chelidonine

Names

[ CAS No. ]:
476-32-4

[ Name ]:
chelidonine

[Synonym ]:
(5bR,6S,12bS)-13-Methyl-5b,6,7,12b,13,14-hexahydro[1,3]dioxolo[4,5]benzo[1,2-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol
EINECS 207-504-1
Chelidonine
Khelidonin
(5bR,6S,12bS)-13-Methyl-5b,6,7,12b,13,14-hexahydro[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phenanthridin-6-ol
MFCD00069660
[1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridin-6-ol, 5b,6,7,12b,13,14-hexahydro-13-methyl-, (5bR,6S,12bS)-
Chelidonin
(5bR,6S,12bS)-13-Méthyl-5b,6,7,12b,13,14-hexahydro[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-i]phénanthridin-6-ol
[5bR-(5ba,6b,12b4a)]-5b,6,7,12b,13,14-hexahydro-13-methyl[1,3]benzodioxolo[5,6-c]-1,3-di oxolo[4,5-i]phenanthridin-6-ol
Diphylline
Helidonine
Stylophorin

Biological Activity

[Description]:

Chelidonine is an isoquinoline alkaloid isolated from Chelidonium majus L., causes G2/M arrest and induces caspase-dependent and caspase-independent apoptosis, with anticancer and antiviral activity[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Infection

[References]

[1]. Lee YK, et al. Chelidonine Induces Caspase-Dependent and Caspase-Independent Cell Death through G2/M Arrest in the T98G Human Glioblastoma Cell Line. Evid Based Complement Alternat Med. 2019 May 26;2019:6318179.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
507.4±50.0 °C at 760 mmHg

[ Melting Point ]:
135-140ºC

[ Molecular Formula ]:
C₂₀H₁₉NO₅

[ Molecular Weight ]:
353.369

[ Flash Point ]:
260.7±30.1 °C

[ Exact Mass ]:
353.126312

[ PSA ]:
60.39000

[ LogP ]:
2.75

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.667

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FL9450000

CHEMICAL NAME :: Chelidonine

CAS REGISTRY NUMBER :: 476-32-4

LAST UPDATED :: 199709

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C20-H19-N-O5

MOLECULAR WEIGHT :: 353.40

WISWESSER LINE NOTATION :: T H5 F6 E6 B665 DN IO KO VO A&O JH WH&&TT&&J D1 PQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 125 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 10,135,1960

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 35 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 5,163,1946

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2750 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: HPBIA9 Herba Polonica. (Ars Polona, POB 1001, 00-068 Warsaw 1, Poland) V.11- 1965- Volume(issue)/page/year: 25,209,1979

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 10,135,1960

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 140 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 10,135,1960

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 360 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 10,135,1960

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 160 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 10,135,1960

Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R20/21/22;R25

[ Safety Phrases ]:
S20-S36/37-S45

[ RIDADR ]:
UN 2811

[ RTECS ]:
FL9450000

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%