CHEBI:71520 - paxanthonin

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ChEBI Name paxanthonin
ChEBI ID CHEBI:71520
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C24H26O6
Net Charge 0
Average Mass 410.45960
Monoisotopic Mass 410.17294
InChI InChI=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
InChIKey GYBUSKWANOPNPI-GXTWGEPZSA-N
SMILES [H][C@@]1(C[C@]([H])(c2c(O)cc3oc4c(OC)c(O)ccc4c(=O)c3c2O)C(C)(C)C1)C(C)=C
Metabolite of Species Details
Hypericum perforatum (NCBI:txid65561) Found in callus (BTO:0001010). See: PubMed
Roles Classification
Chemical Role(s): radical scavenger
A role played by a substance that can react readily with, and thereby eliminate, radicals.
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Number Type Source
7394169 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15715262 PubMed citation Europe PMC
19062051 PubMed citation Europe PMC
Last Modified
14 April 2015