CHEBI:8809 - resiniferatoxin

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ChEBI Name resiniferatoxin
ChEBI ID CHEBI:8809
Definition A heteropentacyclic compound found in Euphorbia poissonii with molecular formula C37H40O9. It is an agonist of the transient receptor potential cation channel subfamily V member 1 (TrpV1).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB7304594, eMolecules:715664, eMolecules:11487000, ZINC000004262463
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Wikipedia License
Resiniferatoxin (RTX) is a naturally occurring chemical found in resin spurge (Euphorbia resinifera), a cactus-like plant commonly found in Morocco, and in Euphorbia poissonii found in northern Nigeria. It is a potent functional analog of capsaicin, the active ingredient in chili peppers.
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Formula C37H40O9
Net Charge 0
Average Mass 628.718
Monoisotopic Mass 628.26723
InChI InChI=1S/C37H40O9/c1-21(2)35-17-23(4)37-27(33(35)44-36(45-35,46-37)19-24-9-7-6-8-10-24)14-26(18-34(41)30(37)13-22(3)32(34)40)20-43-31(39)16-25-11-12-28(38)29(15-25)42-5/h6-15,23,27,30,33,38,41H,1,16-20H2,2-5H3/t23-,27+,30-,33-,34-,35-,36-,37-/m1/s1
InChIKey DSDNAKHZNJAGHN-MXTYGGKSSA-N
SMILES C=1(C=C(C(=CC1)O)OC)CC(OCC2=C[C@@]3([C@]4([C@]5([C@](C2)(C(=O)C(=C5)C)O)[H])O[C@]6(O[C@@]([C@@]3(O6)[H])(C(=C)C)C[C@H]4C)CC=7C=CC=CC7)[H])=O
Metabolite of Species Details
Euphorbia poissonii (NCBI:txid212962) See: Book: Harborne, Phytochemical Dictionary Second Edition, Taylor and Francis (1999), Chapter 52.
Euphorbia resinifera (NCBI:txid457265) See: Book: Harborne, Phytochemical Dictionary Second Edition, Taylor and Francis (1999), Chapter 52.
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
neurotoxin
A poison that interferes with the functions of the nervous system.
analgesic
An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
TRPV1 agonist
An agonist at the transient receptor potential vanilloid 1 (TRPV1).
Application(s): analgesic
An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing resiniferatoxin (CHEBI:8809) has role analgesic (CHEBI:35480)
resiniferatoxin (CHEBI:8809) has role neurotoxin (CHEBI:50910)
resiniferatoxin (CHEBI:8809) has role plant metabolite (CHEBI:76924)
resiniferatoxin (CHEBI:8809) has role TRPV1 agonist (CHEBI:140535)
resiniferatoxin (CHEBI:8809) is a carboxylic ester (CHEBI:33308)
resiniferatoxin (CHEBI:8809) is a diterpenoid (CHEBI:23849)
resiniferatoxin (CHEBI:8809) is a enone (CHEBI:51689)
resiniferatoxin (CHEBI:8809) is a monomethoxybenzene (CHEBI:25235)
resiniferatoxin (CHEBI:8809) is a organic heteropentacyclic compound (CHEBI:38164)
resiniferatoxin (CHEBI:8809) is a ortho ester (CHEBI:71989)
resiniferatoxin (CHEBI:8809) is a phenols (CHEBI:33853)
resiniferatoxin (CHEBI:8809) is a tertiary α-hydroxy ketone (CHEBI:139592)
IUPAC Name
[(2S,3aR,3bS,6aR,9aR,9bR,10R,11aR)-2-benzyl-6a-hydroxy-8,10-dimethyl-7-oxo-11a-(prop-1-en-2-yl)-3a,6,6a,7,9a,10,11,11a-octahydro-3bH-2,9b-epoxyazuleno[4',5':5,6]benzo[1,2-d][1,3]dioxol-5-yl]methyl (4-hydroxy-3-methoxyphenyl)acetate
Synonyms Sources
(+)-resiniferatoxin ChEBI
resiniferatoxin KEGG COMPOUND
resiniferatoxin UniProt
RTX ChemIDplus
Manual Xrefs Databases
6EU PDBeChem
C00003478 KNApSAcK
C09179 KEGG COMPOUND
DB06515 DrugBank
Resiniferatoxin Wikipedia
View more database links
Registry Numbers Types Sources
5371150 Reaxys Registry Number Reaxys
57444-62-9 CAS Registry Number ChemIDplus
Citations
Darmani NA, Henry DA, Zhong W, Chebolu S (2020)
Ultra-low doses of the transient receptor potential vanilloid 1 agonist, resiniferatoxin, prevents vomiting evoked by diverse emetogens in the least shrew (Cryptotis parva).
Behavioural pharmacology 31, 3-14 [PubMed:31503071]
[show Abstract]
Wu Y, Hu Z, Wang D, Lv K, Hu N (2020)
Resiniferatoxin reduces ventricular arrhythmias in heart failure via selectively blunting cardiac sympathetic afferent projection into spinal cord in rats.
European journal of pharmacology 867, 172836 [PubMed:31811858]
[show Abstract]
Nahama A, Ramachandran R, Cisternas AF, Ji H (2020)
The role of afferent pulmonary innervation in ARDS associated with COVID-19 and potential use of resiniferatoxin to improve prognosis: A review.
Medicine in drug discovery 5, 100033 [PubMed:32292906]
[show Abstract]
Javed H, Rehmathulla S, Tariq S, Emerald BS, Ljubisavljevic M, Shehab S (2020)
Perineural application of resiniferatoxin on uninjured L3 and L4 nerves completely alleviates thermal and mechanical hypersensitivity following L5 nerve injury in rats.
The Journal of comparative neurology 528, 2195-2217 [PubMed:32064609]
[show Abstract]
Wang D, Wu Y, Chen Y, Wang A, Lv K, Kong X, He Y, Hu N (2019)
Focal selective chemo-ablation of spinal cardiac afferent nerve by resiniferatoxin protects the heart from pressure overload-induced hypertrophy.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie 109, 377-385 [PubMed:30399572]
[show Abstract]
Zubcevic L, Hsu AL, Borgnia MJ, Lee SY (2019)
Symmetry transitions during gating of the TRPV2 ion channel in lipid membranes.
eLife 8, e45779 [PubMed:31090543]
[show Abstract]
Zou J, Dong X, Li Y, Tong S, Wang J, Liao M, Huang G (2019)
Deep Sequencing Identification of Differentially Expressed miRNAs in the Spinal Cord of Resiniferatoxin-Treated Rats in Response to Electroacupuncture.
Neurotoxicity research 36, 387-395 [PubMed:31124075]
[show Abstract]
Oliveira R, Coelho A, Franquinho F, Sousa MM, Cruz F, D Cruz C (2019)
Effects of early intravesical administration of resiniferatoxin to spinal cord-injured rats in neurogenic detrusor overactivity.
Neurourology and urodynamics 38, 1540-1550 [PubMed:31180583]
[show Abstract]
Unger MD, Pleticha J, Steinauer J, Kanwar R, Diehn F, LaVallee KT, Banck MS, Jones B, Yaksh TL, Maus TP, Beutler AS (2019)
Unilateral Epidural Targeting of Resiniferatoxin Induces Bilateral Neurolysis of Spinal Nociceptive Afferents.
Pain medicine (Malden, Mass.) 20, 897-906 [PubMed:30590777]
[show Abstract]
Raithel SJ, Sapio MR, LaPaglia DM, Iadarola MJ, Mannes AJ (2018)
Transcriptional Changes in Dorsal Spinal Cord Persist after Surgical Incision Despite Preemptive Analgesia with Peripheral Resiniferatoxin.
Anesthesiology 128, 620-635 [PubMed:29271803]
[show Abstract]
Zubcevic L, Le S, Yang H, Lee SY (2018)
Conformational plasticity in the selectivity filter of the TRPV2 ion channel.
Nature structural & molecular biology 25, 405-415 [PubMed:29728656]
[show Abstract]
Kan HW, Chang CH, Lin CL, Lee YC, Hsieh ST, Hsieh YL (2018)
Downregulation of adenosine and adenosine A1 receptor contributes to neuropathic pain in resiniferatoxin neuropathy.
Pain 159, 1580-1591 [PubMed:29672450]
[show Abstract]
Iadarola MJ, Sapio MR, Raithel SJ, Mannes AJ, Brown DC (2018)
Long-term pain relief in canine osteoarthritis by a single intra-articular injection of resiniferatoxin, a potent TRPV1 agonist.
Pain 159, 2105-2114 [PubMed:30015705]
[show Abstract]
Hockman TM, Cisternas AF, Jones B, Butt MT, Osborn KG, Steinauer JJ, Malkmus SA, Yaksh TL (2018)
Target engagement and histopathology of neuraxial resiniferatoxin in dog.
Veterinary anaesthesia and analgesia 45, 212-226 [PubMed:29361418]
[show Abstract]
Hashimoto S, Katoh SI, Kato T, Urabe D, Inoue M (2017)
Total Synthesis of Resiniferatoxin Enabled by Radical-Mediated Three-Component Coupling and 7-endo Cyclization.
Journal of the American Chemical Society 139, 16420-16429 [PubMed:29041773]
[show Abstract]
Muñoz-Carrillo JL, Muñoz-López JL, Muñoz-Escobedo JJ, Maldonado-Tapia C, Gutiérrez-Coronado O, Contreras-Cordero JF, Moreno-García MA (2017)
Therapeutic Effects of Resiniferatoxin Related with Immunological Responses for Intestinal Inflammation in Trichinellosis.
The Korean journal of parasitology 55, 587-599 [PubMed:29320813]
[show Abstract]
Gao Y, Cao E, Julius D, Cheng Y (2016)
TRPV1 structures in nanodiscs reveal mechanisms of ligand and lipid action.
Nature 534, 347-351 [PubMed:27281200]
[show Abstract]
Brown DC (2016)
Resiniferatoxin: The Evolution of the "Molecular Scalpel" for Chronic Pain Relief.
Pharmaceuticals (Basel, Switzerland) 9, E47 [PubMed:27529257]
[show Abstract]
Iadarola MJ, Gonnella GL (2013)
Resiniferatoxin for Pain Treatment: An Interventional Approach to Personalized Pain Medicine.
The open pain journal 6, 95-107 [PubMed:26779292]
[show Abstract]
Szallasi A, Blumberg PM (1989)
Resiniferatoxin, a phorbol-related diterpene, acts as an ultrapotent analog of capsaicin, the irritant constituent in red pepper.
Neuroscience 30, 515-520 [PubMed:2747924]
[show Abstract]
Driedger PE, Blumberg PM (1980)
Different biological targets for resiniferatoxin and phorbol 12-myristate 13-acetate.
Cancer research 40, 1400-1404 [PubMed:7189445]
[show Abstract]
Last Modified
02 September 2021