N-benzyl-N-(4-(dimethylcarbamoyl)phenyl)-2,4-dihydroxy-5-methylbenzamide

ID: ALA3728280

PubChem CID: 117972600

Max Phase: Preclinical

Molecular Formula: C24H24N2O4

Molecular Weight: 404.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C(=O)N(Cc2ccccc2)c2ccc(C(=O)N(C)C)cc2)c(O)cc1O

Standard InChI:  InChI=1S/C24H24N2O4/c1-16-13-20(22(28)14-21(16)27)24(30)26(15-17-7-5-4-6-8-17)19-11-9-18(10-12-19)23(29)25(2)3/h4-14,27-28H,15H2,1-3H3

Standard InChI Key:  HSRXRPVIBOXEKS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -7.7903   -1.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4939   -0.7591    0.0000 C   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
    0.0000   -2.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA3728280

   N-benzyl-N-[4-(dimethylcarbamoyl)phenyl]-2,4-dihydroxy-5-methylbenzamide

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: 404.47

Molecular Weight (Monoisotopic): 404.1736

AlogP: 3.96

#Rotatable Bonds: 5

Polar Surface Area: 81.08

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.23

CX Basic pKa: ┄

CX LogP: 3.86

CX LogD: 3.80

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.67

Np Likeness Score: -0.99

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