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
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 |
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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Inhibitory effects of Egyptian folk medicines on human immunodeficiency virus (HIV) reverse transcriptase. | 1995 Apr |
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A search for anti-viral properties in Panamanian medicinal plants. The effects on HIV and its essential enzymes. | 1999 Jan |
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Inhibitory effects of sudanese medicinal plant extracts on hepatitis C virus (HCV) protease. | 2000 Nov |
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[HPLC investigation of antioxidant components in Solidago herba]. | 2004 |
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Isolation of angiotensin converting enzyme (ACE) inhibitory flavonoids from Sedum sarmentosum. | 2004 Dec |
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[Studies on antiproliferative effect of flavones compounds isolated from Yao herb medicines]. | 2007 Aug |
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Determination of quercetin and its glucosides in onion by electrochemical methods. | 2008 Jun 9 |
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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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Camellia japonica suppresses immunoglobulin E-mediated allergic response by the inhibition of Syk kinase activation in mast cells. | 2008 May |
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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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[Flavones from Helichrysi flos syn]. | 2009 Jun |
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Phenolic compounds in leaves of Alchornea triplinervia: anatomical localization, mutagenicity, and antibacterial activity. | 2010 Aug |
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
Thu Jul 06 01:42:26 UTC 2023
by
admin
on
Thu Jul 06 01:42:26 UTC 2023
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Record UNII |
6HN2PC637T
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C68457
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6HN2PC637T
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C110309
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68352
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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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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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