CHEBI:18388 - apigenin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name apigenin
ChEBI ID CHEBI:18388
Definition A trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4', 5 and 7. It induces autophagy in leukaemia cells.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:12084, CHEBI:2768, CHEBI:22588
Supplier Information ChemicalBook:CB1384541, eMolecules:478202, Selleckchem:Apigenin, ZINC000003871576
Download Molfile XML SDF
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
Formula C15H10O5
Net Charge 0
Average Mass 270.23690
Monoisotopic Mass 270.05282
InChI InChI=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
InChIKey KZNIFHPLKGYRTM-UHFFFAOYSA-N
SMILES Oc1ccc(cc1)-c1cc(=O)c2c(O)cc(O)cc2o1
Metabolite of Species Details
Ficus mucuso (NCBI:txid309328) Found in fruit (BTO:0000486). Methanolic extract of air-dried and powdered figs(fruits) See: PubMed
Roles Classification
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): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 3-methoxyapigenin (CHEBI:1579) has functional parent apigenin (CHEBI:18388)
5,7-dihydroxy-4'-methoxyflavone (CHEBI:15335) has functional parent apigenin (CHEBI:18388)
6,8-di-C-α-L-arabinosylapigenin (CHEBI:142912) 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)
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 7,4'-dimethyl ether (CHEBI:2769) 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-O-neohesperidoside (CHEBI:31227) has functional parent apigenin (CHEBI:18388)
apigenin C-pentoside (CHEBI:131755) 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 Sources
2-(p-hydroxyphenyl)-5,7-dihydroxychromone ChemIDplus
4',5,7-Trihydroxyflavone KEGG COMPOUND
5,7,4'-Trihydroxyflavone KEGG COMPOUND
5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone ChemIDplus
5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one ChemIDplus
Apigenin KEGG COMPOUND
C.I. Natural Yellow 1 ChemIDplus
chamomile ChEBI
spigenin ChEBI
versulin ChEBI
Manual Xrefs Databases
AGI PDBeChem
Apigenin Wikipedia
C00003817 KNApSAcK
C01477 KEGG COMPOUND
CPD-431 MetaCyc
HMDB0002124 HMDB
LMPK12110005 LIPID MAPS
LSM-5206 LINCS
View more database links
Registry Numbers Types Sources
262620 Reaxys Registry Number Reaxys
520-36-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
23 December 2022