rhodiocyanoside A (CHEBI:66305)

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ChEBI Name	rhodiocyanoside A

ChEBI ID	CHEBI:66305

Definition	A cyanogenic glycoside that is (2Z)-2-methylbut-2-enenitrile attached to a β-D-glucopyranosyloxy at position 4. Isolated from Rhodiola quadrifida, it exhibits anti-allergic activity.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C11H17NO6

Net Charge

Average Mass

259.25580

Monoisotopic Mass

259.10559

InChI

InChI=1S/C11H17NO6/c1-6(4-12)2-3-17-11-10(16)9(15)8(14)7(5-13)18-11/h2,7-11,13-16H,3,5H2,1H3/b6-2-/t7-,8-,9+,10-,11-/m1/s1

InChIKey

ZMELGIPFIBWPHX-GMLQCYRESA-N

SMILES

C\C(=C\CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C#N

Metabolite of Species	Details
Rhodiola quadrifida (NCBI:txid487764)	Found in root (BTO:0001188). Underground parts See: PubMed

Roles Classification
Biological Role(s):	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via cyanogenic glycoside )

Application(s):	anti-allergic agent A drug used to treat allergic reactions.

ChEBI Ontology
Outgoing	rhodiocyanoside A (CHEBI:66305) has role anti-allergic agent (CHEBI:50857) rhodiocyanoside A (CHEBI:66305) has role metabolite (CHEBI:25212) rhodiocyanoside A (CHEBI:66305) is a β-D-glucoside (CHEBI:22798) rhodiocyanoside A (CHEBI:66305) is a aliphatic nitrile (CHEBI:80291) rhodiocyanoside A (CHEBI:66305) is a cyanogenic glycoside (CHEBI:23436) rhodiocyanoside A (CHEBI:66305) is a monosaccharide derivative (CHEBI:63367)

IUPAC Name

(2Z)-4-(β-D-glucopyranosyloxy)-2-methylbut-2-enenitrile

Synonym	Source
(2Z)-2-methyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}but-2-enenitrile	IUPAC

Registry Number	Type	Source
7377117	Reaxys Registry Number	Reaxys

Last Modified

01 May 2015