EMBL-EBI | Chemical Biology | ChEBI

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

CHEBI:66597 - lupulin A

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:
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
cyclooxygenase 2 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
cyclooxygenase 1 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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