Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-05-15 00:12:34 UTC
Update Date2025-10-07 16:05:14 UTC
Metabolite IDMMDBc0006813
Metabolite Identification
Common NameOxysporidinone
DescriptionOxysporidinone is a member of the pyridone chemical class, specifically characterized by its hydroxy-substituted cyclohexanone ring. This compound is biosynthesized through a complex process involving phenol dearomatization, although the precise biochemical mechanisms remain to be fully elucidated (PMID:37086399 ). The biosynthetic gene cluster responsible for oxysporidinone production has been identified in the fungus Fusarium oxysporum, highlighting its significance in fungal metabolism (PMID:37086399 ). Oxysporidinone and its derivatives, such as 4,6'-anhydrooxysporidinone, have been shown to exhibit biological activities, including the induction of autophagic and apoptotic cell death in MCF-7 breast cancer cells (PMID:34208033 ). Additionally, 4,6'-anhydrooxysporidinone has demonstrated neuroprotective effects on hippocampal neuronal cell lines (PMID:34208033 ). The compound has also been isolated from various Fusarium species, emphasizing its diverse occurrence in endophytic fungi associated with medicinal plants (PMID:36484574 ; PMID:29915912 ). Furthermore, studies involving biomimetic conversions have provided insights into the structural relationships between oxysporidinone and other tricyclic pyridone alkaloids (PMID:21419624 ).
Structure
SynonymsNot Available
Molecular FormulaC28H43NO6
Average Mass489.653
Monoisotopic Mass489.309038109
IUPAC Name5-(1,2-dihydroxy-4-oxocyclohexyl)-3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-1-methyl-1,2-dihydropyridin-2-one
Traditional Name5-(1,2-dihydroxy-4-oxocyclohexyl)-3-[6-(4,6-dimethyloct-2-en-2-yl)-5-methyloxan-2-yl]-4-hydroxy-1-methylpyridin-2-one
CAS Registry NumberNot Available
SMILES
CCC(C)CC(C)C=C(C)C1OC(CCC1C)C1=C(O)C(=CN(C)C1=O)C1(O)CCC(=O)CC1O
InChI Identifier
InChI=1S/C28H43NO6/c1-7-16(2)12-17(3)13-19(5)26-18(4)8-9-22(35-26)24-25(32)21(15-29(6)27(24)33)28(34)11-10-20(30)14-23(28)31/h13,15-18,22-23,26,31-32,34H,7-12,14H2,1-6H3
InChI KeyCYNJYGDSSURTLH-UHFFFAOYSA-N