CHEBI:69604 - clethroidoside D

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ChEBI Name clethroidoside D
ChEBI ID CHEBI:69604
Definition A triterpenoid saponin that is (3β)-3-hydroxy-13,28-epoxyoleanan-16-one 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
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Formula C52H84O21
Net Charge 0
Average Mass 1045.21080
Monoisotopic Mass 1044.55051
InChI InChI=1S/C52H84O21/c1-46(2)14-15-51-22-67-52(29(51)16-46)13-9-28-48(5)11-10-31(47(3,4)27(48)8-12-49(28,6)50(52,7)17-30(51)56)71-44-40(73-43-39(64)36(61)33(58)24(18-53)68-43)35(60)26(21-66-44)70-45-41(37(62)34(59)25(19-54)69-45)72-42-38(63)32(57)23(55)20-65-42/h23-29,31-45,53-55,57-64H,8-22H2,1-7H3/t23-,24-,25-,26+,27+,28-,29-,31+,32+,33-,34-,35+,36+,37+,38-,39-,40-,41-,42+,43+,44+,45+,48+,49-,50+,51-,52+/m1/s1
InChIKey LXYNMISGVPYMHU-LGZUVIOGSA-N
SMILES CC1(C)CC[C@]23CO[C@@]4(CC[C@@H]5[C@@]6(C)CC[C@H](O[C@@H]7OC[C@H](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O[C@@H]8OC[C@@H](O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)C(C)(C)[C@@H]6CC[C@@]5(C)[C@]4(C)CC2=O)[C@@H]3C1
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 D (CHEBI:69604) has parent hydride oleanane (CHEBI:36481)
clethroidoside D (CHEBI:69604) has role antineoplastic agent (CHEBI:35610)
clethroidoside D (CHEBI:69604) has role plant metabolite (CHEBI:76924)
clethroidoside D (CHEBI:69604) is a cyclic ether (CHEBI:37407)
clethroidoside D (CHEBI:69604) is a cyclic terpene ketone (CHEBI:36130)
clethroidoside D (CHEBI:69604) is a hexacyclic triterpenoid (CHEBI:70994)
clethroidoside D (CHEBI:69604) is a tetrasaccharide derivative (CHEBI:63567)
clethroidoside D (CHEBI:69604) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name
(3β)-16-oxo-13,28-epoxyoleanan-3-yl β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranoside
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-3β-hydroxyolean-16-one ChEBI
Registry Number Type Source
22007804 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
21928797 PubMed citation Europe PMC
Last Modified
20 January 2014