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Miquelianin

CAT: 0804-HY-13930-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-13930-01Size:5 mg
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Description
Miquelianin (Quercetin 3-O-glucuronide) is a metabolite of quercetin and a type of natural flavonoid. Miquelianin is also a CBR1 inhibitor.
CAS Number
22688-79-5
Product Name Alternative
Quercetin 3-O-glucuronide; Quercetin 3-glucuronide
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Endogenous Metabolite
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Applications
Cancer-Kinase/protease
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/Miquelianin.html
Purity
99.96
Solubility
DMSO : ≥ 30 mg/mL
Smiles
O=C1C2=C(O)C=C(O)C=C2OC(C3=CC=C(O)C(O)=C3)=C1O[C@@H]4O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]4O
Molecular Formula
C21H18O13
Molecular Weight
478.36
Precautions
H302, H315, H319, H335
References & Citations
[1]Terao J, e al. Protection by quercetin and quercetin 3-O-beta-D-glucuronide of peroxynitrite-induced antioxidant consumption in human plasma low-density lipoprotein. Free Radic Res. 2001 Dec;35 (6) :925-31.|[2]Juergenliemk G, et al. In vitro studies indicate that miquelianin (quercetin 3-O-beta-D-glucuronopyranoside) is able to reach the CNS from the small intestine. Planta Med. 2003 Nov;69 (11) :1013-7.|[3]Butterweck V, et al. Flavonoids from Hypericum perforatum show antidepressant activity in the forced swimming test. Planta Med. 2000 Feb;66 (1) :3-6.|[4]Yamazaki S, et al. Quercetin-3-O-glucuronide inhibits noradrenaline-promoted invasion of MDA-MB-231 human breast cancer cells by blocking β-adrenergic signaling. Arch Biochem Biophys. 2014 Sep 1;557:18-27.|[5]Ho L, et al. Identification of brain-targeted bioactive dietary quercetin-3-O-glucuronide as a novel intervention for Alzheimer's disease. FASEB J. 2013 Feb;27 (2) :769-81.|[6]Iannuzzi A M, et al. Chemical profile and nutraceutical features of Salsola soda (agretti) : Anti-inflammatory and antidiabetic potential of its flavonoids[J]. Food Bioscience, 2020, 37: 100713.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Querciturone

Miquelianin is a quercetin O-glycoside that consists of quercetin attached to a beta-D-glucuronopyranosyl moiety at position 3 via a glycosidic linkage. Isolated from Salvia and Phaseolus vulgaris, it exhibits antioxidant and antidepressant activities. It has a role as an antioxidant, a metabolite and an antidepressant. It is a beta-D-glucosiduronic acid and a quercetin O-glycoside.

CAS Number22688-79-5
PubChem CID5274585
IUPAC Name(2S,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
Molecular FormulaC21H18O13
Molecular Weight478.4
XLogP0.6
Topological Polar Surface Area224
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count13
Rotatable Bond Count4
Heavy Atom Count34
Formal Charge0
Complexity829
SMILES
C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)O)O)O)O)O)O
InChI
InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)/t14-,15-,16+,19-,21+/m0/s1
InChIKey
DUBCCGAQYVUYEU-ZUGPOPFOSA-N
Chemical Structure
2D Structure
2D structure of Querciturone
CAS: 22688-79-5
CID: 5274585
Formula: C21H18O13
MW: 478.4
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight478.4
XLogP30.6
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count13
Rotatable Bond Count4
Exact Mass478.07474062
Monoisotopic Mass478.07474062
Topological Polar Surface Area224 Ų
Heavy Atom Count34
Formal Charge0
Complexity829
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes