CHEBI:66597 - lupulin A

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ChEBI Name lupulin A
Definition A diterpenoid isolated from Ajuga lupulina and has been shown to exhibit anti-inflammatory and antibacterial activities.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H46O11
Net Charge 0
Average Mass 582.67960
Monoisotopic Mass 582.30401
InChI InChI=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
SMILES [H][C@]1(CC2C[C@H](OC)OC2O1)[C@@]1(C)[C@H](C)C[C@H](OC(C)=O)[C@]2(COC(C)=O)[C@]1([H])C[C@@H](O)[C@H](OC(=O)C(C)CC)[C@]21CO1
Metabolite of Species Details
Ajuga lupulina (NCBI:txid587657) See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
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.
Application(s): anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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)
(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 Number Type Source
8528547 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
17191906 PubMed citation Europe PMC
19946570 PubMed citation Europe PMC
21073945 PubMed citation Europe PMC
8759163 PubMed citation Europe PMC
Last Modified
25 March 2013