CHEBI:2631 - amentoflavone

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ChEBI Name amentoflavone
ChEBI ID CHEBI:2631
Definition A biflavonoid that is obtained by oxidative coupling of two molecules of apigenin resulting in a bond between positions C-3 of the hydroxyphenyl ring and C-8 of the chromene ring. A natural product found particularly in Ginkgo biloba and Hypericum perforatum.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:65403
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Formula C30H18O10
Net Charge 0
Average Mass 538.45790
Monoisotopic Mass 538.090
InChI InChI=1S/C30H18O10/c31-15-4-1-13(2-5-15)24-12-23(38)29-21(36)10-20(35)27(30(29)40-24)17-7-14(3-6-18(17)33)25-11-22(37)28-19(34)8-16(32)9-26(28)39-25/h1-12,31-36H
InChIKey YUSWMAULDXZHPY-UHFFFAOYSA-N
SMILES Oc1ccc(cc1)-c1cc(=O)c2c(O)cc(O)c(-c3cc(ccc3O)-c3cc(=O)c4c(O)cc(O)cc4o3)c2o1
Metabolite of Species Details
Biophytum sensitivum (IPNI:371965-1) See: PubMed
Selaginella braunii (ITIS:17074) See: PubMed
Juniperus occidentalis (NCBI:txid114265) See: PubMed
Cupressus sempervirens (NCBI:txid13469) See: DOI
Selaginella sinensis (NCBI:txid137174) See: PubMed
Selaginella stauntoniana (NCBI:txid137175) See: PubMed
Selaginella tamariscina (NCBI:txid137178) See: PubMed
Selaginella doederleinii (NCBI:txid186426) See: PubMed
Cupressus cashmeriana (NCBI:txid187464) See: DOI
Taxus baccata (NCBI:txid25629) See: INDIAN J CHEM,35B,283
Selaginella uncinata (NCBI:txid307165) See: PubMed
Ginkgo biloba (NCBI:txid3311) See: PubMed
Selaginella davidii (NCBI:txid417315) See: PubMed
Cycas rumphii (NCBI:txid58031) See: PubMed
Thuja orientalis (NCBI:txid58046) See: PubMed
Lanaria lanata (NCBI:txid59087) See: DOI
Hypericum perforatum (NCBI:txid65561) See: PubMed
Selaginella pulvinata (NCBI:txid672198) See: PubMed
Selanginella moellendorfii (NCBI:txid88036) See: PubMed
Taxodium mucronatum (NCBI:txid99812) See: PubMed
Roles Classification
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
P450 inhibitor
An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.
cathepsin B inhibitor
A cysteine protease inhibitor which inhibits cathepsin B (EC 3.4.22.1).
antiviral agent
A substance that destroys or inhibits replication of viruses.
Application(s): angiogenesis inhibitor
An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing amentoflavone (CHEBI:2631) has role angiogenesis inhibitor (CHEBI:48422)
amentoflavone (CHEBI:2631) has role antiviral agent (CHEBI:22587)
amentoflavone (CHEBI:2631) has role cathepsin B inhibitor (CHEBI:64932)
amentoflavone (CHEBI:2631) has role P450 inhibitor (CHEBI:50183)
amentoflavone (CHEBI:2631) has role plant metabolite (CHEBI:76924)
amentoflavone (CHEBI:2631) is a biflavonoid (CHEBI:50128)
amentoflavone (CHEBI:2631) is a hydroxyflavone (CHEBI:24698)
amentoflavone (CHEBI:2631) is a ring assembly (CHEBI:36820)
Incoming 2,3-dihydro-4',4'''-di-O-methylamentoflavone (CHEBI:65770) has functional parent amentoflavone (CHEBI:2631)
ginkgetin (CHEBI:5353) has functional parent amentoflavone (CHEBI:2631)
sciadopitysin (CHEBI:9050) has functional parent amentoflavone (CHEBI:2631)
IUPAC Name
8-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Synonyms Sources
3',8''-Biapigenin KEGG COMPOUND
8-(5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one ChEBI
Didemethyl-ginkgetin HMDB
Manual Xrefs Databases
Amentoflavone Wikipedia
C00001015 KNApSAcK
C10018 KEGG COMPOUND
HMDB0030832 HMDB
LMPK12040009 LIPID MAPS
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Registry Numbers Types Sources
1617-53-4 CAS Registry Number ChemIDplus
380244 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11256492 PubMed citation Europe PMC
12372862 PubMed citation Europe PMC
15130600 PubMed citation Europe PMC
16084098 PubMed citation Europe PMC
18298378 PubMed citation Europe PMC
Last Modified
12 June 2015
General Comment
2012-07-27 INDIAN J CHEM,35B,283