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CHEBI:66827 - orbiculin F

ChEBI IDCHEBI:66827
ChEBI Nameorbiculin F
Stars
DefinitionA dihydroagarofuran sesquiterpenoid that consists of dihydro-β-agarofuran substituted by acetoxy group at position 1, benzoyloxy group at position 9 and furoyloxy groups at positions 2 and 6 (the 1β,9α,2β,6α stereoisomer). Isolated from Celastrus orbiculatus, it exhibits inhibition of both NF-κB activation and nitric oxide production.
Last Modified19 April 2013
DownloadsMolfile
FormulaC34H36O11
Net Charge0
Average Mass620.651
Monoisotopic Mass620.22576
SMILES[H][C@]12C[C@H](OC(=O)c3ccccc3)[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/C34H36O11/c1-19-15-25(42-30(37)22-11-13-39-17-22)28(41-20(2)35)33(5)26(43-29(36)21-9-7-6-8-10-21)16-24-27(34(19,33)45-32(24,3)4)44-31(38)23-12-14-40-18-23/h6-14,17-19,24-28H,15-16H2,1-5H3/t19-,24-,25+,26+,27-,28+,33-,34-/m1/s1
InChIKeyBRLFNCXCWAFVFC-DYQOWCLGSA-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.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
orbiculin F (CHEBI:66827) has functional parent 3-furoic acid (CHEBI:30846)
orbiculin F (CHEBI:66827) has role antineoplastic agent (CHEBI:35610)
orbiculin F (CHEBI:66827) has role metabolite (CHEBI:25212)
orbiculin F (CHEBI:66827) has role NF-κB inhibitor (CHEBI:73240)
orbiculin F (CHEBI:66827) is a acetate ester (CHEBI:47622)
orbiculin F (CHEBI:66827) is a benzoate ester (CHEBI:36054)
orbiculin F (CHEBI:66827) is a bridged compound (CHEBI:35990)
orbiculin F (CHEBI:66827) is a cyclic ether (CHEBI:37407)
orbiculin F (CHEBI:66827) is a dihydroagarofuran sesquiterpenoid (CHEBI:71548)
orbiculin F (CHEBI:66827) is a organic heterotricyclic compound (CHEBI:26979)
IUPAC Name 
(3R,5S,5aR,6R,7S,9R,9aS,10R)-6-(acetyloxy)-5-(benzoyloxy)-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methano-1-benzoxepine-7,10-diyl difuran-3-carboxylate
Synonyms  Source
(1S,2R,4S,5R,6R,7S,9R,12R)-5-acetoxy-7-(benzoyloxy)-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.01,6]dodecane-4,12-diyl di(3-furoate)IUPAC
1β-acetoxy-9α-benzoyloxy-2β,6α-di(3-furoyloxy)-dihydro-β-agarofuranChEBI
Registry NumbersSources
Reaxys:8374098Reaxys
Citations