Basic information

CPKB ID	CP00002
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]acetamide
Synonyms	.Alpha.-Amanitin 2-[(2,3-Dihydroxy-1-Methyl-Propyl)-Dihydroxy-Nonaoxo-Sec-Butyl-[?]Yl]Acetamide 23109-05-9 Alpha--Amanitin Alpha-Amanitin Alpha-Amanitin,-From-Amanita-Phalloides,->=90%-(Hplc),-Powder Alpha-Amanitine Amanitin Bcbcmap01_000054 Bio1_000218 Bio1_000707 Bio1_001196 Cbiol_001932 Cerapp_20658 Dtxsid90860291 Ls-15416 Schembl3506327 Smp1_000013
Source	Amanita phalloides [Division : Plants and Fungi] Taxonomy :67723 (Fungi-Basidiomycota-Agaricales-Agaricomycetes-Amanitaceae Amanita) Wikipedia: Amanita phalloides Galerina marginata [Division : Plants and Fungi] Taxonomy :109633 (Fungi-Basidiomycota-Agaricales-Agaricomycetes-Strophariaceae Galerina) Wikipedia: Galerina marginata Conocybe filaris [Division : Plants and Fungi] Taxonomy :229372 (Fungi-Basidiomycota-Agaricales-Agaricomycetes-Bolbitiaceae Conocybe) Wikipedia: Conocybe filaris PubChem
Family	Amatoxins PubChem
Function	Toxin PubChem
Information	Alpha-Amanitin or α-amanitin is a cyclic peptide of eight amino acids. It is possibly the most deadly of all the amatoxins, toxins found in several members of the Amanita genus of mushrooms, one being the Death cap (Amanita phalloides) as well as the Destroying angel, a complex of similar species, principally A. Virosa and A. Bisporigera. It is also found in the mushrooms Galerina marginata and Conocybe filaris. (L993) PubChem\|2100

Legend

Structure

Molecular Formula	C39H54N10O14S
Molecular Weight	918.3541674 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(N)=O)C(=O)N1CC(O)CC1C(=O)NC(C(C)C(O)CO)C(=O)N2 PubChem\|2100
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)
InChIKey	CIORWBWIBBPXCG-HIKZLMOMNA-N

2D Structure PubChem\|2100

Sequence

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.

Chemical and Physical Properties

CyclicPepedia|Struc2Seq + 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|2100

Amanitin has an unusually strong and specific attraction to the enzyme RNA polymerase II. Upon ingestion, it binds to the RNA polymerase II enzyme, preventing mRNA synthesis and effectively causing cytolysis of hepatocytes (liver cells). (L993)

Metabolism PubChem|2100

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	Amanitin
Bayer healthcare pharmaceuticals	Amanitin
Upsher smith laboratories	Amanitin
Merck	Amanitin

Manufacturers Name	Value
Apotex	Amanitin
Baxter Healthcare Corp	Amanitin
Pharmasources	Amanitin
Novartis	Amanitin
AstraZeneca	Amanitin

Forecasting tools

Forecasting tools	Value
Structure to Sequence	CCC(C)C1NC(=O)CNC(=O)C2Cc3c([nH]c4cc(O)ccc34)S(=O)CC(NC(=O)CNC1=O)C(=O)NC(CC(N)=O)C(=O)N1CC(O)CC1C(=O)NC(C(C)C(O)CO)C(=O)N2
Structure Properties	CCC(C)C1NC(=O)CNC(=O)C2Cc3c([nH]c4cc(O)ccc34)S(=O)CC(NC(=O)CNC1=O)C(=O)NC(CC(N)=O)C(=O)N1CC(O)CC1C(=O)NC(C(C)C(O)CO)C(=O)N2
Sequence to Structure	CNPIWGIG
Sequence Properties	CNPIWGIG
Expasy ProtParam Tool	CNPIWGIG
SEA	RUN SEA Predictions

Information Source

Property Name	Property ID
Patents	CIORWBWIBBPXCG-HIKZLMOMNA-N
pubchem	2100
Drugbank	Amanitin
DRAMP3	Amanitin
Uniprot	Amanitin
Cybase	Amanitin
CONOSERVER	Amanitin
BindingDB	CCC(C)C1NC(=O)CNC(=O)C2Cc3c([nH]c4cc(O)ccc34)S(=O)CC(NC(=O)CNC1=O)C(=O)NC(CC(N)=O)C(=O)N1CC(O)CC1C(=O)NC(C(C)C(O)CO)C(=O)N2
CHEMBL	Amanitin
CTD	Amanitin
Wikipedia	%CE%91-Amanitin
KEGG Compound/Drug	Amanitin
CHEBI	CIORWBWIBBPXCG-HIKZLMOMNA-N
EPA DSSTox	DTXSID90860291
FDA Global Substance Registration System (GSRS)	Amanitin
DTP/NCI	Amanitin
Chemspider	CIORWBWIBBPXCG-HIKZLMOMNA-N
VARIDT	DR00364

Reference

Pubmed_ID	Title	DOI	Journal
14775070	[Choline therapy of toxic diseases of the liver]	10.1007/BF01737300.	Klin Wochenschr
[Choline therapy of toxic diseases of the liver] Abstract No profile to view

Pubmed_ID

Title

DOI

Journal

14775070

[Choline therapy of toxic diseases of the liver]

10.1007/BF01737300.

Klin Wochenschr

[Choline therapy of toxic diseases of the liver]

Abstract

No profile to view

Amanitin

Basic information

Legend

Structure

Download structure

Sequence

Chemical and Physical Properties

Structure Properties

Sequence Properties

Binding Target

Other evidence

Biologic Description

Toxicity PubChem|2100

Metabolism PubChem|2100

Manufacturers

Forecasting tools

Information Source

Reference

[Choline therapy of toxic diseases of the liver]

Abstract