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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:04:14 UTC
Update Date2019-07-23 06:15:37 UTC
HMDB IDHMDB0034266
Secondary Accession Numbers
  • HMDB34266
Metabolite Identification
Common NameL-Coprine
DescriptionL-Coprine 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. This causes the build of of acetaldehyde in the body. 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. L-Coprine is a very strong basic compound (based on its pKa). Outside of the human body, L-Coprine has been detected, but not quantified in, mushrooms. This could make L-coprine a potential biomarker for the consumption of these foods. L-Coprine is a potentially toxic compound. Coprine may cause symptoms such as flushing, headache, nausea, palpitations, dyspnea, dizziness. Coprine interferes with the bodys ability to metabolize alcohol.
Structure
Data?1563862537
Synonyms
ValueSource
CoprineHMDB
N(5)-(1-Hydroxycyclopropyl)-L-glutamineHMDB
N-(1-Hydroxycyclopropyl)-L-glutamineHMDB
2-Amino-4-[(1-hydroxycyclopropyl)-C-hydroxycarbonimidoyl]butanoateGenerator
Chemical FormulaC8H14N2O4
Average Molecular Weight202.2078
Monoisotopic Molecular Weight202.095356946
IUPAC Name2-amino-4-[(1-hydroxycyclopropyl)-C-hydroxycarbonimidoyl]butanoic acid
Traditional Name2-amino-4-[(1-hydroxycyclopropyl)-C-hydroxycarbonimidoyl]butanoic acid
CAS Registry Number58919-61-2
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 KeyOEEZRBUCLFMTLD-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamine 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 FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point197 - 199 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility76.1 g/LALOGPS
logP-3ALOGPS
logP-3.2ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.03ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.14 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity47.43 m³·mol⁻¹ChemAxon
Polarizability20.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9200000000-a122f01177e5d201af45Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-4329000000-a7dd2788543a604a7778Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pi9-6930000000-743d2bc0563132ebf3efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-9500000000-f297023fb8752cf328e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-d6652b0b83bf59e5acffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-2890000000-a0b201fc51831a763e83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9720000000-829295167ea340401a84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-56182246e2fa0629258eSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012597
KNApSAcK IDC00001349
Chemspider ID3677218
KEGG Compound IDC08271
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCoprine
METLIN IDNot Available
PubChem Compound4479242
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (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.. .