Quercetin-3-O-β-glycopyranoside
| Compound Structure: |
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| Synonyms: | Isoquercetin; Isoquercitrin; 482-35-9 ;Hirsutrin ;Quercetin 3-glucoside | ||||||||||||||||||||||||||||||||||||||||||
| Compound ID: | NMPC-1448 | ||||||||||||||||||||||||||||||||||||||||||
| PubChem ID: | |||||||||||||||||||||||||||||||||||||||||||
| Molecular Formula: | C21H20O12 | ||||||||||||||||||||||||||||||||||||||||||
| Canonical SMILES: | C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O | ||||||||||||||||||||||||||||||||||||||||||
| InChIKey: | OVSQVDMCBVZWGM-QSOFNFLRSA-N | ||||||||||||||||||||||||||||||||||||||||||
| About the compound: | Quercetin 3-O-beta-D-glucopyranoside, also known as isoquercetin, isoquercitrin, or isotrifoliin, is a quercetin O-glucoside. It consists of quercetin with a beta-D-glucosyl residue attached at position 3. This compound has been isolated from Lepisoruscontortus and exhibits notable antineoplastic (anti-cancer) activity. It has also been found to decrease the rate of polymerization and sickling of red blood cells. In terms of its roles, quercetin 3-O-beta-D-glucopyranoside functions as an antineoplastic agent, a plant metabolite, a bone density conservation agent, an osteogenesis regulator, an antioxidant, a histamine antagonist, an antipruritic drug, and a geroprotector. Chemically, it is categorized as a quercetin O-glucoside, a tetrahydroxyflavone, a beta-D-glucoside, and a monosaccharide derivative. Isoquercetin has been used in various clinical trials studying its potential in the treatment of conditions like kidney cancer, renal cell carcinoma, and thromboembolism in pancreatic and colorectal cancer. It is found in various plant species including Mangiferaindica (mango) and Rheum nobile (Noble rhubarb), as well as in the leaves of Annonasquamosa, Camellia sinensis (tea), and Vestiafoetida. Current research is investigating isoquercetin for the prevention of thromboembolism in selected cancer patients and as an anti-fatigue agent in kidney cancer patients treated with the drug sunitinib. There's also a single case report noting its successful use in treating prurigonodularis, a challenging skin condition. However, it is important to note that isoquercetin falls under the PAINS (Pan-assay interference compounds) category of chemicals. Compounds in this category are known to interfere with a wide range of assays, which can lead to false positives in drug discovery and other biochemical screening processes. This characteristic necessitates careful interpretation of results and further validation in studies involving isoquercetin. GHS Hazard Statements • H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] • H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] • H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] |
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| Properties: |
Chemical and Physical Properties
Source: PubChem |
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| Source Species: |
Bridelia ferruginea. Newbouldia laevis Physalis angulata |