4-[6-(2,3-dihydro-1H-isoindole-2-carbonyl)-1,2,3,4-tetrahydroquinoline-1-carbonyl]benzene-1,3-diol

ID: ALA3718953

PubChem CID: 117967734

Max Phase: Preclinical

Molecular Formula: C25H22N2O4

Molecular Weight: 414.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccc2c(c1)CCCN2C(=O)c1ccc(O)cc1O)N1Cc2ccccc2C1

Standard InChI:  InChI=1S/C25H22N2O4/c28-20-8-9-21(23(29)13-20)25(31)27-11-3-6-16-12-17(7-10-22(16)27)24(30)26-14-18-4-1-2-5-19(18)15-26/h1-2,4-5,7-10,12-13,28-29H,3,6,11,14-15H2

Standard InChI Key:  XAWMWRRMUXYKPC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -5.2109    0.7445    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9141    2.6966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5404    1.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3505   -0.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8119   -1.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5511    0.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0549    0.2799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8173   -1.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA3718953

   1,3-dihydroisoindol-2-yl-[1-(2,4-dihydroxybenzoyl)-3,4-dihydro-2H-quinolin-6-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: 414.46

Molecular Weight (Monoisotopic): 414.1580

AlogP: 3.85

#Rotatable Bonds: 2

Polar Surface Area: 81.08

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.83

CX Basic pKa: ┄

CX LogP: 3.58

CX LogD: 3.44

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.67

Np Likeness Score: -0.93

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