ContaminantDB: L-Coprine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (8)XML

Record Information

Version

1.0

Creation Date

2009-07-03 20:58:42 UTC

Update Date

2026-04-06 12:32:55 UTC

Accession Number

CHEM002043

Identification

Common Name

L-Coprine

Class

Small Molecule

Description

L-Coprine is found in mushrooms. L-Coprine is present in the moderately toxic ink cap mushroom Coprinus atramentarius (common ink cap). Produces an oversensitivity to ethanol in some people. L-Coprine belongs to the family of Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon)[1]. (Reference: [1] Amino Acid: http://en.wikipedia.org/wiki/Amino_acid).

Contaminant Sources

FooDB Chemicals
T3DB toxins

Contaminant Type

Amide
Amine
Food Toxin
Fungal Toxin
Metabolite
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Coprine	HMDB
N(5)-(1-Hydroxycyclopropyl)-L-glutamine	HMDB
N-(1-Hydroxycyclopropyl)-L-glutamine	HMDB
2-Amino-4-[(1-hydroxycyclopropyl)-C-hydroxycarbonimidoyl]butanoate	Generator

Chemical Formula

C₈H₁₄N₂O₄

Average Molecular Mass

202.208 g/mol

Monoisotopic Mass

202.095 g/mol

CAS Registry Number

58919-61-2

IUPAC Name

2-amino-4-[(1-hydroxycyclopropyl)-C-hydroxycarbonimidoyl]butanoic acid

Traditional Name

2-amino-4-[(1-hydroxycyclopropyl)-C-hydroxycarbonimidoyl]butanoic acid

SMILES

NC(CCC(O)=NC1(O)CC1)C(O)=O

InChI Identifier

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)

InChI Key

OEEZRBUCLFMTLD-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamine and derivatives

Alternative Parents

Substituents

Glutamine or derivatives
Alpha-amino acid
Fatty acyl
Fatty acid
Fatty amide
N-acyl-amine
Carboxamide group
Amino acid
Cyclopropanol
Secondary carboxylic acid amide
Alkanolamine
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary aliphatic amine
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Amine
Organic oxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Chemical Roles

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

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	197 - 199°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.96 g/L	ALOGPS
logP	-3	ALOGPS
logP	-3.2	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	2.03	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	47.43 m³·mol⁻¹	ChemAxon
Polarizability	20.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9200000000-a122f01177e5d201af45	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0udi-4329000000-a7dd2788543a604a7778	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0pi9-6930000000-743d2bc0563132ebf3ef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-9500000000-f297023fb8752cf328e9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-d6652b0b83bf59e5acff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ue9-2890000000-a0b201fc51831a763e83	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9720000000-829295167ea340401a84	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-56182246e2fa0629258e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zmi-9030000000-70eee36f93c8937a7118	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9000000000-f75ff566022137a86f84	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052r-9000000000-a5328f3ba6c2d13c79bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0059-0910000000-b2a6bb3ff18352f8ed6b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-2910000000-13c8f2b44f5609ea9be5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-7355fad45f5d3edf7cb5	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (1)

Mechanism of Toxicity

It 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. (2)

Metabolism

Metabolises to 1-aminocyclopropanol. (2)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Coprine occurs naturally in the otherwise edible mushroom, the common ink cap (Coprinopsis atramentaria). (2)

Minimum Risk Level

Not Available

Health Effects

Coprine interferes with the bodys ability to metabolize alcohol. This causes the build of of acetaldehyde in the body. (3)

Symptoms

Coprine may cause symptoms such as flushing, headache, nausea, palpitations, dyspnea, dizziness. (3)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0034266

FooDB ID

FDB012597

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001349

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Coprine

Chemspider ID

3677218

ChEBI ID

Not Available

PubChem Compound ID

4479242

Kegg Compound ID

C08271

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

L-Coprine (CHEM002043)

Structure for CHEM002043: L-Coprine