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ALPHA-AMANITIN

CAS No.:
23109-05-9
Catalog Number:
AG00BBUN
Molecular Formula:
C39H54N10O14S
Molecular Weight:
918.9697
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥90%
1 week
United States
$300
- +
2mg
99%
1 week
United States
$571
- +
5mg
99%
1 week
United States
$1307
- +
Product Description
Catalog Number:
AG00BBUN
Chemical Name:
ALPHA-AMANITIN
CAS Number:
23109-05-9
Molecular Formula:
C39H54N10O14S
Molecular Weight:
918.9697
MDL Number:
MFCD30207890
IUPAC Name:
2-[(1R,4S,8R,10S,13S,16S,34S)-34-[(2S)-butan-2-yl]-13-[(2R,3R)-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
InChI:
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)/t16-,17-,19+,23-,24-,25-,26-,27-,31-,32-,64?/m0/s1
InChI Key:
CIORWBWIBBPXCG-JAXJKTSHSA-N
SMILES:
OC[C@@H]([C@@H]([C@@H]1NC(=O)[C@@H]2C[C@H](CN2C(=O)[C@H](CC(=O)N)NC(=O)[C@@H]2CS(=O)c3c(C[C@H](NC1=O)C(=O)NCC(=O)N[C@@H]([C@H](CC)C)C(=O)NCC(=O)N2)c1ccc(cc1[nH]3)O)O)C)O
EC Number:
245-432-2
Properties
Complexity:
1840  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
10  
Defined Bond Stereocenter Count:
0
Exact Mass:
918.354g/mol
Formal Charge:
0
Heavy Atom Count:
64  
Hydrogen Bond Acceptor Count:
15  
Hydrogen Bond Donor Count:
13  
Isotope Atom Count:
0
Molecular Weight:
918.977g/mol
Monoisotopic Mass:
918.354g/mol
Rotatable Bond Count:
7  
Topological Polar Surface Area:
400A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
-4.4  
Literature
Title Journal
A breakthrough on Amanita phalloides poisoning: an effective antidotal effect by polymyxin B. Archives of toxicology 20151201
Generation of proliferating human hepatocytes using Upcyte® technology: characterisation and applications in induction and cytotoxicity assays. Xenobiotica; the fate of foreign compounds in biological systems 20121001
Determination of amatoxins in different tissues and development stages of Amanita exitialis. Journal of the science of food and agriculture 20121001
Analysis of microRNAs and their precursors in bovine early embryonic development. Molecular human reproduction 20120901
Conditioned food aversion reconsolidation in snails is impaired by translation inhibitors but not by transcription inhibitors. Brain research 20120727
Biogenesis of Epstein-Barr virus microRNAs. Molecular and cellular biochemistry 20120601
Embryonic genome activation events in buffalo (Bubalus bubalis) preimplantation embryos. Molecular reproduction and development 20120501
Therapeutic potential of amanitin-conjugated anti-epithelial cell adhesion molecule monoclonal antibody against pancreatic carcinoma. Journal of the National Cancer Institute 20120418
Prolonged α-amanitin treatment of cells for studying mutated polymerases causes degradation of DSIF160 and other proteins. RNA (New York, N.Y.) 20120201
Ribosomal biosynthesis of α-amanitin in Galerina marginata. Fungal genetics and biology : FG & B 20120201
Effects of proteasome inhibitors on the nucleolar size of porcine oocytes. The Journal of reproduction and development 20120101
Amanitin intoxication in two beef calves in California. Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc 20120101
Distribution and mechanism of α-amanitin tolerance in mycophagous Drosophila (Diptera: Drosophilidae). Environmental entomology 20111201
Amatoxin and phallotoxin composition in species of the genus Amanita in Colombia: a taxonomic perspective. Toxicon : official journal of the International Society on Toxinology 20111101
Macromolecular synthesis inhibitors perturb glucocorticoid receptor trafficking. The Journal of steroid biochemistry and molecular biology 20110901
Development of a DNA-based macroarray for the detection and identification of Amanita species. Journal of forensic sciences 20110701
The enterohepatic circulation of amanitin: kinetics and therapeutical implications. Toxicology letters 20110610
HOX genes are expressed in bovine and mouse oocytes and early embryos. Molecular reproduction and development 20110601
Benzylpenicyllin and acetylcysteine protection from α-amanitin-induced apoptosis in human hepatocyte cultures. Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie 20110501
A genetic analysis of Plasmodium falciparum RNA polymerase II subunits in yeast. Molecular and biochemical parasitology 20110401
Influence of commonly used clinical antidotes on antioxidant systems in human hepatocyte culture intoxicated with alpha-amanitin. Human & experimental toxicology 20110101
Developmental changes in expression of genes involved in regulation of apoptosis in the bovine preimplantation embryo. Biology of reproduction 20110101
Sequential analysis of global gene expression profiles in immature and in vitro matured bovine oocytes: potential molecular markers of oocyte maturation. BMC genomics 20110101
Argonaute proteins regulate microRNA stability: Increased microRNA abundance by Argonaute proteins is due to microRNA stabilization. RNA biology 20110101
Localization and differential expression of the Krüppel-associated box zinc finger proteins 1 and 54 in early mouse development. DNA and cell biology 20101001
HSP90 and its R2TP/Prefoldin-like cochaperone are involved in the cytoplasmic assembly of RNA polymerase II. Molecular cell 20100924
Benzylpenicillin, acetylcysteine and silibinin as antidotes in human hepatocytes intoxicated with alpha-amanitin. Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie 20100701
Feasibility study for the rapid screening of target molecules using translational diffusion coefficients: diffusion-ordered NMR spectroscopy of biological toxins. Analytical and bioanalytical chemistry 20100201
[Effect of DRB/alpha-Amanitin on localization of Nrf2 in A549 cells]. Zhejiang da xue xue bao. Yi xue ban = Journal of Zhejiang University. Medical sciences 20100101
Single cell analysis of transcriptional activation dynamics. PloS one 20100101
alpha-Amanitin induced apoptosis in primary cultured dog hepatocytes. Folia histochemica et cytobiologica 20100101
Evidence for an RNA polymerization activity in axolotl and Xenopus egg extracts. PloS one 20100101
Comparative antidotal efficacy of benzylpenicillin, ceftazidime and rifamycin in cultured human hepatocytes intoxicated with α-amanitin. Archives of toxicology 20091201
Study on genes with altered expression in alpha-amanitin poisoned mice and evaluation on antagonistic effects of traditional Chinese medicines against toxicity of alpha-amanitin. Acta biologica Hungarica 20090901
Intestinal glucose uptake protects liver from lipopolysaccharide and D-galactosamine, acetaminophen, and alpha-amanitin in mice. The American journal of pathology 20090901
[Toxicity of alpha-amanitin on mice in vivo]. Sichuan da xue xue bao. Yi xue ban = Journal of Sichuan University. Medical science edition 20090901
Chromatin dynamics is correlated with replication timing. Chromosoma 20090801
Apoptotic processes and DNA cytosine methylation in mouse embryos arrested at the 2-cell stage. Zygote (Cambridge, England) 20090801
Ataxia telangiectasia mutated activation by transcription- and topoisomerase I-induced DNA double-strand breaks. EMBO reports 20090801
Transcriptomic and proteomic analysis of global ischemia and cardioprotection in the rabbit heart. Physiological genomics 20090701
Evidence for transcriptional activity in the syncytiotrophoblast of the human placenta. Placenta 20090401
Expression of microRNA processing machinery genes in rhesus monkey oocytes and embryos of different developmental potentials. Molecular reproduction and development 20090301
On the robustness of mammalian circadian oscillators. Cell cycle (Georgetown, Tex.) 20090301
Identification of a novel pathway that selectively modulates apoptosis of breast cancer cells. Cancer research 20090215
Estrogen directly activates AID transcription and function. The Journal of experimental medicine 20090119
Early morphological and functional alterations in canine hepatocytes due to alpha-amanitin, a major toxin of Amanita phalloides. Archives of toxicology 20090101
Failure of benzylpenicillin, N-acetylcysteine and silibinin to reduce alpha-amanitin hepatotoxicity. In vivo (Athens, Greece) 20090101
Characterization of cells expressing RNA polymerase II tagged with green fluorescent protein: effect of ionizing irradiation on RNA synthesis. International journal of radiation biology 20080901
Determination of alpha- and beta-amanitin in clinical urine samples by Capillary Zone Electrophoresis. Journal of pharmaceutical and biomedical analysis 20080805
Structural basis of transcription inhibition by alpha-amanitin and implications for RNA polymerase II translocation. Nature structural & molecular biology 20080801
Juvenile hormone induction of glutathione S-transferase activity in the larval fat body of the common cutworm, Spodoptera litura (Lepidoptera: Noctuidae). Archives of insect biochemistry and physiology 20080801
In response to Tong TC, et al. Comparative treatment of alpha-amanitin poisoning with N-acetylcysteine, benzylpenicillin, cimetidine, thioctic acid, and silybin in a murine model. Annals of emergency medicine 20080801
Jamming the ratchet of transcription. Nature structural & molecular biology 20080801
The RNA polymerase II trigger loop functions in substrate selection and is directly targeted by alpha-amanitin. Molecular cell 20080606
Characterization of organic anion transporting polypeptide 1b2-null mice: essential role in hepatic uptake/toxicity of phalloidin and microcystin-LR. Toxicological sciences : an official journal of the Society of Toxicology 20080501
Dynamic expression of the RNA-binding protein Sam68 during mouse pre-implantation development. Gene expression patterns : GEP 20080501
Cytotoxic constituents of Amanita subjunquillea. Archives of pharmacal research 20080501
Constitutive heterochromatin during mouse oogenesis: the pattern of histone H3 modifications and localization of HP1alpha and HP1beta proteins. Molecular reproduction and development 20080201
Inhibition of mRNA synthesis in the hippocampus impairs consolidation and reconsolidation of spatial memory. Hippocampus 20080101
Synthesis, characterisation, and in vitro evaluation of Pro2-Ile3-S-deoxo-amaninamide and Pro2-D-allo-Ile3-S-deoxo-amaninamide: implications for structure-activity relationships in amanitin conformation and toxicity. Chemistry (Weinheim an der Bergstrasse, Germany) 20080101
Resistance of mitochondrial p53 to dominant inhibition. Molecular cancer 20080101
A bioartificial liver that combines plasma dialysis and whole liver perfusion. Hepato-gastroenterology 20080101
A protocol for studying the kinetics of RNA within cultured cells: application to ribosomal RNA. Nature protocols 20080101
A tunable ratchet driving human RNA polymerase II translocation adjusted by accurately templated nucleoside triphosphates loaded at downstream sites and by elongation factors. The Journal of biological chemistry 20071214
Extragenic accumulation of RNA polymerase II enhances transcription by RNA polymerase III. PLoS genetics 20071101
Nucleolar translocalization of GRA10 of Toxoplasma gondii transfectionally expressed in HeLa cells. The Korean journal of parasitology 20070901
RNA is an integral component of chromatin that contributes to its structural organization. PloS one 20070101
Gonadotropin regulation of NGFI-B messenger ribonucleic acid expression during ovarian follicle development in the rat. Endocrinology 20010701
Growth suppression induced by antitumor drug vitamin K-3 in human hepatoma HepG2 cells is accompanied by downregulation of proliferating cell nuclear antigen expression. International journal of oncology 19970501
Induction of P4502E1 by acetone in isolated rabbit hepatocytes. Role of increased protein and mRNA synthesis. Biochemical pharmacology 19930406
Coordinate and differential regulation of phenylethanolamine N-methyltransferase, tyrosine hydroxylase and proenkephalin mRNAs by neural and hormonal mechanisms in cultured bovine adrenal medullary cells. Brain research 19900305
Study of the protective effect of an anabolic steroid, 19-nortestosterone phenylpropionate (19-NTPP) on the fatty liver induced by high doses of rifampicin in the rat. Archives of toxicology. Supplement. = Archiv fur Toxikologie. Supplement 19800101
Properties