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シクロ[L-Asn-L-t4Hyp-[(3R,4R)-4,5-ジヒドロキシ-3-メチル-L-Nva-]-6-ヒドロキシ-L-Trp2(1)-Gly-3-メチル-L-Nva-Gly-3-オキソメルカプト(1)-L-Ala-]

Cerapp_20658

HCID 2100
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
23109-05-9
標準SMILES
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
InChIKey
CIORWBWIBBPXCG-UHFFFAOYSA-N
分子式
C39H54N10O14S
平均分子量
919 g/mol
単同位体質量
918.35416761

概要

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)

名称と識別子

優先名称
Cerapp_20658
IUPAC
2-[34-butan-2-yl-13-(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
現地名
シクロ[L-Asn-L-t4Hyp-[(3R,4R)-4,5-ジヒドロキシ-3-メチル-L-Nva-]-6-ヒドロキシ-L-Trp2(1)-Gly-3-メチル-L-Nva-Gly-3-オキソメルカプト(1)-L-Ala-]
英語名
ALPHA-AMANITIN
分子式
C39H54N10O14S
分子量
918.98

名称と別名

RefChem:1081352CERAPP_20658DTXCID60209572DTXSID90860291.alpha.-AmanitinC39H54N10O14SCBiol_001932orb1708067SCHEMBL3506327BCBcMAP01_000054MSK7283CIORWBWIBBPXCG-UHFFFAOYSA-N
名称をさらに表示
α-アマニチンシクロ[L-Asn-L-t4Hyp-[(3R,4R)-4,5-ジヒドロキシ-3-メチル-L-Nva-]-6-ヒドロキシ-L-Trp2(1)-Gly-3-メチル-L-Nva-Gly-3-オキソメルカプト(1)-L-Ala-]αアマニチン2-[(1R,4S,8R,10S,13S,16S,34S)-34-(ブタン-2-イル)-13-[(2R,3R)-3,4-ジヒドロキシブタン-2-イル]-8,22-ジヒドロキシ-2,5,11,14,27,30,33,36,39-ノナオキソ-27λ4-チア-3,6,12,15,25,29,32,35,38-ノナアザペンタシクロ[14.12.11.06,10.018,26.019,24]ノナトリアコンタ-18(26),19,21,23-テトラエン-4-イル]アセトアミドアルファアマニチンα-AmanitinA-AMANITINAids004473α-AmatoxinAids-004473AMANITIN, A-ALPHA-AMANTINALPHA-AMANITINalpha-amatoxinALPHA-AMANTINE
Bio1_000218Bio1_000707Bio1_001196SMP1_000013DA-60946LS-15416T13540alpha-Amanitin, from Amanita phalloides, >=90% (HPLC), powder

データベース識別子

CAS
23109-05-9
PubChem CID
2100

物性

構造計算による物性

XLogP
-4.4
極性表面積
400 Ų
水素結合供与体数
13
水素結合受容体数
15
回転可能結合数
7
重原子数
64
形式電荷
0
複雑度
1,840

物理化学的性質

融点
254 · 254-255 °C(lit.)
比旋光度
20 · D20 +191°
沸点
1622.2 · 1622.2±65.0 °C(Predicted)
比重(密度)
1.1626 · 1.1626 (rough estimate)
屈折率
1.74 · 1.7400 (estimate)
貯蔵温度
20 °C · −20°C
溶解性
2 O: · H2O: 1.0 mg/mL
外見
粉
酸解離定数(Pka)
9.63 · 9.63±0.70(Predicted)
色
白色~淡黄色
由来生物
Amanita phalloides
水溶解度
5 mM · Soluble to 5 mM in ethanol and to 5 mM in water
Merck
13 · 13,370
BRN
1071138 · 1071138
InChIKey
CIORWBWIBBPXCG-PWKRRBCNNA-N
SMILES
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)N5CC(O)CC5C(=O)NC(C(C)C(O)CO)C(=O)N2

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

毒性情報

Treatment · 1 件

Treatment is mainly supportive (gastric lavage, activated carbon, fluid resuscitation) but includes various drugs to counter the amatoxins, including intravenous penicillin and cephalosporin derivatives, and, in cases of greater ingestion, can extend to an orthotopic liver transplant. The most reliable method to treat amanitin poisoning is through having the stomach pumped immediately after ingestion; however, the onset of symptoms is generally too late for this to be an option. (A300)

Health Effects · 1 件

Around 15% of those poisoned will die within 10 days, progressing through a comatose stage to renal failure, liver failure, hepatic coma, respiratory failure and death. Those who recover are at risk of permanent liver damage. Diagnosis is difficult, and is established by observation of the clinical symptoms as well as the presence of α-amanitin in the urine. Urine screening is generally most useful within 48 hours of ingestion. (A300)

Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 件

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)

Signs and Symptoms · 1 件

Few effects are reported within 10 hours; it is not unusual for significant effects to take as long as 24 hours after ingestion to appear, with this delay in symptoms making α-amanitin poisoning even more difficult to diagnose and all the more dangerous. By then, it is far past the time in which stomach pumping would yield an efficient result. Diarrhea and cramps are the first symptoms, but those pass, giving a false sign of remission. Typically, on the 4th to 5th day, the toxin starts to have severe effects on the liver and kidneys, leading to total system failure in both. Death usually takes place around a week from ingestion. (L993)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataLD50: 0.1 mg/kg (Oral, Mouse) (L993)

安全データ

F
8-10-18-21
wgk
3
rtecs
BD6195000
ridadr
UN 3462 6.1/PG 2
毒性
LD50 i.p. in albino mice: 0.1 mg/kg (Wieland, Wieland)
hs_code
2934999090
risk_code
26/27/28-33-26/28
hazard_code
T+
safety_code
36/37/39-45-36/37-28
hazard_class
6.1(a)
packing_group
I
Hazard Classifications
Acute Tox. 1 OralSTOT RE 2
ストレージクラス
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
有毒物質データの
23109-05-9(Hazardous Substances Data)

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

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.

用途と製造

Uses · 1 件

It is 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)

応用分野 · 1 件

使用α-Amanitin has been used:for inducing transcriptional arrest in NT2 cells prior to immunofluorescence assayto induce nephrotoxicity in mice renal tissuesto induce and analyse genotoxicity in mice bone marrow cells by cell viability assay, comet assay and chromosomal aberration assay

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化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート