CHEBI:65377 - aiphanol

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ChEBI Name aiphanol
ChEBI ID CHEBI:65377
Definition A lignan that is (2R)-2,3-dihydro-1,4-benzodioxin-2-ylmethanol which is substituted by a 2-(3,5-dihydroxyphenyl)ethenyl group at position 6 and a 4-hydroxy-3,5-dimethoxyphenyl group at position 3. It is a stilbenolignan isolated from the seeds of Aiphanes aculeata and exhibits potent inhibitory efficacy against cyclooxygenase-1 and -2 (COX-1 and COX-2).
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C25H24O8
Net Charge 0
Average Mass 452.45330
Monoisotopic Mass 452.14712
InChI InChI=1S/C25H24O8/c1-30-21-10-16(11-22(31-2)24(21)29)25-23(13-26)32-19-6-5-14(9-20(19)33-25)3-4-15-7-17(27)12-18(28)8-15/h3-12,23,25-29H,13H2,1-2H3/b4-3+/t23-,25-/m1/s1
InChIKey KDMFHGGHQLUIRH-OOODPRFPSA-N
SMILES COc1cc(cc(OC)c1O)[C@H]1Oc2cc(ccc2O[C@@H]1CO)\C=C\c1cc(O)cc(O)c1
Metabolite of Species Details
Aiphanes aculeata (NCBI:txid131249) Found in seed (BTO:0001226). See: PubMed
Roles Classification
Biological Role(s): EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor
A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing aiphanol (CHEBI:65377) has role EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544)
aiphanol (CHEBI:65377) is a aromatic ether (CHEBI:35618)
aiphanol (CHEBI:65377) is a benzodioxine (CHEBI:64096)
aiphanol (CHEBI:65377) is a lignan (CHEBI:25036)
aiphanol (CHEBI:65377) is a stilbenoid (CHEBI:26776)
IUPAC Name
5-{(E)-2-[(2R,3R)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]ethenyl}benzene-1,3-diol
Synonym Source
(+)-aiphanol ChEBI
Registry Number Type Source
8952721 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11440571 PubMed citation Europe PMC
12956057 PubMed citation Europe PMC
Last Modified
31 October 2012