withalongolide H (CHEBI:69112)

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CHEBI:69112 - withalongolide H

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ChEBI ID	CHEBI:69112
ChEBI Name	withalongolide H
Stars
Definition	A withanolide saponin that consists of withaferin A attached to a α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl residue via a glycosidic linkage. Isolated from the aerial parts of Physalis longifolia, it exhibits antineoplastic activity.
Last Modified	29 October 2019
Downloads	Molfile

Formula	C40H58O15
Net Charge	0
Average Mass	778.889
Monoisotopic Mass	778.37757
SMILES	[H][C@@]1(O[C@H]2[C@H](O)[C@@H](O)[C@H](OCC3=C(C)C[C@]([H])([C@@H](C)[C@@]4([H])CC[C@@]5([H])[C@]6([H])C[C@H]7O[C@]78[C@@H](O)C=CC(=O)[C@]8(C)[C@@]6([H])CC[C@@]54C)OC3=O)O[C@@H]2CO)O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
InChI	InChI=1S/C40H58O15/c1-16-12-24(17(2)21-6-7-22-19-13-28-40(55-28)27(43)9-8-26(42)39(40,5)23(19)10-11-38(21,22)4)52-35(49)20(16)15-50-36-33(48)31(46)34(25(14-41)53-36)54-37-32(47)30(45)29(44)18(3)51-37/h8-9,17-19,21-25,27-34,36-37,41,43-48H,6-7,10-15H2,1-5H3/t17-,18-,19-,21+,22-,23-,24+,25+,27-,28+,29-,30+,31+,32+,33+,34+,36+,37-,38+,39-,40+/m0/s1
InChIKey	KWSCHTSFNFDQSG-IPAGGVPOSA-N

Species of Metabolite	Component	Source	Comments
Physalis longifolia (ncbitaxon:161495)	aerial part (BTO:0001658)	PubMed (22098611)	CH2Cl2-MeOH(1:1) extract of the air-dried aerial parts

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)
	withalongolide H (CHEBI:69112) has functional parent withaferin A (CHEBI:69120)
	withalongolide H (CHEBI:69112) has role antineoplastic agent (CHEBI:35610)
	withalongolide H (CHEBI:69112) has role plant metabolite (CHEBI:76924)
	withalongolide H (CHEBI:69112) is a 4-hydroxy steroid (CHEBI:62846)
	withalongolide H (CHEBI:69112) is a disaccharide derivative (CHEBI:63353)
	withalongolide H (CHEBI:69112) is a epoxy steroid (CHEBI:145217)
	withalongolide H (CHEBI:69112) is a ergostanoid (CHEBI:50403)
	withalongolide H (CHEBI:69112) is a withanolide saponin (CHEBI:76344)
	withalongolide H (CHEBI:69112) is a δ-lactone (CHEBI:18946)

IUPAC Name
(4β,5β,6β,22R)-4-hydroxy-1,26-dioxo-5,6:22,26-diepoxyergosta-2,24-dien-27-yl 4-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside

Synonym	Source
27-O-[α-L-rhamnopyranosyl(1→4)]-β-D-glucopyranosylwithaferin A	ChEBI

Registry Numbers	Sources
Reaxys:22217724	Reaxys

Citations