EMBL-EBI | Chemical Biology | ChEBI

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

CHEBI:66826 - orbiculin E

ChEBI IDCHEBI:66826
ChEBI Nameorbiculin E
Stars
DefinitionA dihydroagarofuran sesquiterpenoid that consists of dihydro-β-agarofuran substituted by acetoxy group at positions 1 and 2, a benzoyloxy group at position 9 and furoyloxy groups at position 6 (the 1β,2β,9α,6α). Isolated from Celastrus orbiculatus, it exhibits inhibition of both NF-κB activation and nitric oxide production.
Last Modified19 April 2013
DownloadsMolfile
FormulaC31H36O10
Net Charge0
Average Mass568.619
Monoisotopic Mass568.23085
SMILES[H][C@]12C[C@H](OC(=O)c3ccccc3)[C@]3(C)[C@@H](OC(C)=O)[C@@H](OC(C)=O)C[C@@H](C)[C@@]3(OC1(C)C)[C@@H]2OC(=O)c1ccoc1
InChIInChI=1S/C31H36O10/c1-17-14-23(37-18(2)32)26(38-19(3)33)30(6)24(39-27(34)20-10-8-7-9-11-20)15-22-25(31(17,30)41-29(22,4)5)40-28(35)21-12-13-36-16-21/h7-13,16-17,22-26H,14-15H2,1-6H3/t17-,22-,23+,24+,25-,26+,30-,31-/m1/s1
InChIKeyGAOKKLOHOKIMQT-KBAKPPLISA-N
Species of MetaboliteComponentSourceComments
Celastrus orbiculatus (ncbitaxon:85181) root (BTO:0001188) PubMed (10346948)
Roles Classification
Biological Roles:
NF-kappaB inhibitor  An inhibitor of NF-κB (nuclear factor κ-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
orbiculin E (CHEBI:66826) has functional parent 3-furoic acid (CHEBI:30846)
orbiculin E (CHEBI:66826) has role antineoplastic agent (CHEBI:35610)
orbiculin E (CHEBI:66826) has role metabolite (CHEBI:25212)
orbiculin E (CHEBI:66826) has role NF-κB inhibitor (CHEBI:73240)
orbiculin E (CHEBI:66826) is a acetate ester (CHEBI:47622)
orbiculin E (CHEBI:66826) is a benzoate ester (CHEBI:36054)
orbiculin E (CHEBI:66826) is a bridged compound (CHEBI:35990)
orbiculin E (CHEBI:66826) is a cyclic ether (CHEBI:37407)
orbiculin E (CHEBI:66826) is a dihydroagarofuran sesquiterpenoid (CHEBI:71548)
orbiculin E (CHEBI:66826) is a organic heterotricyclic compound (CHEBI:26979)
IUPAC Name 
(3R,5S,5aR,6R,7S,9R,9aS,10R)-6,7-bis(acetyloxy)-5-(benzoyloxy)-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methano-1-benzoxepin-10-yl furan-3-carboxylate
Synonyms  Source
(1S,2R,4S,5R,6R,7S,9R,12R)-4,5-diacetoxy-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.01,6]dodec-12-yl 3-furoateIUPAC
1β,2β-diacetoxy-9α-benzoyloxy-6α-(3-furoyloxy)-dihydro-β-agarofuranChEBI
Registry NumbersSources
Reaxys:8370943Reaxys
Citations