asphodelin A-4'-O-beta-glucoside (CHEBI:65454)

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CHEBI:65454 - asphodelin A-4'-O-β-glucoside

ChEBI ID	CHEBI:65454
ChEBI Name	asphodelin A-4'-O-β-glucoside
Stars
ASCII Name	asphodelin A-4'-O-beta-glucoside
Definition	A β-D-glucoside in which a β-D-glucopyranosyl residue is attached at position 4' of asphodelin A via a glycosidic linkage. It is isolated from the roots of Asphodelus microcarpus and exhibits antimicrobial activity against bacteria like Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa and fungal microorganisms like Candida albicans and Botrytis cinerea.
Last Modified	26 November 2012
Downloads	Molfile

Formula	C21H20O11
Net Charge	0
Average Mass	448.380
Monoisotopic Mass	448.10056
SMILES	O=c1oc2cc(O)ccc2c(O)c1-c1ccc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1O
InChI	InChI=1S/C21H20O11/c22-7-14-17(26)18(27)19(28)21(32-14)30-9-2-4-10(12(24)6-9)15-16(25)11-3-1-8(23)5-13(11)31-20(15)29/h1-6,14,17-19,21-28H,7H2/t14-,17-,18+,19-,21-/m1/s1
InChIKey	OEZWCAHAQBRTTP-FKRBRYKNSA-N

Species of Metabolite	Component	Source
Asphodelus microcarpus (IPNI:531525-1)
	root (BTO:0001188)	PubMed (17253862)
	bulb (BTO:0000159)	PubMed (17253862)

Roles Classification

Biological Roles:

antifungal agent An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.

antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria.

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)
	asphodelin A-4'-O-β-glucoside (CHEBI:65454) has functional parent asphodelin A (CHEBI:65453)
	asphodelin A-4'-O-β-glucoside (CHEBI:65454) has role antibacterial agent (CHEBI:33282)
	asphodelin A-4'-O-β-glucoside (CHEBI:65454) has role antifungal agent (CHEBI:35718)
	asphodelin A-4'-O-β-glucoside (CHEBI:65454) has role metabolite (CHEBI:25212)
	asphodelin A-4'-O-β-glucoside (CHEBI:65454) is a hydroxycoumarin (CHEBI:37912)
	asphodelin A-4'-O-β-glucoside (CHEBI:65454) is a polyphenol (CHEBI:26195)
	asphodelin A-4'-O-β-glucoside (CHEBI:65454) is a β-D-glucoside (CHEBI:22798)

IUPAC Name
4-(4,7-dihydroxy-2-oxo-2H-chromen-3-yl)-3-hydroxyphenyl β-D-glucopyranoside

Synonym	Source
3-(2'-hydroxy-p-O-β-D-glucopyranosyloxyphenyl)-4,7-dihydroxy-2H-1-benzopyran-2-one	ChEBI

Registry Numbers	Sources
Reaxys:11288781	Reaxys

Citations