CHEBI:69606 - clethroidoside F

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ChEBI Name clethroidoside F
ChEBI ID CHEBI:69606
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C56H90O25
Net Charge 0
Average Mass 1163.29880
Monoisotopic Mass 1162.57712
InChI InChI=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
InChIKey HHORBZPRWXKSQO-LKWZKNPLSA-N
SMILES CC(=O)O[C@H]1[C@H](OC(C)=O)C(C)(C)C[C@@H]2[C@]11CO[C@@]22CC[C@@H]3[C@@]4(C)CC[C@H](O[C@@H]5OC[C@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O[C@@H]6OC[C@@H](O)[C@H](O)[C@H]6O)[C@H](O)[C@H]5O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C(C)(C)[C@@H]4CC[C@@]3(C)[C@]2(C)C[C@H]1O
Metabolite of Species Details
Lysimachia clethroides (NCBI:txid167892) Found in aerial part (BTO:0001658). Air-dried, powdered aerial parts were extracted with 70% aqueous ethyl alcohol. 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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via saponin )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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-tetrahydroxyoleanane ChEBI
Registry Number Type Source
21856528 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21928797 PubMed citation Europe PMC
Last Modified
20 January 2014