N-benzyl-5-chloro-2,4-dihydroxy-N-(4-(3-methyl-5-(N-(pyridin-3-ylmethyl)sulfamoyl)pyridin-2-yl)phenyl)benzamide

ID: ALA3730222

PubChem CID: 117972803

Max Phase: Preclinical

Molecular Formula: C32H27ClN4O5S

Molecular Weight: 615.11

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(S(=O)(=O)NCc2cccnc2)cnc1-c1ccc(N(Cc2ccccc2)C(=O)c2cc(Cl)c(O)cc2O)cc1

Standard InChI:  InChI=1S/C32H27ClN4O5S/c1-21-14-26(43(41,42)36-18-23-8-5-13-34-17-23)19-35-31(21)24-9-11-25(12-10-24)37(20-22-6-3-2-4-7-22)32(40)27-15-28(33)30(39)16-29(27)38/h2-17,19,36,38-39H,18,20H2,1H3

Standard InChI Key:  FKHMXABMILEREF-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3730222

   N-benzyl-5-chloro-2,4-dihydroxy-N-[4-[3-methyl-5-(pyridin-3-ylmethylsulfamoyl)pyridin-2-yl]phenyl]benzamide

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: 615.11

Molecular Weight (Monoisotopic): 614.1391

AlogP: 5.84

#Rotatable Bonds: 9

Polar Surface Area: 132.72

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.99

CX Basic pKa: 4.81

CX LogP: 5.32

CX LogD: 4.73

Aromatic Rings: 5

Heavy Atoms: 43

QED Weighted: 0.19

Np Likeness Score: -1.44

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