Basic information
- CAS
21705-02-2- Standard SMILES
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(C)O)C(=O)N2- InChIKey
OFILNAORONITPV-UHFFFAOYSA-N- Molecular formula
- C39H53N9O14S
- Average molar mass
- 904 g/mol
- Monoisotopic mass
- 903.34326857
Overview
ε-amanitin has been reported in Acanthochlamys bracteata with data available.
Names & identifiers
- Preferred name
- epsilon-Amanitin
- IUPAC
- 2-[34-butan-2-yl-8,22-dihydroxy-13-(3-hydroxybutan-2-yl)-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]acetic acid
- English name
- EPSILON-AMANITIN
- Molecular formula
- C39H53N9O14S
- Molecular weight
- 903.96
Names & synonyms
epsilon-Amanitin21705-02-22-[34-butan-2-yl-8,22-dihydroxy-13-(3-hydroxybutan-2-yl)-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 acidalpha-Amanitin, 1-L-aspartic acid-3-((S)-4-hydroxy-L-isoleucine)-alpha-Amanitin, 1-L-aspartic acid-3-(4-hydroxy-L-isoleucine)-, (S)-9,18-(Iminoethaniminoethaniminoethaniminomethano)pyrrolo(1',2':8,9)(1,5,8,11,14)thiatetraazacyclooctadecino(18,17-b)indole-6-acetic acid, 1,2,3,5,6,7,8,9,10,12,17,18,19,20,21,22,23,23a-octadecahydro-29-sec-butyl-2,14-dihydroxy-21-(2-hydroxy-1-methylpropyl)-5,8,20,23,24,27,30,33-octaoxo-, 11-oxideCyclo(L-alpha-aspartyl-4-hydroxy-L-prolyl-(S)-4-hydroxy-L-isoleucyl-6-hydroxy-2-mercapto-L-tryptophylglycyl-L-isoleucylglycyl-L-cysteinyl), cyclic (4-8)-sulfide, (R)-8-oxidee-Amantin2-((1R,4S,8R,10S,13S,16S,34S)-34-((2S)-butan-2-yl)-2,8,11,14,22,30,33,36,39-nonahydroxy-13-((2R,3S)-3-hydroxybutan-2-yl)-5,27-dioxo-27lambda4-thia-3,6,12,15,25,29,32,35,38-nonaazapentacyclo(14.12.11.06,10.018,26.019,24)nonatriaconta-2,11,14,18(26),19(24),20,22,29,32,35,38-undecaen-4-yl)acetic acid2-(34-butan-2-yl-8,22-dihydroxy-13-(3-hydroxybutan-2-yl)-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 acid2-[(1R,4S,8R,10S,13S,16S,34S)-34-[(2S)-butan-2-yl]-2,8,11,14,22,30,33,36,39-nonahydroxy-13-[(2R,3S)-3-hydroxybutan-2-yl]-5,27-dioxo-27lambda4-thia-3,6,12,15,25,29,32,35,38-nonaazapentacyclo[14.12.11.06,10.018,26.019,24]nonatriaconta-2,11,14,18(26),19(24),20,22,29,32,35,38-undecaen-4-yl]acetic acidRefChem:137411
Show more names
α-Amanitin, 1-L-aspartic acid-3-[(4S)-4-hydroxy-L-isoleucine]-Cyclo[L-Asp-L-t4Hyp-[(4S)-4-hydroxy-L-Ile-]-6-hydroxy-L-Trp2(1)-Gly-3-methyl-L-Nva-Gly-3-oxomercapto(1)-L-Ala-]
orb1691158SCHEMBL29365556DTXSID201028142AKOS040757381DA-59377NS00124014T396492-[34-butan-2-yl-8,22-dihydroxy-13-(3-hydroxybutan-2-yl)-2,5,11,14,27,30,33,36,39-nonaoxo-27|E4-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
Database identifiers
- CAS
21705-02-2- PubChem CID
- 30508
- DTXSID
DTXSID201028142
Properties
Computed structural properties
- XLogP
- -2.7
- Topological polar surface area
- 374 Ų
- Hydrogen bond donors
- 12
- Hydrogen bond acceptors
- 15
- Rotatable bonds
- 6
- Heavy atoms
- 63
- Formal charge
- 0
- Complexity
- 1,820
Physicochemical properties
- Density
- 1.1627 · 1.1627 (rough estimate)
- refractive index
- 1.74 · 1.7400 (estimate)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Treatment
Treatment involves high dose penicillin as well as supportive care in cases of hepatic and renal injury. Cautious attention is given to maintaining hemodynamic stability, although if hepatorenal syndrome has developed the prognosis is guarded at best. (L1774)
Treatment involves high dose penicillin as well as supportive care in cases of hepatic and renal injury. Cautious attention is given to maintaining hemodynamic stability, although if hepatorenal syndrome has developed the prognosis is guarded at best. (L1774)
Health Effects
Amatoxins cause liver damage. They may also affect the kidneys. The most severe effects are toxic hepatitis with centrolobular necrosis and hepatic steatosis, as well as acute tubulointerstitial nephropathy, which altogether induce a severe hepatorenal syndrome. (L1774)
Amatoxins cause liver damage. They may also affect the kidneys. The most severe effects are toxic hepatitis with centrolobular necrosis and hepatic steatosis, as well as acute tubulointerstitial nephropathy, which altogether induce a severe hepatorenal syndrome. (L1774)
Exposure Routes
Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary
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)
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)
Signs and Symptoms
Diarrhea and cramps are the first symptoms. (L993)
Diarrhea and cramps are the first symptoms. (L993)
Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).
No indication of carcinogenicity to humans (not listed by IARC).
Toxicity Data
LD50: 0.3-0.6 mg/kg (Mouse) (T258)
LD50: 0.5 mg/kg (Mouse) (T258)
Chemistry & industry
Uses & manufacturing
Uses
Amatoxins are a subgroup of at least eight toxic compounds 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)
Amatoxins are a subgroup of at least eight toxic compounds 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)
Applications
Usesε-Amanitin, a cyclic peptide isolated from a variety of mushroom species, potently binds to and inhibits the activity of RNA polymerase II[1][2].
Suppliers2 total
MedChemExpress[email protected]
宝欧信特生物科技（苏州）有限公司51288865780 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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