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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 of ISOQUERCETIN

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

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

Sources: DOI: 10.1007/978-1-4614-0535-1_485

Approval Year

AUC

AUC

ValueDoseCo-administeredAnalytePopulation
15 μM × h
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

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Inhibition of HIV infection by flavanoids.
1993 Oct
Inhibitory effects of Egyptian folk medicines on human immunodeficiency virus (HIV) reverse transcriptase.
1995 Apr
Inhibitory effects of sudanese medicinal plant extracts on hepatitis C virus (HCV) protease.
2000 Nov
Inhibitory activity of flavonoids and tannins against HIV-1 protease.
2000 Sep
[Chemical constituents from the leaves of crataegus pinnatifida Bge. var. major N.E.Br].
2001 Oct
[HPLC investigation of antioxidant components in Solidago herba].
2004
Glycosides from Grewia damine and Filicium decipiens.
2004 Dec
[Studies on antiproliferative effect of flavones compounds isolated from Yao herb medicines].
2007 Aug
An unusual C6-C6" linked flavonoid from Miconia cabucu (Melastomataceae).
2007 Jul
[Study on antioxidant activity of constituents from mulberry leaf].
2008 Apr
[Studies on chemical constituents of Primula sikkmensis].
2008 Jan
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
[Chemical constituents from Polygonum capitatum and their antioxidation activities in vitro].
2008 Jul
[Flavones from flowers of Paulownia fortunei].
2008 Nov
Phytochemicals of apple peels: isolation, structure elucidation, and their antiproliferative and antioxidant activities.
2008 Nov 12
[Chemical constituents from Neo-Taraxacum siphonathum].
2009 Apr
[Chemical study on ethyl acetate soluble portion of Kadsura oblongifolia].
2009 Apr
[Chemical constituents in Buddleja albiflora].
2009 Dec
Antioxidant enzymatically modified isoquercitrin suppresses the development of liver preneoplastic lesions in rats induced by beta-naphthoflavone.
2010 Feb 9
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
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.
2011 Dec 15
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
Patents

Sample Use Guides

500 mg or 1000 mg, Once daily, 28 days
Route of Administration: Oral
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
  • Download
Name Type Language
ISOQUERCETIN
INCI  
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
WHO-DD  
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
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
Code System Code Type Description
PUBCHEM
5280804
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY
EPA CompTox
482-35-9
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY
FDA UNII
6HN2PC637T
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY
MESH
C110309
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY
CAS
482-35-9
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY
NCI_THESAURUS
C117288
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY
WIKIPEDIA
ISOQUERCETIN
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY
MERCK INDEX
M6537
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB12665
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
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Repeated chromatography of the n-BuOH soluble fraction yielded this flavonoid glucoside. Has shown antimicrobial activiral activity in other studies.
PARENT -> CONSTITUENT ALWAYS PRESENT
Secondary metabolite detected in developing cacao seeds.