Structure Database (LMSD)
Common Name
N-arachidonoyl vanillylamine
Systematic Name
N-(5Z,8Z,11Z,15Z-eicosatetraenoyl)-vanillylamine
Synonyms
- NAVA
LM ID
LMFA08020154
Formula
Exact Mass
Calculate m/z
439.308644
Sum Composition
Status
Curated
3D model of N-arachidonoyl vanillylamine
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Arvanil is a structural analog of capsaicin, which is the noxious active component of hot peppers of the Capsicum family. It is the amide of vanillylamine and arachidonic acid. Arvanil induces analgesia in rat and mouse models of pain.1 Arvanil has complex interactions with the cannabinoid system, in that it potentiates the agonist activity of endogenous cannabinoids by inhibiting the reuptake of arachidonoyl ethanolamide (AEA). It is an agonist at CB1 (Ki values of 0.25 to 0.52 μM), but not CB2, receptors, and is resistant to hydrolysis by FAAH.2 The vasodilator, analgesic, and anti-inflammatory properties of arvanil are not clearly explained by its interactions with cannabinoid and vanilloid receptors, suggesting other possible sites of action.
This information has been provided by Cayman Chemical
References
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Homo sapiens
(#9606)
Mammalia
(#40674)
Endocannabinoid Oxygenation by Cyclooxygenases, Lipoxygenases, and Cytochromes P450: Cross-Talk between the Eicosanoid and Endocannabinoid Signaling Pathways,
Chem Rev, 2011
Chem Rev, 2011
Pubmed ID:
21923193
DOI:
10.1021/cr2002799
String Representations
InChiKey (Click to copy)
QVLMCRFQGHWOPM-ZKWNWVNESA-N
InChi (Click to copy)
InChI=1S/C28H41NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-28(31)29-24-25-21-22-26(30)27(23-25)32-2/h7-8,10-11,13-14,16-17,21-23,30H,3-6,9,12,15,18-20,24H2,1-2H3,(H,29,31)/b8-7-,11-10-,14-13-,17-16-
SMILES (Click to copy)
C(/C/C=C\C/C=C\CCCCC)=C/C/C=C\CCCC(=O)NCC1C=C(OC)C(O)=CC=1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
32
Rings
1
Aromatic Rings
1
Rotatable Bonds
17
Van der Waals Molecular Volume
485.95
Topological Polar Surface Area
58.56
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
7.16
Molar Refractivity
134.91
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