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CHEBI:69861 - ajugaciliatin B

ChEBI IDCHEBI:69861
ChEBI Nameajugaciliatin B
Stars
DefinitionA diterpene lactone isolated from the whole plants of Ajuga ciliata and has been shown to exhibit neuroprotective activity.
Last Modified2 December 2014
DownloadsMolfile
FormulaC31H45ClO11
Net Charge0
Average Mass629.143
Monoisotopic Mass628.26504
SMILES[H][C@]12[C@H](OC(C)=O)CC[C@](O)(CCl)[C@]1(COC(C)=O)[C@@H](OC(C)=O)C[C@@H](C)[C@]2(C)C[C@H](OC(=O)[C@@H](C)CC)C1=CC(=O)OC1
InChIInChI=1S/C31H45ClO11/c1-8-17(2)28(37)43-24(22-12-26(36)39-14-22)13-29(7)18(3)11-25(42-21(6)35)31(16-40-19(4)33)27(29)23(41-20(5)34)9-10-30(31,38)15-32/h12,17-18,23-25,27,38H,8-11,13-16H2,1-7H3/t17-,18+,23+,24-,25-,27+,29-,30-,31+/m0/s1
InChIKeyLMCZPZLFURXAIA-JKZOSZDYSA-N
Species of MetaboliteComponentSourceComments
Ajuga ciliata (ncbitaxon:199542) whole plant (BTO:0001461) PubMed (21682262) Methanol extract of air-dried whole plant
Roles Classification
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
neuroprotective agent  Any compound that can be used for the treatment of neurodegenerative disorders.
ChEBI Ontology
Outgoing Relation(s)
ajugaciliatin B (CHEBI:69861) has role neuroprotective agent (CHEBI:63726)
ajugaciliatin B (CHEBI:69861) has role plant metabolite (CHEBI:76924)
ajugaciliatin B (CHEBI:69861) is a acetate ester (CHEBI:47622)
ajugaciliatin B (CHEBI:69861) is a butenolide (CHEBI:50523)
ajugaciliatin B (CHEBI:69861) is a carbobicyclic compound (CHEBI:36785)
ajugaciliatin B (CHEBI:69861) is a diterpene lactone (CHEBI:49193)
ajugaciliatin B (CHEBI:69861) is a organochlorine compound (CHEBI:36683)
ajugaciliatin B (CHEBI:69861) is a tertiary alcohol (CHEBI:26878)
IUPAC Name 
(1S)-2-[(1S,2R,4S,4aR,5R,8R,8aR)-4,8-bis(acetyloxy)-4a-[(acetyloxy)methyl]-5-(chloromethyl)-5-hydroxy-1,2-dimethyldecahydronaphthalen-1-yl]-1-(5-oxo-2,5-dihydrofuran-3-yl)ethyl (2S)-2-methylbutanoate
Synonym  Source
(12S,2'''S)-1β,6α,19-triacetoxy-18-chloro-4α-hydroxy-12-(2-methylbutanoyloxy)-neo-clerod-13-en-15,16-olideChEBI
Registry NumbersSources
Reaxys:21728544Reaxys
Citations