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CHEBI:66697 - 5-methoxy-8-(2'-hydroxy-3'-buthoxy-3'-methylbutyloxy)psoralen

ChEBI IDCHEBI:66697
ChEBI Name5-methoxy-8-(2'-hydroxy-3'-buthoxy-3'-methylbutyloxy)psoralen
Stars
DefinitionA member of the class of psoralens that is psoralen substituted by a methoxy group at position 4 and a [(2R)-3-butoxy-2-hydroxy-3-methylbutyl]oxy group at position 9. Isolated from the roots of Angelica dahurica, it exhibits inhibitory activity against COX-2 and 5-lipooxygenase.
Last Modified8 April 2013
DownloadsMolfile
FormulaC21H26O7
Net Charge0
Average Mass390.432
Monoisotopic Mass390.16785
SMILESCCCCOC(C)(C)[C@H](O)COc1c2occc2c(OC)c2ccc(=O)oc12
InChIInChI=1S/C21H26O7/c1-5-6-10-27-21(2,3)15(22)12-26-20-18-14(9-11-25-18)17(24-4)13-7-8-16(23)28-19(13)20/h7-9,11,15,22H,5-6,10,12H2,1-4H3/t15-/m1/s1
InChIKeyHYFWQORTIZQRLZ-OAHLLOKOSA-N
Species of MetaboliteComponentSourceComments
Angelica dahurica (ncbitaxon:48101) root (BTO:0001188) DOI (http://dx.doi.org/10.5012/bkcs.2003.24.11.1699)
Roles Classification
Biological Roles:
cyclooxygenase 2 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor  A lipoxygenase inhibitor that interferes with the action of arachidonate 5-lipoxygenase (EC 1.13.11.34).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
5-methoxy-8-(2'-hydroxy-3'-buthoxy-3'-methylbutyloxy)psoralen (CHEBI:66697) has functional parent psoralen (CHEBI:27616)
5-methoxy-8-(2'-hydroxy-3'-buthoxy-3'-methylbutyloxy)psoralen (CHEBI:66697) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
5-methoxy-8-(2'-hydroxy-3'-buthoxy-3'-methylbutyloxy)psoralen (CHEBI:66697) has role EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor (CHEBI:64964)
5-methoxy-8-(2'-hydroxy-3'-buthoxy-3'-methylbutyloxy)psoralen (CHEBI:66697) has role metabolite (CHEBI:25212)
5-methoxy-8-(2'-hydroxy-3'-buthoxy-3'-methylbutyloxy)psoralen (CHEBI:66697) is a aromatic ether (CHEBI:35618)
5-methoxy-8-(2'-hydroxy-3'-buthoxy-3'-methylbutyloxy)psoralen (CHEBI:66697) is a psoralens (CHEBI:26369)
5-methoxy-8-(2'-hydroxy-3'-buthoxy-3'-methylbutyloxy)psoralen (CHEBI:66697) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
9-{[(2R)-3-butoxy-2-hydroxy-3-methylbutyl]oxy}-4-methoxy-7H-furo[3,2-g]chromen-7-one
Citations