2,4-dihydroxy-N-(4-(methyl(quinoxalin-6-ylmethyl)carbamoyl)phenyl)-N-(thiophen-3-ylmethyl)benzamide

ID: ALA3728227

PubChem CID: 123857956

Max Phase: Preclinical

Molecular Formula: C29H24N4O4S

Molecular Weight: 524.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(Cc1ccc2nccnc2c1)C(=O)c1ccc(N(Cc2ccsc2)C(=O)c2ccc(O)cc2O)cc1

Standard InChI:  InChI=1S/C29H24N4O4S/c1-32(16-19-2-9-25-26(14-19)31-12-11-30-25)28(36)21-3-5-22(6-4-21)33(17-20-10-13-38-18-20)29(37)24-8-7-23(34)15-27(24)35/h2-15,18,34-35H,16-17H2,1H3

Standard InChI Key:  AGIRAUWGTYSFEY-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3728227

   ---

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: 524.60

Molecular Weight (Monoisotopic): 524.1518

AlogP: 5.22

#Rotatable Bonds: 7

Polar Surface Area: 106.86

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.83

CX Basic pKa: 1.70

CX LogP: 4.18

CX LogD: 4.04

Aromatic Rings: 5

Heavy Atoms: 38

QED Weighted: 0.30

Np Likeness Score: -1.59

References

1.  (2015)  Resorcinol n-aryl amide compounds, for 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