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CHEBI:66359 - (+)-α-viniferin

Default Structure
ChEBI IDCHEBI:66359
ChEBI Name(+)-α-viniferin
Stars
ASCII Name(+)-alpha-viniferin
DefinitionA nine-membered macrocycle that incorporates three 6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuranyl moieties as part of the cyclic skeleton. It is isolated from Caragana chamlague Lamarck and exhibits significant inhibitory effect towards the enzyme acetylcholinesterase (EC 3.1.1.7).
Last Modified25 March 2015
DownloadsMolfile
FormulaC42H30O9
Net Charge0
Average Mass678.693
Monoisotopic Mass678.18898
SMILES[H][C@]12c3cc(O)cc4c3[C@@]([H])(c3cc(O)cc5c3[C@@]([H])(c3cc(O)cc(c31)O[C@@H]2c1ccc(O)cc1)[C@H](c1ccc(O)cc1)O5)[C@H](c1ccc(O)cc1)O4
InChIInChI=1S/C42H30O9/c43-22-7-1-19(2-8-22)40-37-28-13-25(46)17-32-35(28)39(42(50-32)21-5-11-24(45)12-6-21)30-15-27(48)18-33-36(30)38(29-14-26(47)16-31(49-40)34(29)37)41(51-33)20-3-9-23(44)10-4-20/h1-18,37-48H/t37-,38-,39+,40+,41+,42-/m1/s1
InChIKeyKUTVNHOAKHJJFL-ZSIJVUTGSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Caragana (ncbitaxon:20483) root (BTO:0001188) PubMed (2337958)
Roles Classification
Biological Roles:
EC 3.1.1.7 (acetylcholinesterase) inhibitor  An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
(+)-α-viniferin (CHEBI:66359) has functional parent resveratrol (CHEBI:27881)
(+)-α-viniferin (CHEBI:66359) has role anti-inflammatory agent (CHEBI:67079)
(+)-α-viniferin (CHEBI:66359) has role EC 3.1.1.7 (acetylcholinesterase) inhibitor (CHEBI:38462)
(+)-α-viniferin (CHEBI:66359) has role plant metabolite (CHEBI:76924)
(+)-α-viniferin (CHEBI:66359) is a 1-benzofurans (CHEBI:38830)
(+)-α-viniferin (CHEBI:66359) is a macrocycle (CHEBI:51026)
(+)-α-viniferin (CHEBI:66359) is a polyphenol (CHEBI:26195)
IUPAC Name 
(2R,2aR,7R,7aR,12S,12aS)-2,7,12-tris(4-hydroxyphenyl)-2,2a,7,7a,12,12a-hexahydrobis[1]benzofuro[3',4':4,5,6;3'',4'':7,8,9]cyclonona[1,2,3-cd][1]benzofuran-4,9,14-triol
Synonym  Source
α-viniferinChEBI
Manual XrefsDatabases
Alpha-ViniferinWikipedia
Registry NumbersSources
Reaxys:3644570Reaxys
CAS:62218-13-7ChemIDplus
Citations