CHEBI:66395 - miquelianin

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ChEBI Name miquelianin
ChEBI ID CHEBI:66395
Definition A quercetin O-glycoside that consists of quercetin attached to a β-D-glucuronopyranosyl moiety at position 3 via a glycosidic linkage. Isolated from Salvia and Phaseolus vulgaris, it exhibits antioxidant and antidepressant activities.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H18O13
Net Charge 0
Average Mass 478.35980
InChI InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)/t14-,15-,16+,19-,21+/m0/s1
InChIKey DUBCCGAQYVUYEU-ZUGPOPFOSA-N
SMILES O[C@H]1[C@@H](O[C@@H]([C@@H](O)[C@@H]1O)C(O)=O)Oc1c(oc2cc(O)cc(O)c2c1=O)-c1ccc(O)c(O)c1
Metabolite of Species Details
Polygonum salicifolium (IPNI:696398-1) Found in aerial part (BTO:0001658). See: PubMed
Foeniculum dulce (IPNI:842661-1) Found in flower (BTO:0000469). See: DOI
Callistemon lanceolatus (NCBI:155884) Found in leaf (BTO:0000713). See: PubMed
Callistemon lanceolatus (NCBI:155884) Found in flower (BTO:0000469). See: PubMed
Salvia (NCBI:21880) See: PubMed
Phaseolus vulgaris (NCBI:3885) See: DOI
Schinus molle (NCBI:43851) Found in leaf (BTO:0000713). See: PubMed
Foeniculum vulgare (NCBI:48038) Found in flower (BTO:0000469). See: DOI
Hypericum perforatum (NCBI:65561) See: PubMed
Hypericum hirsutum (NCBI:673928) See: DOI
Reynoutria sachalinensis (NCBI:76036) Found in flower (BTO:0000469). See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing miquelianin (CHEBI:66395) has role antidepressant (CHEBI:35469)
miquelianin (CHEBI:66395) has role antioxidant (CHEBI:22586)
miquelianin (CHEBI:66395) has role metabolite (CHEBI:25212)
miquelianin (CHEBI:66395) is a β-D-glucosiduronic acid (CHEBI:15341)
miquelianin (CHEBI:66395) is a quercetin O-glycoside (CHEBI:76424)
IUPAC Name
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl β-D-glucopyranosiduronic acid
Synonyms Sources
quercetin 3-O-glucuronide HMDB
quercetin-3-O-β-D-glucuronopyranoside ChEBI
quercituron ChemIDplus
Database Links Databases
HMDB29212 HMDB
LMPK12112173 LIPID MAPS
Miquelianin Wikipedia
View more database links
Registry Numbers Types Sources
22688-79-5 CAS Registry Number ChemIDplus
72004 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10479312 PubMed citation CiteXplore
11809447 PubMed citation CiteXplore
14735439 PubMed citation CiteXplore
15742803 PubMed citation CiteXplore
16521111 PubMed citation CiteXplore
18618463 PubMed citation CiteXplore
Last Modified
26 November 2013