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Isoscopoletin (Standard)

CAT: 0804-HY-N1365R-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N1365R-01Size:1 mg
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Description
Isoscopoletin (Standard) is the analytical standard of Isoscopoletin. This product is intended for research and analytical applications. Isoscopoletin (6-Hydroxy-7-methoxycoumarin) is an active constituent in Artemisia argyi leaves. Isoscopoletin shows substantial inhibition against cell proliferation, with IC50s of 4.0 μM and 1.6 μM for human CCRF-CEM leukaemia cells and multidrug resistant subline CEM/ADR5000, respectively[1]. Isoscopoletin (6-Hydroxy-7-methoxycoumarin) possesses inhibitory activity against HBV replication[2]. Isoscopoletin exhibits anti-inflammatory activity through inhibition of MAPK/NF-κB/STAT/AKT signaling pathway[3].
CAS Number
776-86-3
Product Name Alternative
6-Hydroxy-7-methoxycoumarin (Standard)
UNSPSC
12352005
Target
Akt; ERK; HBV; JNK; NF-κB; p38 MAPK; Reference Standards; STAT
Type
Reference Standards
Related Pathways
Anti-infection; JAK/STAT Signaling; MAPK/ERK Pathway; NF-κB; Others; PI3K/Akt/mTOR; Stem Cell/Wnt
Field of Research
Cancer; Infection; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/isoscopoletin-standard.html
Purity
99.93
Smiles
O=C1C=CC2=CC(O)=C(OC)C=C2O1
Molecular Formula
C10H8O4
Molecular Weight
192.17
References & Citations
[1]Adams M, et al. Activity-guided isolation of scopoletin and isoscopoletin, the inhibitory active principles towards CCRF-CEM leukaemia cells and multi-drug resistant CEM/ADR5000 cells, from Artemisia argyi. Planta Med. 2006 Jul;72 (9) :862-4.|[2]Li H, et al. Evaluation of antiviral activity of compounds isolated from Ranunculus sieboldii and Ranunculus sceleratus. Planta Med. 2005 Dec;71 (12) :1128-33.|[3]Ruan C, et al., Isoscopoletin inhibits hepatocellular carcinoma cell proliferation via regulating glycolysis-related proteins. PLoS One. 2024 Nov 7;19 (11) :e0310530.
Shipping Conditions
Blue Ice
Storage Conditions
4°C, sealed and dry storage, away from light and moisture
Scientific Category
Reference Standards

Chemical Information

Isoscopoletin

Isoscopoletin is a hydroxycoumarin that is esculetin in which the hydroxy group at position 7 is replaced by a methoxy group. It is the major primary metabolite of scoparone. It has a role as a plant metabolite. It is an aromatic ether and a hydroxycoumarin. It is functionally related to an esculetin.

CAS Number776-86-3
PubChem CID69894
IUPAC Name6-hydroxy-7-methoxychromen-2-one
Molecular FormulaC10H8O4
Molecular Weight192.17
XLogP1.5
Topological Polar Surface Area55.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Heavy Atom Count14
Formal Charge0
Complexity261
SMILES
COC1=C(C=C2C=CC(=O)OC2=C1)O
InChI
InChI=1S/C10H8O4/c1-13-9-5-8-6(4-7(9)11)2-3-10(12)14-8/h2-5,11H,1H3
InChIKey
SYTYLPHCLSSCOJ-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Isoscopoletin
CAS: 776-86-3
CID: 69894
Formula: C10H8O4
MW: 192.17
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight192.17
XLogP31.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Exact Mass192.04225873
Monoisotopic Mass192.04225873
Topological Polar Surface Area55.8 Ų
Heavy Atom Count14
Formal Charge0
Complexity261
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

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