CHEBI:2981 - baicalin

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ChEBI Name baicalin
ChEBI ID CHEBI:2981
Definition The glycosyloxyflavone which is the 7-O-glucuronide of baicalein.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H18O11
Net Charge 0
Average Mass 446.36100
Monoisotopic Mass 446.085
InChI InChI=1S/C21H18O11/c22-9-6-10(8-4-2-1-3-5-8)30-11-7-12(14(23)15(24)13(9)11)31-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-7,16-19,21,23-27H,(H,28,29)/t16-,17-,18+,19-,21+/m0/s1
InChIKey IKIIZLYTISPENI-ZFORQUDYSA-N
SMILES O[C@H]1[C@@H](O[C@@H]([C@@H](O)[C@@H]1O)C(O)=O)Oc1cc2oc(cc(=O)c2c(O)c1O)-c1ccccc1
Metabolite of Species Details
Scutellaria baicalensis (NCBI:65409) Found in root (BTO:0001188). See: PubMed
Roles Classification
Biological Role(s): EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
Any EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of prolyl oligopeptidase (EC 3.4.21.26).
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application(s): non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing baicalin (CHEBI:2981) has functional parent baicalein (CHEBI:2979)
baicalin (CHEBI:2981) has role EC 3.4.21.26 (prolyl oligopeptidase) inhibitor (CHEBI:76779)
baicalin (CHEBI:2981) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
baicalin (CHEBI:2981) has role plant metabolite (CHEBI:76924)
baicalin (CHEBI:2981) has role prodrug (CHEBI:50266)
baicalin (CHEBI:2981) is a dihydroxyflavone (CHEBI:38686)
baicalin (CHEBI:2981) is a glucosiduronic acid (CHEBI:24302)
baicalin (CHEBI:2981) is a glycosyloxyflavone (CHEBI:50018)
baicalin (CHEBI:2981) is a monosaccharide derivative (CHEBI:63367)
baicalin (CHEBI:2981) is conjugate acid of baicalin(1−) (CHEBI:61283)
Incoming baicalin(1−) (CHEBI:61283) is conjugate base of baicalin (CHEBI:2981)
IUPAC Name
5,6-dihydroxy-4-oxo-2-phenyl-4H-chromen-7-yl β-D-glucopyranosiduronic acid
Synonyms Sources
5,6,7-trihydroxyflavone 7-O-β-D-glucuronide ChEBI
5,6-dihydroxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl β-D-glucopyranosiduronic acid ChemIDplus
7-D-glucuronic acid-5,6-dihydroxyflavone ChemIDplus
Baicalein 7-O-glucuronide KEGG COMPOUND
Baicalin KEGG COMPOUND
Database Links Databases
Baicalin Wikipedia
C00001024 KNApSAcK
C10025 KEGG COMPOUND
CN102584918 Patent
CPD-12725 MetaCyc
HMDB41832 HMDB
LMPK12111081 LIPID MAPS
WO2012119458 Patent
View more database links
Registry Numbers Types Sources
21967-41-9 CAS Registry Number KEGG COMPOUND
21967-41-9 CAS Registry Number ChemIDplus
70480 Reaxys Registry Number Reaxys
70480 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
10724177 PubMed citation CiteXplore
18650094 PubMed citation CiteXplore
21087019 PubMed citation CiteXplore
22467027 PubMed citation CiteXplore
23302221 PubMed citation CiteXplore
23354080 PubMed citation CiteXplore
23523628 PubMed citation CiteXplore
Last Modified
26 May 2015