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Chemical substance record

Coprine

58919-61-2C8H14N2O4202.21 g/mol
Organic/Inorganic Small MoleculeChEBI source record

A non-proteinogenic L-α-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'). — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values
CAS number58919-61-2ChEBI ↗
Molecular formulaC8H14N2O4ChEBI ↗
Molar mass202.21 g/molChEBI ↗
Monoisotopic mass202.09536 DaChEBI ↗
Formal charge0ChEBI ↗
ChEBI identifierCHEBI:3875ChEBI ↗

Cross-source molecular data

PubChem
Molar mass202.21 g/molPubChem ↗
Exact mass202.09535693 DaPubChem ↗
Computed XLogP-3.4PubChem ↗
Topological polar surface area (Ų)113PubChem ↗
H-bond donors4PubChem ↗
H-bond acceptors5PubChem ↗
Rotatable bonds5PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

Copy any identifier
coprine
N-(1-hydroxycyclopropyl)-L-glutamine
OEEZRBUCLFMTLD-YFKPBYRVSA-N
N[C@@H](CCC(=O)NC1(O)CC1)C(=O)O
InChI=1S/C8H14N2O4/c9-5(7(12)13)1-2-6(11)10-8(14)3-4-8/h5,14H,1-4,9H2,(H,10,11)(H,12,13)/t5-/m0/s1

Names & synonyms

N-(1-hydroxycyclopropyl)-L-glutamine

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology
L-glutamine derivativeChEBI parent class · 24317 ↗dicarboxylic acid monoamideChEBI parent class · 35735 ↗cyclopropanesChEBI parent class · 51454 ↗non-proteinogenic L-alpha-amino acidChEBI parent class · 83822 ↗
carboxylic acidamino acidorganic molecular entity

Roles recorded in ChEBI

metabolitemycotoxinEC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass
Equivalent amount
0.00494535 mol

Uses 202.21 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions
C
Carbon · 8 atoms
47.52%
O
Oxygen · 4 atoms
31.65%
N
Nitrogen · 2 atoms
13.85%
H
Hydrogen · 14 atoms
6.98%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations
Isolation and structural studies of coprine, the disulfiram-like constituent of Coprinus atramentarius. ↗Lloydia · 1975 Nov-Dec · PMID 1241098
[An unusual mushroom mycotoxin: coprine, a deterrent to alcohol abuse]. ↗Pharmazie in unserer Zeit · 1992 Jan · PMID 1553385
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Sources & record history

Checked 27 Sep 2026
EMBL-EBI ChEBI · CHEBI:3875

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

NCBI PubChem · CID 108079 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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