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Cerapp_20658

HCID 2100
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
23109-05-9
Standard 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
Molecular formula
C39H54N10O14S
Average molar mass
919 g/mol
Monoisotopic mass
918.35416761

Overview

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)

Names & identifiers

Preferred name
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
English name
ALPHA-AMANITIN
Molecular formula
C39H54N10O14S
Molecular weight
918.98

Names & synonyms

RefChem:1081352CERAPP_20658DTXCID60209572DTXSID90860291.alpha.-AmanitinC39H54N10O14SCBiol_001932orb1708067SCHEMBL3506327BCBcMAP01_000054MSK7283CIORWBWIBBPXCG-UHFFFAOYSA-N
Show more names
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

Database identifiers

CAS
23109-05-9
PubChem CID
2100

Properties

Computed structural properties

XLogP
-4.4
Topological polar surface area
400 Ų
Hydrogen bond donors
13
Hydrogen bond acceptors
15
Rotatable bonds
7
Heavy atoms
64
Formal charge
0
Complexity
1,840

Physicochemical properties

Melting point
254 · 254-255 °C(lit.)
alpha
20 · D20 +191°
Boiling point
1622.2 · 1622.2±65.0 °C(Predicted)
Density
1.1626 · 1.1626 (rough estimate)
refractive index
1.74 · 1.7400 (estimate)
storage temp.
20 °C · −20°C
solubility
2 O: · H2O: 1.0 mg/mL
form
powder
pka
9.63 · 9.63±0.70(Predicted)
color
white to light yellow
biological source
Amanita phalloides
optical activity
19120 · +19120 (H2O)
Water Solubility
5 mM · Soluble to 5 mM in ethanol and to 5 mM in water
ε(extinction coefficient)
13 · 13,500 at 310nm in H2O at 1M
Merck
13 · 13,370
BRN
1071138 · 1071138

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 · 1 item

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 item

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 item

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 item

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)

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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.

Uses & manufacturing

Uses · 1 item

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)

Applications · 1 item

Usesα-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

Suppliers63 total

北京华美互利生物化工010-56205725 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
Hebei baicao biology science and technology co., ltd+86-19131911055 17824879454 · [email protected]
广州佳途科技股份有限公司

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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
EWG's Food Scores
1 · 1
FDA UNII
4 K0QZ999 · E04K0QZ999
UNSPSC Code
12352202 · 12352202
NACRES
32 · NA.32
Symbol(GHS)
6 · GHS06,GHS08
Signal word
Danger
Hazard statements
300 · H300-H373
Precautionary statements
260 · P260-P264-P270-P301+P310-P314-P405
target organs
Kidney,Blood,Liver,Gastrointestinal tract,Respiratory Tract,Central nervous system
PPE
2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes
T+
Risk Statements
26 · 26/27/28-33-26/28
Safety Statements
36 · 36/37/39-45-36/37-28
RIDADR
3462 · UN 3462 6.1/PG 2
WGK Germany
3 · 3
RTECS
6195000 · BD6195000
F
8 · 8-10-18-21
HazardClass
6.1 · 6.1(a)
PackingGroup
I
HS Code
2934999090 · 2934999090
Storage Class
6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications
1 OralSTOT · Acute Tox. 1 OralSTOT RE 2
Hazardous Substances Data
23109 · 23109-05-9(Hazardous Substances Data)
Toxicity
50 i.p · LD50 i.p. in albino mice: 0.1 mg/kg (Wieland, Wieland)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataLD50: 0.1 mg/kg (Oral, Mouse) (L993)

Safety data

F
8-10-18-21
PPE
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
3
rtecs
BD6195000
ridadr
UN 3462 6.1/PG 2
hs_code
2934999090
Toxicity
LD50 i.p. in albino mice: 0.1 mg/kg (Wieland, Wieland)
risk_code
26/27/28-33-26/28
Signal word
Danger
Symbol(GHS)
GHS06,GHS08
hazard_code
T+
safety_code
36/37/39-45-36/37-28
hazard_class
6.1(a)
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group
I
target organs
Kidney,Blood,Liver,Gastrointestinal tract,Respiratory Tract,Central nervous system
Hazard statements
H300-H373
Hazard Classifications
Acute Tox. 1 OralSTOT RE 2
Precautionary statements
P260-P264-P270-P301+P310-P314-P405
Hazardous Substances Data
23109-05-9(Hazardous Substances Data)
81960175-877 18933936954 · [email protected]
成都健腾生物技术有限公司028-85159085 18080455027 · [email protected]
河南闰霖化工有限公司+86-18738066252; +86-18738066252 · [email protected]
Hebei shuoxi biotechnology co. LTD+8613081092107
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
湖北魏氏化学试剂股份有限公司027-59102966 18717199209 · [email protected]
淄博容纳生物科技有限公司+86-86-13583358881 +8618560316533 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
湖北广奥生物科技有限公司027-02702759223056 18162699093 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
吉林中科研伸科技有限公司18143011203 · [email protected]
广东元丰化学试剂有限公司0751-2829979 13376591640 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
泰州市众致生物科技有限公司[email protected] 15066129350 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
上海喀露蓝科技有限公司18149758185 18149758185 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
Chongqing jooe co., ltd+86-15223382610 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
上海皓元医药股份有限公司021-58950125 · [email protected]
四川精萃天成药物科技有限公司028-87865381 18108190480 · [email protected]
广东翁江化学试剂有限公司0751-2815987 13927875076 · [email protected]
上海阿拉丁生化科技股份有限公司6206333 13167063860 · [email protected]
上海前衍生物科技有限公司02781293128 · [email protected]
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成都华纯科技有限公司400-1166-196 15982826727 · [email protected]
南京肽业生物科技有限公司025-58361106-805 15951641583 · [email protected]
山东小野化学股份有限公司0539-6362799 20)
Shanghai Acmec Biochemical Technology Co., Ltd.+86-18621343501 · [email protected]
ChemExpress+86-021-58950125 · [email protected]
Musechem+1-800-259-7612 · [email protected]
南京安美科技有限公司18936879710 18851749494 · [email protected]
career henan chemical co+86-0371-86658258 · [email protected]
范德(北京)生物科技有限责任公司15911056312 · [email protected]
Aladdin Scientific[email protected]
陕西缔都医药化工有限公司029-029-029-81148696 18161915376 · [email protected]
湖北信康医药化工有限公司027-027-59308705 18871579363 · [email protected]
南京旭泽风生物科技有限公司13270865186 · [email protected]
常州翔龙医药科技有限公司18661161657 · [email protected]
山西诺诚生物科技有限公司17835231871 · [email protected]
SHANGHAI KEAN TECHNOLOGY CO., LTD.+8613817748580 · [email protected]
湖北萃园生物科技有限公司18162795156 18162795156 · [email protected]