CHEBI:66425 - (3β,16α)-16-hydroxy-13,28-epoxyoleanan-3-yl α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-arabinopyranoside

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ChEBI Name (3β,16α)-16-hydroxy-13,28-epoxyoleanan-3-yl α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-arabinopyranoside
ChEBI ID CHEBI:66425
ChEBI ASCII Name (3beta,16alpha)-16-hydroxy-13,28-epoxyoleanan-3-yl alpha-L-Rhap-(1->2)-beta-D-Glcp-(1->4)-[beta-D-Glcp-(1->2)]-alpha-L-arabinopyranoside
Definition A triterpenoid saponin isolated from Myrsine australis and Ardisia japonica and has been shown to exhibit antineoplastic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C53H88O21
Net Charge 0
Average Mass 1061.25320
Monoisotopic Mass 1060.58181
InChI InChI=1S/C53H88O21/c1-23-32(57)36(61)39(64)43(68-23)74-42-38(63)34(59)25(20-55)70-46(42)71-26-21-66-45(41(35(26)60)73-44-40(65)37(62)33(58)24(19-54)69-44)72-31-11-12-49(6)27(48(31,4)5)9-13-50(7)28(49)10-14-53-29-17-47(2,3)15-16-52(29,22-67-53)30(56)18-51(50,53)8/h23-46,54-65H,9-22H2,1-8H3/t23-,24+,25+,26-,27-,28+,29+,30+,31-,32-,33+,34+,35-,36+,37-,38-,39+,40+,41+,42+,43-,44-,45-,46-,49-,50+,51-,52+,53-/m0/s1
InChIKey MIBQGVWGYOOZBJ-ZDFBONGQSA-N
SMILES [H][C@@]1(CO[C@@]([H])(O[C@H]2CC[C@@]3(C)[C@@]([H])(CC[C@]4(C)[C@]3([H])CC[C@]35OC[C@@]6(CCC(C)(C)C[C@@]36[H])[C@H](O)C[C@@]45C)C2(C)C)[C@H](O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@]1([H])O[C@@H](C)[C@H](O)[C@@H](O)[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
Ardisia japonica (NCBI:txid276775) Found in whole plant (BTO:0001461). See: PubMed
Myrsine australis (NCBI:txid450843) Found in leaf (BTO:0000713). See: PubMed
Myrsine australis (NCBI:txid450843) Found in twig (BTO:0001411). 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.
(via (3beta,16alpha)-16-hydroxy-13,28-epoxyoleanan-3-yl alpha-L-Rhap-(1->2)-beta-D-Glcp-(1->4)-[beta-D-Glcp-(1->2)]-alpha-L-arabinopyranoside )
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.
(via (3beta,16alpha)-16-hydroxy-13,28-epoxyoleanan-3-yl alpha-L-Rhap-(1->2)-beta-D-Glcp-(1->4)-[beta-D-Glcp-(1->2)]-alpha-L-arabinopyranoside )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (3β,16α)-16-hydroxy-13,28-epoxyoleanan-3-yl α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-arabinopyranoside (CHEBI:66425) has role antineoplastic agent (CHEBI:35610)
(3β,16α)-16-hydroxy-13,28-epoxyoleanan-3-yl α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-arabinopyranoside (CHEBI:66425) has role plant metabolite (CHEBI:76924)
(3β,16α)-16-hydroxy-13,28-epoxyoleanan-3-yl α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-arabinopyranoside (CHEBI:66425) is a bridged compound (CHEBI:35990)
(3β,16α)-16-hydroxy-13,28-epoxyoleanan-3-yl α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-arabinopyranoside (CHEBI:66425) is a hexacyclic triterpenoid (CHEBI:70994)
(3β,16α)-16-hydroxy-13,28-epoxyoleanan-3-yl α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-arabinopyranoside (CHEBI:66425) is a tetrasaccharide derivative (CHEBI:63567)
(3β,16α)-16-hydroxy-13,28-epoxyoleanan-3-yl α-L-Rhap-(1→2)-β-D-Glcp-(1→4)-[β-D-Glcp-(1→2)]-α-L-arabinopyranoside (CHEBI:66425) 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)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranoside
Registry Number Type Source
11058763 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17243725 PubMed citation Europe PMC
21928797 PubMed citation Europe PMC
7807121 PubMed citation Europe PMC
Last Modified
20 January 2014