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
References
1. Appendino G, Cascio MG, Bacchiega S, Moriello AS, Minassi A, Thomas A, Ross R, Pertwee R, De Petrocellis L, Di Marzo V. (2006)
First "hybrid" ligands of vanilloid TRPV1 and cannabinoid CB2 receptors and non-polyunsaturated fatty acid-derived CB2-selective ligands.
FEBS Lett., 580 (2): 568-74. [PMID:16406364]
2. Appendino G, De Petrocellis L, Trevisani M, Minassi A, Daddario N, Moriello AS, Gazzieri D, Ligresti A, Campi B, Fontana G et al.. (2005)
Development of the first ultra-potent "capsaicinoid" agonist at transient receptor potential vanilloid type 1 (TRPV1) channels and its therapeutic potential.
J. Pharmacol. Exp. Ther., 312 (2): 561-70. [PMID:15356216]
3. Luviano A, Aguiñiga-Sánchez I, Demare P, Tiburcio R, Ledesma-Martínez E, Santiago-Osorio E, Regla I. (2014)
Antineoplastic activity of rinvanil and phenylacetylrinvanil in leukaemia cell lines.
Oncol Lett, 7 (5): 1651-1656. [PMID:24765194]
4. Sánchez-Sánchez L, Alvarado-Sansininea JJ, Escobar ML, López-Muñoz H, Hernández-Vázquez JM, Monsalvo-Montiel I, Demare P, Regla I, Weiss-Steider B. (2015)
Evaluation of the antitumour activity of Rinvanil and Phenylacetylrinvanil on the cervical cancer tumour cell lines HeLa, CaSKi and ViBo.
Eur. J. Pharmacol., 758: 129-36. [PMID:25864613]