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CHEBI:66829 - orbiculin H

Default Structure
ChEBI IDCHEBI:66829
ChEBI Nameorbiculin H
Stars
DefinitionA 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.
Last Modified19 April 2013
DownloadsMolfile
FormulaC29H34O11
Net Charge0
Average Mass558.580
Monoisotopic Mass558.21011
SMILES[H][C@@]12[C@@H](OC(=O)c3ccoc3)[C@]3(OC1(C)C)[C@H](C)CC[C@H](OC(C)=O)[C@@]3(C)[C@@H](OC(=O)c1ccoc1)[C@@H]2OC(C)=O
InChIInChI=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
InChIKeyCVKSZMJJSHWLSE-QFRBWOKISA-N
Species of MetaboliteComponentSourceComments
Celastrus orbiculatus (ncbitaxon:85181) root (BTO:0001188) PubMed (11809076)
Roles Classification
Biological Roles:
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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
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  Source
(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-agarofuranChEBI
Registry NumbersSources
Reaxys:9100608Reaxys
Citations