CHEBI:65426 - ardisianoside B

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ChEBI Name ardisianoside B
ChEBI ID CHEBI:65426
Definition A triterpenoid saponin that is composed of (3β,16α)-13,28-epoxyoleanane-3,16-diol having a β-D-Glcp-(1→2)-{β-D-Xylp-(1→2)-[β-D-Glcp-(1→3)-β-D-Glcp-(1→3)]-β-D-Glcp-(1→4)}-α-L-Arap moiety attached to 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 C64H106O31
Net Charge 0
Average Mass 1371.50780
Monoisotopic Mass 1370.67181
InChI InChI=1S/C64H106O31/c1-58(2)14-15-63-24-85-64(33(63)16-58)13-9-32-60(5)11-10-35(59(3,4)31(60)8-12-61(32,6)62(64,7)17-34(63)70)91-56-50(94-54-46(81)43(78)38(73)27(19-66)87-54)41(76)30(23-84-56)90-57-51(95-52-44(79)36(71)25(69)22-83-52)49(40(75)29(21-68)89-57)93-55-47(82)48(39(74)28(20-67)88-55)92-53-45(80)42(77)37(72)26(18-65)86-53/h25-57,65-82H,8-24H2,1-7H3/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+,50-,51-,52+,53+,54+,55+,56+,57+,60+,61-,62+,63-,64+/m1/s1
InChIKey OCSVOVNGBJMZTD-JKDSUZQNSA-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]4O[C@H](CO)[C@@H](O)[C@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@H]4O)[C@H]3O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[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 B (CHEBI:65426) has functional parent (3β,16α)-13,28-epoxyoleanane-3,16-diol (CHEBI:70987)
ardisianoside B (CHEBI:65426) has parent hydride oleanane (CHEBI:36481)
ardisianoside B (CHEBI:65426) has role antineoplastic agent (CHEBI:35610)
ardisianoside B (CHEBI:65426) has role plant metabolite (CHEBI:76924)
ardisianoside B (CHEBI:65426) is a bridged compound (CHEBI:35990)
ardisianoside B (CHEBI:65426) is a cyclic ether (CHEBI:37407)
ardisianoside B (CHEBI:65426) is a hexacyclic triterpenoid (CHEBI:70994)
ardisianoside B (CHEBI:65426) is a hexasaccharide derivative (CHEBI:63565)
ardisianoside B (CHEBI:65426) is a secondary alcohol (CHEBI:35681)
ardisianoside B (CHEBI:65426) is a triterpenoid saponin (CHEBI:61778)
IUPAC Name
(3β,16α)-16-hydroxy-13,28-epoxyoleanan-3-yl β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranoside
Synonyms Sources
3β-O-β-D-Glcp-(1→2)-{β-D-Xylp-(1→2)-[β-D-Glcp-(1→3)-β-D-Glcp-(1→3)]-β-D-Glcp-(1→4)}-α-L-Arap-13β,28-epoxy-16α-hydroxyoleanane ChEBI
3β-O-β-D-glucopyranosyl-(1→2)-{β-D-xylopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)}-α-L-arabinopyranosyl-13β,28-epoxy-16α-hydroxyoleanane ChEBI
Registry Number Type Source
11058762 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
17243725 PubMed citation Europe PMC
Last Modified
20 January 2014