Compound: Amentoflavone
SMILES: O=c1c2c(oc(c1)-c3ccc(O)cc3)c(c(O)cc2O)-c4c(O)ccc(c4)-c5oc6c(c(O)cc(c6)O)c(c5)=O
InChIKey: YUSWMAULDXZHPY-UHFFFAOYSA-N
Synonyms: Amentoflavone, 1617-53-4, Didemethyl-ginkgetin, 3',8''-Biapigenin, Tridemethylsciadopitysin, DTXSID20167225, 9I1VC79L77, 4H-1-Benzopyran-4-one, 8-[5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-, NSC-295677, CHEBI:2631, 8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one, 4H-1-Benzopyran-4-one, 8-(5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-, 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, 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, 8-(5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one, RefChem:111894, DTXCID1089716, Amenthoflavone, MFCD00017470, 8-(5-(5,7-Dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one, I3',II8-BIAPIGENIN, MLS000574827, 8-[5-(5,7-dihydroxy-4-oxo-chromen-2-yl)-2-hydroxy-phenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one, 8-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one, SMR000156235, SR-01000721725, UNII-9I1VC79L77, AMentotaxus biflavone, Apigenin Impurity 3, 3'8''-biapigenin, NSC 295677, Amentoflavone (Standard), A1D6Q, BIDD:PXR0028, GINKGETIN, DIDEMETHYL-, SCHEMBL312563, MEGxp0_000924, orb1304220, orb3140672, SCHEMBL29497539, SCHEMBL29929632, HY-N0662R, med.21724, Compound 138, Amentoflavone, analytical standard, BDBM429466, HMS2228B12, HMS3343J17, HMS3885A08, HMS6018F20, HY-N0662, Amentoflavone, >=99.0% (HPLC), LMPK12040009, MFCD20275041, NSC295677, s3833, AKOS015896819, CCG-269950, CS-4945, EBC-457103, FA65485, 3',8-Bi[4',5,7-trihydroxyflavone], NCGC00247542-01, NCGC00247542-02, AC-34718, BS-15502, SY055524, DB-043499, A2544, NS00074071, A11476, AO-229/40763433, Q4742425, SR-01000721725-2, SR-01000721725-3, 4',5,7-Trihydroxyflavone(3'->8)-4',5,7-trihydroxyflavone, 3''',8-BIFLAVONE, 4',4''',5,5'',7,7''-HEXAHYDROXY, 4',4''',5,5'',7,7''-Hexahydroxy-3''',8-biflavone, 8CI, 4H-1-Benzopyran-4-one, 8-[5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)
Theoretical properties:
molecular_formula: C30H18O10
molecular_weight: 538.5 g/mol
exact_mass: 538.08999677 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 10
rotatable_bond_count: 3
heavy_atom_count: 40
topological_polar_surface_area: 174 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 300 °C
Descriptions:
pubchem: Amentoflavone is 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. It has a role as an antiviral agent, an angiogenesis inhibitor, a P450 inhibitor, a cathepsin B inhibitor and a plant metabolite. It is a hydroxyflavone, a ring assembly and a biflavonoid.
chebi: 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 <em>Ginkgo biloba</em> and <em>Hypericum perforatum</em>.
chembl: AMENTOFLAVONE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Amentoflavone is a biflavonoid (bis-apigenin coupled at 8 and 3′ positions, or 3′,8″-biapigenin) constituent of a number of plants including Ginkgo biloba, Chamaecyparis obtusa (hinoki), Biophytum sensitivum, Selaginella tamariscina, Hypericum perforatum (St. John's Wort) and Xerophyta plicata.
Amentoflavone can interact with many medications by being a potent inhibitor of CYP3A4 and CYP2C9, which are enzymes responsible for the metabolism of some drugs in the body. It is also an inhibitor of human cathepsin B.
Amentoflavone has a variety of in vitro activities including antimalarial activity, anticancer activity (which may, at least in part, be mediated by its inhibition of fatty acid synthase), and antagonist activity at the κ-opioid receptor (Ke = 490 nmol L−1) as well as activity at the allosteric benzodiazepine site of the GABAA receptor as a negative allosteric modulator.