N-(4-(2-chloro-5-methylpyrimidin-4-yl)phenyl)-2,4-dihydroxy-N-(4-((3-methoxypyrrolidin-1-yl)methyl)benzyl)benzamide

ID: ALA3729144

PubChem CID: 127035936

Max Phase: Preclinical

Molecular Formula: C31H31ClN4O4

Molecular Weight: 559.07

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1CCN(Cc2ccc(CN(C(=O)c3ccc(O)cc3O)c3ccc(-c4nc(Cl)ncc4C)cc3)cc2)C1

Standard InChI:  InChI=1S/C31H31ClN4O4/c1-20-16-33-31(32)34-29(20)23-7-9-24(10-8-23)36(30(39)27-12-11-25(37)15-28(27)38)18-22-5-3-21(4-6-22)17-35-14-13-26(19-35)40-2/h3-12,15-16,26,37-38H,13-14,17-19H2,1-2H3

Standard InChI Key:  WYUKVGVZYSCCDJ-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3729144

   ---

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: 559.07

Molecular Weight (Monoisotopic): 558.2034

AlogP: 5.58

#Rotatable Bonds: 8

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: 4.34

CX LogD: 4.06

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.27

Np Likeness Score: -1.10

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