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 8504	2.3 µM [IC50]
Aldose reductase 45 Target ID: CHEMBL1900 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26529431	Inhibitor 8504	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 8504	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 8504

Conditions

Condition	Modality	Highest Phase	Product
Inflammation 105 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 609 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
In vitro effects of some flavones on human pyruvate kinase isoenzyme M2.	2015-03	25388478
Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives.	2010-12-20	21053930
Isoform-selective inhibition of chrysin towards human cytochrome P450 1A2. Kinetics analysis, molecular docking, and molecular dynamics simulations.	2010-10-15	20832301
Structure-affinity relationship of flavones on binding to serum albumins: effect of hydroxyl groups on ring A.	2010-07	20306480
Use of glucuronidation fingerprinting to describe and predict mono- and dihydroxyflavone metabolism by recombinant UGT isoforms and human intestinal and liver microsomes.	2010-06-07	20297805
Comprehensive review of Clerodendrum phlomidis: a traditionally used bitter.	2010-06	20550872
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.	2010-06	20346546
2-(4-Bromo-phen-yl)-6-methyl-4H-1-benzopyran-4-one (4'-bromo-6-methyl-flavone).	2010-03-27	21580767
Methylation of dietary flavones increases their metabolic stability and chemopreventive effects.	2009-11-18	20087474
AKR1C3 as a potential target for the inhibitory effect of dietary flavonoids.	2009-03-16	19007764
Mechanism of CYP2C9 inhibition by flavones and flavonols.	2009-03	19074529
Intestinal first-pass glucuronidation activities of selected dihydroxyflavones.	2009-01-21	18809479
Metabolism and pharmacokinetics of 3,3',4',7-tetrahydroxyflavone (fisetin), 5-hydroxyflavone, and 7-hydroxyflavone and antihemolysis effects of fisetin and its serum metabolites.	2009-01-14	19090755
Ground and excited state proton transfer and antioxidant activity of 7-hydroxyflavone in model membranes: absorption and fluorescence spectroscopic studies.	2009-01	18977065
Inhibition of fatty acid amide hydrolase by kaempferol and related naturally occurring flavonoids.	2008-09	18552875
Protein engineering on biphenyl dioxygenase for conferring activity to convert 7-hydroxyflavone and 5,7-dihydroxyflavone (chrysin).	2008-08	18804053
Empirically predicted 13C NMR chemical shifts for 8-hydroxyflavone starting from 7,8,4'-trihydroxyflavone and from 7,8-dihydroxyflavone.	2008-07	18389493
Phytoestrogens and breast cancer prevention: possible mechanisms of action.	2008-04	18414622
Antimetastatic potentials of flavones on oral cancer cell via an inhibition of matrix-degrading proteases.	2008-03	17936716
Interaction of 7-hydroxyflavone with human serum albumin: a spectroscopic study.	2008-01-30	18068375
Multi-substrate flavonol O-glucosyltransferases from strawberry (Fragaria x ananassa) achene and receptacle.	2008	18487633
Aromatase inhibition by bioavailable methylated flavones.	2007-10	17624765
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
Phytoestrogens as inhibitors of the human progesterone metabolizing enzyme AKR1C1.	2006-10-19	16962702
Methylated flavonoids have greatly improved intestinal absorption and metabolic stability.	2006-10	16868069
[Study on the non-covalent interaction of 7-hydroxy flavone and its phosphate with DNA by fluorescence method].	2006-03	16830759
Effect of different flavonoids on collagen synthesis in human fibroblasts.	2006-03	16642409
Microbial metabolism. Part 6. Metabolites of 3- and 7-hydroxyflavones.	2006-03	16508185
Characterization of polyphenols from plant materials through their silylation and 29Si NMR spectroscopy-line assignment through 29Si, 13C spin-spin couplings.	2005-10	16041773
Induction and inhibition of aromatase (CYP19) activity by natural and synthetic flavonoid compounds in H295R human adrenocortical carcinoma cells.	2004-11	15319488
Vasorelaxing effects of flavonoids: investigation on the possible involvement of potassium channels.	2004-10	15378228
The inhibitory effects of flavonoids and antiestrogens on the Glut1 glucose transporter in human erythrocytes.	2003-12-15	14642735
Manganese-based complexes of radical scavengers as neuroprotective agents.	2003-05-15	12713845
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	12162852
Evaluation of 7-hydroxy-flavones as inhibitors of oestrone and oestradiol biosynthesis.	2001-11	11916147
No evidence for the in vivo activity of aromatase-inhibiting flavonoids.	2001-09	11595503
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.	2001-03	11258977
Inhibitors of human and rat testes microsomal 17beta-hydroxysteroid dehydrogenase (17beta-HSD) as potential agents for prostatic cancer.	2001-01	11496833
Effect of simple phenolic compounds on azoxymethane-induced aberrant crypt foci in rat colon.	2001	12094612
Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates.	1994-09-01	7835232
Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds.	1994-08-03	7520698
Differential inhibitory effects of various flavonoids on the activities of reverse transcriptase and cellular DNA and RNA polymerases.	1990-07-05	1695572

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

NSC-94258

Preferred Name

English

7-HYDROXYFLAVONE

Systematic Name

English

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

Systematic Name

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