CHEBI:66830 - orbiculin I

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ChEBI Name orbiculin I
ChEBI ID CHEBI:66830
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C32H34O12
Net Charge 0
Average Mass 610.60520
Monoisotopic Mass 610.20503
InChI InChI=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
InChIKey TUOQDKWZMVPMKF-FWBAFIGCSA-N
SMILES [H][C@]12C[C@H](OC(=O)c3ccoc3)[C@]3(C)[C@@H](OC(C)=O)[C@H](C[C@@H](C)[C@@]3(OC1(C)C)[C@@H]2OC(=O)c1ccoc1)OC(=O)c1ccoc1
Metabolite of Species Details
Celastrus orbiculatus (NCBI:txid85181) Found in root (BTO:0001188). 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.
NF-kappaB inhibitor
An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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-agarofuran ChEBI
Registry Number Type Source
9103566 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
11809076 PubMed citation Europe PMC
Last Modified
18 April 2013