CHEBI:68932 - yadanziolide B

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ChEBI Name yadanziolide B
ChEBI ID CHEBI:68932
Definition A quassinoid that is 13,20-epoxypicras-3-ene substituted by hydroxy groups at positions 1, 6, 11, 12, 14, 15 and 21 and oxo groups at positions 2 and 16. Isolated from the ethanol extract of the stem of Brucea mollis, it exhibits cytotoxic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C20H26O11
Net Charge 0
Average Mass 442.41380
Monoisotopic Mass 442.14751
InChI InChI=1S/C20H26O11/c1-6-3-7(22)12(25)17(2)8(6)9(23)15-18-5-30-19(4-21,13(26)10(24)11(17)18)20(18,29)14(27)16(28)31-15/h3,8-15,21,23-27,29H,4-5H2,1-2H3/t8-,9-,10-,11-,12-,13+,14+,15-,17+,18+,19-,20+/m1/s1
InChIKey QPBBQXZJTIVCTO-VWXLKGNHSA-N
SMILES CC1=CC(=O)[C@@H](O)[C@@]2(C)[C@H]1[C@@H](O)[C@H]1OC(=O)[C@H](O)[C@@]3(O)[C@]4(CO)OC[C@]13[C@@H]2[C@@H](O)[C@@H]4O
Metabolite of Species Details
Brucea mollis (NCBI:txid43723) Found in stem (BTO:0001300). Ethanolic extract of air-dried and powdered stems 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.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing yadanziolide B (CHEBI:68932) has parent hydride picrasane (CHEBI:36506)
yadanziolide B (CHEBI:68932) has role antineoplastic agent (CHEBI:35610)
yadanziolide B (CHEBI:68932) has role plant metabolite (CHEBI:76924)
yadanziolide B (CHEBI:68932) is a δ-lactone (CHEBI:18946)
yadanziolide B (CHEBI:68932) is a enone (CHEBI:51689)
yadanziolide B (CHEBI:68932) is a heptol (CHEBI:62610)
yadanziolide B (CHEBI:68932) is a organic heteropentacyclic compound (CHEBI:38164)
yadanziolide B (CHEBI:68932) is a quassinoid (CHEBI:72485)
yadanziolide B (CHEBI:68932) is a secondary α-hydroxy ketone (CHEBI:2468)
IUPAC Name
(1β,6α,11β,12α,15β)-1,6,11,12,14,15,21-heptahydroxy-13,20-epoxypicras-3-ene-2,16-dione
Registry Number Type Source
5664336 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22070654 PubMed citation Europe PMC
Last Modified
06 February 2018