ISOQUERCETIN

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H20O12
Molecular Weight	464.3771
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1cc(c(cc1-c2c(c(=O)c3c(cc(cc3o2)O)O)O[C@@]4([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O4)O)O)O)O)O

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	464.3771
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 1343
Oxidative Stress 149 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 7728
Sodium/potassium-transporting ATPase 32 Target ID: CHEMBL2095186 Sources: DOI: 10.1007/978-1-4614-0535-1_485	Inhibitor 7728
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 7728	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 643	Unknown Approved Use Unknown
Kidney cancer 9 Sources: https://clinicaltrials.gov/ct2/show/NCT02446795	Secondary	Phase II 1101	Unknown Approved Use Unknown
Chronic kidney disease 52 Sources: https://clinicaltrials.gov/ct2/show/NCT02552888	Primary	Phase II 1101	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
Inhibition of HIV infection by flavanoids.	1993 Oct	8279812
Inhibitory effects of Egyptian folk medicines on human immunodeficiency virus (HIV) reverse transcriptase.	1995 Apr	7541317
[HPLC investigation of antioxidant components in Solidago herba].	2004	16316050
[Studies on chemical constituents from Salvia roborowskii Maxim].	2005 Feb	15981878
[Study on chemical constituents of Lagotis yunnanensis].	2005 Sep	16447867
[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
Constituents from the leaves of Phellodendron amurense and their antioxidant activity.	2006 Sep	16946541
Development of an HPLC-PAD-MS assay for the identification and quantification of major phenolic edelweiss (Leontopodium alpium Cass.) constituents.	2006 Sep-Oct	17019930
Simultaneous determination of seven flavonoids in Potentilla multifida by HPLC.	2007 Apr	17504571
The anti-thrombotic active constituents from Centella asiatica.	2007 May	17473438
[Isolation and preparation of flavones from the leaves of Lindera aggregata using high speed counter-current chromatography].	2007 Sep	18161329
[Study on antioxidant activity of constituents from mulberry leaf].	2008 Apr	18661822
[Studies on chemical constituents of Primula sikkmensis].	2008 Jan	18589747
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 Jan 25	18032389
[Chemical constituents from Polygonum capitatum and their antioxidation activities in vitro].	2008 Jul	18973013
Soil quality effects on Chenopodium album flavonoid content and antioxidant potential.	2008 Jul 9	18553886
Determination of quercetin and its glucosides in onion by electrochemical methods.	2008 Jun 9	18486637
[Studies on chemical constituents of Arachniodes rhomboidea].	2008 Mar	18590191
Deconjugation and degradation of flavonol glycosides by pig cecal microbiota characterized by Fluorescence in situ hybridization (FISH).	2008 Mar 26	18303842
Camellia japonica suppresses immunoglobulin E-mediated allergic response by the inhibition of Syk kinase activation in mast cells.	2008 May	18261158
Pharmacological basis for use of Pistacia integerrima leaves in hyperuricemia and gout.	2008 May 22	18420362
Determination of the relative contribution of quercetin and its glucosides to the antioxidant capacity of onion by cyclic voltammetry and spectrophotometric methods.	2008 May 28	18454541
Taxodione, a DNA-binding compound from Taxodium distichum L. (Rich.).	2008 May-Jun	18669020
[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
Light filtering by epidermal flavonoids during the resistant response of cotton to Xanthomonas protects leaf tissue from light-dependent phytoalexin toxicity.	2008 Sep	18617197
Deep supercooling xylem parenchyma cells of katsura tree (Cercidiphyllum japonicum) contain flavonol glycosides exhibiting high anti-ice nucleation activity.	2008 Sep	18518920
Chemical composition of the stem bark and leaves of Ficus pandurata Hance.	2009	19731141
[Chemical constituents from Neo-Taraxacum siphonathum].	2009 Apr	19639786
[Chemical study on ethyl acetate soluble portion of Kadsura oblongifolia].	2009 Apr	19623983
[Chemical constituents in Buddleja albiflora].	2009 Dec	20222420
[Study on chemical constituents of Herba Cirsii].	2009 Jan	19445122
[Flavones from Helichrysi flos syn].	2009 Jun	19771867
[Chemical constituents of Galium verum].	2009 Nov	20209910
[Chemical constituents from leaves of Sterculia foetida].	2009 Oct	20069901
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
Phenolic compounds in leaves of Alchornea triplinervia: anatomical localization, mutagenicity, and antibacterial activity.	2010 Aug	20839624
Antioxidant enzymatically modified isoquercitrin or melatonin supplementation reduces oxidative stress-mediated hepatocellular tumor promotion of oxfendazole in rats.	2010 Feb	20033131
Antioxidant enzymatically modified isoquercitrin suppresses the development of liver preneoplastic lesions in rats induced by beta-naphthoflavone.	2010 Feb 9	20045035
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 Jan	20087995
[Flavonoids of Lysimachia paridiformis var. stenophylla].	2010 Jul	20939277
[Glycosides from Periploca forrestii].	2010 Mar	20506822
[Flavonoids and phenolic acid derivatives from flos farfarae].	2010 May	20707069
Preparative isolation and purification of four flavonoids from the petals of Nelumbo nucifera by high-speed counter-current chromatography.	2010 May-Jun	20020439
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 Apr 28	21295105
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.	2011 Dec 15	21872416
Effect of enzymatically modified isoquercitrin on preneoplastic liver cell lesions induced by thioacetamide promotion in a two-stage hepatocarcinogenesis model using rats.	2013 Mar 8	23318833

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 `Sat Jun 26 06:16:24 UTC 2021` Edited by `admin` on `Sat Jun 26 06:16:24 UTC 2021`
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