Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C39H53N9O15S |
| Molecular Weight | 919.954 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 11 / 11 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12C[C@@H](O)CN1C(=O)[C@]([H])(CC(O)=O)NC(=O)[C@]3([H])C[S@@](=O)C4=C(C[C@H](NC(=O)[C@@]([H])(NC2=O)[C@@H](C)[C@@H](O)CO)C(=O)NCC(=O)N[C@@]([H])([C@@H](C)CC)C(=O)NCC(=O)N3)C5=CC=C(O)C=C5N4
InChI
InChIKey=IEQCUEXVAPAFMQ-SXZCQOKQSA-N
InChI=1S/C39H53N9O15S/c1-4-16(2)31-36(60)41-11-28(53)42-25-15-64(63)38-21(20-6-5-18(50)7-22(20)45-38)9-23(33(57)40-12-29(54)46-31)43-37(61)32(17(3)27(52)14-49)47-35(59)26-8-19(51)13-48(26)39(62)24(10-30(55)56)44-34(25)58/h5-7,16-17,19,23-27,31-32,45,49-52H,4,8-15H2,1-3H3,(H,40,57)(H,41,60)(H,42,53)(H,43,61)(H,44,58)(H,46,54)(H,47,59)(H,55,56)/t16-,17-,19+,23-,24-,25-,26-,27-,31-,32-,64+/m0/s1
β-Amanitin is an extremely toxic constituent of the mushroom, Amanita phalloides, that inhibits Rpb (eukaryotic RNA polymerase II) and eukaryotic RNA polymerase III. This toxin is synthesized as a proprotein, on ribosomes, 34 to 35 amino acids in length and then cleaved at specific proline residues by an enzyme belonging to the prolyl oligopeptidase (POP) subfamily. β-Amanitin shows remarkable binding affinity for eukaryotic RNA polymerase II, slightly binds to RNA polymerase III, and shows no activity on RNA polymerase I; it has been used to determine which types of RNA polymerase are present in a given sample. The toxin works by binding to the bridging helix of RNA polymerase II inhibiting the translocation of RNA and DNA needed to empty the site for the next round of synthesis; thereby slowing the rate of transcription by over 1000 fold.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Evaluation and comparison of alpha- and beta-amanitin toxicity on MCF-7 cell line. | 2014 |
|
| Simultaneous determination of mushroom toxins α-amanitin, β-amanitin and muscarine in human urine by solid-phase extraction and ultra-high-performance liquid chromatography coupled with ultra-high-resolution TOF mass spectrometry. | 2015 Jun |
|
| Fabrication of a biomimetic adsorbent imprinted with a common specificity determinant for the removal of α- and β-amanitin from plasma. | 2016 Aug 12 |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Lethal Dose: 0.1 mg/kg for an adult human. http://www.t3db.ca/toxins/T3D3585
PROBABLE ORAL LETHAL DOSE (HUMAN) 5-50 MG/KG
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: Beta-amanitin in the labeled conjugate was able to inhibit the growth of A 431 cells at a concentration of 28 nM, 80 times lower than for native beta-amanitin and 20 times lower than for poly-L-ornithine-bound beta-amanitin without the hrEGFL label. https://www.ncbi.nlm.nih.gov/pubmed/2397216
The MCF-7 breast cancer cell line was used, and specific concentrations of β-Amanitin (100, 10, 1, 0.1, and 0.01 ug/mL) were applied to the cells.
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3459
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244-244-8
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m1637
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beta-Amanitin
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DTXSID50897720
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SUBSTANCE RECORD
