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
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
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: WP402 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28413477 |
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Target ID: CHEMBL2095186 Sources: DOI: 10.1007/978-1-4614-0535-1_485 |
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Target ID: CHEMBL5422 |
2.5 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | Unknown Approved UseUnknown |
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Secondary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Inhibition of HIV infection by flavanoids. | 1993 Oct |
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Inhibitory effects of Egyptian folk medicines on human immunodeficiency virus (HIV) reverse transcriptase. | 1995 Apr |
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Inhibitory effects of sudanese medicinal plant extracts on hepatitis C virus (HCV) protease. | 2000 Nov |
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Inhibitory activity of flavonoids and tannins against HIV-1 protease. | 2000 Sep |
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[Chemical constituents from the leaves of crataegus pinnatifida Bge. var. major N.E.Br]. | 2001 Oct |
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[HPLC investigation of antioxidant components in Solidago herba]. | 2004 |
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Glycosides from Grewia damine and Filicium decipiens. | 2004 Dec |
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[Studies on antiproliferative effect of flavones compounds isolated from Yao herb medicines]. | 2007 Aug |
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An unusual C6-C6" linked flavonoid from Miconia cabucu (Melastomataceae). | 2007 Jul |
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[Study on antioxidant activity of constituents from mulberry leaf]. | 2008 Apr |
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[Studies on chemical constituents of Primula sikkmensis]. | 2008 Jan |
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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 |
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[Chemical constituents from Polygonum capitatum and their antioxidation activities in vitro]. | 2008 Jul |
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[Flavones from flowers of Paulownia fortunei]. | 2008 Nov |
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Phytochemicals of apple peels: isolation, structure elucidation, and their antiproliferative and antioxidant activities. | 2008 Nov 12 |
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[Chemical constituents from Neo-Taraxacum siphonathum]. | 2009 Apr |
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[Chemical study on ethyl acetate soluble portion of Kadsura oblongifolia]. | 2009 Apr |
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[Chemical constituents in Buddleja albiflora]. | 2009 Dec |
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Antioxidant enzymatically modified isoquercitrin suppresses the development of liver preneoplastic lesions in rats induced by beta-naphthoflavone. | 2010 Feb 9 |
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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 |
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Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation. | 2011 Dec 15 |
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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
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02195232
500 mg or 1000 mg, Once daily, 28 days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28413477
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
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admin
on
Edited
Sat Jun 26 06:16:24 UTC 2021
by
admin
on
Sat Jun 26 06:16:24 UTC 2021
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Record UNII |
6HN2PC637T
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C68457
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5280804
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482-35-9
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6HN2PC637T
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C110309
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482-35-9
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C117288
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ISOQUERCETIN
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M6537
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DB12665
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
CALENDULA OFFICINALIS FLOWER Flavonoid
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Repeated chromatography of the n-BuOH soluble
fraction yielded this flavonoid glucoside.
Has shown antimicrobial activiral activity in other studies.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Secondary metabolite detected in developing cacao seeds.
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