compound 5a [PMID: 27536893]   

GtoPdb Ligand ID: 9300

Compound class: Synthetic organic
Comment: Compound 5a causes microtubule fragmentation via modulation of the hydrolase activity of katanin [1]. The precise binding site has not been determined, but could reside within catalytic site of KATNA1 (p60 subunit) due to the purine scaffold of 5a. A docking model suggests that 5a may bind in a position which stabilizes the p60 structure and enhances the microtubule severing activity of katanin.
Katanin-modulating compounds could provide an alternative to vinca alkaloid and taxane microtubule targeting agents (MTAs), which suffer from issues of drug-induced resistance developing in clinical use.
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 124.6
Molecular weight 405.14
XLogP 2.29
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCOc1ccc(cc1)c1nc(C(=O)N)c2c(n1)n(c(=O)[nH]2)c1ccccc1OC
Isomeric SMILES CCOc1ccc(cc1)c1nc(C(=O)N)c2c(n1)n(c(=O)[nH]2)c1ccccc1OC
InChI InChI=1S/C21H19N5O4/c1-3-30-13-10-8-12(9-11-13)19-23-16(18(22)27)17-20(25-19)26(21(28)24-17)14-6-4-5-7-15(14)29-2/h4-11H,3H2,1-2H3,(H2,22,27)(H,24,28)
InChI Key FFKCRLSRMMVTAN-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
IUPAC Name
2-(4-ethoxyphenyl)-9-(2-methoxyphenyl)-8-oxo-7H-purine-6-carboxamide
Comments
Compound 5a causes microtubule fragmentation via modulation of the hydrolase activity of katanin [1]. The precise binding site has not been determined, but could reside within catalytic site of KATNA1 (p60 subunit) due to the purine scaffold of 5a. A docking model suggests that 5a may bind in a position which stabilizes the p60 structure and enhances the microtubule severing activity of katanin.
Katanin-modulating compounds could provide an alternative to vinca alkaloid and taxane microtubule targeting agents (MTAs), which suffer from issues of drug-induced resistance developing in clinical use.
Database Links
GtoPdb PubChem SID 318164819
PubChem CID 7196946
Search Google for chemical match using the InChIKey FFKCRLSRMMVTAN-UHFFFAOYSA-N
Search Google for chemicals with the same backbone FFKCRLSRMMVTAN
Search UniChem for chemical match using the InChIKey FFKCRLSRMMVTAN-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone FFKCRLSRMMVTAN