ISOQUERCETIN

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H20O12
Molecular Weight	464.3763
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C4=CC=C(O)C(O)=C4)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=OVSQVDMCBVZWGM-QSOFNFLRSA-N

InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H20O12
Molecular Weight	464.3763
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=763386 | DOI: 10.1007/978-1-4614-0535-1_485 | https://www.ncbi.nlm.nih.gov/pubmed/28097231 | https://www.ncbi.nlm.nih.gov/pubmed/20826184 | https://www.ncbi.nlm.nih.gov/pubmed/28413477

Isoquercetin is a flavonoid, derivative of quercetin. It was isolated from various plant species including Ammothamnus Lehmanii, Caragana alaica, Cicer baldshuanicum, C. macroconthum, C. pungens, Euphorbia cyparissias, E. helioscapia, E. lathyris, E. lucida, E. purporata and others. It demonstrated radical scavenging activity, inhibitory effects on Na+/K+-ATPase and positive inotropic activity. It is protein disulfide isomerase (PDI) inhibitor. As a PDI inhibitor, this agent blocks PDI-mediated platelet activation, and fibrin generation, which prevents thrombus formation after vascular injury. Isoquercetin inhibited the replication of both influenza A and B viruses at the lowest effective concentration. Isoquercetin activates the ERK1/2-Nrf2 pathway and protects against cerebral ischemia-reperfusion injury in vivo and in vitro. It is being investigated for prevention of thromboembolism in selected cancer patients and as an anti-fatigue agent in kidney cancer patients treated with sunitinib.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
ERK1 - ERK2 MAPK cascade 7 Target ID: WP402 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28413477	Activator 1430
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25312183 \| https://www.ncbi.nlm.nih.gov/pubmed/26166137 \| 10.1007/978-1-4614-0535-1_485	Inhibitor 8297
Sodium/potassium-transporting ATPase 39 Target ID: CHEMBL2095186 Sources: DOI: 10.1007/978-1-4614-0535-1_485	Inhibitor 8297
Protein disulfide-isomerase 4 Target ID: CHEMBL5422 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28097231 \| https://www.ncbi.nlm.nih.gov/pubmed/24677236	Inhibitor 8297	2.5 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Thrombosis, cancer associated 1 Sources: https://clinicaltrials.gov/ct2/show/NCT02195232 http://adisinsight.springer.com/trials/700247597	Preventing	Phase III 656	Unknown Approved Use Unknown
Kidney cancer 10 Sources: https://clinicaltrials.gov/ct2/show/NCT02446795	Secondary	Phase II 1132	Unknown Approved Use Unknown
Chronic kidney disease 56 Sources: https://clinicaltrials.gov/ct2/show/NCT02552888	Primary	Phase II 1132	Unknown Approved Use Unknown

AUC

Value	Dose	Co-administered	Analyte	Population
15 μM × h OTHER GOV'T https://clinicaltrials.gov/ct2/show/results/NCT01722669	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		QUERCETIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00360R	https://www.1pchem.com/search?query=1P00360R
AK Scientific	V0296	https://aksci.com/item_detail.php?cat=V0296
Angene	AGN-PC-0RYY9L	http://www.angenechemical.com/productshow/AGN-PC-0RYY9L.html
Apollo Scientific	BIDF1022	http://www.apolloscientific.co.uk/chemical_results.php?qstext=BIDF1022&product_group=%25&search_fieldname=header_search
AstaTech	44263	http://astatechinc.com/CPSResult.php?CRNO=44263
BOC Sciences	21637-25-2	http://www.bocsci.com/description.asp?cas=21637-25-2
BioSynth	Q-100268	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-100268
Biopurify Phytochemicals	BP0793	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP0793&searchhtmp=simplesearch&t=1
Chem Scene	CS-0016884	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0016884
ChemShuttle	181523	https://www.chemshuttle.com/catalogsearch/result/?q=181523
Combi-Blocks	QC-6151	http://www.combi-blocks.com/cgi-bin/find.cgi?QC-6151
KeyOrganics	AS-35335	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-35335
MedChem Express	HY-N1445	https://www.medchemexpress.com/search.html?q=HY-N1445&ft=&fa=&fp=
MolPort	MolPort-001-740-247	https://www.molport.com/shop/molecule-link/MolPort-001-740-247
Oakwood	99483	http://www.oakwoodchemical.com/ProductsList.aspx?txtSearch=099483
TargetMol	BBP01921	https://www.targetmol.com/search?keyword=BBP01921
TargetMol	T4902	https://www.targetmol.com/search?keyword=T4902
TargetMol	T5S0754	https://www.targetmol.com/search?keyword=T5S0754
W&J PharmaChem	50C516196	http://wjpharmachem.com/new/searcht.php?keyword=50C516196
W&J PharmaChem	50C516197	http://wjpharmachem.com/new/searcht.php?keyword=50C516197
eMolecules	485752	https://orderbb.emolecules.com/search/#?query=485752
eNovation Chemicals	D659311	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D659311&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-1611345094	https://mcule.com/MCULE-1611345094/
mcule	MCULE-2852848721	https://mcule.com/MCULE-2852848721/

PubMed

Title	Date	PubMed
A search for anti-viral properties in Panamanian medicinal plants. The effects on HIV and its essential enzymes.	1999 Jan	10075118
Inhibitory effects of sudanese medicinal plant extracts on hepatitis C virus (HCV) protease.	2000 Nov	11054840
Inhibitory activity of flavonoids and tannins against HIV-1 protease.	2000 Sep	10993207
Antioxidative components from the aerial parts of Lactuca scariola L.	2001 Oct	11693545
Inhibitory effect of quercetin on carrageenan-induced inflammation in rats.	2003 Dec 26	14654164
Glycosides from Grewia damine and Filicium decipiens.	2004 Dec	15595608
[Studies on chemical constituents from flowers of Apocynum venetum].	2005 Sep	16323543
Quantitative determination of major active components in Ginkgo biloba dietary supplements by liquid chromatography/mass spectrometry.	2006	16921563
Inhibition of human cytochrome CYP 1 enzymes by flavonoids of St. John's wort.	2006 Jan 16	16271822
Development of an HPLC-PAD-MS assay for the identification and quantification of major phenolic edelweiss (Leontopodium alpium Cass.) constituents.	2006 Sep-Oct	17019930
Soil quality effects on Chenopodium album flavonoid content and antioxidant potential.	2008 Jul 9	18553886
[Studies on chemical constituents of Arachniodes rhomboidea].	2008 Mar	18590191
Camellia japonica suppresses immunoglobulin E-mediated allergic response by the inhibition of Syk kinase activation in mast cells.	2008 May	18261158
[Flavones from flowers of Paulownia fortunei].	2008 Nov	19216158
Phytochemicals of apple peels: isolation, structure elucidation, and their antiproliferative and antioxidant activities.	2008 Nov 12	18828600
Flavonoid glycosides isolated from Salicornia herbacea inhibit matrix metalloproteinase in HT1080 cells.	2008 Oct	18715546
[Chemical constituents of Galium verum].	2009 Nov	20209910
Nondigestible saccharides suppress the bacterial degradation of quercetin aglycone in the large intestine and enhance the bioavailability of quercetin glucoside in rats.	2009 Oct 28	19807098

Patents

Sample Use Guides

In Vivo Use Guide

500 mg or 1000 mg, Once daily, 28 days

Route of Administration: Oral

In Vitro Use Guide

The protein expression of Nrf2 in rat hippocampal neurons in the 100 ug/ml group increased by 200% compared with the OGD/R (oxygen-glucose deprivation followed by reoxygenation) group.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:29:21 GMT 2023` Edited by `admin` on `Fri Dec 15 18:29:21 GMT 2023`
Record UNII	6HN2PC637T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOQUERCETIN

Official Name

English

QUERCETIN-3-O-.BETA.-D-GLUCOSIDE

Systematic Name

English

QUERCETIN 3.BETA.-GLUCOSIDE

Common Name

English

ISOQUERCETIN [INCI]

Common Name

English

QUERCETIN-3-O-GLUCOSIDE

Common Name

English

3',4',5,7-TETRAHYDROXYFLAVONE-3-.BETA.-D-GLUCOPYRANOSIDE

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-3-(.BETA.-D-GLUCOPYRANOSYLOXY)-5,7-DIHYDROXY-

Common Name

English

ISOQUERCITRIN [MI]

Common Name

English

NSC-115918

Code

English

QUERCETIN-3-.BETA.-GLUCOPYRANOSIDE

Common Name

English

QUERCETIN 3-O-GLUCOSIDE

Common Name

English

GLUCOSYL-3-QUERCETIN

Common Name

English

Quercetin 3-O-glucopyranoside [WHO-DD]

Common Name

English

QUERCETIN GLUCOSIDE

Common Name

English

3-GLUCOSYLQUERCETIN

Common Name

English

QUERCETIN 3-D-GLUCOSIDE

Common Name

English

QUERCETIN 3-O-.BETA.-D-GLUCOPYRANOSIDE

Common Name

English

3-O-.BETA.-D-GLUCOPYRANOSYLQUERCETIN

Common Name

English

QUERCETOL 3-MONOGLUCOSIDE

Common Name

English

QUERCETIN 3-O-GLUCOPYRANOSIDE

Common Name

English

CONTIGOSIDE B

Common Name

English

QUERCETIN-3-GLUCOSE

Common Name

English

ISOQUERCETIN, (-)-

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 2- (3,4-DIHYDROXYPHENYL)-3- (SS-D-GLUCOFURANOSYLOXY)-5,7-DIHYDROXY-

Systematic Name

English

QUERCETIN 3-O-GLUCOSIDE (CONSTITUENT OF GINKGO) [DSC]

Common Name

English

HIRSUTRIN

Common Name

English

RONACARE ISOQUERCETIN

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C68457