N5-(1-ヒドロキシシクロプロピル)-L-グルタミン
Coprine
基本情報
- CAS
58919-61-2- 標準SMILES
N[C@@H](CCC(=O)NC1(O)CC1)C(=O)O- InChIKey
OEEZRBUCLFMTLD-YFKPBYRVSA-N- 分子式
- C8H14N2O4
- 平均分子量
- 202.21 g/mol
- 単同位体質量
- 202.09535693
概要
Coprine is a non-proteinogenic L-alpha-amino acid that is L-glutamine in which one of the hydrogens attached to the amide nitrogen is replaced by a 1-hydroxycyclopropyl group. Found in the ink-cap mushroom, Coprinus atramentarius, it causes an unpleasant hypersensitivity to alcohol (the 'disulfiram effect'). It has a role as a metabolite, a mycotoxin and an EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor. It is a L-glutamine derivative, a dicarboxylic acid monoamide, a member of cyclopropanes and a non-proteinogenic L-alpha-amino acid.
名称と識別子
- 優先名称
- Coprine
- IUPAC
- (2S)-2-amino-5-[(1-hydroxycyclopropyl)amino]-5-oxopentanoic acid
- 現地名
- N5-(1-ヒドロキシシクロプロピル)-L-グルタミン
- 英語名
- coprine
- 分子式
- C8H14N2O4
- 分子量
- 202.21
名称と別名
Coprine58919-61-2n-(1-hydroxycyclopropyl)-l-glutamineN(5)-(1-Hydroxycyclopropyl)-L-glutamine(2S)-2-amino-5-[(1-hydroxycyclopropyl)amino]-5-oxopentanoic acid28L2R8DM94L-Glutamine, N-(1-hydroxycyclopropyl)-CHEBI:3875DTXSID00974419(2S)-2-amino-5-((1-hydroxycyclopropyl)amino)-5-oxopentanoic acidRefChem:919030DTXCID601401847
名称をさらに表示
コプリンN5-(1-ヒドロキシシクロプロピル)-L-グルタミン(2S)-2-アミノ-4-[(1-ヒドロキシシクロプロピル)カルバモイル]ブタン酸N5-(1-Hydroxycyclopropyl)-L-glutamine
L-coprineSCHEMBL320268UNII-28L2R8DM94orb1697735n5-(1-hydroxycyclopropyl)glutamine(2S)-5-amino-2-[(1-hydroxycyclopropyl)amino]-5-oxopentanoic acidAKOS040751246DA-52051
データベース識別子
- CAS
58919-61-2- PubChem CID
- 108079
- DTXSID
物性
構造計算による物性
- XLogP
- -3.4
- 極性表面積
- 113 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 5
- 回転可能結合数
- 5
- 重原子数
- 14
- 形式電荷
- 0
- 複雑度
- 250
物理化学的性質
- 沸点
- 533.4 · 533.4±50.0 °C(Predicted)
- 比重(密度)
- 1.4 · 1.40±0.1 g/cm3(Predicted)
- 酸解離定数(Pka)
- 2.22 · 2.22±0.10(Predicted)
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
Health EffectsCoprine interferes with the bodys ability to metabolize alcohol. This causes the build of of acetaldehyde in the body. (L1671)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity SummaryIt metabolises to 1-aminocyclopropanol, a closely-related chemical to Disulfiram and exhibits the same mechanism of action: inhibition of the enzyme acetaldehyde dehydrogenase, which is required for alchohol metabolism. (L1015)
Signs and SymptomsCoprine may cause symptoms such as flushing, headache, nausea, palpitations, dyspnea, dizziness. (L1671)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
安全データ
- ridadr
- 1544
- 毒性
- A compound produced by edible mushrooms of the genus Coprinus that on ingestion causes a marked ethanol sensitivity. The mechanism appears to be inhibition of the low Km form of liver acetaldehyde dehydrogenase by the active metabolite cyclopropanone hydrate. Although the overall effect resembles that of disulfiram, coprine does not affect dopamine-β-decarboxylase and is a more potent ethanol sensitizing agent.
- hazard_class
- 6.1(b)
- packing_group
- III
化学と産業
薬理情報
Metabolism/MetabolitesMetabolises to 1-aminocyclopropanol. (L1015)
用途と製造
UsesCoprine occurs naturally in the otherwise edible mushroom, the common ink cap (Coprinopsis atramentaria). (L1015)
応用分野
使用Coprine is a poisonous toxin that is found in mushrooms resulting in coprinus syndrome.
補足説明
定義ChEBI: A non-proteinogenic L-alpha-amino acid that is L-glutamine in which one of the hydrogens attached to the amide nitrogen is replaced by a 1-hydroxycyclopropyl group. Found in the ink-cap mushroom, Cop inus atramentarius, it causes an unpleasant hypersensitivity to alcohol (the 'disulfiram effect').
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