CHEBI:141296 - (1R,4R,5R,8S)-8-hydroxy-4,8-dimethyl-2-oxabicyclo[3.3.1]nonan-3-one

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ChEBI Name (1R,4R,5R,8S)-8-hydroxy-4,8-dimethyl-2-oxabicyclo[3.3.1]nonan-3-one
ChEBI ID CHEBI:141296
ChEBI ASCII Name (1R,4R,5R,8S)-8-hydroxy-4,8-dimethyl-2-oxabicyclo[3.3.1]nonan-3-one
Definition An organic heterobicyclic compound that is 2-oxabicyclo[3.3.1]nonan-3-one which has been substituted by an oxo group at position 3, methyl groups at positions 4 and 8, and by a hydroxy group at position 8 (the 1R,4R,5R,8S stereoisomer). Isolated from the plant endophytic fungus Pestalotiopsis foedan.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter R. Stephan
Supplier Information
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Formula C10H16O3
Net Charge 0
Average Mass 184.233
Monoisotopic Mass 184.10994
InChI InChI=1S/C10H16O3/c1-6-7-3-4-10(2,12)8(5-7)13-9(6)11/h6-8,12H,3-5H2,1-2H3/t6-,7-,8-,10+/m1/s1
InChIKey NIVFCUNTHUULDF-DQUBFYRCSA-N
SMILES O1[C@]2([C@](CC[C@@]([C@H](C1=O)C)(C2)[H])(O)C)[H]
Metabolite of Species Details
Neopestalotiopsis foedans (NCBI:txid290095) See: PubMed
Roles Classification
Biological Role(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
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ChEBI Ontology
Outgoing (1R,4R,5R,8S)-8-hydroxy-4,8-dimethyl-2-oxabicyclo[3.3.1]nonan-3-one (CHEBI:141296) has role antifungal agent (CHEBI:35718)
(1R,4R,5R,8S)-8-hydroxy-4,8-dimethyl-2-oxabicyclo[3.3.1]nonan-3-one (CHEBI:141296) has role fungal metabolite (CHEBI:76946)
(1R,4R,5R,8S)-8-hydroxy-4,8-dimethyl-2-oxabicyclo[3.3.1]nonan-3-one (CHEBI:141296) is a δ-lactone (CHEBI:18946)
(1R,4R,5R,8S)-8-hydroxy-4,8-dimethyl-2-oxabicyclo[3.3.1]nonan-3-one (CHEBI:141296) is a monoterpenoid (CHEBI:25409)
(1R,4R,5R,8S)-8-hydroxy-4,8-dimethyl-2-oxabicyclo[3.3.1]nonan-3-one (CHEBI:141296) is a organic heterobicyclic compound (CHEBI:27171)
(1R,4R,5R,8S)-8-hydroxy-4,8-dimethyl-2-oxabicyclo[3.3.1]nonan-3-one (CHEBI:141296) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(1R,4R,5R,8S)-8-hydroxy-4,8-dimethyl-2-oxabicyclo[3.3.1]nonan-3-one
Citation Waiting for Citations Type Source
27448166 PubMed citation Europe PMC
Last Modified
07 May 2021