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

HIDE SMILES / InChI

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

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
Identification of quercetin glucuronides in human plasma by high-performance liquid chromatography-tandem mass spectrometry.	2001 Apr 5	11334336
The in vitro inhibitory effect of flavonoid astilbin on 3-hydroxy-3-methylglutaryl coenzyme A reductase on Vero cells.	2001 Jul	11584575
Variability in the content of the constituents of Hypericum perforatum L. and some commercial extracts.	2001 Jul	11548855
Role of flavonoids in controlling the phototoxicity of Hypericum perforatum extracts.	2001 Jul	11515722
Domestic processing of onion bulbs (Allium cepa) and asparagus spears (Asparagus officinalis): effect on flavonol content and antioxidant status.	2001 Jul	11453754
Antioxidant and antiradical activities of flavonoids.	2001 Jun	11409965
Isolation and characterization of structurally novel antimutagenic flavonoids from spinach (Spinacia oleracea).	2001 Jun	11409964
Chemoprotective potentials of homoisoflavonoids and chalcones of Dracaena cinnabari: modulations of drug-metabolizing enzymes and antioxidant activity.	2001 Mar	11268108
Two new glycosides from Astragalus caprinus.	2001 May	11374969
Comparative evaluation of St. John's wort from different Italian regions.	2001 May-Jul	11482784
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
Antimicrobial and pesticidal activity of partially purified flavonoids of Annona squamosa.	2002 Jan	11838282
Dietary flavonols: chemistry, food content, and metabolism.	2002 Jan	11827770
Quercetin metabolism in the lens: role in inhibition of hydrogen peroxide induced cataract.	2002 Jul 1	12086683
The flavonol quercetin activates basolateral K(+) channels in rat distal colon epithelium.	2002 Mar	11877325
Flavonoids as anticancer agents: structure-activity relationship study.	2002 Nov	12678721
Novel two-band ratiometric fluorescence probes with different location and orientation in phospholipid membranes.	2002 Nov	12445770
Flavonol and flavone intakes in US health professionals.	2002 Oct	12396158
Myb-related genes of the Kyoho grape ( Vitis labruscana) regulate anthocyanin biosynthesis.	2002 Oct	12355152
Electrochromic modulation of excited-state intramolecular proton transfer: the new principle in design of fluorescence sensors.	2002 Oct 16	12371881
Induction of antioxidant flavonol biosynthesis in fresh-cut potatoes. Effect of domestic cooking.	2002 Oct 9	12358461
The relation between dietary flavonol intake and coronary heart disease mortality: a meta-analysis of prospective cohort studies.	2003 Aug	12879084
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
Cuticular waxes and flavonol aglycones of mistletoes.	2003 Jul-Aug	12939028
Dietary compounds inhibit proliferation and contraction of keloid and hypertrophic scar-derived fibroblasts in vitro: therapeutic implication for excessive scarring.	2003 Jun	12813346
Divergent evolution of flavonoid 2-oxoglutarate-dependent dioxygenases in parsley.	2003 Jun 5	12782296
Inhibitory effect of the plant flavonoid galangin on rat vas deferens in vitro.	2003 May 16	12706486
Evolutionary rate variation in anthocyanin pathway genes.	2003 Nov	12885963
Purification and characterization of a flavonol 3-O-beta-heterodisaccharidase from the dried herb of Fagopyrum esculentum Moench.	2003 Sep	12943757
Hepatoprotective activity of polyhydroxylated 2-styrylchromones against tert-butylhydroperoxide induced toxicity in freshly isolated rat hepatocytes.	2003 Sep	12879211

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:44:40 GMT 2023` Edited by `admin` on `Fri Dec 15 18:44:40 GMT 2023`
Record UNII	ZTG9LSS5QH
Record Status	`Validated (UNII)`
Record Version

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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