CHEBI:66828 - orbiculin G

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ChEBI Name orbiculin G
ChEBI ID CHEBI:66828
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C38H40O9
Net Charge 0
Average Mass 640.71880
Monoisotopic Mass 640.26723
InChI InChI=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
InChIKey ULAZFRGMLIIKAD-MNRUEBDGSA-N
SMILES [H][C@]12C[C@H](OC(=O)c3ccccc3)[C@]3(C)[C@@H](OC(C)=O)[C@H](C[C@@H](C)[C@@]3(OC1(C)C)[C@@H]2OC(=O)c1ccccc1)OC(=O)c1ccccc1
Metabolite of Species Details
Microtropis fokienensis (NCBI:txidtxid1089417) Found in root (BTO:0001188). See: PubMed
Celastrus orbiculatus (NCBI:txidtxid85181) Found in root (BTO:0001188). See: PubMed
Roles Classification
Biological Role(s): 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.
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.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antitubercular agent
A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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-agarofuran ChEBI
Registry Number Type Source
8373955 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10346948 PubMed citation Europe PMC
17315960 PubMed citation Europe PMC
Last Modified
14 April 2015