CHEBI:66825 - orbiculin D

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ChEBI Name orbiculin D
ChEBI ID CHEBI:66825
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C27H32O9
Net Charge 0
Average Mass 500.53760
Monoisotopic Mass 500.20463
InChI InChI=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
InChIKey PYVZLPAEJQAONU-ZNUYPWKISA-N
SMILES [H][C@]12C[C@H](OC(=O)c3ccoc3)[C@]3(C)[C@H](CC[C@@H](C)[C@@]3(OC1(C)C)[C@@H]2OC(=O)c1ccoc1)OC(C)=O
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 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-agarofuran ChEBI
Registry Number Type Source
8366521 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
10346948 PubMed citation Europe PMC
Last Modified
19 April 2013