CHEBI:66359 - (+)-α-viniferin

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ChEBI Name (+)-α-viniferin
ChEBI ID CHEBI:66359
ChEBI ASCII Name (+)-alpha-viniferin
Definition A 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).
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C42H30O9
Net Charge 0
Average Mass 678.68220
Monoisotopic Mass 678.18898
InChI InChI=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
InChIKey KUTVNHOAKHJJFL-ZSIJVUTGSA-N
SMILES [H][C@@]12[C@H](Oc3cc(O)cc(c13)[C@@]1([H])[C@@H](Oc3cc(O)cc(c13)[C@@]1([H])[C@@H](Oc3cc(O)cc2c13)c1ccc(O)cc1)c1ccc(O)cc1)c1ccc(O)cc1
Metabolite of Species Details
Caragana (NCBI:txid20483) Found in root (BTO:0001188). See: PubMed
Roles Classification
Biological Role(s): 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(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (+)-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-viniferin ChEBI
Manual Xref Database
Alpha-Viniferin Wikipedia
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Registry Numbers Types Sources
3644570 Reaxys Registry Number Reaxys
62218-13-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
14531020 PubMed citation Europe PMC
20424383 PubMed citation Europe PMC
22209460 PubMed citation Europe PMC
2337958 PubMed citation Europe PMC
Last Modified
25 March 2015