CHEBI:65427 - ardisianoside C

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ChEBI Name ardisianoside C
ChEBI ID CHEBI:65427
Definition A triterpenoid saponin that is composed of (3β,16α)-13,28-epoxyoleanane-3,16-diol having a α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-α-L-Arap moiety attached at position 3 by a glycosidic linkage. It is isolated from the whole plants of Ardisia japonica and exhibits significant cytotoxicity against a panel of human cancer cell lines.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C47H78O16
Net Charge 0
Average Mass 899.11260
Monoisotopic Mass 898.52899
InChI InChI=1S/C47H78O16/c1-22-30(50)33(53)36(56)39(59-22)63-37-34(54)31(51)23(19-48)60-40(37)61-24-20-57-38(35(55)32(24)52)62-29-11-12-43(6)25(42(29,4)5)9-13-44(7)26(43)10-14-47-27-17-41(2,3)15-16-46(27,21-58-47)28(49)18-45(44,47)8/h22-40,48-56H,9-21H2,1-8H3/t22-,23+,24-,25-,26+,27+,28+,29-,30-,31+,32-,33+,34-,35+,36+,37+,38-,39-,40-,43-,44+,45-,46+,47-/m0/s1
InChIKey HERCSTJVHFDRGB-JTWYRERBSA-N
SMILES [H][C@@]12CC[C@]3(C)[C@]([H])(CC[C@]45OC[C@@]6(CCC(C)(C)C[C@@]46[H])[C@H](O)C[C@@]35C)[C@@]1(C)CC[C@H](O[C@@H]1OC[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@H](O)[C@H]1O)C2(C)C
Metabolite of Species Details
Ardisia japonica (NCBI:txid276775) Found in whole plant (BTO:0001461). 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 ardisianoside C (CHEBI:65427) has functional parent (3β,16α)-13,28-epoxyoleanane-3,16-diol (CHEBI:70987)
ardisianoside C (CHEBI:65427) has parent hydride oleanane (CHEBI:36481)
ardisianoside C (CHEBI:65427) has role antineoplastic agent (CHEBI:35610)
ardisianoside C (CHEBI:65427) has role plant metabolite (CHEBI:76924)
ardisianoside C (CHEBI:65427) is a bridged compound (CHEBI:35990)
ardisianoside C (CHEBI:65427) is a cyclic ether (CHEBI:37407)
ardisianoside C (CHEBI:65427) is a hexacyclic triterpenoid (CHEBI:70994)
ardisianoside C (CHEBI:65427) is a secondary alcohol (CHEBI:35681)
ardisianoside C (CHEBI:65427) is a trisaccharide derivative (CHEBI:63571)
ardisianoside C (CHEBI:65427) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name
(3β,16α)-16-hydroxy-13,28-epoxyoleanan-3-yl 6-deoxy-α-L-mannopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranoside
Synonyms Sources
3β-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl-13β,28-epoxy-16α-hydroxyoleanane ChEBI
3β-O-α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-α-L-Arap-13β,28-epoxy-16α-hydroxyoleanane ChEBI
Registry Number Type Source
22932248 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17243725 PubMed citation Europe PMC
22940450 PubMed citation Europe PMC
Last Modified
20 January 2014