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Isosinensetin

CAT: 0804-HY-N1941-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N1941-01Size:5 mg
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Description
Isosinensetin is a flavonoid compound and an inhibitor of HIV-1 protease and PTP1B (IC50: 2.61 µM; Ki: 0.92 µM) . Isosinensetin inhibits P-glycoprotein (P-gp) in MDR1-MDCKII cells. Isosinensetin has multiple activities such as anti-tumor, anti-viral, anti-inflammatory, and antioxidant effects. Isosinensetin can be used in the research of various diseases including cancer, inflammation, osteoporosis, diabetes, etc[1][2][3][4][5].
CAS Number
17290-70-9
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Bacterial; Calcium Channel; ERK; HIV Protease; JNK; NF-κB; p38 MAPK; P-glycoprotein; Phosphatase; Reactive Oxygen Species (ROS)
Type
Natural Products
Related Pathways
Anti-infection; Immunology/Inflammation; MAPK/ERK Pathway; Membrane Transporter/Ion Channel; Metabolic Enzyme/Protease; Neuronal Signaling; NF-κB; Stem Cell/Wnt
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Infection; Metabolic Disease; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/isosinensetin.html
Purity
99.90
Solubility
DMSO : 12.5 mg/mL (ultrasonic)
Smiles
O=C1C=C(C2=CC=C(OC)C(OC)=C2)OC3=C(OC)C(OC)=CC(OC)=C13
Molecular Formula
C20H20O7
Molecular Weight
372.37
Precautions
H302, H315, H319, H335
References & Citations
[1]Bai J, et al. Inhibitory effects of flavonoids on P-glycoprotein in vitro and in vivo: Food/herb-drug interactions and structure-activity relationships. Toxicol Appl Pharmacol. 2019 Apr 15;369:49-59.|[2]Qin Y, et al. Isosinensetin alleviates estrogen deficiency-induced osteoporosis via suppressing ROS-mediated NF-κB/MAPK signaling pathways. Biomed Pharmacother. 2023 Apr;160:114347.|[3]Trang N M, et al. Inhibition of PTP1B by isosinensetin, a polymethoxylated flavone isolated from trifoliate orange peel: Kinetic studies, molecular docking, and molecular dynamics simulation. Chemical Papers, 2023, 77 (3) : 1751-1757.|[4]Jiang Y, et al. Isolation of adenosine, iso-sinensetin and dimethylguanosine with antioxidant and HIV-1 protease inhibiting activities from fruiting bodies of Cordyceps militaris. Phytomedicine. 2011 Jan 15;18 (2-3) :189-93.|[5]Lee SH, et al. Isosinensetin Stimulates Glucagon-like Peptide-1 Secretion via Activation of hTAS2R50 and the Gβγ-Mediated Signaling Pathway. Int J Mol Sci. 2023 Feb 12;24 (4) :3682.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Isosinensetin

Isosinensetin is an ether and a member of flavonoids.

CAS Number17290-70-9
PubChem CID632135
IUPAC Name2-(3,4-dimethoxyphenyl)-5,7,8-trimethoxychromen-4-one
Molecular FormulaC20H20O7
Molecular Weight372.4
XLogP3
Topological Polar Surface Area72.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count7
Rotatable Bond Count6
Heavy Atom Count27
Formal Charge0
Complexity548
SMILES
COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3OC)OC)OC)OC
InChI
InChI=1S/C20H20O7/c1-22-13-7-6-11(8-15(13)23-2)14-9-12(21)18-16(24-3)10-17(25-4)19(26-5)20(18)27-14/h6-10H,1-5H3
InChIKey
UYCWETIUOAGWIL-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Isosinensetin
CAS: 17290-70-9
CID: 632135
Formula: C20H20O7
MW: 372.4
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight372.4
XLogP33
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count7
Rotatable Bond Count6
Exact Mass372.12090297
Monoisotopic Mass372.12090297
Topological Polar Surface Area72.5 Ų
Heavy Atom Count27
Formal Charge0
Complexity548
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes