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(O)=C(O)C=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 1447
Oxidative Stress 162 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 8504
Sodium/potassium-transporting ATPase 34 Target ID: CHEMBL2095186 Sources: DOI: 10.1007/978-1-4614-0535-1_485	Inhibitor 8504
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 8504	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 665	Unknown Approved Use Unknown
Kidney cancer 10 Sources: https://clinicaltrials.gov/ct2/show/NCT02446795	Secondary	Phase II 1147	Unknown Approved Use Unknown
Chronic kidney disease 55 Sources: https://clinicaltrials.gov/ct2/show/NCT02552888	Primary	Phase II 1147	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
Biopurify Phytochemicals	BP0793	https://www.phytopurify.com/search.do?a=s&searchtype=3&psize=10&q=BP0793&searchhtmp=simplesearch&t=1
BioSynth	Q-100268	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-100268
BOC Sciences	21637-25-2	http://www.bocsci.com/description.asp?cas=21637-25-2
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
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
KeyOrganics	AS-35335	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-35335
mcule	MCULE-1611345094	https://mcule.com/MCULE-1611345094/
mcule	MCULE-2852848721	https://mcule.com/MCULE-2852848721/
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

PubMed

Title	Date	PubMed
Effect of enzymatically modified isoquercitrin on preneoplastic liver cell lesions induced by thioacetamide promotion in a two-stage hepatocarcinogenesis model using rats.	2013-03-08	23318833
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.	2011-12-15	21872416
Concomitant apoptosis and regeneration of liver cells as a mechanism of liver-tumor promotion by β-naphthoflavone involving TNFα-signaling due to oxidative cellular stress in rats.	2011-04-28	21295105
Phenolic compounds in leaves of Alchornea triplinervia: anatomical localization, mutagenicity, and antibacterial activity.	2010-08	20839624
[Flavonoids of Lysimachia paridiformis var. stenophylla].	2010-07	20939277
[Flavonoids and phenolic acid derivatives from flos farfarae].	2010-05	20707069
[Glycosides from Periploca forrestii].	2010-03	20506822
Antioxidant enzymatically modified isoquercitrin suppresses the development of liver preneoplastic lesions in rats induced by beta-naphthoflavone.	2010-02-09	20045035
Antioxidant enzymatically modified isoquercitrin or melatonin supplementation reduces oxidative stress-mediated hepatocellular tumor promotion of oxfendazole in rats.	2010-02	20033131
Who is the king? The alpha-hydroxy-beta-oxo-alpha,beta-enone moiety or the catechol B ring: relationship between the structure of quercetin derivatives and their pro-oxidative abilities.	2010-01	20087995
Preparative isolation and purification of four flavonoids from the petals of Nelumbo nucifera by high-speed counter-current chromatography.	2009-12-19	20020439
[Chemical constituents in Buddleja albiflora].	2009-12	20222420
[Chemical constituents of Galium verum].	2009-11	20209910
Nondigestible saccharides suppress the bacterial degradation of quercetin aglycone in the large intestine and enhance the bioavailability of quercetin glucoside in rats.	2009-10-28	19807098
[Chemical constituents from leaves of Sterculia foetida].	2009-10	20069901
[Flavones from Helichrysi flos syn].	2009-06	19771867
[Chemical constituents from Neo-Taraxacum siphonathum].	2009-04	19639786
[Chemical study on ethyl acetate soluble portion of Kadsura oblongifolia].	2009-04	19623983
[Study on chemical constituents of Herba Cirsii].	2009-01	19445122
[Flavonoid constituents from herbs of Sarcopyramis bodinieri var. delicata].	2009-01	19385178
Chemical composition of the stem bark and leaves of Ficus pandurata Hance.	2009	19731141
Phytochemicals of apple peels: isolation, structure elucidation, and their antiproliferative and antioxidant activities.	2008-11-12	18828600
[Flavones from flowers of Paulownia fortunei].	2008-11	19216158
Flavonoid glycosides isolated from Salicornia herbacea inhibit matrix metalloproteinase in HT1080 cells.	2008-10	18715546
Light filtering by epidermal flavonoids during the resistant response of cotton to Xanthomonas protects leaf tissue from light-dependent phytoalexin toxicity.	2008-09	18617197
Deep supercooling xylem parenchyma cells of katsura tree (Cercidiphyllum japonicum) contain flavonol glycosides exhibiting high anti-ice nucleation activity.	2008-09	18518920
Taxodione, a DNA-binding compound from Taxodium distichum L. (Rich.).	2008-08-02	18669020
Soil quality effects on Chenopodium album flavonoid content and antioxidant potential.	2008-07-09	18553886
[Chemical constituents from Polygonum capitatum and their antioxidation activities in vitro].	2008-07	18973013
Determination of quercetin and its glucosides in onion by electrochemical methods.	2008-06-09	18486637
Determination of the relative contribution of quercetin and its glucosides to the antioxidant capacity of onion by cyclic voltammetry and spectrophotometric methods.	2008-05-28	18454541
Pharmacological basis for use of Pistacia integerrima leaves in hyperuricemia and gout.	2008-05-22	18420362
Camellia japonica suppresses immunoglobulin E-mediated allergic response by the inhibition of Syk kinase activation in mast cells.	2008-05	18261158
[Study on antioxidant activity of constituents from mulberry leaf].	2008-04	18661822
Deconjugation and degradation of flavonol glycosides by pig cecal microbiota characterized by Fluorescence in situ hybridization (FISH).	2008-03-26	18303842
[Studies on chemical constituents of Arachniodes rhomboidea].	2008-03	18590191
Quercetin 3-glucoside protects neuroblastoma (SH-SY5Y) cells in vitro against oxidative damage by inducing sterol regulatory element-binding protein-2-mediated cholesterol biosynthesis.	2008-01-25	18032389
[Studies on chemical constituents of Primula sikkmensis].	2008-01	18589747
Three new 3-benzylbenzofuran-2-one derivatives from Homalium brachybotrys (Flacourtiaceae/Salicaceae s. l.).	2007-11	17987500
[Isolation and preparation of flavones from the leaves of Lindera aggregata using high speed counter-current chromatography].	2007-09	18161329
[Studies on antiproliferative effect of flavones compounds isolated from Yao herb medicines].	2007-08	18074851
An unusual C6-C6" linked flavonoid from Miconia cabucu (Melastomataceae).	2007-07	17540417
The anti-thrombotic active constituents from Centella asiatica.	2007-05	17473438
Simultaneous determination of seven flavonoids in Potentilla multifida by HPLC.	2007-04	17504571
Development of an HPLC-PAD-MS assay for the identification and quantification of major phenolic edelweiss (Leontopodium alpium Cass.) constituents.	2006-10-06	17019930
Constituents from the leaves of Phellodendron amurense and their antioxidant activity.	2006-09	16946541
Quantitative determination of major active components in Ginkgo biloba dietary supplements by liquid chromatography/mass spectrometry.	2006	16921563
[Study on chemical constituents of Lagotis yunnanensis].	2005-09	16447867
Inhibitory effects of Egyptian folk medicines on human immunodeficiency virus (HIV) reverse transcriptase.	1995-04	7541317
Inhibition of HIV infection by flavanoids.	1993-10	8279812

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 `Mon Mar 31 19:13:23 GMT 2025` Edited by `admin` on `Mon Mar 31 19:13:23 GMT 2025`
Record UNII	6HN2PC637T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOQUERCETIN

Official Name

English

QUERCETIN 3-O-GLUCOPYRANOSIDE

Preferred Name

English

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

Systematic Name

English

QUERCETIN 3.BETA.-GLUCOSIDE

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

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