CX LogP: 3.82

CX LogD: 3.68

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.84

Np Likeness Score: -0.48

References

1.  (2015)  Tetrahydroisoquinoline compounds and their use as pyruvate dehydrogenase kinase inhibitors, 

2. Morrell, J A JA and 5 more authors.  2003-12  AZD7545 is a selective inhibitor of pyruvate dehydrogenase kinase 2.  [PMID:14641019]

3. Moore, Jonathan D and 12 more authors.  2014-12-30  VER-246608, a novel pan-isoform ATP competitive inhibitor of pyruvate dehydrogenase kinase, disrupts Warburg metabolism and induces context-dependent cytostasis in cancer cells.  [PMID:25404640]

4. Tso, Shih-Chia and 9 more authors.  2017-02-09  Development of Dihydroxyphenyl Sulfonylisoindoline Derivatives as Liver-Targeting Pyruvate Dehydrogenase Kinase Inhibitors.  [PMID:28085286]

Source

Source(1):

• Patent Bioactivity Data