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

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 5-methoxy-8-(2'-hydroxy-3'-buthoxy-3'-methylbutyloxy)psoralen
ChEBI ID CHEBI:66697
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C21H26O7
Net Charge 0
Average Mass 390.42690
Monoisotopic Mass 390.16785
InChI InChI=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
InChIKey HYFWQORTIZQRLZ-OAHLLOKOSA-N
SMILES CCCCOC(C)(C)[C@H](O)COc1c2occc2c(OC)c2ccc(=O)oc12
Metabolite of Species Details
Angelica dahurica (NCBI:txid48101) Found in root (BTO:0001188). See: DOI
Roles Classification
Biological Role(s): 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).
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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
Citation Waiting for Citations Type Source
18481018 PubMed citation Europe PMC
Last Modified
08 April 2013
General Comment
2013-04-08 Bull. Korean Chem. Soc. (2003), 24(11), 1699-1701.