EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:10552 - epi-tulipinolide

ChEBI IDCHEBI:10552
ChEBI Nameepi-tulipinolide
Stars
ASCII Nameepi-tulipinolide
DefinitionA germacranolide with formula C17H22O4, originally isolated from Liriodendron tulipifera. It exhibits anti-cancer and anti-oxidant properties.
Last Modified14 August 2017
DownloadsMolfile
FormulaC17H22O4
Net Charge0
Average Mass290.359
Monoisotopic Mass290.15181
SMILES[H][C@@]12/C=C(\C)CC/C=C(\C)C[C@@H](OC(C)=O)[C@@]1([H])C(=C)C(=O)O2
InChIInChI=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
InChIKeyUPNVKIZABMRHNR-PWCAFIOLSA-N
Species of MetaboliteComponentSourceComments
Apis cerana (ncbitaxon:7461) - MetaboLights (MTBLS379)
Liriodendron chinense (ncbitaxon:3414) - Article (Acta Botanica Yunnanica 23(1): 115-120, 134)
Liriodendron tulipifera (ncbitaxon:3415) leaf (BTO:0000713) PubMed (24705566)
Paramichelia baillonii (ncbitaxon:86754) - Article (Acta Botanica Yunnanica 23(1): 115-120, 134)
Roles Classification
Chemical Role:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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  Source
epitulipinolideChEBI
Eupatolide acetateChemIDplus
Manual XrefsDatabases
4444839ChemSpider
C00003379KNApSAcK
C09566KEGG COMPOUND
Registry NumbersSources
Reaxys:1626294Reaxys
CAS:24164-13-4KEGG COMPOUND
CAS:24164-13-4ChemIDplus
Citations