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CHEBI:66824 - orbiculin A

ChEBI IDCHEBI:66824
ChEBI Nameorbiculin A
Stars
DefinitionA dihydroagarofuran sesquiterpenoid that consists of dihydro-β-agarofuran substituted by an acetoxy groups at positions 1 and 2 and benzoyloxy groups at positions 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 Modified19 April 2013
DownloadsMolfile
FormulaC33H38O9
Net Charge0
Average Mass578.658
Monoisotopic Mass578.25158
SMILES[H][C@]12C[C@H](OC(=O)c3ccccc3)[C@]3(C)[C@@H](OC(C)=O)[C@@H](OC(C)=O)C[C@@H](C)[C@@]3(OC1(C)C)[C@@H]2OC(=O)c1ccccc1
InChIInChI=1S/C33H38O9/c1-19-17-25(38-20(2)34)28(39-21(3)35)32(6)26(40-29(36)22-13-9-7-10-14-22)18-24-27(33(19,32)42-31(24,4)5)41-30(37)23-15-11-8-12-16-23/h7-16,19,24-28H,17-18H2,1-6H3/t19-,24-,25+,26+,27-,28+,32-,33-/m1/s1
InChIKeyKYEKMLQQOXNBSD-HJJCBLRASA-N
Species of MetaboliteComponentSourceComments
Celastrus orbiculatus (ncbitaxon:85181) root (BTO:0001188) PubMed (9461657)
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 A (CHEBI:66824) has role antineoplastic agent (CHEBI:35610)
orbiculin A (CHEBI:66824) has role metabolite (CHEBI:25212)
orbiculin A (CHEBI:66824) has role NF-κB inhibitor (CHEBI:73240)
orbiculin A (CHEBI:66824) is a acetate ester (CHEBI:47622)
orbiculin A (CHEBI:66824) is a benzoate ester (CHEBI:36054)
orbiculin A (CHEBI:66824) is a bridged compound (CHEBI:35990)
orbiculin A (CHEBI:66824) is a cyclic ether (CHEBI:37407)
orbiculin A (CHEBI:66824) is a dihydroagarofuran sesquiterpenoid (CHEBI:71548)
orbiculin A (CHEBI:66824) is a organic heterotricyclic compound (CHEBI:26979)
IUPAC Name 
(3R,5S,5aR,6R,7S,9R,9aS,10R)-6,7-bis(acetyloxy)-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methano-1-benzoxepine-5,10-diyl dibenzoate
Synonyms  Source
(1S,2R,4S,5R,6R,7S,9R,12R)-4,5-diacetoxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.01,6]dodecane-7,12-diyl dibenzoateIUPAC
1β,2β-diacetoxy-6α,9α-bis(benzoyloxy)dihydro-β-agarofuranChEBI
Registry NumbersSources
Reaxys:7959601Reaxys
Citations