CHEBI:65742 - 5-O-demethylpaxanthonin

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ChEBI Name 5-O-demethylpaxanthonin
ChEBI ID CHEBI:65742
ChEBI ASCII Name 5-O-demethylpaxanthonin
Definition A member of the class of xanthones consisting of paxanthonin in which the methoxy group at position 5 is replaced by a hydroxy group. Isolated from the roots of Hypericum roeperianum and leaves of Hypericum styphelioides, it exhibits antioxidant and antifungal activities.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C23H24O6
Net Charge 0
Average Mass 396.43310
Monoisotopic Mass 396.15729
InChI InChI=1S/C23H24O6/c1-10(2)11-7-13(23(3,4)9-11)17-15(25)8-16-18(21(17)28)19(26)12-5-6-14(24)20(27)22(12)29-16/h5-6,8,11,13,24-25,27-28H,1,7,9H2,2-4H3/t11-,13+/m0/s1
InChIKey LYMUFMGSOHLCHO-WCQYABFASA-N
SMILES [H][C@@]1(C[C@]([H])(c2c(O)cc3oc4c(O)c(O)ccc4c(=O)c3c2O)C(C)(C)C1)C(C)=C
Metabolite of Species Details
Hypericum styphelioides (IPNI:433886-1) Found in leaf (BTO:0000713). See: PubMed
Hypericum roeperianum (NCBI:txid269018) Found in root (BTO:0001188). See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 5-O-demethylpaxanthonin (CHEBI:65742) has functional parent paxanthonin (CHEBI:71520)
5-O-demethylpaxanthonin (CHEBI:65742) has role antifungal agent (CHEBI:35718)
5-O-demethylpaxanthonin (CHEBI:65742) has role antioxidant (CHEBI:22586)
5-O-demethylpaxanthonin (CHEBI:65742) has role metabolite (CHEBI:25212)
5-O-demethylpaxanthonin (CHEBI:65742) is a polyphenol (CHEBI:26195)
5-O-demethylpaxanthonin (CHEBI:65742) is a xanthones (CHEBI:51149)
Incoming 1,3,5-trihydroxy-2-(2',2'-dimethyl-4'-isopropenyl)cyclopentanylxanthone (CHEBI:66053) has functional parent 5-O-demethylpaxanthonin (CHEBI:65742)
IUPAC Name
2-[(1S,4S)-2,2-dimethyl-4-(prop-1-en-2-yl)cyclopentyl]-1,3,5,6-tetrahydroxy-9H-xanthen-9-one
Synonym Source
1,3,5,6-tetrahydroxy-2-(2',2'-dimethyl-4'-isopropenyl)-cyclopentanylxanthone ChEBI
Manual Xref Database
13100107 ChemSpider
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Registry Number Type Source
7665231 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15165152 PubMed citation Europe PMC
8862040 PubMed citation Europe PMC
Last Modified
26 February 2013