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CHEBI:191933 - pennicitrinone C

ChEBI IDCHEBI:191933
ChEBI Namepennicitrinone C
Stars
DefinitionA pyranoxanthene that is 3,5-dihydro-2H-pyrano[4,3,2-kl]xanthene substituted by methyl groups at positions 2R, 3S, 4, and 10, by an oxo group at position 5, by hydroxy groups at positions 8 and 10, and by a (2S,3S)-3-hydroxybutan-2-yl group at position 9. It is a natural product isolated from the fungus Penicillium citrinum B-57.
Last Modified17 May 2022
SubmitterAdnan
DownloadsMolfile
FormulaC23H26O6
Net Charge0
Average Mass398.455
Monoisotopic Mass398.17294
SMILESCc1c([C@H](C)[C@H](C)O)c(O)c2oc3cc(=O)c(C)c4c-3c(c2c1O)O[C@H](C)[C@H]4C
InChIInChI=1S/C23H26O6/c1-8(12(5)24)17-11(4)20(26)19-22-18-15(29-23(19)21(17)27)7-14(25)10(3)16(18)9(2)13(6)28-22/h7-9,12-13,24,26-27H,1-6H3/t8-,9-,12+,13-/m1/s1
InChIKeyHESPWWKIRCFDQL-MNUQUWEESA-N
Species of MetaboliteComponentSourceComments
Penicillium citrinum (ncbitaxon:5077) - PubMed (18281952) Strain: B-57
Roles Classification
Chemical Role:
radical scavenger  A role played by a substance that can react readily with, and thereby eliminate, radicals.
Biological Role:
fungal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
ChEBI Ontology
Outgoing Relation(s)
pennicitrinone C (CHEBI:191933) has role fungal metabolite (CHEBI:76946)
pennicitrinone C (CHEBI:191933) has role radical scavenger (CHEBI:48578)
pennicitrinone C (CHEBI:191933) is a phenols (CHEBI:33853)
pennicitrinone C (CHEBI:191933) is a pyranoxanthene (CHEBI:64515)
pennicitrinone C (CHEBI:191933) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(2R,3S)-8,11-dihydroxy-9-[(2S,3S)-3-hydroxybutan-2-yl]-2,3,4,10-tetramethyl-2,3-dihydro-5H-pyrano[4,3,2-kl]xanthen-5-one
Synonym  Source
(14S,15R)-3,6-dihydroxy-5-[(2S,3S)-3-hydroxybutan-2-yl]-4,12,14,15-tetramethyl-8,16-dioxatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,12-hexaen-11-oneIUPAC
Manual XrefsDatabases
23340845ChemSpider
Citations