| Identification | Back Directory | [Name]
ALPHA-AMANITIN | [CAS]
23109-05-9 | [Synonyms]
Aids004473
Α-AMANITIN
A-AMANITIN
α-Amanitin
Aids-004473
AMANITIN, A-
ALPHA-AMANTIN
ALPHA-AMANTINE
ALPHA-AMANITIN
alpha-amatoxin
ALPHA-AMANITINE
AMANITIN, a-(RG)
ulfide,(r)-s-oxide
Α-AMANITIN;Α-AMATOXIN
AMANITIN, a-(RG)(CALL)
α-Amanitin
DISCONTINUED
alpha-Amanitin
(α-Amanitin
ALPHA-AMANITIN, AMANITA SPECIES
A-AMANITIN FROM AMANITA PHALLOIDES
A-AMANTINE, FROM AMANITA PHALLOIDES
α-Amanitin, from Amanita Phalloides
ALPHA-AMANITIN FROM AMANITA PHALLOIDES
alpha-AMantine, froM AManita Phalloides
alpha-Amanitine, from Amanita Phalloides
y-2-mercapto-l-tryptophylglycyl-l-isoleucylglycyl-l-cysteinyl),cyclic(4-8)-s
cyclic(l-asparaginyl-4-hydroxy-l-prolyl-(r)-4,5-dihydroxy-l-isoleucyl-6-hydrox
Cyclo[L-Asn-L-t4Hyp-[(3R,4R)-4,5-dihydroxy-3-methyl-L-Nva-]-6-hydroxy-L-Trp2(1)-Gly-3-methyl-L-Nva-Gly-3-oxomercapto(1)-L-Ala-]
cyclo[L-Asparaginyl-4-hydroxy-L-proly-(R-4,5-dihydroxy-L-isoleucyl-6-hydroxy-2-mercapto-L-tryptophylglycyl-L-isoleucylglycyl-L-cysteinyl]cyclic(4-8)-sulfide(R)-S-oxide | [EINECS(EC#)]
245-432-2 | [Molecular Formula]
C39H54N10O14S | [MDL Number]
MFCD00215842 | [MOL File]
23109-05-9.mol | [Molecular Weight]
918.97 |
| Chemical Properties | Back Directory | [Melting point ]
254-255 °C(lit.)
| [alpha ]
D20 +191° | [Boiling point ]
1622.2±65.0 °C(Predicted) | [density ]
1.1626 (rough estimate) | [refractive index ]
1.7400 (estimate) | [storage temp. ]
−20°C
| [solubility ]
H2O: 1.0 mg/mL
| [form ]
powder
| [pka]
9.63±0.70(Predicted) | [color ]
white to light yellow
| [biological source]
Amanita phalloides | [Optical Rotation]
+19120 (H2O) | [Water Solubility ]
Soluble to 5 mM in ethanol and to 5 mM in water | [ε(extinction coefficient)]
13,500 at 310nm in H2O at 1M | [Merck ]
13,370 | [BRN ]
1071138 | [InChIKey]
CIORWBWIBBPXCG-PWKRRBCNNA-N | [SMILES]
CCC(C)C1NC(=O)CNC(=O)C2Cc3c([nH]c4cc(O)ccc34)S(=O)CC(NC(=O)CNC1=O)C(=O)NC(CC(N)=O)C(=O)N5CC(O)CC5C(=O)NC(C(C)C(O)CO)C(=O)N2 |
| Hazard Information | Back Directory | [Uses]
Inhibits eukaryotic RNA-polymerase II with high efficiency, but not eukaryotic RNA-polymerase I, or bacterial or viral RNA-polymerases. Inhibits mammalian protein synthesis. | [Biological Activity]
α-amanitin, the most deleterious toxin of a. phalloides to humans, inhibits rna polymerase ii (rnapii), causing hepatic and renal failure. | [Biochem/physiol Actions]
The major toxic constituent of the mushroom, Amanita phalloides, inhibits eukaryotic RNA polymerase II and III, but does not inhibit RNA polymerase I or bacterial RNA polymerase. Inhibits mammalian protein synthesis. | [Enzyme inhibitor]
This bicyclic octapeptide toxin (FW = 918.98 g/mol; CAS 23109-05-9;
LD50 = 0.1 mg/kg i.p in albino mice) from the the death-cap fungus
Amanita phalloides binds very tightly to eukaryotic RNA polymerase II (Ki
≈ 10 nM) and less tightly to eukaryotic RNA polymerase III (Ki ≈ 1 μM),
blocking mRNA synthesis and inducing cytolysis of hepatocytes and
kidney cells. a-Amanitin istable at room temperature, soluble in water and
ethanol, and melts with decomposition at 254-255°C. Caution: Gloves
should be worn, and measures should be taken to avoid inhalation.
Symptoms of a toxic dose may not appear for 6-15 hours after exposure.
More than 90% of deaths caused by mushroom poisonings are due to A.
phalloides and related species. Target (s) : RNA polymerase II;
RNA polymerase III; yeast RNA polymerase B; RNA
polymerase I; certain plant RNA polymerases (e.g., plant RNA
polymerase II (); DNA-directed DNA polymerase; DNA-directed
RNA polymerase. | [in vivo]
The intravenous LD50 dose of alpha-Amanitin is 0.327 mg/kg body weight after intravenous injection into BALB/c mice. After 12 h of alpha-Amanitin injection in caudal vein, the levels of WBC, RBC and HGB decrease significantly, while those of BUN and Crea increase significantly in serum. alpha-Amanitin inhibits some genes (Hsp90b1, Irx4, etc.), whose encoded proteins regulate the RNA polymerase II activity. alpha-Amanitin down-regulates some proteins (Nmi, Trpc5, etc.) taking part in the transcription progress[1]. alpha-Amanitin has potent activity in DTC suppression. Mice injected with alpha-Amanitin (0.4 mg/kg, i.p.)-treated cells maintain their body weight, while those receiving a peritoneal injection of MKN45 cells show a constant decrease in body weight[2]. | [IC 50]
Traditional Cytotoxic Agents | [storage]
-20°C, protect from light,unstable in solution, ready to use. |
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