CHEBI:132386 - wilformine

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ChEBI Name wilformine
ChEBI ID CHEBI:132386
Definition A sesquiterpene alkaloid that has been isolated from Tripterygium wilfordii and exhibits immunosuppressive and insecticidal properties. It was found to be identical with euonine, previously isolated from Euonymous sieboldiana.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter qingping liu
qingping liu
Secondary ChEBI IDs CHEBI:132514
Supplier Information
Download Molfile XML SDF
Formula C38H47NO18
Net Charge 0
Average Mass 805.777
Monoisotopic Mass 805.27931
InChI InChI=1S/C38H47NO18/c1-17-12-13-25-24(11-10-14-39-25)34(47)50-15-35(8)26-27(51-19(3)41)31(54-22(6)44)37(16-49-18(2)40)32(55-23(7)45)28(52-20(4)42)30(56-33(17)46)36(9,48)38(37,57-35)29(26)53-21(5)43/h10-11,14,17,26-32,48H,12-13,15-16H2,1-9H3/t17-,26+,27+,28-,29+,30-,31+,32-,35-,36-,37+,38-/m0/s1
InChIKey QIHHQEWWGMEJTH-VWEYKOQISA-N
SMILES [C@@H]1([C@H]([C@@]2([C@@H](OC(=O)C)[C@H]([C@]3([C@]([C@]42[C@H](OC(=O)C)[C@]1([H])[C@@](COC(=O)C5=C(N=CC=C5)CC[C@@H](C(O3)=O)C)(C)O4)(C)O)[H])OC(C)=O)COC(=O)C)OC(=O)C)OC(C)=O
Metabolite of Species Details
Peritassa campestris (NCBI:txid123445) Found in root (BTO:0001188). See: PubMed
Tripterygium wilfordii (NCBI:txid458696) See: PubMed
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.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
insecticide
Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing wilformine (CHEBI:132386) has role immunosuppressive agent (CHEBI:35705)
wilformine (CHEBI:132386) has role insecticide (CHEBI:24852)
wilformine (CHEBI:132386) has role plant metabolite (CHEBI:76924)
wilformine (CHEBI:132386) is a acetate ester (CHEBI:47622)
wilformine (CHEBI:132386) is a dihydroagarofuran sesquiterpenoid (CHEBI:71548)
wilformine (CHEBI:132386) is a macrolide (CHEBI:25106)
wilformine (CHEBI:132386) is a pyridine alkaloid (CHEBI:26416)
wilformine (CHEBI:132386) is a sesquiterpene alkaloid (CHEBI:26657)
Synonyms Sources
(8alpha)-8-(Acetyloxy)-8-deoxoevonimine KNApSAcK
Euonine KNApSAcK
Manual Xrefs Databases
101335373 PubChem
C00013118 KNApSAcK
FR2728466 Patent
WO9113627 Patent
View more database links
Registry Numbers Types Sources
41758-69-4 CAS Registry Number KNApSAcK
5418533 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11738408 PubMed citation Europe PMC
12579877 PubMed citation Europe PMC
14738378 PubMed citation Europe PMC
16933883 PubMed citation Europe PMC
18998413 PubMed citation Europe PMC
23852638 PubMed citation Europe PMC
2618700 PubMed citation Europe PMC
Last Modified
21 November 2017