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CHEBI:66825 - orbiculin D

Default Structure
ChEBI IDCHEBI:66825
ChEBI Nameorbiculin D
Stars
DefinitionA dihydroagarofuran sesquiterpenoid that consists of dihydro-β-agarofuran substituted by acetoxy group at position 1 and furoyloxy groups at positions 6 and 9 (the 1β,6α,9α stereoisomer). Isolated from Celastrus orbiculatus, it exhibits inhibition of both NF-κB activation and nitric oxide production.
Last Modified19 April 2013
DownloadsMolfile
FormulaC27H32O9
Net Charge0
Average Mass500.544
Monoisotopic Mass500.20463
SMILES[H][C@]12C[C@H](OC(=O)c3ccoc3)[C@]3(C)[C@@H](OC(C)=O)CC[C@@H](C)[C@@]3(OC1(C)C)[C@@H]2OC(=O)c1ccoc1
InChIInChI=1S/C27H32O9/c1-15-6-7-20(33-16(2)28)26(5)21(34-23(29)17-8-10-31-13-17)12-19-22(27(15,26)36-25(19,3)4)35-24(30)18-9-11-32-14-18/h8-11,13-15,19-22H,6-7,12H2,1-5H3/t15-,19-,20+,21+,22-,26+,27-/m1/s1
InChIKeyPYVZLPAEJQAONU-ZNUYPWKISA-N
Species of MetaboliteComponentSourceComments
Celastrus orbiculatus (ncbitaxon:85181) root (BTO:0001188) PubMed (10346948)
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 D (CHEBI:66825) has functional parent 3-furoic acid (CHEBI:30846)
orbiculin D (CHEBI:66825) has role metabolite (CHEBI:25212)
orbiculin D (CHEBI:66825) has role NF-κB inhibitor (CHEBI:73240)
orbiculin D (CHEBI:66825) is a acetate ester (CHEBI:47622)
orbiculin D (CHEBI:66825) is a bridged compound (CHEBI:35990)
orbiculin D (CHEBI:66825) is a cyclic ether (CHEBI:37407)
orbiculin D (CHEBI:66825) is a dihydroagarofuran sesquiterpenoid (CHEBI:71548)
orbiculin D (CHEBI:66825) is a organic heterotricyclic compound (CHEBI:26979)
IUPAC Name 
(3R,5S,5aS,6S,9R,9aS,10R)-6-(acetyloxy)-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methano-1-benzoxepine-5,10-diyl difuran-3-carboxylate
Synonym  Source
1β-acetoxy-6α,9α-di(3-furoyloxy)-dihydro-β-agarofuranChEBI
Registry NumbersSources
Reaxys:8366521Reaxys
Citations