.BETA.-AMANITIN

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

Structure Search

SMILES

CC[C@H](C)[C@@H]1NC(=O)CNC(=O)[C@@H]2CC3=C(NC4=C3C=CC(O)=C4)[S@](=O)C[C@H](NC(=O)CNC1=O)C(=O)N[C@@H](CC(O)=O)C(=O)N5C[C@H](O)C[C@H]5C(=O)N[C@@H]([C@@H](C)[C@@H](O)CO)C(=O)N2

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16198510 | https://www.ncbi.nlm.nih.gov/pubmed/1248586 | https://www.scbt.com/scbt/product/beta-amanitin-21150-22-1 | http://www.t3db.ca/toxins/T3D3585

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

Targets

Primary Target	Pharmacology	Condition	Potency
RNA polymerase II activity 1 Target ID: GO:0001055 Sources: http://www.abcam.com/beta-amanitin-ab144513.html \| https://www.scbt.com/scbt/product/beta-amanitin-21150-22-1 \| http://www.t3db.ca/toxins/T3D3585	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2397216 https://www.google.com/patents/US20120100161 http://www.google.com.pg/patents/EP1661584A1	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Fabrication of a biomimetic adsorbent imprinted with a common specificity determinant for the removal of α- and β-amanitin from plasma.	2016-08-12	27394089
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.	2015-06	25916793
Evaluation and comparison of alpha- and beta-amanitin toxicity on MCF-7 cell line.	2014	25539537

Patents

Sample Use Guides

In Vivo Use Guide

PROBABLE ORAL LETHAL DOSE (HUMAN) 5-50 MG/KG

Route of Administration: Oral

In Vitro Use Guide

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.

Name

Type

Language

.BETA.-AMANITIN

Common Name

English

.ALPHA.-AMANITIN, 1-L-ASPARTIC ACID-

Preferred Name

English

CYCLO(L-.ALPHA.-ASPARTYL-(4R)-4-HYDROXY-L-PROLYL-(4R)-4,5-DIHYDROXY-L-ISOLEUCYL-6-HYDROXY-2-MERCAPTO-L-TRYPTOPHYLGLYCYL-L-ISOLEUCYLGLYCYL-L-CYSTEINYL) CYCLIC (4->8)-THIOETHER (R)-S-OXIDE

Systematic Name

English

.BETA.-AMANITINE

Common Name

English

1-L-ASPARTIC ACID .ALPHA.-AMANITIN

Common Name

English

.BETA.-AMATOXIN [HSDB]

Common Name

English

.BETA.-AMANITIN [MI]

Common Name

English

AMANITIN, .BETA.-

Common Name

English

Code System Code Type Description

HSDB

3459