EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:66597 - lupulin A

Default Structure
ChEBI IDCHEBI:66597
ChEBI Namelupulin A
Stars
DefinitionA diterpenoid isolated from Ajuga lupulina and has been shown to exhibit anti-inflammatory and antibacterial activities.
Last Modified25 March 2013
DownloadsMolfile
FormulaC30H46O11
Net Charge0
Average Mass582.687
Monoisotopic Mass582.30401
SMILES[H][C@]12C[C@@H](O)[C@H](OC(=O)C(C)CC)[C@]3(CO3)[C@]1(COC(C)=O)[C@@H](OC(C)=O)C[C@@H](C)[C@]2(C)[C@]1([H])CC2C[C@H](OC)OC2O1
InChIInChI=1S/C30H46O11/c1-8-15(2)26(34)41-25-20(33)12-21-28(6,22-10-19-11-24(35-7)40-27(19)39-22)16(3)9-23(38-18(5)32)29(21,13-36-17(4)31)30(25)14-37-30/h15-16,19-25,27,33H,8-14H2,1-7H3/t15?,16-,19?,20-,21-,22+,23+,24-,25+,27?,28+,29+,30-/m1/s1
InChIKeyUEZOFWAZJUOMCN-HKDNVZQMSA-N
Species of MetaboliteComponentSourceComments
Ajuga lupulina (ncbitaxon:587657) - PubMed (8759163)
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
cyclooxygenase 1 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
cyclooxygenase 2 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
Application:
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
ChEBI Ontology
Outgoing Relation(s)
lupulin A (CHEBI:66597) has role anti-inflammatory agent (CHEBI:67079)
lupulin A (CHEBI:66597) has role antibacterial agent (CHEBI:33282)
lupulin A (CHEBI:66597) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
lupulin A (CHEBI:66597) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
lupulin A (CHEBI:66597) has role metabolite (CHEBI:25212)
lupulin A (CHEBI:66597) is a acetate ester (CHEBI:47622)
lupulin A (CHEBI:66597) is a diterpenoid (CHEBI:23849)
lupulin A (CHEBI:66597) is a epoxide (CHEBI:32955)
lupulin A (CHEBI:66597) is a furofuran (CHEBI:47790)
IUPAC Name 
(1R,2S,3R,4aR,5S,6R,8S,8aR)-8-(acetyloxy)-8a-[(acetyloxy)methyl]-3-hydroxy-5-[(2S,5R)-5-methoxyhexahydrofuro[2,3-b]furan-2-yl]-5,6-dimethyloctahydro-2H-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylbutanoate
Registry NumbersSources
Reaxys:8528547Reaxys
Citations