Ellipticine
K00071 · LP00531 · CS-1794 · icig770 · CP-3025 · CCG36483 · CCG 36483 · DB-052047
Identifiers & Physical Properties
| CAS No. | 519-23-3 |
|---|---|
| Molecular formula | C17H14N2 |
| Average molar mass | 246.31 g/mol |
| Monoisotopic mass | 246.11569845 g/mol |
| SMILES | Cc1c2ccncc2c(C)c2c1[nH]c1ccccc12 |
| InChIKey | CTSPAMFJBXKSOY-UHFFFAOYSA-N |
| PubChem CID | 3213 |
| ChEMBL | CHEMBL123 |
| ChEBI | CHEBI:4776 |
| EC No. | 208-264-0 |
| DTXSID | DTXSID30199855 |
Chemical & Physical Properties
| XLogP | 4.8 |
|---|---|
| Topological polar surface area | 28.7 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 0 |
| Heavy atoms | 19 |
| Formal charge | 0 |
| Complexity | 342 |
| LogP (partition coefficient) | 4.8 |
| Melting point | 316-318°C |
| Boiling point | 379.31°C (rough estimate) |
| Density | 1.257±0.06 g/cm3 (20 ºC 760 Torr) |
| Refractive index | 1.5794 (estimate) |
| Storage conditions | Keep in dark place,Sealed in dry,2-8°C |
| Solubility | DMSO: soluble |
| Physical state | Bright yellow solid |
| pKa (acidity coefficient) | 16.59±0.40(Predicted) |
| Color | Light yellow to yellow |
| Merck | 13,3581 |
| InChI | 1S/C17H14N2/c1-10-14-9-18-8-7-12(14)11(2)17-16(10)13-5-3-4-6-15(13)19-17/h3-9,19H,1-2H3 |
| InChIKey | CTSPAMFJBXKSOY-UHFFFAOYSA-N |
| SMILES | [nH]1c2c(c4c1cccc4)c(c3c(c2C)ccnc3)C |
| LogP (partition coefficient) | 4.800 |
| CAS DataBase Reference | 519-23-3(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 117VLW7484 |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
| GHS pictogram | GHS06 |
| Signal word | Danger |
| GHS hazard statements | H301 |
| GHS precautionary statements | P264-P270-P301+P310-P405-P501 |
| Hazard symbols | T |
| Risk statements (R) | 25 |
| Safety statements (S) | 45 |
| UN transport number | UN 3462 6.1/PG 3 |
| Water hazard class (WGK) | 3 |
| RTECS number | UU8825000 |
| Hazard class | 6.1(b)Acute Tox. 3 Oral |
| Packing group | III |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Toxicity | LD50 in mice (mg/kg): 19.5-22.4 i.v.178-204 orally (Rakieten) |
Safety & Regulations
| GHS classification | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 3 (100%) |
| Water hazard class (WGK) | 3 |
| RTECS number | UU8825000 |
| UN transport number | UN 3462 6.1/PG 3 |
| Toxicity | LD50 in mice (mg/kg): 19.5-22.4 i.v.178-204 orally (Rakieten) |
| Risk statements (R) | 25 |
| Signal word | Danger |
| GHS pictogram | GHS06 |
| Hazard symbols | T |
| Safety statements (S) | 45 |
| Hazard class | 6.1(b)Acute Tox. 3 Oral |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Packing group | III |
| GHS hazard statements | H301 |
| GHS precautionary statements | P264-P270-P301+P310-P405-P501 |
Applications & Uses
Description
Ellipticine is an alkaloid isolated from Apocyanaceae plants that exhibits antitumor activities by intercalating into DNA and/or inhibiting DNA topoisomerase II. It forms covalent adducts in DNA after being enzymatically activated with cytochrome P450 isoforms (e.g., CYP3A4, CYP1A1, or CYP1A2) or by peroxidases in target tissues. Ellipticine has been shown to inhibit the proliferation of human breast adenocarcinoma MCF-7 cells, leukemia HL-60 and CCRF-CEM cells, neuroblastoma IMR-32, UKF-NB-3, and UKF-NB-4 cells, and U87MG glioblastoma cells with IC50 values ranging from 0.27-4.7 μM.
Uses
Ellipticine is a DNA intercalating agent and exhibits antitumor activities.
General Description
A topoisomerase II inhibitor. Acts as an intercalative alkaloid that stimulates topoisomerase II-mediated DNA breakage. Is also capable of uncoupling mitochondrial oxidative phosphorylation.