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

Default Structure
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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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).
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