4-[2-(pyridin-3-yl)-1,2,3,4-tetrahydroquinoline-1-carbonyl]benzene-1,3-diol

ID: ALA3716343

PubChem CID: 117967819

Max Phase: Preclinical

Molecular Formula: C21H18N2O3

Molecular Weight: 346.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(O)cc1O)N1c2ccccc2CCC1c1cccnc1

Standard InChI:  InChI=1S/C21H18N2O3/c24-16-8-9-17(20(25)12-16)21(26)23-18-6-2-1-4-14(18)7-10-19(23)15-5-3-11-22-13-15/h1-6,8-9,11-13,19,24-25H,7,10H2

Standard InChI Key:  XRQPVXUTZFDCGK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -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
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    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
    5.1929   -0.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4908   -1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4885   -3.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1883   -3.7510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904   -2.9990    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
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 26 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3716343

   (2,4-dihydroxyphenyl)-(2-pyridin-3-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: 346.39

Molecular Weight (Monoisotopic): 346.1317

AlogP: 3.83

#Rotatable Bonds: 2

Polar Surface Area: 73.66

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.82

CX Basic pKa: 4.79

CX LogP: 3.37

CX LogD: 3.23

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.74

Np Likeness Score: -0.38

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