clethroidoside B (CHEBI:69602)

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CHEBI:69602 - clethroidoside B

ChEBI ID	CHEBI:69602
ChEBI Name	clethroidoside B
Stars
Definition	A triterpenoid saponin that is barringtogenol C which is acetylated at position 28 and attached to a β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl residue at position 3 via a glycosidic linkage. It has been isolated from the aerial parts of Lysimachia clethroides.
Last Modified	20 January 2014
Downloads	Molfile

Formula	C49H80O20
Net Charge	0
Average Mass	989.159
Monoisotopic Mass	988.52429
SMILES	[H][C@@]1(O[C@H]2CO[C@@]([H])(O[C@H]3CC[C@]4(C)[C@@]5([H])CC=C6[C@]7([H])CC(C)(C)[C@@H](O)[C@H](O)[C@]7(COC(C)=O)[C@H](O)C[C@@]6(C)[C@]5(C)CC[C@@]4([H])C3(C)C)[C@H](O[C@]3([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]2O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI	InChI=1S/C49H80O20/c1-21(52)64-20-49-23(15-44(2,3)39(61)40(49)62)22-9-10-28-46(6)13-12-30(45(4,5)27(46)11-14-47(28,7)48(22,8)16-29(49)53)68-43-38(69-42-37(60)35(58)32(55)25(18-51)66-42)33(56)26(19-63-43)67-41-36(59)34(57)31(54)24(17-50)65-41/h9,23-43,50-51,53-62H,10-20H2,1-8H3/t23-,24+,25+,26-,27-,28+,29+,30-,31+,32+,33-,34-,35-,36+,37+,38+,39-,40-,41-,42-,43-,46-,47+,48+,49-/m0/s1
InChIKey	WJBKGNOXYGTIHU-FTWMTZRVSA-N

Species of Metabolite	Component	Source	Comments
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.

ChEBI Ontology

Outgoing Relation(s)
	clethroidoside B (CHEBI:69602) has functional parent barringtogenol C (CHEBI:2994)
	clethroidoside B (CHEBI:69602) has parent hydride oleanane (CHEBI:36481)
	clethroidoside B (CHEBI:69602) has role plant metabolite (CHEBI:76924)
	clethroidoside B (CHEBI:69602) is a acetate ester (CHEBI:47622)
	clethroidoside B (CHEBI:69602) is a pentacyclic triterpenoid (CHEBI:25872)
	clethroidoside B (CHEBI:69602) is a triol (CHEBI:27136)
	clethroidoside B (CHEBI:69602) is a trisaccharide derivative (CHEBI:63571)
	clethroidoside B (CHEBI:69602) is a triterpenoid saponin (CHEBI:61778)

IUPAC Name
(3β,16α,21β,22α)-3-{[β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl]oxy}-16,21,22-trihydroxyolean-12-en-28-yl acetate

Synonym	Source
3-O-β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl-28-acetyl-3β,16α,21β,22α,28-pentahydroxyolean-12-ene	ChEBI

Registry Numbers	Sources
Reaxys:22007802	Reaxys

Citations