1,2-Dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridinium
Chelerythrine
Grundinformationen
- CAS
34316-15-9- Standard-SMILES
COc1ccc2c(c[n+](C)c3c4cc5c(cc4ccc23)OCO5)c1OC- InChIKey
LLEJIEBFSOEYIV-UHFFFAOYSA-N- Summenformel
- C21H18NO4+
- Durchschnittliche Molmasse
- 348,4 g/mol
- Monoisotopische Masse
- 348,12358306
Überblick
Chelerythrine is a benzophenanthridine alkaloid isolated from the root of Zanthoxylum simulans, Chelidonium majus L., and other Papaveraceae. It has a role as an antibacterial agent, an antineoplastic agent and an EC 2.7.11.13 (protein kinase C) inhibitor. It is an organic cation and a benzophenanthridine alkaloid.
Namen und Bezeichner
- Bevorzugter Name
- Chelerythrine
- IUPAC
- 1,2-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium
- Lokaler Name
- 1,2-Dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridinium
- Englischer Name
- Chelerythrine
- Summenformel
- C21H18NO4+
- Molmasse
- 348.37192
Namen und Synonyme
chelerythrine34316-15-9ToddalincheleritrineToddalinebroussonpapyrine[1,3]Benzodioxolo[5,6-c]phenanthridinium, 1,2-dimethoxy-12-methyl-1,2-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-12-iumE3B045W6X0CHEBI:783731,2-Dimethoxy-12-methyl(1,3)benzodioxolo(5,6-c)phenanthridinium1,2-Dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridinium
Weitere Namen anzeigen
Chelerythrine chlorideSibutramine Impurity 7helerythrineEinecs 251-930-0Chelerythrine (6CI)Chelerythrine chlorichelerythrine/toddaline
DTXSID20861211(1,3)BENZODIOXOLO(5,6-C)PHENANTHRIDINIUM, 1,2-DIMETHOXY-12-METHYL-1,2-DIMETHOXY-12-METHYL(1,3)DIOXOLO)4',5':4,5)BENZO(1,2-C)PHENANTHRIDINIUM1,2-dimethoxy-12-methyl-(1,3)benzodioxolo(5,6-c)phenanthridin-12-ium17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo(11.8.0.0^(2,10).0^(4,8).0^(14,19))henicosa-1(13),2,4(8),9,11,14,16,18,20-nonaen-21-ium17,18-dimethoxy-21-methyl-5,7-dioxa-21-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{14,19}]henicosa-1(13),2,4(8),9,11,14,16,18,20-nonaen-21-iumRefChem:32228DTXCID30208572
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,6
- Polarare Oberfläche (TPSA)
- 40,8 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 26
- Formalladung
- 1
- Komplexität
- 516
Physikochemische Eigenschaften
- Schmelzpunkt
- 195 · 195-205°C
- Siedepunkt
- 496.37 °C · 496.37°C (rough estimate)
- Dichte
- 1.2985 · 1.2985 (rough estimate)
- Brechungsindex
- 1.5614 · 1.5614 (estimate)
- storage temp.
- -20 °C · Desiccate at -20°C
- Löslichkeit
- Chloroform (Slightly, Sonicated), DMSO (Slightly, Sonicated), Methanol (Slightly）
- Aggregatzustand
- Solid
- Farbe
- Light Yellow to Dark Orange
- Stabilität
- Hygroscopic
- InChI
- InChI=1S/C21H18NO4/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22/h4-10H,11H2,1-3H3/q+1
- InChIKey
- LLEJIEBFSOEYIV-UHFFFAOYSA-N
- SMILES
- C[N+]1=CC2=C(C(OC)=CC=C2C2C=CC3C=C4OCOC4=CC=3C1=2)OC
- LogP
- -0.401 · -0.401 (est)
- CAS Datenbank
- 34316 · 34316-15-9(CAS DataBase Reference)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H300 (50%): Fatal if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 2 (50%)
Toxikologische Informationen
Toxicity Summary
Chelerythrine is a potent, selective, and cell-permeable protein kinase C (PKC) inhibitor. It is also the major active natural product found in the plant Zanthoxylum clava-herculis, exhibiting anti-bacterial activity against Staphylococcus aureus. (Wikipedia) Chelerythrine is a selective inhibitor of group A and B PKC isoforms with an antitumor activity. Inhibition of PKC with chelerythrine chloride induces apoptosis by activation of a neutral sphingomyelinase, accumulation of ceramide, and depletion of sphingomyelin. Chelerythrine is at least 100-fold more selective for PKCs than for other kinases. Chelerythrine competes for the conserved catalytic sites of PKC and seems to be a potent and specific inhibitor of the group A and group B kinases. Chelerythrine exhibited cytotoxic activity against nine human tumor cell lines tested in vitro. Radioresistant and chemoresistant squamous cell carcinoma lines (HNSCC) undergo apoptosis rapidly after treatment with chelerythrine in vitro. Chelerythrine treatment of nude mice bearing SQ-20B HNSCC cells is associated with significant tumor growth delay. Also, treatment with chelerythrine resulted in minimal toxicity. (A15441)
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Substances that inhibit the growth or reproduction of BACTERIA.
Vor- und nachgelagerte Produkte
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