Coptisine chloride: Overview, Structure, Properties, and Formulas
Coptisine, Q-100696, or NSC-119754, is an isoquinoline-alkaloid that was isolated from Coptidis Rhizoma. It has anti-diabetic as well as antimicrobial properties and also antiviral, antiviral, and anti-hepatoma characteristics. Coptisine Chloride is an effective non-competitive IDO inhibitor with an IC50 value of 6.3 millimeters and Ki levels of 5.8 millimoles. For buying these chemicals and other research chemicals many online stores are available. From any store, you can buy chemicals online.
IUPAC name
5,7,17,19-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;chloride
InChI
InChI=1S/C19H14NO4.ClH/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;1H/q+1;/p-1
InChI Key
LUXPUVKJHVUJAV-UHFFFAOYSA-M
Properties
| Property Name | Property Value | Reference |
| Molecular Weight | 355.8 | Computed by PubChem 2.1 (PubChem release 2021.05.07) |
| Hydrogen Bond Donor Count | 0 | Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07) |
| Hydrogen Bond Acceptor Count | 5 | Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07) |
| Rotatable Bond Count | 0 | Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07) |
| Exact Mass | 355.0611356 | Computed by PubChem 2.1 (PubChem release 2021.05.07) |
| Monoisotopic Mass | 355.0611356 | Computed by PubChem 2.1 (PubChem release 2021.05.07) |
| Topological Polar Surface Area | 40.8 Ų | Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07) |
| Heavy Atom Count | 25 | Computed by PubChem |
| Formal Charge | 0 | Computed by PubChem |
| Complexity | 502 | Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07) |
| Isotope Atom Count | 0 | Computed by PubChem |
| Defined Atom Stereocenter Count | 0 | Computed by PubChem |
| Undefined Atom Stereocenter Count | 0 | Computed by PubChem |
| Defined Bond Stereocenter Count | 0 | Computed by PubChem |
| Undefined Bond Stereocenter Count | 0 | Computed by PubChem |
| Covalently-Bonded Unit Count | 2 | Computed by PubChem |
| Compound Is Canonicalized | Yes | Computed by PubChem (release 2021.05.07) |
Biological Tests Results
| Activity | Value, µM Activity | Activity Type | Target Name | BioAssay Name |
| Active | 3.3 | GI50 | Antiproliferative activity against rat VSMC assessed as cell growth inhibition | |
| Active | 3.35 | GI50 | Growth inhibition against rat VSMC after 72 hrs by MTT assay | |
| Active | 4.49 | GI50 | Growth inhibition against rat A10 cells after 72 hrs by MTT assay | |
| Active | 5.59 | IC50 | Cytotoxicity against human HCT8 cells assessed as growth inhibition rate after 96 hrs by MTT assay |
Chemicals properties
| PubChem ID | 72321 | Appearance | Orange powder |
| Formula | C19H14NO4Cl | M.Wt | 355.77 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | DMSO : 10.75 mg/mL (30.22 mM; Need ultrasonic and warming) | ||
| SMILES | C1C[N+]2=C(C=C3C=CC4=C(C3=C2)OCO4)C5=CC6=C(C=C51)OCO6.[Cl-] | ||
| Standard InChIKey | LUXPUVKJHVUJAV-UHFFFAOYSA-M | ||
| Standard InChI | InChI=1S/C19H14NO4.ClH/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;1H/q+1;/p-1 | ||
| General tips | We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. | ||
Biological activity
| Description | Coptisine is an isoquinoline alkaloid isolated from Coptidis Rhizoma with anti-diabetic, antimicrobial, antiviral, anti-hepatoma, and anti-leukemia effects. It protects rat heart against myocardial ischemia/reperfusion injury by suppressing myocardial apoptosis and inflammation. Coptisine chloride can be absorbed across intestinal epithelial cells, and completely absorbed compounds. |
| In vitro | [Absorption of coptisine chloride and berberrubine across human intestinal epithelial by using human Caco-2 cell monolayers].
Zhongguo Zhong Yao Za Zhi. 2007 Dec;32(23):2523-7. To study the absorption of Coptisine chloride (COP) and berberrubine (BRB) as chemical constituents of some traditional Chinese medicines in human intestinal epithelial. The P(app) values of Coptisine chloride, BRB were (1.103 +/- 0.162) x 10(-5), (1.309 +/- 0.102) x 10(-5) cm x s(-1 from AP side to BL side, and (0.300 +/- 0.041) x 10(-5) and (1.955 +/- 0.055) x 10(-5) cm x s(-1) from BL side to AP side, respectively. Their P(app) values were identical with those of propranolol [(2.23 +/- 0.10) x 10(-5 cm x s(-1)], which is a transcellular transport marker and as a control substance for high permeability. On the other hand, the efflux transport of BRB was higher 1.49 times more than its influx transport with 0.67 rate of P(app A–>B)/P(app B–>A). But P(app A–>B)/P(app B–>A value of Coptisine chloride was 3.67, which suggested that the efflux transport have not been involved in its absorbed mechanism in Caco-2 cells monolayers. |
Conclusion
Coptisine chloride can be absorbed through intestinal epithelial cells. Thus, BRB may have been involved in the efflux mechanism in the Caco-2 cells monolayers model from the basolateral-to-apical direction.
