FLAVONOL

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

Structure Search

SMILES

OC1=C(OC2=CC=CC=C2C1=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

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20346546
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	Potency
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19592245	Antagonist 2778	23.5 µM [IC50]
Carbonic anhydrase XII 30 Target ID: CHEMBL3242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22487176	Inhibitor 8297	6.59 µM [IC50]
Carbonic anhydrase IX 35 Target ID: CHEMBL3594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22487176	Inhibitor 8297	5.63 µM [IC50]
Carbonic anhydrase I 62 Target ID: CHEMBL261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22487176	Inhibitor 8297	5.63 µM [IC50]
Pregnane X receptor 35 Target ID: CHEMBL3401 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26238175	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Inflammatory bowel disease 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26238175	Primary		Basic research	Unknown Approved Use Unknown
Type 2 diabetes mellitus 259 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20346546	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Anti-HIV prenylated flavonoids from Monotes africanus.	2001 Apr	11325248
Determination of polyphenolic profiles of Basque cider apple varieties using accelerated solvent extraction.	2001 Aug	11513662
[Research on the selecting suspension cell line of higher productivity of flavonol glycoside by hypoxia stress as well as the stability in subcultures].	2001 Jan	11330197
Domestic processing of onion bulbs (Allium cepa) and asparagus spears (Asparagus officinalis): effect on flavonol content and antioxidant status.	2001 Jul	11453754
Determination of flavone, flavonol, and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry.	2001 Jun	11401161
A stress-responsive gene from groundnut, Gdi-15, is homologous to flavonol 3-O-glucosyltransferase involved in anthocyanin biosynthesis.	2001 Jun 15	11396938
Overexpression of petunia chalcone isomerase in tomato results in fruit containing increased levels of flavonols.	2001 May	11329019
Superoxide scavenging by polyphenols: effect of conjugation and dimerization.	2002	12625945
Chalcones and flavonoids as anti-tuberculosis agents.	2002 Aug	12057669
Bioactive constituents of Chinese natural medicines. VII. Inhibitors of degranulation in RBL-2H3 cells and absolute stereostructures of three new diarylheptanoid glycosides from the bark of Myrica rubra.	2002 Feb	11848211
Caffeine, quercetin and alizarin stimulate the exhalation of metabolic products of [14C]-N-nitrosodiethylamine in mice.	2002 Jun	12587722
Structure and biological activity of a new rotenoid from Pongamia pinnata.	2002 Oct	12434992
Flavonol and flavone intakes in US health professionals.	2002 Oct	12396158
High-flavonol tomatoes resulting from the heterologous expression of the maize transcription factor genes LC and C1.	2002 Oct	12368501
Silencing of the tapetum-specific zinc finger gene TAZ1 causes premature degeneration of tapetum and pollen abortion in petunia.	2002 Oct	12368491
Myb-related genes of the Kyoho grape ( Vitis labruscana) regulate anthocyanin biosynthesis.	2002 Oct	12355152
The unique occurrence of the flavone aglycone tricetin in Myrtaceae pollen.	2002 Sep-Oct	12440738
Profound difference in pharmacokinetics between morin and its isomer quercetin in rats.	2003 Feb	12631412
Six new isoflavones and a 5-deoxyflavonol glycoside from the leaves of Ateleiaherbert-smithii.	2003 Feb	12608851
Enhanced sensitivity of human oral tumours to the flavonol, morin, during cancer progression: involvement of the Akt and stress kinase pathways.	2003 Feb	12584164
Liquid chromatographic/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (Theobroma cacao).	2003 Jan	12526004
Malonylated flavonol glycosides from the petals of Clitoria ternatea.	2003 Jan	12482461
Two xanthones from Polygala paniculata and confirmation of the 1-hydroxy-2,3,5-trimethoxy-xanthone at trace level by HRGC-MS.	2003 Jul-Aug	12939033
Divergent evolution of flavonoid 2-oxoglutarate-dependent dioxygenases in parsley.	2003 Jun 5	12782296
Anti-inflammatory effect of rutin on rat paw oedema, and on neutrophils chemotaxis and degranulation.	2003 Mar	12710715
Perturbation of planarity as the possible mechanism of solvent-dependent variations of fluorescence quantum yield in 2-aryl-3-hydroxychromones.	2003 Mar 1	12609629
Protective effects of flavonoids on the cytotoxicity of linoleic acid hydroperoxide toward rat pheochromocytoma PC12 cells.	2003 Mar 6	12606158
Evolutionary rate variation in anthocyanin pathway genes.	2003 Nov	12885963
A novel Mg(2+)-dependent O-methyltransferase in the phenylpropanoid metabolism of Mesembryanthemum crystallinum.	2003 Nov 7	12941960
Purification and characterization of a flavonol 3-O-beta-heterodisaccharidase from the dried herb of Fagopyrum esculentum Moench.	2003 Sep	12943757

Patents

Sample Use Guides

In Vivo Use Guide

Rats were treated with as dose 50 mg/kg

Route of Administration: Oral

In Vitro Use Guide

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

Name

Type

Language

FLAVONOL

Systematic Name

English

NSC-57653

Code

English

3-HYDROXY-2-PHENYL-4H-CHROMEN-4-ONE

Systematic Name

English

3-HYDROXYFLAVONE [HSDB]

Common Name

English

NSC-58585

Code

English

3-HYDROXY-2-PHENYLCHROMONE

Systematic Name

English

NSC-58587

Code

English

FLAVON-3-OL

Systematic Name

English

4H-1-BENZOPYRAN-4-ONE, 3-HYDROXY-2-PHENYL-

Systematic Name

English

NSC-58586

Code

English

Code System Code Type Description

EPA CompTox

DTXSID4060365