CHEBI:66827 - orbiculin F

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ChEBI Name orbiculin F
ChEBI ID CHEBI:66827
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C34H36O11
Net Charge 0
Average Mass 620.64300
Monoisotopic Mass 620.22576
InChI InChI=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
InChIKey BRLFNCXCWAFVFC-DYQOWCLGSA-N
SMILES [H][C@]12C[C@H](OC(=O)c3ccccc3)[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:txidtxid85181) 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.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
(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-agarofuran ChEBI
Registry Number Type Source
8374098 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
10346948 PubMed citation Europe PMC
Last Modified
19 April 2013