α-Amanitin - Moligand™, ≥90% , CAS No.23109-05-9

CAS: 23109-05-9 Cat. No.: A133283 Molecular Weight: 918.97 Beilstein Registry Number: 1071138 EC Number: 245-432-2 PubChem CID: 2100

GRADE & PURITY Moligand™, ≥90%

Synonyms

Bio1_001196 | Bio1_000707 | Bio1_000218 | alpha-Amanitin, from Amanita phalloides, >=90% (HPLC), powder | 2-[(2,3-dihydroxy-1-methyl-propyl)-dihydroxy-nonaoxo-sec-butyl-[?]yl]acetamide | BCBcMAP01_000054 | CBiol_001932 | alpha-amanitin | Amanitin | SCHEMB

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Product Describtion:

A selective RNA polymerase II inhibitor；
Alpha-amanitin is the main toxin of several deadly poisonous mushrooms, exerting its toxic effects by inhibiting RNA polymerase II

α-Amanitin is the major toxic bicyclic octapeptide of the Amanita phalloides mushroom that has been used in biochemical research for decades. 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. α-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. α-Amanitin is an inhibitor of Pol III.
A specific and potent inhibitor of eukaryotic RNA pol II and a mild inhibitor of RNA pol III.

Specifications

Synonyms

Bio1_001196 | Bio1_000707 | Bio1_000218 | alpha-Amanitin, from Amanita phalloides, >=90% (HPLC), powder | 2-[(2, 3-dihydroxy-1-methyl-propyl)-dihydroxy-nonaoxo-sec-butyl-[?]yl]acetamide | BCBcMAP01_000054 | CBiol_001932 | alpha-amanitin | Amanitin | SCHEMB

Specifications & Purity

Moligand™, ≥90%

Biochemical and Physiological Mechanisms

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.Potent and selective RNA polymerase II

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥90%

Names and Identifiers

• Canonical Smiles: CCC(C)C1C(=O)NCC(=O)NC2CS(=O)C3=C(CC(C(=O)NCC(=O)N1)NC(=O)C(NC(=O)C4CC(CN4C(=O)C(NC2=O)CC(=O)N)O)C(C)C(CO)O)C5=C(N3)C=C(C=C5)O
• IUPAC Name: 2-[34-butan-2-yl-13-(3,4-dihydroxybutan-2-yl)-8,22-dihydroxy-2,5,11,14,27,30,33,36,39-nonaoxo-27λ4-thia-3,6,12,15,25,29,32,35,38-nonazapentacyclo[14.12.11.06,10.018,26.019,24]nonatriaconta-18(26),19(24),20,22-tetraen-4-yl]acetamide
• InChIKey: CIORWBWIBBPXCG-UHFFFAOYSA-N
• INCHI: 1S/C39H54N10O14S/c1-4-16(2)31-36(60)42-11-29(55)43-25-15-64(63)38-21(20-6-5-18(51)7-22(20)46-38)9-23(33(57)41-12-30(56)47-31)44-37(61)32(17(3)27(53)14-50)48-35(59)26-8-19(52)13-49(26)39(62)24(10-28(40)54)45-34(25)58/h5-7,16-17,19,23-27,31-32,46,50-53H,4,8-15H2,1-3H3,(H2,40,54)(H,41,57)(H,42,60)(H,43,55)(H,44,61)(H,45,58)(H,47,56)(H,48,59)
• Isomeric SMILES: CCC(C)C1C(=O)NCC(=O)NC2CS(=O)C3=C(CC(C(=O)NCC(=O)N1)NC(=O)C(NC(=O)C4CC(CN4C(=O)C(NC2=O)CC(=O)N)O)C(C)C(CO)O)C5=C(N3)C=C(C=C5)O
• WGK Germany: 3
• RTECS: BD6195000
• PubChem CID: 2100
• Molecular Weight: 918.97
• Beilstein: 1071138

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Peptides
          • Level6 Cyclic peptides
            • Level7 Amatoxins

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Peptides - Cyclic peptides
• Direct Parent: Amatoxins
• Alternative Parents: Oligopeptides 3-alkylindoles Alpha amino acids and derivatives Hydroxyindoles 1-hydroxy-2-unsubstituted benzenoids Tertiary carboxylic acid amides Heteroaromatic compounds Pyrroles Pyrrolidines Secondary alcohols Lactams Secondary carboxylic acid amides Sulfoxides Primary carboxylic acid amides Sulfinyl compounds Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Primary alcohols
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Amatoxin skeleton - Alpha-oligopeptide - Alpha-amino acid or derivatives - Hydroxyindole - 3-alkylindole - Indole - Indole or derivatives - 1-hydroxy-2-unsubstituted benzenoid - Benzenoid - Pyrrole - Pyrrolidine - Heteroaromatic compound - Tertiary carboxylic acid amide - Carboxamide group - Lactam - Primary carboxylic acid amide - Secondary alcohol - Secondary carboxylic acid amide - Sulfoxide - Azacycle - Sulfinyl compound - Organoheterocyclic compound - Hydrocarbon derivative - Organic oxide - Primary alcohol - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Organopnictogen compound - Carbonyl group - Alcohol - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as amatoxins. These are cyclic peptides containing eight amino acid residues arranged in a macrobicyclic motif.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in water (1.0 mg/ml), ethanol (5 mM), DMSO, DMF, methanol, and acetonitrile.
• Sensitivity: Light sensitive
• Melt Point(°C): 254-255° C
• Molecular Weight: 919.000 g/mol
• XLogP3: -4.400
• Hydrogen Bond Donor Count: 13
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 7
• Exact Mass: 918.354 Da
• Monoisotopic Mass: 918.354 Da
• Topological Polar Surface Area: 400.000 Ų
• Heavy Atom Count: 64
• Formal Charge: 0
• Complexity: 1840.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 11
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yanwen Wang, Miao Cai, Yue Lou, Siran Zhang, Xiaoli Liu.  (2022)  ZBTB20-AS1 promoted Alzheimer's disease progression through ZBTB20/GSK-3β/Tau pathway.  BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS,      [PMID:36502636] [10.1016/j.bbrc.2022.11.107]