N-{[1-(2,4-dihydroxybenzoyl)-1,2,3,4-tetrahydroquinolin-2-yl]methyl}-2,2,2-trifluoroacetamide

ID: ALA3716039

PubChem CID: 117967524

Max Phase: Preclinical

Molecular Formula: C19H17F3N2O4

Molecular Weight: 394.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(O)cc1O)N1c2ccccc2CCC1CNC(=O)C(F)(F)F

Standard InChI:  InChI=1S/C19H17F3N2O4/c20-19(21,22)18(28)23-10-12-6-5-11-3-1-2-4-15(11)24(12)17(27)14-8-7-13(25)9-16(14)26/h1-4,7-9,12,25-26H,5-6,10H2,(H,23,28)

Standard InChI Key:  QOMVKWOSNCOMEE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -5.1815    5.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1852    3.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8880    3.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870    3.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5835    5.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5428    5.8519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2193    5.8633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2907    2.9981    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
   -0.2489    3.5938    0.0000 O   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 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
    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
   -3.9122    1.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2109    0.7445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5121    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8109    0.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5141    2.6924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8513    1.3383    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8491    0.1384    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8090   -0.4597    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
  6  7  1  0
  2  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  1  0
 10 15  1  0
 12 13  1  0
 13 14  1  0
 14 16  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 12 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
 24 27  1  0
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3716039

   N-[[1-(2,4-dihydroxybenzoyl)-3,4-dihydro-2H-quinolin-2-yl]methyl]-2,2,2-trifluoroacetamide

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: 394.35

Molecular Weight (Monoisotopic): 394.1140

AlogP: 2.74

#Rotatable Bonds: 3

Polar Surface Area: 89.87

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.33

CX Basic pKa: ┄

CX LogP: 3.02

CX LogD: 2.68

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.75

Np Likeness Score: -0.55

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