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CHEBI:66829 - orbiculin H

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:
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.
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