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

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/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
Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates.	1994 Sep-Oct	7835232
No evidence for the in vivo activity of aromatase-inhibiting flavonoids.	2001 Sep	11595503
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
Manganese-based complexes of radical scavengers as neuroprotective agents.	2003 May 15	12713845
Vasorelaxing effects of flavonoids: investigation on the possible involvement of potassium channels.	2004 Oct	15378228
Effect of different flavonoids on collagen synthesis in human fibroblasts.	2006 Mar	16642409
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
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
Intestinal first-pass glucuronidation activities of selected dihydroxyflavones.	2009 Jan 21	18809479
AKR1C3 as a potential target for the inhibitory effect of dietary flavonoids.	2009 Mar 16	19007764
Methylation of dietary flavones increases their metabolic stability and chemopreventive effects.	2009 Nov 18	20087474
Structure-function relationships of inhibition of human cytochromes P450 1A1, 1A2, 1B1, 2C9, and 3A4 by 33 flavonoid derivatives.	2010 Dec 20	21053930
Structure-affinity relationship of flavones on binding to serum albumins: effect of hydroxyl groups on ring A.	2010 Jul	20306480
Comprehensive review of Clerodendrum phlomidis: a traditionally used bitter.	2010 Jun	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 Jun	20346546
Use of glucuronidation fingerprinting to describe and predict mono- and dihydroxyflavone metabolism by recombinant UGT isoforms and human intestinal and liver microsomes.	2010 Jun 7	20297805
2-(4-Bromo-phen-yl)-6-methyl-4H-1-benzopyran-4-one (4'-bromo-6-methyl-flavone).	2010 Mar 27	21580767
Isoform-selective inhibition of chrysin towards human cytochrome P450 1A2. Kinetics analysis, molecular docking, and molecular dynamics simulations.	2010 Oct 15	20832301
In vitro effects of some flavones on human pyruvate kinase isoenzyme M2.	2015 Mar	25388478

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:31:30 GMT 2023` Edited by `admin` on `Fri Dec 15 18:31:30 GMT 2023`
Record UNII	ZE72458E4L
Record Status	`Validated (UNII)`
Record Version

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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