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CHEBI:66828 - orbiculin G

ChEBI IDCHEBI:66828
ChEBI Nameorbiculin G
Stars
DefinitionA dihydroagarofuran sesquiterpenoid that consists of dihydro-β-agarofuran substituted by an acetoxy group at position 1 and benzoyloxy groups at positions 2, 6 and 9 (the 1β,2β,6α,9α stereoisomers). Isolated from the roots of Celastrus orbiculatus and Microtropis fokienensis and exhibits cytotoxic and antitubercular properties.
Last Modified14 April 2015
DownloadsMolfile
FormulaC38H40O9
Net Charge0
Average Mass640.729
Monoisotopic Mass640.26723
SMILES[H][C@]12C[C@H](OC(=O)c3ccccc3)[C@]3(C)[C@@H](OC(C)=O)[C@@H](OC(=O)c4ccccc4)C[C@@H](C)[C@@]3(OC1(C)C)[C@@H]2OC(=O)c1ccccc1
InChIInChI=1S/C38H40O9/c1-23-21-29(44-33(40)25-15-9-6-10-16-25)32(43-24(2)39)37(5)30(45-34(41)26-17-11-7-12-18-26)22-28-31(38(23,37)47-36(28,3)4)46-35(42)27-19-13-8-14-20-27/h6-20,23,28-32H,21-22H2,1-5H3/t23-,28-,29+,30+,31-,32+,37-,38-/m1/s1
InChIKeyULAZFRGMLIIKAD-MNRUEBDGSA-N
Species of MetaboliteComponentSourceComments
Microtropis fokienensis (ncbitaxon:1089417) root (BTO:0001188) PubMed (17315960)
Celastrus orbiculatus (ncbitaxon:85181) root (BTO:0001188) PubMed (10346948)
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.
antitubercular agent  A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Applications:
antitubercular agent  A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
orbiculin G (CHEBI:66828) has role antineoplastic agent (CHEBI:35610)
orbiculin G (CHEBI:66828) has role antitubercular agent (CHEBI:33231)
orbiculin G (CHEBI:66828) has role NF-κB inhibitor (CHEBI:73240)
orbiculin G (CHEBI:66828) has role plant metabolite (CHEBI:76924)
orbiculin G (CHEBI:66828) is a acetate ester (CHEBI:47622)
orbiculin G (CHEBI:66828) is a benzoate ester (CHEBI:36054)
orbiculin G (CHEBI:66828) is a bridged compound (CHEBI:35990)
orbiculin G (CHEBI:66828) is a cyclic ether (CHEBI:37407)
orbiculin G (CHEBI:66828) is a dihydroagarofuran sesquiterpenoid (CHEBI:71548)
orbiculin G (CHEBI:66828) is a organic heterotricyclic compound (CHEBI:26979)
Incoming Relation(s)
15-acetoxyorbiculin G (CHEBI:65364) has functional parent orbiculin G (CHEBI:66828)
IUPAC Name 
(3R,5S,5aR,6R,7S,9R,9aS,10R)-6-(acetyloxy)-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methano-1-benzoxepine-5,7,10-triyl tribenzoate
Synonym  Source
1β-acetoxy-2β,6α,9α-tribenzoyloxy-dihydro-β-agarofuranChEBI
Registry NumbersSources
Reaxys:8373955Reaxys
Citations