Harringtonine
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Harringtonine
structure -
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CAS No:
26833-85-2
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Formula:
C28H37NO9
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Chemical Name:
Harringtonine
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Synonyms:
Cephalotaxine,3-[4-methyl (2R)-2-hydroxy-2-(3-hydroxy-3-methylbutyl)butanedioate];Harringtonine;Cephalotaxine,4-methyl 2-hydroxy-2-(3-hydroxy-3-methylbutyl)butanedioate (ester),[3(R)]-;Cephalotaxine,4-methyl (2R)-2-hydroxy-2-(3-hydroxy-3-methylbutyl)butanedioate (ester);4H-Cyclopenta[a][1,3]dioxolo[4,5-h]pyrrolo[2,1-b][3]benzazepine,cephalotaxine deriv.;Harringtonin;2′R-Harringtonine;NSC 124147;25302-09-4;88455-80-5
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CAS No:
Description
Harringtonine is a natural Cephalotaxus alkaloid that inhibits protein synthesis.
Harringtonine is an alkaloid.
Characteristics
123.99000
2.12850
white solid
1.4±0.1 g/cm3
73-75ºC
679.4ºC at 760 mmHg
364.7±31.5 °C
1.610
2.17E-19mmHg at 25°C
Safety Information
II
6.1(a)
1544
|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|P260, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P304+P340, P310, P320, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Harringtonine Use and Manufacturing
A natural product with significant antitumor activities. Harringtonine is an alkaloid extracted from the branches, leaves and bark of the cedar tree that is unique to southern China. The mechanism of action is to inhibit the synthesis of nucleoprotein bodies to depolymerize polynucleoprotein bodies and release new life. Peptide chain and protein synthesis stop, can obviously reduce the mitosis of cancer cells, have inhibitory effect on various animal tumors, and have no cross-resistance with alkylating agents and purines. Harringtonine is a cycle non-specific drug; it has the most obvious effect on the S phase, and it also has a blocking effect on the G2-M and G1-S phases. In addition, this product has an immunosuppressive effect, obviously inhibiting cellular immunity and humoral immunity. Clinically, it is mainly used to treat acute myelogenous leukemia, acute monocytic leukemia and malignant lymphoma. It is also used for polycythemia vera, chronic myelogenous leukemia and promyelocytic leukemia.
Computed Properties
Molecular Weight:531.6
XLogP3:0.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:10
Exact Mass:531.24683176
Monoisotopic Mass:531.24683176
Topological Polar Surface Area:124
Heavy Atom Count:38
Complexity:953
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Anti-tumor drug. This product is a non-specific drug for the cell cycle, but it has a more obvious effect on the S phase, increasing the number of cells in the G1 phase and reducing the number of cells in the S phase and G2M phase. Its mechanism of action is to inhibit the initial stage of protein synthesis, inhibit the activity of DNA polymerase α, lead to a decrease in DNA synthesis, and severely inhibit protein synthesis. This product also has the effects of inducing cell differentiation, increasing cAMP content, and inhibiting glycoprotein synthesis.
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