Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H10O2 |
| Molecular Weight | 222.2387 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C1C=C(OC2=C1C=CC=C2)C3=CC=CC=C3
InChI
InChIKey=VHBFFQKBGNRLFZ-UHFFFAOYSA-N
InChI=1S/C15H10O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-10H
| Molecular Formula | C15H10O2 |
| Molecular Weight | 222.2387 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Flavone belongs to the class of organic compounds known as flavones. Flavones are mainly found in cereals and herbs. Flavone is a less potent inhibitor of CYP1A1 than CYP1A2. Flavone inhibited the estrogen action without binding to the estrogen receptor by acting as a competitive agonist for aryl hydrocarbon receptor. This naturally occurring flavone was shown to be an effective inducer of benzpyrene hydroxylase in human liver microsomes in in vitro assays, and the inducing effect of the flavone was concentration-dependent.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Advanced glycation end-products formation Sources: DOI: 10.1007/s00044-017-2078-4 |
116.5 µM [IC50] | ||
Target ID: CHEMBL2922 |
0.14 µM [IC50] | ||
Target ID: CHEMBL1075125 |
0.066 µM [IC50] | ||
Target ID: CHEMBL3201 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Modification of flavonoid using lipase in non-conventional media: effect of the water content. | 2003-02-27 |
|
| 2,3-Diarylbenzopyran derivatives as a novel class of selective cyclooxygenase-2 inhibitors. | 2003-02-10 |
|
| Studies on the chemical constituents of stem bark of Millettia leucantha: isolation of new chalcones with cytotoxic, anti-herpes simplex virus and anti-inflammatory activities. | 2003-02 |
|
| Flavone C-glycoside, phenolic acid, and nitrogen contents in leaves of barley subject to organic fertilization treatments. | 2003-01-29 |
|
| Insect antifeedant activity of flavones and chromones against Spodoptera litura. | 2003-01-15 |
|
| 2D-IR correlation analysis of deteriorative process of traditional Chinese medicine 'Qing Kai Ling' injection. | 2003-01-01 |
|
| Urinary pharmacokinetics of baicalein, wogonin and their glycosides after oral administration of Scutellariae Radix in humans. | 2003-01 |
|
| Flavopiridol, a cyclin dependent kinase (CDK) inhibitor, induces apoptosis by regulating Bcl-x in oral cancer cells. | 2003-01 |
|
| Baicalein and genistein display differential actions on estrogen receptor (ER) transactivation and apoptosis in MCF-7 cells. | 2002-12-10 |
|
| Combination of vascular targeting agents with thermal or radiation therapy. | 2002-12-01 |
|
| Two flavones from Scutellaria baicalensis Georgi and their binding affinities to the benzodiazepine site of the GABAA receptor complex. | 2002-12 |
|
| Flavone-coumarin hybrids from Gnidia socotrana. | 2002-12 |
|
| Phase I clinical and pharmacokinetic trial of the cyclin-dependent kinase inhibitor flavopiridol. | 2002-12 |
|
| The unique occurrence of the flavone aglycone tricetin in Myrtaceae pollen. | 2002-11-21 |
|
| Antiproliferative activities of citrus flavonoids against six human cancer cell lines. | 2002-10-09 |
|
| [Quantitative genetic analysis and multiple trait selection of pharmaceutical composition on Ginkgo biloba L. leaves]. | 2002-10 |
|
| Flavonol and flavone intakes in US health professionals. | 2002-10 |
|
| Self-modelling analysis applied to nanosecond transient absorption spectroscopy of flavone: an aid to elucidate and characterise reaction intermediates. | 2002-10 |
|
| Accurate prediction of xanthine oxidase inhibition based on the structure of flavonoids. | 2002-09-13 |
|
| Refinement and evaluation of a pharmacophore model for flavone derivatives binding to the benzodiazepine site of the GABA(A) receptor. | 2002-09-12 |
|
| The antitumour activity of 5,6-dimethylxanthenone-4-acetic acid (DMXAA) in TNF receptor-1 knockout mice. | 2002-08-12 |
|
| GABA(A)-receptor ligands of flavonoid structure. | 2002-08 |
|
| Chalcones and flavonoids as anti-tuberculosis agents. | 2002-08 |
|
| Flavones from Scutellaria baicalensis Georgi attenuate apoptosis and protein oxidation in neuronal cell lines. | 2002-07-03 |
|
| Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids. | 2002-07 |
|
| QSAR aspects of flavonoids as a plentiful source of new drugs. | 2002-07 |
|
| Activation of the antitumor agent aminoflavone (NSC 686288) is mediated by induction of tumor cell cytochrome P450 1A1/1A2. | 2002-07 |
|
| Interactions of different phenolic acids and flavonoids with soy proteins. | 2002-06-18 |
|
| Induction of endothelial cell apoptosis by the antivascular agent 5,6-Dimethylxanthenone-4-acetic acid. | 2002-06-17 |
|
| Cytotoxic flavonoids from the stem bark of Lonchocarpus aff. fluvialis. | 2002-06 |
|
| Arginine to lysine 108 substitution in recombinant CYP1A2 abolishes methoxyresorufin metabolism in lymphoblastoid cells. | 2002-06 |
|
| A novel combretastatin A-4 derivative, AC7700, strongly stanches tumour blood flow and inhibits growth of tumours developing in various tissues and organs. | 2002-05-20 |
|
| Protection of flavonoids against lipid peroxidation: the structure activity relationship revisited. | 2002-05 |
|
| [Antibacterial constituents against Helicobacter pylori of Brazilian medicinal plant, Pariparoba]. | 2002-04 |
|
| Novel FMN-containing rotenone-insensitive NADH dehydrogenase from Trypanosoma brucei mitochondria: isolation and characterization. | 2002-03-05 |
|
| Luteolin, a flavone, does not suppress postprandial glucose absorption through an inhibition of alpha-glucosidase action. | 2002-03 |
|
| Activation of isoflavone biosynthesis in excised cotyledons of Lupinus seedlings by jasmonoids and excess light. | 2002-02-12 |
|
| Evidence that a type-2 NADH:quinone oxidoreductase mediates electron transfer to particulate methane monooxygenase in methylococcus capsulatus. | 2002-02-01 |
|
| Diterpenoids from Salvia ceratophylla. | 2002-02 |
|
| Flavone glucoside uptake into barley mesophyll and Arabidopsis cell culture vacuoles. Energization occurs by H(+)-antiport and ATP-binding cassette-type mechanisms. | 2002-02 |
|
| Determination of non-steroidal estrogens in breast milk, plasma, urine and hair by gas chromatography/mass spectrometry. | 2002 |
|
| Uptake of the antivascular agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA) and activation of NF-kappaB in human tumor cell lines. | 2002 |
|
| Activation of bone sialoprotein gene transcription by flavonoids is mediated through an inverted CCAAT box in ROS 17/2.8 cells. | 2002 |
|
| Interactions of flavones and other phytochemicals with adenosine receptors. | 2002 |
|
| A straightforward means of coupling preparative high-performance liquid chromatography and mass spectrometry. | 2002 |
|
| Synthesis, antiplatelet and vasorelaxing effects of monooxygenated flavones and flavonoxypropanolamines. | 2001-12 |
|
| Acute effects of vascular modifying agents in solid tumors assessed by noninvasive laser Doppler flowmetry and near infrared spectroscopy. | 2001-10-15 |
|
| Modulation by insulin rather than blood glucose of the pain threshold in acute physiological and flavone induced antinociception in mice. | 2001-10 |
|
| Role of protein kinase C, PI3-kinase and tyrosine kinase in activation of MAP kinase by glucose and agonists of G-protein coupled receptors in INS-1 cells. | 2001 |
|
| A new antibacterial diterpene from the roots of Salvia caespitosa. | 2001 |
Patents
| Substance Class |
Chemical
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| Record UNII |
S2V45N7G3B
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| Record Status |
Validated (UNII)
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| Record Version |
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