Haemanthamine

Category	Influenza Virus
CAS	466-75-1
Description	Haemanthamine is a crinine-type alkaloid isolated from the Amaryllidaceae plants with anticancer, pro-apoptotic, antioxidant, antiviral, antimalarial and anticonvulsant activities. It targets ribosomal that inhibits protein biosynthesis during the translational elongation phase.

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Product Information

Synonyms	(+)-Haemanthamine; Natalensin; 3-Epicrinamine; NSC403140; Natalensine; Haemanthamin; Hemanthamine; (3β,11R,13β,19α)-3-Methoxy-1,2-didehydrocrinan-11-ol; 3H,6H-5,11b-Ethano[1,3]dioxolo[4,5-j]phenanthridin-12-ol, 4,4a-dihydro-3-methoxy-, (3S,4aS,11bS,12R)-; (3β,5α,11R,13β,19α)-1,2-Didehydro-3-methoxycrinan-11-ol
IUPAC Name	(1S,13S,15S,18R)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraen-18-ol
Molecular Weight	301.34
Molecular Formula	C17H19NO4
Canonical SMILES	COC1CC2C3(C=C1)C(CN2CC4=CC5=C(C=C34)OCO5)O
InChI	InChI=1S/C17H19NO4/c1-20-11-2-3-17-12-6-14-13(21-9-22-14)4-10(12)7-18(8-16(17)19)15(17)5-11/h2-4,6,11,15-16,19H,5,7-9H2,1H3/t11-,15+,16+,17+/m1/s1
InChIKey	YGPRSGKVLATIHT-HSHDSVGOSA-N
Boiling Point	467.5±45.0°C at 760 mmHg
Flash Point	236.5°C
Purity	≥95%
Density	1.4±0.1 g/cm3
Solubility	In Vitro: DMSO : 100 mg/mL(331.85 mM;Need ultrasonic)
Appearance	White to off-white (Solid)
Storage	Powder: -20°C: 3 years 4°C: 2 years In solvent: -80°C: 6 months -20°C: 1 month
Complexity	497
Exact Mass	301.13140809
Index Of Refraction	1.679
In Vitro	Haemanthamine (1-100 µM; 24-48 hours; A2780 cells) treatment shows a time- and dose-dependent decrease in cell viability. Haemanthamine (10 µM; 24-72 hours; A2780 cells) treatment leads to a significant inhibition of A2780 cell proliferation. Haemanthamine binds at the A-site cleft of the peptidyl transferase center on the large ribosomal subunit, creating unique molecular interactions with the 25S rRNA. Haemanthamine has a highly specific inhibitory effect on pre-rRNA processing, leading to the activation of a p53-dependent antitumoral surveillance pathway known as nucleolar stress.
In Vivo	A pharmacokinetic study of Haemanthamine in rats shows a rapid distribution phase of 30 min, a half-life of 70.4 min, and a major clearance through renal elimination. The high distribution volume of 13.7 L/kg suggests a high intracellular penetration, and its plasmatic concentration remains higher than 1 μM for at least 1 hr after a single 10-mg/kg administration.
PSA	51.16000
Target	Apoptosis; Influenza Virus; Parasite
Vapor Pressure	1.53E-09mmHg at 25°C
XLogP3-AA	1.3