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CHEBI:18388 - apigenin

ChEBI IDCHEBI:18388
ChEBI Nameapigenin
Stars
DefinitionA trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4', 5 and 7. It induces autophagy in leukaemia cells.
Secondary ChEBI IDsCHEBI:2768, CHEBI:12084, CHEBI:22588
Last Modified23 December 2022
DownloadsMolfile
FormulaC15H10O5
Net Charge0
Average Mass270.240
Monoisotopic Mass270.05282
SMILESO=c1cc(-c2ccc(O)cc2)oc2cc(O)cc(O)c12
InChIInChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
InChIKeyKZNIFHPLKGYRTM-UHFFFAOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Ficus mucuso (ncbitaxon:309328) fruit (BTO:0000486) PubMed (21619045) Methanolic extract of air-dried and powdered figs(fruits)
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
apigenin (CHEBI:18388) has role antineoplastic agent (CHEBI:35610)
apigenin (CHEBI:18388) has role metabolite (CHEBI:25212)
apigenin (CHEBI:18388) is a trihydroxyflavone (CHEBI:27116)
apigenin (CHEBI:18388) is conjugate acid of apigenin-7-olate (CHEBI:58470)
Incoming Relation(s)
3-methoxyapigenin (CHEBI:1579) has functional parent apigenin (CHEBI:18388)
5,7-dihydroxy-4'-methoxyflavone (CHEBI:15335) has functional parent apigenin (CHEBI:18388)
6-C-(α-L-arabinosyl)-8-C-(β-L-arabinosyl)apigenin (CHEBI:131754) has functional parent apigenin (CHEBI:18388)
6-C-D-Xylopyranosyl-8-C-L-arabinopyranosylapigenin (CHEBI:142908) has functional parent apigenin (CHEBI:18388)
6-C-L-arabinopyranosyl-8-C-D-xylopyranosylapigenin (CHEBI:142907) has functional parent apigenin (CHEBI:18388)
6,8-di-C-α-L-arabinosylapigenin (CHEBI:142912) has functional parent apigenin (CHEBI:18388)
7-O-[β-D-arabinopyranosyl-(1→6)-β-D-glucosyl]apigenin (CHEBI:75556) has functional parent apigenin (CHEBI:18388)
8-C-glucopyranosyl-6-C-xylopyranosylapigenin (CHEBI:142913) has functional parent apigenin (CHEBI:18388)
apigenin C-pentoside (CHEBI:131755) has functional parent apigenin (CHEBI:18388)
apigenin 7-O-neohesperidoside (CHEBI:31227) has functional parent apigenin (CHEBI:18388)
apigenin 7-O-β-D-glucoside (CHEBI:16778) has functional parent apigenin (CHEBI:18388)
apigenin 7-O-β-L-glucoside (CHEBI:132818) has functional parent apigenin (CHEBI:18388)
apigenin 7,4'-dimethyl ether (CHEBI:2769) has functional parent apigenin (CHEBI:18388)
apigenin-7-O-gentiobioside (CHEBI:145768) has functional parent apigenin (CHEBI:18388)
apiin (CHEBI:15932) has functional parent apigenin (CHEBI:18388)
genkwanin (CHEBI:75718) has functional parent apigenin (CHEBI:18388)
hinokiflavone (CHEBI:5721) has functional parent apigenin (CHEBI:18388)
isoschaftoside (CHEBI:75589) has functional parent apigenin (CHEBI:18388)
isoscutellarein (CHEBI:6059) has functional parent apigenin (CHEBI:18388)
isovitexin (CHEBI:18330) has functional parent apigenin (CHEBI:18388)
neoschaftoside (CHEBI:7513) has functional parent apigenin (CHEBI:18388)
ochnaflavone (CHEBI:194126) has functional parent apigenin (CHEBI:18388)
schaftoside (CHEBI:9047) has functional parent apigenin (CHEBI:18388)
scutellarein (CHEBI:9062) has functional parent apigenin (CHEBI:18388)
swertisin (CHEBI:131838) has functional parent apigenin (CHEBI:18388)
vitexin (CHEBI:16954) has functional parent apigenin (CHEBI:18388)
apigenin-7-olate (CHEBI:58470) is conjugate base of apigenin (CHEBI:18388)
IUPAC Name 
5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Synonyms  Source
ApigeninKEGG COMPOUND
4',5,7-TrihydroxyflavoneKEGG COMPOUND
5,7,4'-TrihydroxyflavoneKEGG COMPOUND
5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyroneChemIDplus
5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChemIDplus
2-(p-hydroxyphenyl)-5,7-dihydroxychromoneChemIDplus
Manual XrefsDatabases
C01477KEGG COMPOUND
LMPK12110005LIPID MAPS
CPD-431MetaCyc
HMDB0002124HMDB
ApigeninWikipedia
C00003817KNApSAcK
AGIPDBeChem
LSM-5206LINCS
Registry NumbersSources
Reaxys:262620Reaxys
CAS:520-36-5KEGG COMPOUND
CAS:520-36-5ChemIDplus
Citations