(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 (CHEBI:66425)

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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 ID	CHEBI:66425
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
Stars
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.
Last Modified	20 January 2014
Downloads	Molfile

Formula	C53H88O21
Net Charge	0
Average Mass	1061.266
Monoisotopic Mass	1060.58181
SMILES	[H][C@@]1(O[C@H]2[C@H](O[C@@]3([H])CO[C@@]([H])(O[C@H]4CC[C@]5(C)[C@@]6([H])CC[C@]78OC[C@@]9(CCC(C)(C)C[C@]97[H])[C@H](O)C[C@@]8(C)[C@]6(C)CC[C@@]5([H])C4(C)C)[C@H](O[C@]4([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H]3O)O[C@H](CO)[C@@H](O)[C@@H]2O)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
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

Species of Metabolite	Component	Source	Comments
Myrsine australis (ncbitaxon:450843)
	leaf (BTO:0000713)	PubMed (7807121)
	twig (BTO:0001411)	PubMed (7807121)
Ardisia japonica (ncbitaxon:276775)	whole plant (BTO:0001461)	PubMed (17243725)
Lysimachia clethroides (ncbitaxon:167892)	aerial part (BTO:0001658)	PubMed (21928797)	Air-dried, powdered aerial parts were extracted with 70% aqueous ethyl alcohol.

Roles Classification

Biological Roles:	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.
Application:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	(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 Numbers	Sources
Reaxys:11058763	Reaxys

Citations