Compound: 7,8-dihydroxyflavone
SMILES: O=c1c2c(oc(c1)-c3ccccc3)c(O)c(O)cc2
InChIKey: COCYGNDCWFKTMF-UHFFFAOYSA-N
Synonyms: 7,8-dihydroxyflavone, 38183-03-8, 7,8-dihydroxy-2-phenyl-4H-chromen-4-one, 7,8-DHF, 4H-1-Benzopyran-4-one, 7,8-dihydroxy-2-phenyl-, 7,8-dihydroxy-2-phenylchromen-4-one, 7,8-Dihydroxy-flavone, 7,8-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one, 7,8-Dihydroxy-2-phenyl-4-benzopyrone, ADB6MA8ZV2, NSC-750341, FEMA NO. 4830, CHEBI:140464, DTXSID00191568, RefChem:105589, DTXCID40114059, 253-812-4, 7,8-Dihydroxyflavone hydrate, 7,8-Dihydroxy-2-phenyl-chromen-4-one, MFCD00006836, CHEMBL75267, 7,8-bis(oxidanyl)-2-phenyl-chromen-4-one, EINECS 253-812-4, BRN 0234350, 7,8-Dihydroxy-2-phenyl-4H-chromen-4-one; 7,8-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one;, UK9, 7,8-diOH-Flavone, Spectrum_001087, Spectrum2_000952, Spectrum3_000213, Spectrum4_001823, Spectrum5_000585, UNII-ADB6MA8ZV2, 8-DHF, BSPBio_001825, KBioGR_002491, KBioSS_001567, SPECTRUM201315, 5-18-04-00079 (Beilstein Handbook Reference), BIDD:ER0103, DivK1c_000371, SCHEMBL419316, SPBio_000944, MEGxp0_001683, orb1304985, 7,8-dihydroxy-2-phenylchromone, SCHEMBL29374601, HMS501C13, KBio1_000371, KBio2_001567, KBio2_004135, KBio2_006703, KBio3_001325, NINDS_000371, GLXC-06252, HMS1923A03, HMS3263G12, HMS3743I05, HMS3886D10, Tox21_501075, BDBM50093539, CCG-39038, NSC750341, s8319, SBB000930, AKOS015856571, CS-W014088, EBC-462088, FD46341, HY-W013372, NSC 750341, SDCCGMLS-0066465.P001, IDI1_000371, NCGC00095217-01, NCGC00095217-02, NCGC00095217-03, NCGC00095217-04, NCGC00095217-09, NCGC00095217-12, NCGC00178976-01, NCGC00261760-01, AC-23011, DS-16246, PD002189, ST057268, SY111956, DB-049244, D1916, NS00009738, 7,8-Dihydroxyflavone hydrate, >=98% (HPLC), C74948, AR-683/43483642, F222816, SR-05000002499, SR-05000002499-1, BRD-K49535716-001-02-4, BRD-K49535716-001-03-2, Q19596931
Theoretical properties:
molecular_formula: C15H10O4
molecular_weight: 254.24 g/mol
exact_mass: 254.05790880 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 1
heavy_atom_count: 19
topological_polar_surface_area: 66.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: Very slightly soluble
Descriptions:
{"pubchem": "7,8-dihydroxyflavone is a dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A naturally occurring flavonoid produced by several plants, including the weed Tridax procumbens (coalbuttons or tridax daisy) and the tree Godmania aesculifolia, In animal models, it has shown efficacy against several diseases of the nervous system, including Alzheimer's, Parkinson's, and Huntington's. It has a role as a tropomyosin-related kinase B receptor agonist, an antioxidant, an antidepressant, an antineoplastic agent and a plant metabolite.", "chebi": "A dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A naturally occurring flavonoid produced by several plants, including the weed <em>Tridax procumbens</em> (coalbuttons or tridax daisy) and the tree <em>Godmania aesculifolia</em>, In animal models, it has shown efficacy against several diseases of the nervous system, including Alzheimer's, Parkinson's, and Huntington's.", "chembl": "7,8-DIHYDROXYFLAVONE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Tropoflavin, also known as 7,8-dihydroxyflavone (7,8-DHF), is a naturally occurring flavone found in Godmania aesculifolia, Tridax procumbens, and Primula vulgaris. It has been found to act as a potent and selective small-molecule agonist of the tropomyosin receptor kinase B (TrkB) (Kd \u2248 320 nM), the main signaling receptor of the neurotrophin brain-derived neurotrophic factor (BDNF). Tropoflavin is both orally bioavailable and able to penetrate the blood\u2013brain barrier. A prodrug of tropoflavin with greatly improved potency and pharmacokinetics, R13 (and, formerly, R7), is under development for the treatment of Alzheimer's disease.\nTropoflavin has demonstrated therapeutic efficacy in animal models of a variety of central nervous system disorders, including depression, Alzheimer's disease, cognitive deficits in schizophrenia, Parkinson's disease, Huntington's disease, amyotrophic lateral sclerosis, traumatic brain injury, cerebral ischemia, fragile X syndrome, and Rett syndrome. Tropoflavin also shows efficacy in animal models of age-associated cognitive impairment and enhances memory consolidation and emotional learning in healthy rodents. In addition, tropoflavin possesses powerful antioxidant activity independent of its actions on the TrkB receptor, and protects against glutamate-induced excitotoxicity, 6-hydroxydopamine-induced dopaminergic neurotoxicity, and oxidative stress-induced genotoxicity. It was also found to block methamphetamine-induced dopaminergic neurotoxicity, an effect which, in contrast to the preceding, was found to be TrkB-dependent.\nIn 2017, evidence was published suggesting that tropoflavin and various other reported small-molecule TrkB agonists might not actually be direct agonists of the TrkB and might be mediating their observed effects by other means.\nTropoflavin has been found to act as a weak aromatase inhibitor in vitro (Ki = 10 \u03bcM), though there is evidence to suggest that this might not be the case in vivo. In addition, it has been found to inhibit aldehyde dehydrogenase and estrogen sulfotransferase in vitro (Ki = 35 \u03bcM and 1\u20133 \u03bcM, respectively), although similarly to the case of aromatase, these activities have not yet been confirmed in vivo. Unlike many other flavonoids, tropoflavin does not show any inhibitory activity on 17\u03b2-hydroxysteroid dehydrogenase. Tropoflavin has also been observed to possess in vitro antiestrogenic effects at very high concentrations (Ki = 50 \u03bcM).\nA variety of close structural analogues of tropoflavin have also been found to act as TrkB agonists in vitro, including diosmetin (5,7,3'-trihydroxy-4'-methoxyflavone), norwogonin (5,7,8-trihydroxyflavone), eutropoflavin (4'-dimethylamino-7,8-dihydroxyflavone), 7,8,3'-trihydroxyflavone, 7,3'-dihydroxyflavone, 7,8,2'-trihydroxyflavone, 3,7,8,2'-tetrahydroxyflavone, and 3,7-dihydroxyflavone. The highly hydroxylated analogue gossypetin (3,5,7,8,3',4'-hexahydroxyflavone), conversely, appears to be an antagonist of TrkB in vitro.\nTropoflavin was also found to decrease mouse sleep in dark phase and reduce hypothalamus level of orexin A, but not orexin B, in mice."}