CHEBI:66829 - orbiculin H

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ChEBI Name orbiculin H
ChEBI ID CHEBI:66829
Definition A dihydroagarofuran sesquiterpenoid that consists of dihydro-β-agarofuran substituted by acetoxy groups at positions 1 and 8 and furoyloxy groups at positions 6 and 9 (the 1β,8β,6α,9α stereoisomer). Isolated from Celastrus orbiculatus and 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 C29H34O11
Net Charge 0
Average Mass 558.57370
Monoisotopic Mass 558.21011
InChI InChI=1S/C29H34O11/c1-15-7-8-20(36-16(2)30)28(6)24(39-26(33)19-10-12-35-14-19)22(37-17(3)31)21-23(29(15,28)40-27(21,4)5)38-25(32)18-9-11-34-13-18/h9-15,20-24H,7-8H2,1-6H3/t15-,20+,21-,22-,23-,24+,28+,29-/m1/s1
InChIKey CVKSZMJJSHWLSE-QFRBWOKISA-N
SMILES [H][C@]12[C@@H](OC(C)=O)[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: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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing orbiculin H (CHEBI:66829) has functional parent 3-furoic acid (CHEBI:30846)
orbiculin H (CHEBI:66829) has role metabolite (CHEBI:25212)
orbiculin H (CHEBI:66829) has role NF-κB inhibitor (CHEBI:73240)
orbiculin H (CHEBI:66829) is a acetate ester (CHEBI:47622)
orbiculin H (CHEBI:66829) is a bridged compound (CHEBI:35990)
orbiculin H (CHEBI:66829) is a cyclic ether (CHEBI:37407)
orbiculin H (CHEBI:66829) is a dihydroagarofuran sesquiterpenoid (CHEBI:71548)
orbiculin H (CHEBI:66829) is a organic heterotricyclic compound (CHEBI:26979)
IUPAC Name
(3R,4R,5R,5aS,6S,9R,9aS,10R)-4,6-bis(acetyloxy)-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methano-1-benzoxepine-5,10-diyl difuran-3-carboxylate
Synonyms Sources
(1S,2R,5S,6S,7R,8R,9R,12R)-5,8-Diacetoxy-2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.01,6]dodecane-7,12-diyl di(3-furoate) IUPAC
1β,8β-diacetoxy-6α,9α-di(furoyloxy)-dihydro-β-agarofuran ChEBI
Registry Number Type Source
9100608 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
11809076 PubMed citation Europe PMC
Last Modified
19 April 2013