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CHEBI:141332 - guignardone N

Default Structure
ChEBI IDCHEBI:141332
ChEBI Nameguignardone N
Stars
DefinitionA meroterpenoid found in Guignardia and Fusarium species and shown to exhibit inhibitory activity against Candida albicans growth.
Last Modified17 August 2023
SubmitterR. Stephan
DownloadsMolfile
FormulaC17H24O6
Net Charge0
Average Mass324.373
Monoisotopic Mass324.15729
SMILES[H][C@@]12CC3=C(O[C@]1(C)CC[C@@]2([H])[C@](C)(O)CO)[C@@H]1C[C@@](O)(CO1)C3=O
InChIInChI=1S/C17H24O6/c1-15(20,7-18)10-3-4-16(2)11(10)5-9-13(23-16)12-6-17(21,8-22-12)14(9)19/h10-12,18,20-21H,3-8H2,1-2H3/t10-,11+,12+,15-,16-,17-/m1/s1
InChIKeyOPYPWMGWBUCOSQ-RZNLEFLGSA-N
Species of MetaboliteComponentSourceComments
Fusarium sp. (ncbitaxon:29916) cell suspension culture (BTO:0000221) PubMed (35541335 )
Guignardia sp. (ncbitaxon:1715232) cell suspension culture (BTO:0000221) PubMed (26577190)
Roles Classification
Biological Roles:
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
guignardone N (CHEBI:141332) has role antifungal agent (CHEBI:35718)
guignardone N (CHEBI:141332) has role fungal metabolite (CHEBI:76946)
guignardone N (CHEBI:141332) is a meroterpenoid (CHEBI:64419)
guignardone N (CHEBI:141332) is a organic heterotetracyclic compound (CHEBI:38163)
guignardone N (CHEBI:141332) is a organic hydroxy compound (CHEBI:33822)
guignardone N (CHEBI:141332) is a primary alcohol (CHEBI:15734)
guignardone N (CHEBI:141332) is a tertiary alcohol (CHEBI:26878)
guignardone N (CHEBI:141332) is a tertiary α-hydroxy ketone (CHEBI:139592)
guignardone N (CHEBI:141332) is a triol (CHEBI:27136)
IUPAC Name 
(1S,4R,6aS,7R,9aR)-7-[(2S)-1,2-dihydroxypropan-2-yl]-4-hydroxy-9a-methyl-3,4,6,6a,7,8,9,9a-octahydro-1,4-methanocyclopenta[5,6]pyrano[2,3-c]oxepin-5(1H)-one
Synonym  Source
guignardone NChEBI
Registry NumbersSources
Reaxys:28851661Reaxys
Citations