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
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
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 |
|---|---|---|---|
Target ID: WP402 |
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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 |
|---|---|---|---|---|
| Preventing | Unknown Approved UseUnknown |
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| Secondary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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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| Depsides from the petals of Papaver rhoeas. | 2004 Apr |
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| Glycosides from Grewia damine and Filicium decipiens. | 2004 Dec |
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| Isolation of angiotensin converting enzyme (ACE) inhibitory flavonoids from Sedum sarmentosum. | 2004 Dec |
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| [Studies on the chemical constituents of Knoxia corymbosa]. | 2004 Jun |
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| [Studies on chemical constituents from Salvia roborowskii Maxim]. | 2005 Feb |
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| [Applications of two-dimensional liquid chromatography coupled to mass spectrometry for the separation and identification of compounds in ginkgo biloba extracts]. | 2005 Jan |
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| [Study on chemical constituents of Lagotis yunnanensis]. | 2005 Sep |
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| [Studies on chemical constituents from flowers of Apocynum venetum]. | 2005 Sep |
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| Quantitative determination of major active components in Ginkgo biloba dietary supplements by liquid chromatography/mass spectrometry. | 2006 |
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| Inhibition of human cytochrome CYP 1 enzymes by flavonoids of St. John's wort. | 2006 Jan 16 |
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| Constituents from the leaves of Phellodendron amurense and their antioxidant activity. | 2006 Sep |
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| Development of an HPLC-PAD-MS assay for the identification and quantification of major phenolic edelweiss (Leontopodium alpium Cass.) constituents. | 2006 Sep-Oct |
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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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| The anti-thrombotic active constituents from Centella asiatica. | 2007 May |
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| [Isolation and preparation of flavones from the leaves of Lindera aggregata using high speed counter-current chromatography]. | 2007 Sep |
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| [Study on antioxidant activity of constituents from mulberry leaf]. | 2008 Apr |
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| [Chemical constituents from Polygonum capitatum and their antioxidation activities in vitro]. | 2008 Jul |
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| Soil quality effects on Chenopodium album flavonoid content and antioxidant potential. | 2008 Jul 9 |
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| Determination of quercetin and its glucosides in onion by electrochemical methods. | 2008 Jun 9 |
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| [Studies on chemical constituents of Arachniodes rhomboidea]. | 2008 Mar |
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| Deconjugation and degradation of flavonol glycosides by pig cecal microbiota characterized by Fluorescence in situ hybridization (FISH). | 2008 Mar 26 |
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| Pharmacological basis for use of Pistacia integerrima leaves in hyperuricemia and gout. | 2008 May 22 |
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| 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 |
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| Taxodione, a DNA-binding compound from Taxodium distichum L. (Rich.). | 2008 May-Jun |
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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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| Flavonoid glycosides isolated from Salicornia herbacea inhibit matrix metalloproteinase in HT1080 cells. | 2008 Oct |
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| Light filtering by epidermal flavonoids during the resistant response of cotton to Xanthomonas protects leaf tissue from light-dependent phytoalexin toxicity. | 2008 Sep |
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| Chemical composition of the stem bark and leaves of Ficus pandurata Hance. | 2009 |
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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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| [Flavonoid constituents from herbs of Sarcopyramis bodinieri var. delicata]. | 2009 Jan |
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| [Flavones from Helichrysi flos syn]. | 2009 Jun |
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| [Chemical constituents of Galium verum]. | 2009 Nov |
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| [Chemical constituents from leaves of Sterculia foetida]. | 2009 Oct |
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| Phenolic compounds in leaves of Alchornea triplinervia: anatomical localization, mutagenicity, and antibacterial activity. | 2010 Aug |
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| Antioxidant enzymatically modified isoquercitrin or melatonin supplementation reduces oxidative stress-mediated hepatocellular tumor promotion of oxfendazole in rats. | 2010 Feb |
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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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| 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 |
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| [Flavonoids of Lysimachia paridiformis var. stenophylla]. | 2010 Jul |
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| [Glycosides from Periploca forrestii]. | 2010 Mar |
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| [Flavonoids and phenolic acid derivatives from flos farfarae]. | 2010 May |
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| Preparative isolation and purification of four flavonoids from the petals of Nelumbo nucifera by high-speed counter-current chromatography. | 2010 May-Jun |
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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
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NCI_THESAURUS |
C68457
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28299
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115918
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5280804
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DTXSID3041110
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6HN2PC637T
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C110309
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68352
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482-35-9
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C117288
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ISOQUERCETIN
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300000017646
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m6537
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DB12665
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SUBSTANCE RECORD
