ardisianoside B (CHEBI:65426)

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CHEBI:65426 - ardisianoside B

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ChEBI ID	CHEBI:65426
ChEBI Name	ardisianoside B
Stars
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.
Last Modified	20 January 2014
Downloads	Molfile

Formula	C64H106O31
Net Charge	0
Average Mass	1371.521
Monoisotopic Mass	1370.67181
SMILES	[H][C@]12CC[C@]34OC[C@@]5(CCC(C)(C)C[C@]53[H])[C@H](O)C[C@@]4(C)[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](O[C@@H]3OC[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]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[C@H]5O)[C@H]4O[C@@H]4OC[C@@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)CC[C@]21C
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

Species of Metabolite	Component	Source	Comments
Ardisia japonica (ncbitaxon:276775)	whole plant (BTO:0001461)	PubMed (17243725)

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)
	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	Source
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
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

Registry Numbers	Sources
Reaxys:11058762	Reaxys

Citations