4-[6-(3-methylpyridin-2-yl)-2-(pyridin-3-yl)-1,2,3,4-tetrahydroquinoline-1-carbonyl]benzene-1,3-diol

ID: ALA3719351

PubChem CID: 117967774

Max Phase: Preclinical

Molecular Formula: C27H23N3O3

Molecular Weight: 437.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccnc1-c1ccc2c(c1)CCC(c1cccnc1)N2C(=O)c1ccc(O)cc1O

Standard InChI:  InChI=1S/C27H23N3O3/c1-17-4-2-13-29-26(17)19-7-11-23-18(14-19)6-10-24(20-5-3-12-28-16-20)30(23)27(33)22-9-8-21(31)15-25(22)32/h2-5,7-9,11-16,24,31-32H,6,10H2,1H3

Standard InChI Key:  XWHRRPRMSJTOHZ-UHFFFAOYSA-N

Molfile:  

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   -3.8985    3.0030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA3719351

   (2,4-dihydroxyphenyl)-[6-(3-methylpyridin-2-yl)-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: 437.50

Molecular Weight (Monoisotopic): 437.1739

AlogP: 5.20

#Rotatable Bonds: 3

Polar Surface Area: 86.55

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.82

CX Basic pKa: 5.16

CX LogP: 4.70

CX LogD: 4.56

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.46

Np Likeness Score: -0.52

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