N-((1H-imidazol-4-yl)methyl)-5-chloro-N-(4-(dimethylcarbamoyl)phenyl)-2,4-dihydroxybenzamide

ID: ALA3732408

PubChem CID: 127037321

Max Phase: Preclinical

Molecular Formula: C20H19ClN4O4

Molecular Weight: 414.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)C(=O)c1ccc(N(Cc2c[nH]cn2)C(=O)c2cc(Cl)c(O)cc2O)cc1

Standard InChI:  InChI=1S/C20H19ClN4O4/c1-24(2)19(28)12-3-5-14(6-4-12)25(10-13-9-22-11-23-13)20(29)15-7-16(21)18(27)8-17(15)26/h3-9,11,26-27H,10H2,1-2H3,(H,22,23)

Standard InChI Key:  RGBARTAXHIZUBY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3383   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024    2.6977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8964   -0.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1931   -1.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1885   -3.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8871   -3.7554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5904   -3.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -1.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8793   -5.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5762   -6.0007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9156   -5.8612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5700   -7.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5399   -5.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8525    1.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8524    0.2390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0978   -1.0574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6317   -0.7404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  3  8  1  0
  4  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  6 20  1  0
 17 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
 22 25  1  0
 13 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3732408

   ---

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: 414.85

Molecular Weight (Monoisotopic): 414.1095

AlogP: 3.02

#Rotatable Bonds: 5

Polar Surface Area: 109.76

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.05

CX Basic pKa: 6.17

CX LogP: 1.53

CX LogD: 1.30

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.59

Np Likeness Score: -1.18

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