Coprine
Grundinformationen
- CAS
58919-61-2- Standard-SMILES
N[C@@H](CCC(=O)NC1(O)CC1)C(=O)O- InChIKey
OEEZRBUCLFMTLD-YFKPBYRVSA-N- Summenformel
- C8H14N2O4
- Durchschnittliche Molmasse
- 202,21 g/mol
- Monoisotopische Masse
- 202,09535693
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Coprine
- IUPAC
- (2S)-2-amino-5-[(1-hydroxycyclopropyl)amino]-5-oxopentanoic acid
- Englischer Name
- coprine
- Summenformel
- C8H14N2O4
- Molmasse
- 202.21
Namen und Synonyme
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
Weitere Namen anzeigen
N5-(1-Hydroxycyclopropyl)-L-glutamine
L-coprineSCHEMBL320268UNII-28L2R8DM94orb1697735n5-(1-hydroxycyclopropyl)glutamine(2S)-5-amino-2-[(1-hydroxycyclopropyl)amino]-5-oxopentanoic acidAKOS040751246DA-52051
Datenbank-Bezeichner
- CAS
58919-61-2- PubChem CID
- 108079
- DTXSID
DTXSID00974419- ChEBI
CHEBI:3875- UNII
- 28L2R8DM94
- Nikkaji
- J14.665J
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -3,4
- Polarare Oberfläche (TPSA)
- 113 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 14
- Formalladung
- 0
- Komplexität
- 250
Physikochemische Eigenschaften
- Siedepunkt
- 533.4 · 533.4±50.0 °C(Predicted)
- Dichte
- 1.4 · 1.40±0.1 g/cm3(Predicted)
- pka
- 2.22 · 2.22±0.10(Predicted)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Toxikologische Informationen
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).
Sicherheitsdaten
- ridadr
- 1544
- Toxizität
- 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
Chemie und Industrie
Pharmakologische Informationen
Metabolism/MetabolitesMetabolises to 1-aminocyclopropanol. (L1015)
Verwendung und Herstellung
UsesCoprine occurs naturally in the otherwise edible mushroom, the common ink cap (Coprinopsis atramentaria). (L1015)
Anwendungen
VerwendenCoprine is a poisonous toxin that is found in mushrooms resulting in coprinus syndrome.
Anbieter4 Anbieter
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
TargetMol中国（陶术生物）15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354 · [email protected]
Ergänzende Hinweise
DefinitionChEBI: 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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