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CHEBI:71520 - paxanthonin

ChEBI IDCHEBI:71520
ChEBI Namepaxanthonin
Stars
DefinitionA member of the class of xanthones that is 9H-xanthen-9-one substituted by a 2,2-dimethyl-4-(prop-1-en-2-yl)cyclopentyl group at position 2, hydroxy groups at positions 1, 3 and 6 and a methoxy group at position 5. It is isolated from the callus of Hypericum perforatum and exhibits antioxidant and antimicrobial activities.
Last Modified14 April 2015
Submitternamrata
DownloadsMolfile
FormulaC24H26O6
Net Charge0
Average Mass410.466
Monoisotopic Mass410.17294
SMILES[H][C@@]1(C(=C)C)CC(C)(C)[C@@]([H])(c2c(O)cc3oc4c(OC)c(O)ccc4c(=O)c3c2O)C1
InChIInChI=1S/C24H26O6/c1-11(2)12-8-14(24(3,4)10-12)18-16(26)9-17-19(21(18)28)20(27)13-6-7-15(25)23(29-5)22(13)30-17/h6-7,9,12,14,25-26,28H,1,8,10H2,2-5H3/t12-,14+/m0/s1
InChIKeyGYBUSKWANOPNPI-GXTWGEPZSA-N
Species of MetaboliteComponentSourceComments
Hypericum perforatum (ncbitaxon:65561) callus (BTO:0001010) PubMed (15715262)
Roles Classification
Chemical Role:
radical scavenger  A role played by a substance that can react readily with, and thereby eliminate, radicals.
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
ChEBI Ontology
Outgoing Relation(s)
paxanthonin (CHEBI:71520) has role antimicrobial agent (CHEBI:33281)
paxanthonin (CHEBI:71520) has role plant metabolite (CHEBI:76924)
paxanthonin (CHEBI:71520) has role radical scavenger (CHEBI:48578)
paxanthonin (CHEBI:71520) is a aromatic ether (CHEBI:35618)
paxanthonin (CHEBI:71520) is a polyphenol (CHEBI:26195)
paxanthonin (CHEBI:71520) is a xanthones (CHEBI:51149)
Incoming Relation(s)
5-O-demethylpaxanthonin (CHEBI:65742) has functional parent paxanthonin (CHEBI:71520)
IUPAC Name 
2-[(1S,4S)-2,2-dimethyl-4-(prop-1-en-2-yl)cyclopentyl]-1,3,6-trihydroxy-5-methoxy-9H-xanthen-9-one
Registry NumbersSources
Reaxys:7394169Reaxys
Citations