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ペニトレムA

(1S,2R,5S,6R,8S,9S,10R,12S,15R,16S,25R,27S)-21-chloro-15,16,33,33-tetramethyl-24-methylidene-10-prop-1-en-2-yl-7,11,32-trioxa-18-azadecacyclo[25.4.2.02,16.05,15.06,8.06,12.017,31.019,30.022,29.025,28]tritriaconta-17(31),19,21,29-tetraene-5,9,28-triol

HCID 337313
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
12627-35-9
標準SMILES
C=C(C)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O)(CC[C@H]4[C@@H]5OC(C)(C)[C@H]6C[C@@H]7C(=C)Cc8c(Cl)cc9[nH]c(c5c9c8C76O)[C@@]43C)[C@@]23O[C@H]3[C@H]1O
InChIKey
JDUWHZOLEDOQSR-JHMXYHNCSA-N
分子式
C37H44ClNO6
平均分子量
634.2 g/mol
単同位体質量
633.2857158

概要

Penitrem A is a tremorgenic mycotoxin and neurotoxin found on ryegrass. It is produced by certain species of Aspergillus, Claviceps, and Penicillium. Penicillium crustosum in particular is a common foodborne fungus that causes spoilage in a wide variety of foods, including meat, cereals, nuts, cheese, eggs, fruit, and processed and refrigerated foods. Tremorgenic mycotoxins affect central nervous system activity and have been implicated in a number of neurologic diseases of horses and cattle collectively known as "staggers syndromes". (L1959, A2989)

名称と識別子

優先名称
(1S,2R,5S,6R,8S,9S,10R,12S,15R,16S,25R,27S)-21-chloro-15,16,33,33-tetramethyl-24-methylidene-10-prop-1-en-2-yl-7,11,32-trioxa-18-azadecacyclo[25.4.2.02,16.05,15.06,8.06,12.017,31.019,30.022,29.025,28]tritriaconta-17(31),19,21,29-tetraene-5,9,28-triol
IUPAC
(1S,2R,5S,6R,8S,9S,10R,12S,15R,16S,25R,27S)-21-chloro-15,16,33,33-tetramethyl-24-methylidene-10-prop-1-en-2-yl-7,11,32-trioxa-18-azadecacyclo[25.4.2.02,16.05,15.06,8.06,12.017,31.019,30.022,29.025,28]tritriaconta-17(31),19,21,29-tetraene-5,9,28-triol
現地名
ペニトレムA
英語名
PENITREM A
分子式
C37H44ClNO6
分子量
634.2

名称と別名

NSC354845Q7163053ペニトレムAペニトレムA, PENICILLIUM PAXILLI(1S,2R,5S,6S,8R,9S,10R,12S,15R,16S,25R,27S,28R)-21-クロロ-15,16,33,33-テトラメチル-24-メチリデン-10-(プロパ-1-エン-2-イル)-7,11,32-トリオキサ-18-アザデカシクロ[25.4.2.02,16.05,15.06,8.06,12.017,31.019,30.022,29.025,28]トリトリアコンタ-17(31),19,21,29-テトラエン-5,9,28-トリオールPENITREM ATREMORTIN AJDUWHZOLEDOQSR-JKPSMKLGSA-NPenitrem A Nsc354845Penitrem A, blocker of KCa1.1PENITREM A, PENICILLIUM PAXILLIPenitrem A from Penicillium paxilli
名称をさらに表示
penitrem A from penicillium palitans7,8-(Epoxymethano)-2H,6H-cyclobuta[5,6]benz[1,2-e]oxireno[4',4'a]-1-benzopyrano[5',6':6,7]indeno[1,2-b]indole-3,4b,7d(5H,7H)-triol, 12-chloro-3,3a,6a,8,9,9a,10,11,14,14b,14c,15,16,16a-tetradecahydro-14b,14c,17,17-tetramethyl-10-methylene-2-(1-methylethenyl)-, (2R,3S,3aR,4aS,4bS,6aR,7S,7dR,8R,9aR,14b...2R,3S,3aR,4aS,4bS,6aR,7S,7dR,8R,9aR,14bS,14cR,16aS)-12-chloro-3,3a,6a,8,9,9a,10,11,14,14b,14c,15,16,16a-tetradecahydro-14b,14c,17,17-tetramethyl-10-methylene-2-(1-methylethenyl)-7,8-(epoxymethano)-2H,6H-cyclobuta[5,6]benz[1,2-e]oxireno[4',4'a]-1-benzopyrano[5',6':6,7]indeno[1,2-b]indole-3,4b,7d(5H,7H)-triol

物性

構造計算による物性

XLogP
3.8
極性表面積
107 Ų
水素結合供与体数
4
水素結合受容体数
6
回転可能結合数
1
重原子数
45
形式電荷
0
複雑度
1,420

物理化学的性質

融点
238 °C · 238°C
比重(密度)
1.0241 · 1.0241 (rough estimate)
屈折率
1.6 · 1.6000 (estimate)
貯蔵温度
2 · 2-8°C
溶解性
DMSO に可溶 (最大 6 mg/ml)
外見
白い固体。
酸解離定数(Pka)
13.22 · 13.22±0.70(Predicted)
色
非晶質固体
安定性
-20 °C · -20°C の DMSO 溶液で最大 3 か月間保存できます。
InChIKey
JDUWHZOLEDOQSR-JKPSMKLGSA-N

化学的性質

化学的特性Solid

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

To control severe tremors caused by tremorgenic mycotoxins, methocarbamol should be administered. Generalized seizures may be treated with diazepam followed by methocarbamol or a barbiturate such as pentobarbital sodium. Gastric lavage should be performed and activated charcoal administered to limit further absorption of toxins. (A744)

Health EffectsTremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of horses and cattle known as "staggers syndrome". Penitrem A is also genotoxic and causes DNA damage. (A2974, A3026)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 件

Tremorgenic mycotoxins exert their toxic effects by interfering with neurotransmitter release, possibly by causing degeneration of nerve terminals. They are thought to inhibit gamma-aminobutyric acid (GABA) receptors, both pre- and postsynaptic, as well as inhibit transmitter breakdown at the GABA-T receptors. This would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, then lead to decreased levels of neurotransmitter in the synapse. Penitrem A is also know to increase the spontaneous release of the neurotransmitters glutamate and aspartate from cerebrocortical synaptosomes. In addition, it inhibits presynaptic high-conductance Ca+2 activated maxi-K+ channels in the smooth muscle. Penitrem A is also genotoxic and causes DNA damage. (A2976, A2991, A2993, A3026)

Signs and Symptoms · 1 件

Penitrem A causes an tremorgenic syndrom consisting of acute tremor followed by chronic ataxia. Other symptoms include severe muscle fasciculations, vomiting, convulsions, tachycardia, and seizures, possibly leading to massive liver necrosis and death. Tremorgenic mycotoxins cause a neurological disease of cattle known as "staggers syndrome", which is characterized by muscle tremors and hyperexcitability. (A2974, L1959, A2989, A2990)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Penitrem A is extensively metabolized in the liver to at least five metabolites that are less toxic and more hydrophilic than the parent compound. These metabolites are an oxidated metabolite, an oxidated, dehydrated metabolite, a water adduct, a dioxidated metabolite, and a product of water addition and oxidation. (A2992)

用途と製造

Uses · 1 件

Penitrem A (tremortin) is a tremorgenic mycotoxin and neurotoxin found on ryegrass. It is produced by certain species of Aspergillus, Claviceps, and Penicillium. Penicillium crustosum in particular is a common foodborne fungus that causes spoilage in a wide variety of foods, including meat, cereals, nuts, cheese, eggs, fruit, and processed and refrigerated foods. (L1959, A2989)

応用分野

天然物の起源A series of closely related metabolites of Penicillium crustosum has recently been isolated and the components separated chromatographically. Penitrem A forms colourless crystals from EtOH.

使用Penitrem A is a tremorgenic mycotoxin isolated from Penicillium species. Penitrem A is a selective blocker of high-conductance Ca2+-activated potassium channels.

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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

データベース識別子

CAS
12627-35-9
PubChem CID
337313
Toxicity DataLD50: 10 mg/kg (Oral, Mouse) (A2992) LD50: 1.1 mg/kg (Intraperitoneal, Mouse) (A2992)

安全データ

wgk
3
rtecs
RY7535000
ridadr
UN 2811 6.1/PG 2
毒性
LD50 orl-mus: 10 mg/kg 41KEAL -,108,78
hs_code
29349990
risk_code
26/27/28
hazard_code
T+,T
safety_code
36/37/39-45
hazard_class
6.1(a)
packing_group
II
Hazard Classifications
Acute Tox. 2 Oral
ストレージクラス
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
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