N-benzyl-2,4-dihydroxy-5-methyl-N-(4-(methyl(quinoxalin-6-ylmethyl)carbamoyl)phenyl)benzamide

ID: ALA3732285

PubChem CID: 117972700

Max Phase: Preclinical

Molecular Formula: C32H28N4O4

Molecular Weight: 532.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C(=O)N(Cc2ccccc2)c2ccc(C(=O)N(C)Cc3ccc4nccnc4c3)cc2)c(O)cc1O

Standard InChI:  InChI=1S/C32H28N4O4/c1-21-16-26(30(38)18-29(21)37)32(40)36(20-22-6-4-3-5-7-22)25-11-9-24(10-12-25)31(39)35(2)19-23-8-13-27-28(17-23)34-15-14-33-27/h3-18,37-38H,19-20H2,1-2H3

Standard InChI Key:  YZZSZNYNWZBIOJ-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3732285

   N-benzyl-2,4-dihydroxy-5-methyl-N-[4-[methyl(quinoxalin-6-ylmethyl)carbamoyl]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: 532.60

Molecular Weight (Monoisotopic): 532.2111

AlogP: 5.47

#Rotatable Bonds: 7

Polar Surface Area: 106.86

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.23

CX Basic pKa: 1.70

CX LogP: 4.91

CX LogD: 4.85

Aromatic Rings: 5

Heavy Atoms: 40

QED Weighted: 0.29

Np Likeness Score: -1.13

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