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CHEBI:69606 - clethroidoside F

ChEBI IDCHEBI:69606
ChEBI Nameclethroidoside F
Stars
DefinitionA triterpenoid saponin that is 3,16-dihydroxy-13,28-epoxyoleanane-21,22-diyl diacetate attached to a tetrasaccharide residue at position 3 via a glycosidic linkage. Isolated from the aerial parts of Lysimachia clethroides, it exhibits antineoplastic activity.
Last Modified20 January 2014
DownloadsMolfile
FormulaC56H90O25
Net Charge0
Average Mass1163.311
Monoisotopic Mass1162.57712
SMILES[H][C@@]1(O[C@@H]2[C@@H](O)[C@@]([H])(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@]3([H])O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3O)CO[C@@]2([H])O[C@H]2CC[C@]3(C)[C@@]4([H])CC[C@@]56OC[C@]7([C@H](O)C[C@@]5(C)[C@]4(C)CC[C@@]3([H])C2(C)C)[C@@H](OC(C)=O)[C@H](OC(C)=O)C(C)(C)C[C@]76[H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChIInChI=1S/C56H90O25/c1-23(59)74-44-45(75-24(2)60)55-22-73-56(31(55)16-50(44,3)4)15-11-30-52(7)13-12-33(51(5,6)29(52)10-14-53(30,8)54(56,9)17-32(55)62)79-48-42(81-47-41(70)38(67)35(64)26(18-57)76-47)37(66)28(21-72-48)78-49-43(39(68)36(65)27(19-58)77-49)80-46-40(69)34(63)25(61)20-71-46/h25-49,57-58,61-70H,10-22H2,1-9H3/t25-,26-,27-,28+,29+,30-,31-,32-,33+,34+,35-,36-,37+,38+,39+,40-,41-,42-,43-,44+,45+,46+,47+,48+,49+,52+,53-,54+,55+,56+/m1/s1
InChIKeyHHORBZPRWXKSQO-LKWZKNPLSA-N
Species of MetaboliteComponentSourceComments
Lysimachia clethroides (ncbitaxon:167892) aerial part (BTO:0001658) PubMed (21928797) Air-dried, powdered aerial parts were extracted with 70% aqueous ethyl alcohol.
Roles Classification
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
clethroidoside F (CHEBI:69606) has parent hydride oleanane (CHEBI:36481)
clethroidoside F (CHEBI:69606) has role antineoplastic agent (CHEBI:35610)
clethroidoside F (CHEBI:69606) has role plant metabolite (CHEBI:76924)
clethroidoside F (CHEBI:69606) is a acetate ester (CHEBI:47622)
clethroidoside F (CHEBI:69606) is a cyclic ether (CHEBI:37407)
clethroidoside F (CHEBI:69606) is a hexacyclic triterpenoid (CHEBI:70994)
clethroidoside F (CHEBI:69606) is a secondary alcohol (CHEBI:35681)
clethroidoside F (CHEBI:69606) is a tetrasaccharide derivative (CHEBI:63567)
clethroidoside F (CHEBI:69606) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name 
(3β,16α,21β,22α)-3-{[β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl]oxy}-16-hydroxy-13,28-epoxyoleanane-21,22-diyl diacetate
Synonym  Source
3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl-13β,28-epoxy-21,22-diacetyl-3β,16α,21β,22α-tetrahydroxyoleananeChEBI
Registry NumbersSources
Reaxys:21856528Reaxys
Citations