4-[2-(3,5-dimethyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydroquinoline-1-carbonyl]benzene-1,3-diol

ID: ALA3717293

PubChem CID: 117967677

Max Phase: Preclinical

Molecular Formula: C21H21N3O3

Molecular Weight: 363.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1n[nH]c(C)c1C1CCc2ccccc2N1C(=O)c1ccc(O)cc1O

Standard InChI:  InChI=1S/C21H21N3O3/c1-12-20(13(2)23-22-12)18-10-7-14-5-3-4-6-17(14)24(18)21(27)16-9-8-15(25)11-19(16)26/h3-6,8-9,11,18,25-26H,7,10H2,1-2H3,(H,22,23)

Standard InChI Key:  PUHWWAJTHDKCGR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -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   -1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2449   -0.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2469   -1.9962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4950   -3.2941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0282   -2.9800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1305   -3.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4892    0.2949    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
 18 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 21  2  0
 25 26  1  0
 22 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3717293

   (2,4-dihydroxyphenyl)-[2-(3,5-dimethyl-1H-pyrazol-4-yl)-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: 363.42

Molecular Weight (Monoisotopic): 363.1583

AlogP: 3.77

#Rotatable Bonds: 2

Polar Surface Area: 89.45

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.82

CX Basic pKa: 3.79

CX LogP: 3.23

CX LogD: 3.09

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.65

Np Likeness Score: -0.61

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