7-HYDROXYFLAVONE

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=CC2=C(C=C1)C(=O)C=C(O2)C3=CC=CC=C3

InChI

InChIKey=MQGPSCMMNJKMHQ-UHFFFAOYSA-N

InChI=1S/C15H10O3/c16-11-6-7-12-13(17)9-14(18-15(12)8-11)10-4-2-1-3-5-10/h1-9,16H

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16962702 | https://www.ncbi.nlm.nih.gov/pubmed/15319488 | https://www.ncbi.nlm.nih.gov/pubmed/26529431 | https://www.ncbi.nlm.nih.gov/pubmed/28295316 | https://www.ncbi.nlm.nih.gov/pubmed/24664133

7-hydroxyflavone belongs to the flavone subgroup of flavonoids. It is a potent inhibitor of 20alpha-hydroxysteroid dehydrogenase (AKR1C1), aromatase (cytochrome P450 19; CYP19), aldo-keto reductases AKR1B10 and AKR1B1. It can inhibit LPS-induced inflammation via attenuating the production of NO, PGE2, TNF-alpha and IL-6, indicating that it may be lead compound for developing anti-inflammatory agent. 7-hydroxyflavone may serve as potential protective agents in the treatment of patients with chronic EV71 infection.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Aldo-keto reductase family 1 member C1 4 Target ID: CHEMBL5905 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16962702	Inhibitor 8297	2.3 µM [IC50]
Aldose reductase 44 Target ID: CHEMBL1900 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26529431	Inhibitor 8297	12.3 µM [IC50]
Aldo-keto reductase family 1 member B10 7 Target ID: CHEMBL5983 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26529431	Inhibitor 8297	8.3 µM [IC50]
3C proteases of Enterovirus 71 1 Target ID: 3C proteases of Enterovirus 71 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24664133	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28295316	Primary	Basic research	Unknown Approved Use Unknown
Enterovirus infections 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24664133	Primary	Basic research	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9763404 https://www.ncbi.nlm.nih.gov/pubmed/28587286	Preventing	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds.	1994 Aug 3	7520698
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.	2001 Mar	11258977
Evaluation of 7-hydroxy-flavones as inhibitors of oestrone and oestradiol biosynthesis.	2001 Nov	11916147
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 Jul	12162852
Vasorelaxing effects of flavonoids: investigation on the possible involvement of potassium channels.	2004 Oct	15378228
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Methylated flavonoids have greatly improved intestinal absorption and metabolic stability.	2006 Oct	16868069
Empirically predicted 13C NMR chemical shifts for 8-hydroxyflavone starting from 7,8,4'-trihydroxyflavone and from 7,8-dihydroxyflavone.	2008 Jul	18389493
Antimetastatic potentials of flavones on oral cancer cell via an inhibition of matrix-degrading proteases.	2008 Mar	17936716
Inhibition of fatty acid amide hydrolase by kaempferol and related naturally occurring flavonoids.	2008 Sep	18552875
Ground and excited state proton transfer and antioxidant activity of 7-hydroxyflavone in model membranes: absorption and fluorescence spectroscopic studies.	2009 Jan	18977065
Metabolism and pharmacokinetics of 3,3',4',7-tetrahydroxyflavone (fisetin), 5-hydroxyflavone, and 7-hydroxyflavone and antihemolysis effects of fisetin and its serum metabolites.	2009 Jan 14	19090755
Mechanism of CYP2C9 inhibition by flavones and flavonols.	2009 Mar	19074529
A comparative study of flavonoid analogues on streptozotocin-nicotinamide induced diabetic rats: quercetin as a potential antidiabetic agent acting via 11beta-hydroxysteroid dehydrogenase type 1 inhibition.	2010 Jun	20346546
Isoform-selective inhibition of chrysin towards human cytochrome P450 1A2. Kinetics analysis, molecular docking, and molecular dynamics simulations.	2010 Oct 15	20832301

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 40 mg/kg of bodyweight

Route of Administration: Intragastric

In Vitro Use Guide

Renal proximal tubule (NRK52E) cells were pre-treated with 20 uM 7-Hydroxyflavone overnight prior to treatment with 200 uM nicotine and cell viability was determined 24 hours later. Nicotine significantly decreases cell viability, which was prevented by pretreatment with 7-Hydroxyflavone.

Name

Type

Language

7-HYDROXYFLAVONE

Systematic Name

English

4H-1-BENZOPYRAN-4-ONE, 7-HYDROXY-2-PHENYL-

Systematic Name

English

NSC-94258

Code

English

7-HYDROXY FLAVONE

Systematic Name

English

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

Systematic Name

English

2-PHENYL-CHROMEN-4-ONE

Systematic Name

English

7--HYDROXY-2-PHENYL-4-BENZOPYRONE

Common Name

English

HYDROXYFLAVONE, 7-

Systematic Name

English

Code System Code Type Description

CAS

6665-86-7