VCE-004.3   

GtoPdb Ligand ID: 10030

Compound class: Synthetic organic
Comment: VCE-004.3 is a semi-synthetic cannabidiol quinone derivative [2]. It acts as a dual PPARγ/CB2 receptor agonist and CB1 receptor modulator. The structure is claimed in patent WO2015158381 [1]. VCE-004.3 is functional (promotes transactivation) on PPARγ via a binding site that is distinct from the canonical rosiglitazone binding site on this nuclear receptor.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 11
Topological polar surface area 66.4
Molecular weight 413.29
XLogP 7.3
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES CCCCCNC1=C(CCCCC)C(=O)C(=O)C(=C1O)C1C=C(C)CCC1C(=C)C
Isomeric SMILES CCCCCNC1=C(CCCCC)C(=O)C(=O)C(=C1O)[C@@H]1C=C(C)CC[C@H]1C(=C)C
InChI InChI=1S/C26H39NO3/c1-6-8-10-12-20-23(27-15-11-9-7-2)25(29)22(26(30)24(20)28)21-16-18(5)13-14-19(21)17(3)4/h16,19,21,27,29H,3,6-15H2,1-2,4-5H3/t19-,21+/m0/s1
InChI Key CIEWIZBPWBLHSB-PZJWPPBQSA-N
Classification
Compound class Synthetic organic
IUPAC Name
4-hydroxy-3-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-6-pentyl-5-(pentylamino)cyclohexa-3,5-diene-1,2-dione
Database Links
GtoPdb PubChem SID 375973218
PubChem CID 91972027
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