CHEBI:8809 - resiniferatoxin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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 ZINC000004097440
Download Molfile XML SDF
more structures >>
Wikipedia License
Prednisolone is a corticosteroid, a steroid hormone used to treat certain types of allergies, inflammatory conditions, autoimmune disorders, and cancers, electrolyte imbalances and skin conditions. Some of these conditions include adrenocortical insufficiency, high blood calcium, rheumatoid arthritis, dermatitis, eye inflammation, asthma, multiple sclerosis, and phimosis. It can be taken by mouth, injected into a vein, used topically as a skin cream, or as eye drops. It differs from the similarly named prednisone in having a hydroxyl at the 11th carbon instead of a ketone. Common side effects with short-term use include nausea, difficulty concentrating, insomnia, increased appetite, and fatigue. More severe side effects include psychiatric problems, which may occur in about 5% of people. Common side effects with long-term use include bone loss, weakness, yeast infections, and easy bruising. While short-term use in the later part of pregnancy is safe, long-term use or use in early pregnancy is occasionally associated with harm to the baby. It is a glucocorticoid made from hydrocortisone (cortisol). Prednisolone was discovered and approved for medical use in 1955. It is on the World Health Organization's List of Essential Medicines. It is available as a generic drug. In 2022, it was the 136th most commonly prescribed medication in the United States, with more than 4 million prescriptions.
Read full article at Wikipedia
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 Types Sources
26779292 PubMed citation Europe PMC
27281200 PubMed citation Europe PMC
2747924 PubMed citation Europe PMC
27529257 PubMed citation Europe PMC
29041773 PubMed citation Europe PMC
29271803 PubMed citation Europe PMC
29320813 PubMed citation Europe PMC
29361418 PubMed citation Europe PMC
29672450 PubMed citation Europe PMC
29728656 PubMed citation Europe PMC
30015705 PubMed citation Europe PMC
30399572 PubMed citation Europe PMC
30590777 PubMed citation Europe PMC
31090543 PubMed citation Europe PMC
31124075 PubMed citation Europe PMC
31180583 PubMed citation Europe PMC
31503071 PubMed citation Europe PMC
31811858 PubMed citation Europe PMC
32064609 PubMed citation Europe PMC
32292906 PubMed citation Europe PMC
7189445 PubMed citation Europe PMC
Last Modified
02 September 2021