N-(4-(2-chloro-5-methylpyrimidin-4-yl)phenyl)-N-(3-(2-(dimethylamino)ethoxy)benzyl)-2,4-dihydroxybenzamide

ID: ALA3730414

PubChem CID: 127024755

Max Phase: Preclinical

Molecular Formula: C29H29ClN4O4

Molecular Weight: 533.03

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cnc(Cl)nc1-c1ccc(N(Cc2cccc(OCCN(C)C)c2)C(=O)c2ccc(O)cc2O)cc1

Standard InChI:  InChI=1S/C29H29ClN4O4/c1-19-17-31-29(30)32-27(19)21-7-9-22(10-8-21)34(28(37)25-12-11-23(35)16-26(25)36)18-20-5-4-6-24(15-20)38-14-13-33(2)3/h4-12,15-17,35-36H,13-14,18H2,1-3H3

Standard InChI Key:  UKVBAJDPXOGHTO-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3730414

   ---

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: 533.03

Molecular Weight (Monoisotopic): 532.1877

AlogP: 5.30

#Rotatable Bonds: 9

Polar Surface Area: 99.02

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.78

CX Basic pKa: 8.73

CX LogP: 4.36

CX LogD: 4.07

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.28

Np Likeness Score: -1.17

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