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CHEBI:2631 - amentoflavone

ChEBI IDCHEBI:2631
ChEBI Nameamentoflavone
Stars
DefinitionA 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.
Secondary ChEBI IDCHEBI:65403
Last Modified12 June 2015
DownloadsMolfile
FormulaC30H18O10
Net Charge0
Average Mass538.464
Monoisotopic Mass538.09000
SMILESO=c1cc(-c2ccc(O)c(-c3c(O)cc(O)c4c(=O)cc(-c5ccc(O)cc5)oc34)c2)oc2cc(O)cc(O)c12
InChIInChI=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
InChIKeyYUSWMAULDXZHPY-UHFFFAOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Taxus baccata (ncbitaxon:25629) - Article (INDIAN J CHEM,35B,283)
Lanaria lanata (ncbitaxon:59087) - DOI (10.1021/np50075a007)
Juniperus occidentalis (ncbitaxon:114265) - PubMed (12372862)
Cupressus sempervirens (ncbitaxon:13469) - DOI (10.1021/np50051a032)
Selaginella pulvinata (ncbitaxon:672198) - PubMed (11256492)
Selanginella moellendorfii (ncbitaxon:88036) - PubMed (11256492)
Thuja orientalis (ncbitaxon:58046) - PubMed (19280159)
Biophytum sensitivum (IPNI:371965-1) - PubMed (18298378)
Selaginella braunii (ITIS:17074) - PubMed (11256492)
Ginkgo biloba (ncbitaxon:3311) - PubMed (3212094)
Selaginella stauntoniana (ncbitaxon:137175) - PubMed (11256492)
Selaginella tamariscina (ncbitaxon:137178) - PubMed (11256492)
Selaginella davidii (ncbitaxon:417315) - PubMed (11256492)
Cupressus cashmeriana (ncbitaxon:187464) - DOI (10.1021/np50051a032)
Hypericum perforatum (ncbitaxon:65561) - PubMed (16084098)
Cycas rumphii (ncbitaxon:58031) - PubMed (15130600)
Selaginella uncinata (ncbitaxon:307165) - PubMed (11256492)
Taxodium mucronatum (ncbitaxon:99812) - PubMed (16084098)
Selaginella sinensis (ncbitaxon:137174) - PubMed (11256492)
Selaginella doederleinii (ncbitaxon:186426) - PubMed (11256492)
Roles Classification
Biological Roles:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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.
P450 inhibitor  An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.
Application:
angiogenesis inhibitor  An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
3',8''-BiapigeninKEGG 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-oneChEBI
Didemethyl-ginkgetinHMDB
Manual XrefsDatabases
C10018KEGG COMPOUND
LMPK12040009LIPID MAPS
HMDB0030832HMDB
AmentoflavoneWikipedia
C00001015KNApSAcK
Registry NumbersSources
Reaxys:380244Reaxys
CAS:1617-53-4KEGG COMPOUND
CAS:1617-53-4ChemIDplus
Citations