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Coptisine

CAT: 0804-HY-N0430-03Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0430-03Size:5 mg
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Description
Coptisine is an alkaloid from Chinese goldthread, and acts as an efficient uncompetitive IDO inhibitor with a Ki value of 5.8 μM and an IC50 value of 6.3 μM.
CAS Number
3486-66-6
Product Name Alternative
Coptisin
UNSPSC
12352005
Target
Indoleamine 2,3-Dioxygenase (IDO)
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Applications
Metabolism-protein/nucleotide metabolism
Field of Research
Cancer; Metabolic Disease
Assay Protocol
https://www.medchemexpress.com/Coptisine.html
Solubility
10 mM in DMSO
Smiles
C1(C(CC[N+]2=C1C=C(C=C3)C(C4=C3OCO4)=C2)=C5)=CC6=C5OCO6
Molecular Formula
C19H14NO4
Molecular Weight
320.32
References & Citations
[1]Yu D, et al. The IDO inhibitor coptisine ameliorates cognitive impairment in a mouse model of Alzheimer's disease. J Alzheimers Dis. 2015;43 (1) :291-302.|[2]He K, et al. The safety and anti-hypercholesterolemic effect of coptisine in Syrian golden hamsters. Lipids. 2015 Feb;50 (2) :185-94.|[3]Rao PC, et al. Coptisine-induced cell cycle arrest at G2/M phase and reactive oxygen species-dependent mitochondria-mediated apoptosis in non-small-cell lung cancer A549 cells. Tumour Biol. 2017 Mar;39 (3) :1010428317694565.
Shipping Conditions
Room temperature
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
IDO
Citation 01
DNA Cell Biol. 2020 Oct 2.|J Oncol. 2022 Jun 26:2022:9864411.|SSRN. 2024 Apr 1.|Int Immunopharmacol. 2024 Feb 15:128:111433.|Molecules. 2024 May 14.|Naunyn Schmiedebergs Arch Pharmacol. 2025 May;398 (5) :5465-5474.|Phytomedicine. 2025 Oct 21:148:157446.|Planta Med. 2024 Jun;90 (7-08) :523-533.

Chemical Information

Coptisine

Coptisine is a natural product found in Coptis japonica. It has a role as a metabolite.

CAS Number3486-66-6
PubChem CID72322
IUPAC Name5,7,17,19-tetraoxa-13-azoniahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-1(13),2,4(8),9,14,16(20),21,23-octaene
Molecular FormulaC19H14NO4+
Molecular Weight320.3
XLogP3.5
Topological Polar Surface Area40.8
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count0
Heavy Atom Count24
Formal Charge1
Complexity502
SMILES
C1C[N+]2=C(C=C3C=CC4=C(C3=C2)OCO4)C5=CC6=C(C=C51)OCO6
InChI
InChI=1S/C19H14NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,5-8H,3-4,9-10H2/q+1
InChIKey
XYHOBCMEDLZUMP-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Coptisine
CAS: 3486-66-6
CID: 72322
Formula: C19H14NO4+
MW: 320.3
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight320.3
XLogP33.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count0
Exact Mass320.09228293
Monoisotopic Mass320.09228293
Topological Polar Surface Area40.8 Ų
Heavy Atom Count24
Formal Charge1
Complexity502
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

Alternative Products

CatalogName
N1737-20Coptisine
N2494-20Coptisine Sulfate
A14548-50Coptisine 50mg
A14548-1Coptisine 1mg
GTR19168938-01Coptisine chloride
A14548-25Coptisine 25mg

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