N-[1-(2,4-dihydroxybenzoyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-methylpropanamide

ID: ALA3717058

PubChem CID: 117967921

Max Phase: Preclinical

Molecular Formula: C20H22N2O4

Molecular Weight: 354.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C(=O)Nc1ccc2c(c1)CCCN2C(=O)c1ccc(O)cc1O

Standard InChI:  InChI=1S/C20H22N2O4/c1-12(2)19(25)21-14-5-8-17-13(10-14)4-3-9-22(17)20(26)16-7-6-15(23)11-18(16)24/h5-8,10-12,23-24H,3-4,9H2,1-2H3,(H,21,25)

Standard InChI Key:  JCMGJBTYTUCSSM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    5.2037   -5.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9072   -5.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -5.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -3.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8969   -2.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985   -3.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5685   -5.8503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2450   -5.8341    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
    0.2613   -3.5999    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
   -3.9122    1.4966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2109    0.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2090   -0.4555    0.0000 O   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
   -7.5506    0.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5141    2.6924    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
  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
 12 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3717058

   N-[1-(2,4-dihydroxybenzoyl)-3,4-dihydro-2H-quinolin-6-yl]-2-methylpropanamide

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: 354.41

Molecular Weight (Monoisotopic): 354.1580

AlogP: 3.29

#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: 7.83

CX Basic pKa: ┄

CX LogP: 3.29

CX LogD: 3.15

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.79

Np Likeness Score: -1.13

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