CHEBI:10552 - epi-tulipinolide

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ChEBI Name epi-tulipinolide
ChEBI ID CHEBI:10552
ChEBI ASCII Name epi-tulipinolide
Definition A germacranolide with formula C17H22O4, originally isolated from Liriodendron tulipifera. It exhibits anti-cancer and anti-oxidant properties.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C17H22O4
Net Charge 0
Average Mass 290.355
Monoisotopic Mass 290.15181
InChI InChI=1S/C17H22O4/c1-10-6-5-7-11(2)9-15-16(12(3)17(19)21-15)14(8-10)20-13(4)18/h6,9,14-16H,3,5,7-8H2,1-2,4H3/b10-6+,11-9+/t14-,15-,16-/m1/s1
InChIKey UPNVKIZABMRHNR-PWCAFIOLSA-N
SMILES O1[C@]2([C@](C(C1=O)=C)([C@H](OC(=O)C)CC(=CCCC(=C2)C)C)[H])[H]
Metabolite of Species Details
Liriodendron chinense (NCBI:txid3414) See: Acta Botanica Yunnanica 23(1): 115-120, 134
Liriodendron tulipifera (NCBI:txid3415) Found in leaf (BTO:0000713). See: PubMed
Apis cerana (NCBI:txid7461) See: MetaboLights Study
Paramichelia baillonii (NCBI:txid86754) See: Acta Botanica Yunnanica 23(1): 115-120, 134
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing epi-tulipinolide (CHEBI:10552) has role antineoplastic agent (CHEBI:35610)
epi-tulipinolide (CHEBI:10552) has role antioxidant (CHEBI:22586)
epi-tulipinolide (CHEBI:10552) has role plant metabolite (CHEBI:76924)
epi-tulipinolide (CHEBI:10552) is a acetate ester (CHEBI:47622)
epi-tulipinolide (CHEBI:10552) is a germacranolide (CHEBI:73011)
IUPAC Name
(3aR,4R,6E,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-2,3,3a,4,5,8,9,11a-octahydrocyclodeca[b]furan-4-yl acetate
Synonyms Sources
epitulipinolide ChEBI
Eupatolide acetate ChemIDplus
Manual Xrefs Databases
4444839 ChemSpider
C00003379 KNApSAcK
C09566 KEGG COMPOUND
View more database links
Registry Numbers Types Sources
1626294 Reaxys Registry Number Reaxys
24164-13-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
24705566 PubMed citation Europe PMC
347132 Chinese Abstracts citation Europe PMC
5446985 PubMed citation Europe PMC
Last Modified
14 August 2017