EMBL-EBI | Chemical Biology | ChEBI

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

CHEBI:66830 - orbiculin I

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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
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