phenylacetylrinvanil   

GtoPdb Ligand ID: 4283

Synonyms: 12-Phenylacetyl-ricinoleoyl-vanillamide [1] | compound 1e [PMID: 15356216] | IDN5890 | PhAR
Compound class: Synthetic organic
Comment: Phenylacetylrinvanil is a 'capsaicinoid' type compound that is a potent agonist/activator at the transient receptor potential vanilloid type 1 (TRPV1) channel [2]. Structurally it is a hybrid molecule that combines a vanillamide TRPV1 agonist with a non-polyunsaturated fatty acid-derived cannabinoid CB2 receptor-selective ligand. Phenylacetylrinvanil has demonstrated some antineoplastic activity against leukaemia cells in vitro and in vivo [3] and against cervical cancer tumour cell lines [4].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 23
Topological polar surface area 84.86
Molecular weight 551.36
XLogP 9.12
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES CCCCCCC(OC(=O)Cc1ccccc1)CC=CCCCCCCCC(=O)NCc1ccc(c(c1)OC)O
Isomeric SMILES CCCCCC[C@@H](OC(=O)Cc1ccccc1)C/C=C/CCCCCCCC(=O)NCc1ccc(c(c1)OC)O
InChI InChI=1S/C34H49NO5/c1-3-4-5-15-20-30(40-34(38)26-28-18-13-12-14-19-28)21-16-10-8-6-7-9-11-17-22-33(37)35-27-29-23-24-31(36)32(25-29)39-2/h10,12-14,16,18-19,23-25,30,36H,3-9,11,15,17,20-22,26-27H2,1-2H3,(H,35,37)/b16-10+/t30-/m1/s1
InChI Key LXLBUUJANYSIKU-SSBKBLCMSA-N
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CB2 receptor Hs Agonist Agonist 6.5 pKi - 2
pKi 6.5 (Ki 3x10-7 M) [2]
Description: Binding affinity for recombinant human CB2 receptors expressed in COS cells, displacing [3H]-CP-55,940.
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
TRPV1 Hs Activator - - - - 2
[2]