2,4-dihydroxy-N-(4-(3-methylquinolin-2-yl)phenyl)-N-(4-(2-(pyrrolidin-1-yl)ethoxy)benzyl)benzamide

ID: ALA3729356

PubChem CID: 127024845

Max Phase: Preclinical

Molecular Formula: C36H35N3O4

Molecular Weight: 573.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2ccccc2nc1-c1ccc(N(Cc2ccc(OCCN3CCCC3)cc2)C(=O)c2ccc(O)cc2O)cc1

Standard InChI:  InChI=1S/C36H35N3O4/c1-25-22-28-6-2-3-7-33(28)37-35(25)27-10-12-29(13-11-27)39(36(42)32-17-14-30(40)23-34(32)41)24-26-8-15-31(16-9-26)43-21-20-38-18-4-5-19-38/h2-3,6-17,22-23,40-41H,4-5,18-21,24H2,1H3

Standard InChI Key:  VAEZIOUPBWPWKT-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3729356

   ---

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: 573.69

Molecular Weight (Monoisotopic): 573.2628

AlogP: 6.94

#Rotatable Bonds: 9

Polar Surface Area: 86.13

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.80

CX Basic pKa: 8.89

CX LogP: 5.82

CX LogD: 5.52

Aromatic Rings: 5

Heavy Atoms: 43

QED Weighted: 0.20

Np Likeness Score: -1.03

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. Meng, Tao T and 10 more authors.  2014-12-11  Discovery and optimization of 4,5-diarylisoxazoles as potent dual inhibitors of pyruvate dehydrogenase kinase and heat shock protein 90.  [PMID:25383915]

4. 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]

5. Narayan, Satya S and 7 more authors.  2019-01-01  ASR352, A potent anticancer agent: Synthesis, preliminary SAR, and biological activities against colorectal cancer bulk, 5-fluorouracil/oxaliplatin resistant and stem cells.  [PMID:30384048]

Source

Source(1):

• Patent Bioactivity Data