(+)-lyoniresinol (CHEBI:68168)

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CHEBI:68168 - (+)-lyoniresinol

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ChEBI ID	CHEBI:68168
ChEBI Name	(+)-lyoniresinol
Stars
Definition	A lignan that is tetralin substituted by a 4-hydroxy-3,5-dimethoxy group at position 4, hydroxymethyl groups at positions 2 and 3, methoxy groups at positions 5 and 7 and a hydroxy group at position 6. Isolated from Machilus robusta and Sinocalamus affinis, it exhibits antineoplastic activity.
Last Modified	27 March 2013
Downloads	Molfile

Formula	C22H28O8
Net Charge	0
Average Mass	420.458
Monoisotopic Mass	420.17842
SMILES	COc1cc([C@H]2c3c(cc(OC)c(O)c3OC)C[C@@H](CO)[C@@H]2CO)cc(OC)c1O
InChI	InChI=1S/C22H28O8/c1-27-15-7-12(8-16(28-2)20(15)25)18-14(10-24)13(9-23)5-11-6-17(29-3)21(26)22(30-4)19(11)18/h6-8,13-14,18,23-26H,5,9-10H2,1-4H3/t13-,14-,18+/m0/s1
InChIKey	ZDVZKBOFCHOPLM-SUNYJGFJSA-N

Species of Metabolite	Component	Source	Comments
Sinocalamus affinis (IPNI:421970-1)	stem (BTO:0001300)	PubMed (21469695)	95% Ethanolic extract of skin-removed, air-dried, powdered stems.
Machilus robusta (ncbitaxon:460780)	bark (BTO:0001301)	PubMed (21627109)	95%aqueous EtOH extract of air-dried bark

Roles Classification

Biological Role:	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)
	(+)-lyoniresinol (CHEBI:68168) has role antineoplastic agent (CHEBI:35610)
	(+)-lyoniresinol (CHEBI:68168) has role metabolite (CHEBI:25212)
	(+)-lyoniresinol (CHEBI:68168) is a dimethoxybenzene (CHEBI:51681)
	(+)-lyoniresinol (CHEBI:68168) is a lignan (CHEBI:25036)
	(+)-lyoniresinol (CHEBI:68168) is a polyphenol (CHEBI:26195)
	(+)-lyoniresinol (CHEBI:68168) is a primary alcohol (CHEBI:15734)
	(+)-lyoniresinol (CHEBI:68168) is a tetralins (CHEBI:36786)
Incoming Relation(s)
	(+)-lyoniresinol 4,4'-bis-O-β-D-glucopyranoside (CHEBI:66605) has functional parent (+)-lyoniresinol (CHEBI:68168)
	(+)-lyoniresinol-3-α-O-β-D-glucopyranoside (CHEBI:66606) has functional parent (+)-lyoniresinol (CHEBI:68168)

IUPAC Name
(6R,7R,8S)-8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)-1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-ol

Manual Xrefs	Databases
JP2010150152	Patent

Registry Numbers	Sources
Reaxys:2191984	Reaxys

Citations