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CHEBI:65377 - aiphanol

ChEBI IDCHEBI:65377
ChEBI Nameaiphanol
Stars
DefinitionA 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).
Last Modified31 October 2012
DownloadsMolfile
FormulaC25H24O8
Net Charge0
Average Mass452.459
Monoisotopic Mass452.14712
SMILESCOc1cc([C@H]2Oc3cc(/C=C/c4cc(O)cc(O)c4)ccc3O[C@@H]2CO)cc(OC)c1O
InChIInChI=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
InChIKeyKDMFHGGHQLUIRH-OOODPRFPSA-N
Species of MetaboliteComponentSourceComments
Aiphanes aculeata (ncbitaxon:131249) seed (BTO:0001226) PubMed (11440571)
Roles Classification
Biological Role:
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.
ChEBI Ontology
Outgoing Relation(s)
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
(+)-aiphanolChEBI
Registry NumbersSources
Reaxys:8952721Reaxys
Citations