ardisianoside D (CHEBI:65428)

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CHEBI:65428 - ardisianoside D

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ChEBI ID	CHEBI:65428
ChEBI Name	ardisianoside D
Stars
Definition	A triterpenoid saponin that is composed of (3β,16α)-13,28-epoxyoleanane-3,16-diol having a β-D-Xylp-(1→2)-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	C46H76O16
Net Charge	0
Average Mass	885.098
Monoisotopic Mass	884.51334
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]4O[C@@H]4OC[C@@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)CC[C@]21C
InChI	InChI=1S/C46H76O16/c1-40(2)14-15-45-21-58-46(27(45)16-40)13-9-26-42(5)11-10-29(41(3,4)25(42)8-12-43(26,6)44(46,7)17-28(45)49)61-37-35(55)32(52)24(20-57-37)60-39-36(33(53)31(51)23(18-47)59-39)62-38-34(54)30(50)22(48)19-56-38/h22-39,47-55H,8-21H2,1-7H3/t22-,23-,24+,25+,26-,27-,28-,29+,30+,31-,32+,33+,34-,35-,36-,37+,38+,39+,42+,43-,44+,45-,46+/m1/s1
InChIKey	DYAQVNOJMUMVBF-XKXSQMESSA-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 D (CHEBI:65428) has functional parent (3β,16α)-13,28-epoxyoleanane-3,16-diol (CHEBI:70987)
	ardisianoside D (CHEBI:65428) has parent hydride oleanane (CHEBI:36481)
	ardisianoside D (CHEBI:65428) has role antineoplastic agent (CHEBI:35610)
	ardisianoside D (CHEBI:65428) has role plant metabolite (CHEBI:76924)
	ardisianoside D (CHEBI:65428) is a bridged compound (CHEBI:35990)
	ardisianoside D (CHEBI:65428) is a cyclic ether (CHEBI:37407)
	ardisianoside D (CHEBI:65428) is a hexacyclic triterpenoid (CHEBI:70994)
	ardisianoside D (CHEBI:65428) is a secondary alcohol (CHEBI:35681)
	ardisianoside D (CHEBI:65428) is a trisaccharide derivative (CHEBI:63571)
	ardisianoside D (CHEBI:65428) is a triterpenoid saponin (CHEBI:61778)

IUPAC Name
(3β,16α)-16-hydroxy-13,28-epoxyoleanan-3-yl β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranoside

Synonyms	Source
3β-O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl-13β,28-epoxy-16α-hydroxyoleanane	ChEBI
3β-O-β-D-Xylp-(1→2)-β-D-Glcp-(1→4)-α-L-Arap-13β,28-epoxy-16α-hydroxyoleanane	ChEBI

Registry Numbers	Sources
Reaxys:22932249	Reaxys

Citations