N-(4-((N-(4-(2-chloro-5-methylpyrimidin-4-yl)phenyl)-2,4-dihydroxybenzamido)methyl)benzyl)thiophene-2-carboxamide

ID: ALA3732329

PubChem CID: 117972644

Max Phase: Preclinical

Molecular Formula: C31H25ClN4O4S

Molecular Weight: 585.09

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cnc(Cl)nc1-c1ccc(N(Cc2ccc(CNC(=O)c3cccs3)cc2)C(=O)c2ccc(O)cc2O)cc1

Standard InChI:  InChI=1S/C31H25ClN4O4S/c1-19-16-34-31(32)35-28(19)22-8-10-23(11-9-22)36(30(40)25-13-12-24(37)15-26(25)38)18-21-6-4-20(5-7-21)17-33-29(39)27-3-2-14-41-27/h2-16,37-38H,17-18H2,1H3,(H,33,39)

Standard InChI Key:  QTUKYQAPKFQRDT-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3732329

   N-[[4-[[4-(2-chloro-5-methylpyrimidin-4-yl)-N-(2,4-dihydroxybenzoyl)anilino]methyl]phenyl]methyl]thiophene-2-carboxamide

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: 585.09

Molecular Weight (Monoisotopic): 584.1285

AlogP: 6.36

#Rotatable Bonds: 8

Polar Surface Area: 115.65

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.83

CX Basic pKa: 0.29

CX LogP: 6.29

CX LogD: 6.15

Aromatic Rings: 5

Heavy Atoms: 41

QED Weighted: 0.18

Np Likeness Score: -1.49

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