Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H10O3 |
| Molecular Weight | 238.2381 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=C(OC2=C(C=CC=C2)C1=O)C3=CC=CC=C3
InChI
InChIKey=HVQAJTFOCKOKIN-UHFFFAOYSA-N
InChI=1S/C15H10O3/c16-13-11-8-4-5-9-12(11)18-15(14(13)17)10-6-2-1-3-7-10/h1-9,17H
| Molecular Formula | C15H10O3 |
| Molecular Weight | 238.2381 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19592245 | https://www.ncbi.nlm.nih.gov/pubmed/28640852 | https://www.ncbi.nlm.nih.gov/pubmed/21805085 | https://www.ncbi.nlm.nih.gov/pubmed/26238175
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19592245 | https://www.ncbi.nlm.nih.gov/pubmed/28640852 | https://www.ncbi.nlm.nih.gov/pubmed/21805085 | https://www.ncbi.nlm.nih.gov/pubmed/26238175
Flavonol (3-Hydroxyflavone) is a practically insole synthetic compound, which is not found naturally in plants. 3-hydroxyflavone can be found in a number of food items such as brassicas, pomegranate, red raspberry, and fenugreek, which makes 3-hydroxyflavone a potential biomarker for the consumption of these food products. Flavonol serves as a model molecule as it possesses an excited-state intramolecular proton transfer (ESIPT) effect to serve as a fluorescent probe to study membranes for example or intermembrane proteins.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1871 |
23.5 µM [IC50] | ||
Target ID: CHEMBL3242 |
6.59 µM [IC50] | ||
Target ID: CHEMBL3594 |
5.63 µM [IC50] | ||
Target ID: CHEMBL261 |
5.63 µM [IC50] | ||
Target ID: CHEMBL3401 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| A novel Mg(2+)-dependent O-methyltransferase in the phenylpropanoid metabolism of Mesembryanthemum crystallinum. | 2003-11-07 |
|
| Evolutionary rate variation in anthocyanin pathway genes. | 2003-11 |
|
| Purification and characterization of a flavonol 3-O-beta-heterodisaccharidase from the dried herb of Fagopyrum esculentum Moench. | 2003-09 |
|
| Hepatoprotective activity of polyhydroxylated 2-styrylchromones against tert-butylhydroperoxide induced toxicity in freshly isolated rat hepatocytes. | 2003-09 |
|
| Two xanthones from Polygala paniculata and confirmation of the 1-hydroxy-2,3,5-trimethoxy-xanthone at trace level by HRGC-MS. | 2003-08-27 |
|
| Cuticular waxes and flavonol aglycones of mistletoes. | 2003-08-27 |
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| Quality and enhancement of bioactive phenolics in cv. Napoleon table grapes exposed to different postharvest gaseous treatments. | 2003-08-27 |
|
| Identification and determination of flavonoids in buckwheat (Fagopyrum esculentum Moench, Polygonaceae) by high-performance liquid chromatography with electrospray ionisation mass spectrometry and photodiode array ultraviolet detection. | 2003-08-16 |
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| Identification of flavonol and xanthone glycosides from mango (Mangifera indica L. Cv. "Tommy Atkins") peels by high-performance liquid chromatography-electrospray ionization mass spectrometry. | 2003-08-13 |
|
| The relation between dietary flavonol intake and coronary heart disease mortality: a meta-analysis of prospective cohort studies. | 2003-08 |
|
| Naringin, a citrus flavonone, protects against radiation-induced chromosome damage in mouse bone marrow. | 2003-07 |
|
| Divergent evolution of flavonoid 2-oxoglutarate-dependent dioxygenases in parsley. | 2003-06-05 |
|
| Flavonoids inhibit VEGF/bFGF-induced angiogenesis in vitro by inhibiting the matrix-degrading proteases. | 2003-06-01 |
|
| Dietary compounds inhibit proliferation and contraction of keloid and hypertrophic scar-derived fibroblasts in vitro: therapeutic implication for excessive scarring. | 2003-06 |
|
| Fisetin, a flavonol, inhibits TH2-type cytokine production by activated human basophils. | 2003-06 |
|
| Flavonol and drimane-type sesquiterpene glycosides of Warburgia stuhlmannii leaves. | 2003-06 |
|
| Inhibitory effect of the plant flavonoid galangin on rat vas deferens in vitro. | 2003-05-16 |
|
| Profiling of flavonoid conjugates in Lupinus albus and Lupinus angustifolius responding to biotic and abiotic stimuli. | 2003-05 |
|
| Solvent influence on excited-state intramolecular proton transfer in 3-hydroxychromone derivatives studied by cryogenic high-resolution fluorescence spectroscopy. | 2003-05 |
|
| A rationale for the shift in colour towards blue in transgenic carnation flowers expressing the flavonoid 3',5'-hydroxylase gene. | 2003-05 |
|
| Protective effects of flavonoids on the cytotoxicity of linoleic acid hydroperoxide toward rat pheochromocytoma PC12 cells. | 2003-03-06 |
|
| Perturbation of planarity as the possible mechanism of solvent-dependent variations of fluorescence quantum yield in 2-aryl-3-hydroxychromones. | 2003-03-01 |
|
| Anti-inflammatory effect of rutin on rat paw oedema, and on neutrophils chemotaxis and degranulation. | 2003-03 |
|
| Profound difference in pharmacokinetics between morin and its isomer quercetin in rats. | 2003-02 |
|
| Six new isoflavones and a 5-deoxyflavonol glycoside from the leaves of Ateleiaherbert-smithii. | 2003-02 |
|
| Enhanced sensitivity of human oral tumours to the flavonol, morin, during cancer progression: involvement of the Akt and stress kinase pathways. | 2003-02 |
|
| Liquid chromatographic/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (Theobroma cacao). | 2003-01 |
|
| Malonylated flavonol glycosides from the petals of Clitoria ternatea. | 2003-01 |
|
| Mechanism of action of St John's wort in depression : what is known? | 2003 |
|
| Valorization of grape (Vitis vinifera) byproducts. Antioxidant and biological properties of polyphenolic fractions differing in procyanidin composition and flavonol content. | 2002-12-18 |
|
| The unique occurrence of the flavone aglycone tricetin in Myrtaceae pollen. | 2002-11-21 |
|
| Determination of flavonol metabolites in plasma and tissues of rats by HPLC-radiocounting and tandem mass spectrometry following oral ingestion of [2-(14)C]quercetin-4'-glucoside. | 2002-11-06 |
|
| Rat kidney antioxidant response to long-term exposure to flavonol rich red wine. | 2002-11-01 |
|
| Flavonoids as anticancer agents: structure-activity relationship study. | 2002-11 |
|
| Novel two-band ratiometric fluorescence probes with different location and orientation in phospholipid membranes. | 2002-11 |
|
| Electrochromic modulation of excited-state intramolecular proton transfer: the new principle in design of fluorescence sensors. | 2002-10-16 |
|
| Analysis of wine phenolics by high-performance liquid chromatography using a monolithic type column. | 2002-10-11 |
|
| Induction of antioxidant flavonol biosynthesis in fresh-cut potatoes. Effect of domestic cooking. | 2002-10-09 |
|
| Structure and biological activity of a new rotenoid from Pongamia pinnata. | 2002-10 |
|
| Flavonol and flavone intakes in US health professionals. | 2002-10 |
|
| Expression of genes involved in anthocyanin biosynthesis in relation to anthocyanin, proanthocyanidin, and flavonol levels during bilberry fruit development. | 2002-10 |
|
| High-flavonol tomatoes resulting from the heterologous expression of the maize transcription factor genes LC and C1. | 2002-10 |
|
| Silencing of the tapetum-specific zinc finger gene TAZ1 causes premature degeneration of tapetum and pollen abortion in petunia. | 2002-10 |
|
| Myb-related genes of the Kyoho grape ( Vitis labruscana) regulate anthocyanin biosynthesis. | 2002-10 |
|
| Antitumor-promoting constituents from Dioscorea bulbifera L. in JB6 mouse epidermal cells. | 2002-09 |
|
| Flavonoids suppress the cytotoxicity of linoleic acid hydroperoxide toward PC12 cells. | 2002-08 |
|
| 7-OH-flavone is sulfated in the human liver and duodenum, whereas 5-OH-flavone and 3-OH-flavone are potent inhibitors of SULT1A1 activity and 7-OH-flavone sulfation rate. | 2002-07 |
|
| Caffeine, quercetin and alizarin stimulate the exhalation of metabolic products of [14C]-N-nitrosodiethylamine in mice. | 2002-06 |
|
| Superoxide scavenging by polyphenols: effect of conjugation and dimerization. | 2002 |
|
| Effect of simple phenolic compounds on azoxymethane-induced aberrant crypt foci in rat colon. | 2001 |
Sample Use Guides
The rat renal proximal tubule cell line (NRK52E) was used for activity evaluation. Microplate assay using oxidant-sensitive 20,70-dichlorofluorescein-diacetate (DCFDA; Invitrogen, Grand Island, NY) measured the intracellular generation of ROS. Cells grown in T25 flasks were pretreated with either 20 μM3HF (Flavonol) or 20 μM7HF for overnight as required and isolated with trypsinization. After washing and counting, cells were loaded with 100 μM DCFDA in HBSS for 30 min at 37ÊC. After incubation, the excess dye was removed by washing with fresh HBSS and placed in wells of a 96-well plate (0.5 x 10^6 cells/well). 200 μMNIC was added to the appropriate wells and the increase in fluorescence was monitored in a fluorescence plate reader (Fluorocount, Packard) at 485 nmexc/530 nmem. ROS production was calculated as changes in fluorescence/30 min/0.5 x 10^6 cells and expressed as the percentage of untreated values
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:19:49 GMT 2025
by
admin
on
Mon Mar 31 19:19:49 GMT 2025
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| Record UNII |
ZTG9LSS5QH
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| Record Status |
Validated (UNII)
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| Record Version |
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3-Hydroxyflavone
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