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Alpha-Amanitin

Basic information

CPKB ID CP00295
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-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]acetamide
Synonyms
11000-43-4
23109-05-9
Akos024457936
Alpha-Amanitin
Chembl3792970
Cs-5321
Cyclo[L-Asparaginyl-4-Hydroxy-L-Proly-(R-4,5-Dihydroxy-L-Isoleucyl-6-Hydroxy-2-Mercapto-L-Tryptophylglycyl-L-Isoleucylglycyl-L-Cysteinyl]Cyclic-(4?8)-Sulfide-(R)-S-Oxide
Hy-19610
Schembl16491633
Source

Galerina marginata [Division : Plants and Fungi]

Taxonomy :109633 (Fungi-Basidiomycota-Agaricales-Agaricomycetes-Strophariaceae Galerina)  

Wikipedia: Galerina marginata

Amanita verna [Division : Plants and Fungi]

Taxonomy :112270 (Fungi-Basidiomycota-Agaricales-Agaricomycetes-Amanitaceae Amanita)  

Wikipedia: Amanita verna

Uniprot  

Family

Alpha-Amanitin   Cybase  

Information

Alpha-Amanitin is a natural product found in Galerina marginata, Amanita verna, and other organisms with data available.

PubChem|441541   Uniprot|P85421   Cybase|518  

Legend

Structure

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similarity structure
Molecular Formula

C39H54N10O14S
Molecular Weight 918.3541674 g/mol
SMILES

RUN SEA Predictions

 CC[C@H](C)[C@@H]1NC(=O)CNC(=O)[C@@H]2Cc3c([nH]c4cc(O)ccc34)S(=O)C[C@H](NC(=O)CNC1=O)C(=O)N[C@@H](CC(N)=O)C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H]([C@@H](C)[C@@H](O)CO)C(=O)N2  

PubChem|441541
InChIKey
CIORWBWIBBPXCG-ZHJKGNQFNA-N
2D Structure
PubChem|441541
3D Structure
PDB|3CQZ  PDB|6EXV 
3D Structure (Complex)
PDB|1K83  PDB|2VUM  PDB|3CQZ  PDB|6EXV 

Sequence

Graph alignment
Local alignment
One-letter code

IWGIGCNP

Cybase|518
IUPAC Condensed
ILE-TRP-GLY-ILE-GLY-CYS-ASN-PRO  

CyclicPepedia|PP
Amino acid chain
ILE--TRP--GLY--ILE--GLY--CYS--ASN--PRO  

CyclicPepedia|PP
Graph representation
ILE,TRP,GLY,ILE,GLY,CYS,ASN,PRO  

CyclicPepedia|PP
One letter code from Structure
CNPIWGIG  

CyclicPepedia|Struct2seq
Amino acid chain from Structure
Ile(1)--Gly--Cys(2)--Asn--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.

Biologic Determination

BioAssay Results

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Active 0.0025 Equal to

IC50

 1293409 336870822

Chemical and Physical Properties

CyclicPepedia|PP

Structure Properties

Property Name Property Value
Exact Mass 918.3541674
Number of Rings 5.0
Complexity 0.875
XlogP3 AA -5.9202
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 222.2636
Rule_of_Five 0.0
Number of Atoms 64.0
Topological Polar Surface Area 380.88
Refractivity 222.2636
Veber Rule 0.0
Ghose Filter 0.0
Property Name Property Value
RDKit Fingerprint
11101111111110101111110011111011111111110111011010111011101011001110101111111111111111101110110011110111111111111010111111110111111001111111111111011111000110011101101010111111110111011111111110110110111101101000100110011000010101000111111111101110111111111111001111111111110111101111111110101011111011010111111111010001110111101111111111011110111101100111111101111101001111000011011100101010011101011111100110101110100110111101101000111011111111110110011110111111111011011001100001001110001111011111100101101111111100111110110011111101000110000101111111010111111101101110010111101001010110111100111110111001101110111010101010111001110100111100111111110111111101111110111110111111010111011101111101111000101111100000100111110111111101111111111010111011111110111011111110111000101111111011111110011111001111111111110001101101111011111100111011111101111101110111011100111111101110100101111010010011100101001110111111111110111110011011110001011110101000011110111101111010011101011111101011110101111101011010010011111001111111110111110110111111111011101011010111111010101101100111110111001101110111111101101101011111110011101010110110101101010111001111111001011000111110111110100111101111011111011111101011000111110001101111111111100111111101110111011111111011101111010110101111101110110001111111110101111001011111111101101111101101100101111011111111110101110110111011111011110101111101011111011111100011110001011110111111100101101111101101010011111111101101011011111110111110111101111101110101111111011011000111100100110111111001101101011011011110111111110101011111111001111101100111111111111111100110000011100111111111010110100111111111111110101100011110010011011111100011110111111011100101010000111100111111110100110111010111010111011000100111111111011011111101111111010111100000111110100011111011101111111111111111111101101111110011111110111111111011111111101111111010111111101111010100001111111110111110101101100101011001110111101110111111110110110111011011111111111111011111101111100111111111111100111111011110101111101110010110100100111111110011
Morgan Fingerprint
0100011000100000000100000000110011000000001000000000000000000000010000000000000010000000001000000000000000000100000100010000000000100000000010000001000000000000000000000000000000000000000000000010000000000000000000000000001000010001010000000000000000000010000000000000100000000000000100001100001000100100000000000010100000000000000001000000000000000000000010000100000000000000000001000000000000000000000000000000000010000000000000000000000010000000000000000000000000000000000000000010000000001000100000010000100000000001100000000000000000000000000000010000000000000000000000000011000000000011000010000000000100001000010000000100000000000000000000000010001000000000010001000000000000001000000000000000000010000100000100000100001000000000000100000100000000000000000000000000000000000000000000000000001000000001000000000000000000000001000000001010001101000100000010000001000000110000000000001100010100000000000000000000000000000010000000011000000000000000001000000000000000000000011000000000000000000011000010000000000000010000
MACCS Keys
00000000000000000000000000000000000010000000000100010110000111000101000011000001111111001011100111001110110001110111110011101101110110001111111110101111111111111111110

Sequence Properties

Property Name Property Value
Boman Index -1.08625
Instability -18.4249999999999
Charge -0.0639904165326108
Aliphatic Index 97.5

Binding Target

Other evidence

Property Name Property ID
DrugMAP DM59IT4

Biologic Description

Toxicity PubChem|441541

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

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

1686757

 Physical dependence liability of dynorphin A analogs in rodents 10.1016/0014-2999(91)90343-o.

Eur J Pharmacol

Physical dependence liability of dynorphin A analogs in rodents

Abstract

  • To assess the physical dependence liability of dynorphin A analogs, mice were given repeated injections of various dynorphin A analogs twice daily for 5 days, and rats were given repeated administration of N-methyl-Tyr1,N-methyl-Arg7,D-Leu8dynorphin-A-(1-8) ethylamide (E-2078) twice daily for up to 7 weeks. Mice that had received repeated D-Cys2,Cys5,N-methyl-Arg7,D-Leu8dynorphin-A-(1-9) amide displayed jumping behavior after subcutaneous injection of naloxone, an opioid receptor antagonist. In contrast, the animals that had received repeated E-2078 or N-methyl-Tyr1,Phe4(p-NO2),N-methyl-Arg7,D-Leu8dynorphin-A-(1-8) ethylamide displayed very few jumps after naloxone administration. Rats that had received repeated E-2078 administration did not display withdrawal signs, such as weight loss, after either abrupt withdrawal or naloxone administration. These results indicate that E-2078 and N-methyl-Tyr1,Phe4(p-NO2),N-methyl-Arg7,D-Leu8dynorphin-A-(1-8) ethylamide may have little dependence liability and that D-Cys2,Cys5,N-methyl-Arg7,D-Leu8dynorphin-A-(1-9) amide can cause physical dependence.

1980641

 Synthesis and biological activity of MeTyr1,MeArg7,D-Leu8-dynorphin A(1-9)-NHEt and D-Cys2-Cys5,MeArg7,D-Leu8-dynorphin A(1-9)-NH2 10.1248/cpb.38.2274.

Chem Pharm Bull (Tokyo)

Synthesis and biological activity of MeTyr1,MeArg7,D-Leu8-dynorphin A(1-9)-NHEt and D-Cys2-Cys5,MeArg7,D-Leu8-dynorphin A(1-9)-NH2

Abstract

  • The opioid activities of MeTyr1-Dyn(1-7)-NH2, MeTyr1,D-Leu8-Dyn(1-8)-NH2, MeTyr1,D-Leu8-Dyn(1-9)-NH2, MeTyr1,D-Leu8-Dyn(1-10)-NH2, MeTyr1,D-Leu8-Dyn(1-11)-NH2, and MeTyr1,D-Leu8,12-Dyn(1-13)-NH2 were examined in the bioassays (guinea pig ileum, mouse vas deferens and rabbit vas deferens). Because MeTyr1,D-Leu8-Dyn(1-9)-NH2 showed the most potent opioid activity of the peptides tested, the biological activities of two kinds of Dyn(1-9) analogues, MeTyr1,MeArg7,D-Leu8-Dyn(1-9)-NHEt and D-Cys2-Cys5,MeArg7,D-Leu8-Dyn(1-9)-NH2 were determined and compared with those of MeTyr1,MeArg7,D-Leu8-Dyn(1-8)-NHEt and D-Cys2-Cys5,MeArg7,D-Leu8-Dyn(1-8)-NHEt in the three bioassays, in the receptor binding assays, and in the mouse tail pinch test after subcutaneous administration. The results suggest that the extension of the C-terminal in the peptide chain of MeArg7,D-Leu8-Dyn(1-8)-NH2 analogues by Arg is ineffective for increasing the kappa-opioid activities, kappa-receptor selectivity and/or analgesic effects of the peptides.