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CHEBI:66830 - orbiculin I

Default Structure
ChEBI IDCHEBI:66830
ChEBI Nameorbiculin I
Stars
DefinitionA dihydroagarofuran sesquiterpenoid that consists of dihydro-β-agarofuran substituted by an acetoxy group at position 1 and furoyloxy groups at positions 2, 6 and 9 (the 1β,2β,6α,9α stereoisomer). Isolated from Celastrus orbiculatus, it exhibits inhibition of both NF-κB activation and nitric oxide production.
Last Modified18 April 2013
DownloadsMolfile
FormulaC32H34O12
Net Charge0
Average Mass610.612
Monoisotopic Mass610.20503
SMILES[H][C@]12C[C@H](OC(=O)c3ccoc3)[C@]3(C)[C@@H](OC(C)=O)[C@@H](OC(=O)c4ccoc4)C[C@@H](C)[C@@]3(OC1(C)C)[C@@H]2OC(=O)c1ccoc1
InChIInChI=1S/C32H34O12/c1-17-12-23(41-27(34)19-6-9-37-14-19)26(40-18(2)33)31(5)24(42-28(35)20-7-10-38-15-20)13-22-25(32(17,31)44-30(22,3)4)43-29(36)21-8-11-39-16-21/h6-11,14-17,22-26H,12-13H2,1-5H3/t17-,22-,23+,24+,25-,26+,31-,32-/m1/s1
InChIKeyTUOQDKWZMVPMKF-FWBAFIGCSA-N
Species of MetaboliteComponentSourceComments
Celastrus orbiculatus (ncbitaxon:85181) root (BTO:0001188) PubMed (11809076)
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.
ChEBI Ontology
Outgoing Relation(s)
orbiculin I (CHEBI:66830) has functional parent 3-furoic acid (CHEBI:30846)
orbiculin I (CHEBI:66830) has role metabolite (CHEBI:25212)
orbiculin I (CHEBI:66830) has role NF-κB inhibitor (CHEBI:73240)
orbiculin I (CHEBI:66830) is a acetate ester (CHEBI:47622)
orbiculin I (CHEBI:66830) is a bridged compound (CHEBI:35990)
orbiculin I (CHEBI:66830) is a cyclic ether (CHEBI:37407)
orbiculin I (CHEBI:66830) is a dihydroagarofuran sesquiterpenoid (CHEBI:71548)
orbiculin I (CHEBI:66830) is a organic heterotricyclic compound (CHEBI:26979)
IUPAC Name 
(3R,5S,5aR,6R,7S,9R,9aS,10R)-6-(acetyloxy)-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methano-1-benzoxepine-5,7,10-triyl trifuran-3-carboxylate
Synonym  Source
1β-acetoxy-2β,6α,9α-tri(3-furoyloxy)-dihydro-β-agarofuranChEBI
Registry NumbersSources
Reaxys:9103566Reaxys
Citations