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Beta-Amanitin

Basic information

CPKB ID CP00003
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-27lambda4-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]acetic acid
Synonyms
.Beta.-Amanitin
2-[34-Butan-2-Yl-13-(3,4-Dihydroxybutan-2-Yl)-8,22-Dihydroxy-2,5,11,14,27,30,33,36,39-Nonaoxo-27Lambda4-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]Acetic-Acid
21150-22-1
Beta--Amanitin
Beta-Amanitin
Beta-Amanitin-From-Amanita-Phalloides,-~90%-(Hplc)
Chembl1978871
J-013881
Nci60_008881
Nsc627727
Nsc-627727
Schembl3505949
Source

Amanita phalloides [Division : Plants and Fungi]

Taxonomy :67723 (Fungi-Basidiomycota-Agaricales-Agaricomycetes-Amanitaceae Amanita)  

Wikipedia: Amanita phalloides

Conocybe [Division : Plants and Fungi]

Taxonomy :71669 (Fungi-Basidiomycota-Agaricales-Agaricomycetes-Bolbitiaceae Unassigned)  

Wikipedia: Conocybe

Galerina [Division : Plants and Fungi]

Taxonomy :109632 (Fungi-Basidiomycota-Agaricales-Agaricomycetes-Strophariaceae Unassigned)  

Wikipedia: Galerina

Lepiota [Division : Plants and Fungi]

Taxonomy :37314 (Fungi-Basidiomycota-Agaricales-Agaricomycetes-Agaricaceae Unassigned)  

Wikipedia: Lepiota

PubChem  

Family

Amatoxins   PubChem  

Function

Toxin   PubChem  

Information

Beta-Amanitin is one of a group of at least eight Amatoxins found in several genera of poisonous mushrooms, most notably Amanita phalloides and several other members of the genus Amanita, as well as some Conocybe, Galerina and Lepiota mushroom species. (L1774)

PubChem|2276  

Legend

Structure

Download structure
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similarity structure
Molecular Formula

C39H53N9O15S
Molecular Weight 919.338183 g/mol
SMILES

RUN SEA Predictions

 CCC(C)C1NC(=O)CNC(=O)C2Cc3c([nH]c4cc(O)ccc34)S(=O)CC(NC(=O)CNC1=O)C(=O)NC(CC(=O)O)C(=O)N1CC(O)CC1C(=O)NC(C(C)C(O)CO)C(=O)N2  

PubChem|2276
InChI
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)  
InChIKey
IEQCUEXVAPAFMQ-RDTCRXGGNA-N
2D Structure
PubChem|2276

Sequence

Graph alignment
Local alignment
One letter code from Structure
CDPIWGIG  

CyclicPepedia|Struct2seq
Amino acid chain from Structure
Ile(1)--Gly--Cys(2)--Asp--4OH-Pro--Ile--Trp(2)--Gly(1)  

CyclicPepedia|Struct2seq
Description of the conversion sequence The one letter code and Amino acid chain derived from the structural transformation may be inconsistent, with the Amino acid chain containing Essential Amino acid and the one letter code not.

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + PP

Structure Properties

Property Name Property Value
Exact Mass 919.338183
Number of Rings 5.0
Complexity 0.859375
XlogP3 AA -5.3209
Heavy Atom Count 64.0
Hydrogen Bond Donor Count 13.0
Hydrogen Bond Acceptor Count 14.0
Rotatable Bond Count 7.0
Property Name Property Value
Formal Charge 0.0
Refractivity 220.705
Rule_of_Five 0.0
Number of Atoms 64.0
Topological Polar Surface Area 375.09
Refractivity 220.705
Veber Rule 0.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
11101111111110101111110011111011111111110111011010111011101011001110101111111110111111101110110011110111111111111010111111110111111001111111111111011111000110011101101010111111110111011111111110110110111101101000100110011000010101000111111111101110111111111111001111111111110111101111111110101011111011010111111111010001110111101111111111011110111101110111111101111101001111000011111100101010011101011111100110101110100110111101101000111011111111110110011110111111111011011001100001001110001111011111100101101111111100111110110011111101000110000101111111010111111101101110010111101101010110111100111110110001101110111010101010111001110100111100110111110111111111111110111110111111010111011101111101111000111111100000100111110111111101111111111010111011111110111011111110111000101111111011111110011111001111111111100001101101111011111100111011111101111101110111011100111111101110100101111010010011100101001110111111111110111110011111110001011110101000011110111101111010011101011111101011110101111101011010010011111001111111110111110110111111111011101011010111111010101101100111110111001101110111111101101101111111110011101010110110101101010110010111101001011000111110111110100111101111011111011111101011000111110001101111111111100111111111110111011111111011101111010110101111101110110001111111110101111001011111111101101111101101100101111011111111110101110110111111111011110101111101011111011101100011110001011110111111100101101111101101010011111111101101011011111110101110111101111101110101111111011011000111100100110111111001101101011011011110111111110101011111111001111101100111111111111111100110000011100111111111011110100111111111111110101100011110010011011111100011100111111011100101010000111100111111110100100111010111010111011000100111111111011011111101111111010111100010111110100011111011101101111111111111111101101111110011111110111111111011111111101111111010111111101111010100001111111110111110101101100101011001110111101110111111110110110111011011111111111111011111101111100111111111111000111111011110101111101110010110100100111011110011
Morgan Fingerprint
0100011000100000000100000000110011000000001000000000000000000000010000000000000010000000001000000000000000000100000100010000000000100000000000000000000000000000000000000000000000000000000000000010000000000000000000000000001000010001010000000000000000000010000000000000100000000000000100001100001000100100000000000010100000000000000001000000000000000000000010000100000000000000000001000000010000000000000000000000000010000000000000000000000010000000000000000000000000000000000000000010000000001000100000010000100000000001100000000000000000000000000000010000000000000000000000000011000000000011000010000000000100001000010000000100000000000000000000000010001000000000010001000000000000001000000000000000000010000100010100000110001000000000000100000100000000000000000000000000000000000000000000000000000000000001000000000000000000000001000000001010000101000100000010000001000000010000000000001100010100000000000000000000000000000010000000011000000000000000001000000000000000000000011000000000000000000011000010000000000000010000
MACCS Keys
00000000000000000000000000000000000010000000000100010110000111000101000011000001011101001011100111001110110001110111110011111101110110001111111110101111111111111111110

Sequence Properties

Property Name Property Value
Boman Index -0.826249999999999
Instability 9.25
Charge -1.0635439323776
Aliphatic Index 97.5

Biologic Description

Toxicity PubChem|2276

The major toxic mechanism of amatoxins is the inhibition of RNA polymerase II, a vital enzyme in the synthesis of messenger RNA (mRNA), microRNA, and small nuclear RNA (snRNA). Without mRNA, essential protein synthesis, and hence cell metabolism, grind to a halt and the cell dies. (L1774)

Metabolism PubChem|2276

Free toxin may be removed by opsonization via the reticuloendothelial system (primarily the liver and kidneys) or it may be degraded through cellular internalization via the lysosomes. Lysosomes are membrane-enclosed organelles that contain an array of digestive enzymes, including several proteases.

Manufacturers

Manufacturers Name Value
CreativePeptides
Bayer healthcare pharmaceuticals
Upsher smith laboratories
Merck
Manufacturers Name Value
Apotex
Baxter Healthcare Corp
Pharmasources
Novartis
AstraZeneca

Forecasting tools

Information Source

Reference

Pubmed_ID Title DOI Journal

2087697

 Cytotoxicity on L1210 leukemic cells of beta-amanitin-concanavalin A and phallacidin-concanavalin A conjugates 10.1016/0041-0101(90)90102-d.

Toxicon

Cytotoxicity on L1210 leukemic cells of beta-amanitin-concanavalin A and phallacidin-concanavalin A conjugates

Abstract

  • The conjugates beta-amanitin-concanavalin A and phallacidin concanavalin A were tested for direct cytotoxicity on L1210 lymphocytic leukemia cells by a combined in vitro-in vivo bioassay. Both conjugates exerted strong direct cytotoxicity on the tumour cells.

2397216

 Epidermal growth factor labeled beta-amanitin-poly-L-ornithine: preparation and evidence for specific cytotoxicity 10.1021/bi00481a012.

Biochemistry

Epidermal growth factor labeled beta-amanitin-poly-L-ornithine: preparation and evidence for specific cytotoxicity

Abstract

  • Poly-L-ornithine with an average molecular weight of 32K was reacted with beta-amanitin hydroxysuccinimide ester to form an amide-linked toxin conjugate. Loading of the polymeric chain with amanitin was high, corresponding to up to 35% of the total weight. To this amatoxin vehicle we attached a targeting molecule, human recombinant leucine-21 epidermal growth factor (hrEGFL), via a disulfide-containing linker moiety. A typical average stoichiometry of the hrEGFL labeled toxin conjugate was (L-Orn)164(beta-amanitin)19(COC2H4SSC2H4CO-hrEGFL)2. The affinity for EGF receptors of hrEGFL bound in this conjugate was tested by using A 431 cells. The affinity was eight times lower than that of unsubstituted hrEGFL but regarded as high enough for studying specific toxicity effects with cells bearing EGF receptors. We found that 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. The approximately 20-fold enhancement of cytotoxicity suggests a specific internalization of the toxin conjugate mediated by the hormone label. This idea is supported by the fact that also in another transformed fibroblast cell line, with an increased though smaller number of EGF receptors than A 431 cells, the corresponding enhancement of cytotoxicity was demonstrable but less pronounced (7-fold). The hormone-mediated increase in cytotoxicity of EGF labeled poly-L-ornithine-beta-amanitin conjugates, combined with their moderate toxicity in the mouse, encourages further examination of such compounds in tumor model systems in vivo.(ABSTRACT TRUNCATED AT 250 WORDS)

3124301

 Preparation of a beta-amanitin-concanavalin A conjugate of low toxicity 10.1016/0041-0101(87)90161-9.

Toxicon

Preparation of a beta-amanitin-concanavalin A conjugate of low toxicity

Abstract

  • Pure beta-amanitin was isolated by combined adsorption chromatography of a crude methanol extract from Amanita phalloides on Sephasorb HP Ultrafine and Sephadex LH-20. The beta-amanitin was coupled to concanavalin A by the carbodiimide method. The conjugate was purified by fractionation on a column of Sephadex G-75. The molar ratio beta-amanitin to concanavalin A in this conjugate was 4.14. The purified conjugate was tested by thin-layer chromatography and showed characteristic (for amatoxins) bright purple staining but different mobility. The ultraviolet spectrum of the conjugate was different from the spectra of the native beta-amanitin and the native concanavalin A. The toxicity of the conjugate was determined by in vivo toxicological studies and was four-fold lower than that of the native beta-amanitin. These results suggest that this conjugate may be used for immunization procedures and for the production of amatoxin-specific antibodies.