L-Coprine (T3D2454)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (8)XML
Targets (8)
Record Information
Version2.0
Creation Date2009-07-03 20:58:42 UTC
Update Date2014-12-24 20:25:31 UTC
Accession NumberT3D2454
Identification
Common NameL-Coprine
ClassSmall Molecule
DescriptionL-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).
Compound Type
  • Amide
  • Amine
  • Food Toxin
  • Fungal Toxin
  • Metabolite
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Coprine
N(5)-(1-Hydroxycyclopropyl)-L-glutamine
N-(1-Hydroxycyclopropyl)-L-Glutamine
Chemical FormulaC8H14N2O4
Average Molecular Mass202.208 g/mol
Monoisotopic Mass202.095 g/mol
CAS Registry Number58919-61-2
IUPAC Name2-amino-4-[(1-hydroxycyclopropyl)-C-hydroxycarbonimidoyl]butanoic acid
Traditional Name2-amino-4-[(1-hydroxycyclopropyl)-C-hydroxycarbonimidoyl]butanoic acid
SMILESNC(CCC(O)=NC1(O)CC1)C(O)=O
InChI IdentifierInChI=1/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 KeyInChIKey=OEEZRBUCLFMTLD-UHFFFAOYNA-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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point197 - 199°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.96 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9200000000-a122f01177e5d201af452017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-4329000000-a7dd2788543a604a77782017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pi9-6930000000-743d2bc0563132ebf3ef2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-9500000000-f297023fb8752cf328e92016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-d6652b0b83bf59e5acff2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-2890000000-a0b201fc51831a763e832016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9720000000-829295167ea340401a842016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-56182246e2fa0629258e2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zmi-9030000000-70eee36f93c8937a71182021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-f75ff566022137a86f842021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-9000000000-a5328f3ba6c2d13c79bd2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0910000000-b2a6bb3ff18352f8ed6b2021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2910000000-13c8f2b44f5609ea9be52021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-7355fad45f5d3edf7cb52021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (1)
Mechanism of ToxicityIt 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. (3)
MetabolismMetabolises to 1-aminocyclopropanol. (3)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesCoprine occurs naturally in the otherwise edible mushroom, the common ink cap (Coprinopsis atramentaria). (3)
Minimum Risk LevelNot Available
Health EffectsCoprine interferes with the bodys ability to metabolize alcohol. This causes the build of of acetaldehyde in the body. (4)
SymptomsCoprine may cause symptoms such as flushing, headache, nausea, palpitations, dyspnea, dizziness. (4)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB34266
PubChem Compound ID4479242
ChEMBL IDNot Available
ChemSpider ID3677218
KEGG IDC08271
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDCoprine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkCoprine#Similarly_acting_substances
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  3. Wikipedia. Disulfiram. Last Updated 14 June 2009. [Link]
  4. eMedicine (2009). Toxicity, Mushroom - Disulfiramlike Toxins. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Aldehyde dehydrogenase X, mitochondrial
General Function:
Aldehyde dehydrogenase (nad) activity
Specific Function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular Weight:
57205.93 Da
References
  1. Wikipedia. Disulfiram. Last Updated 14 June 2009. [Link]
Target Details
2. Aldehyde dehydrogenase family 1 member A3
General Function:
Thyroid hormone binding
Specific Function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular Weight:
56107.995 Da
References
  1. Wikipedia. Disulfiram. Last Updated 14 June 2009. [Link]
Target Details
3. Aldehyde dehydrogenase family 16 member A1
General Function:
Aldehyde dehydrogenase (nad) activity
Specific Function:
Not Available
Gene Name:
ALDH16A1
Uniprot ID:
Q8IZ83
Molecular Weight:
85126.605 Da
References
  1. Wikipedia. Disulfiram. Last Updated 14 June 2009. [Link]
Target Details
4. Aldehyde dehydrogenase family 3 member B1
General Function:
Aldehyde dehydrogenase [nad(p)+] activity
Specific Function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular Weight:
51839.245 Da
References
  1. Wikipedia. Disulfiram. Last Updated 14 June 2009. [Link]
Target Details
5. Aldehyde dehydrogenase family 3 member B2
General Function:
Aldehyde dehydrogenase [nad(p)+] activity
Specific Function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular Weight:
42634.6 Da
References
  1. Wikipedia. Disulfiram. Last Updated 14 June 2009. [Link]
Target Details
6. Aldehyde dehydrogenase family 8 member A1
General Function:
Retinal dehydrogenase activity
Specific Function:
Converts 9-cis-retinal to 9-cis-retinoic acid. Has lower activity towards 13-cis-retinal. Has much lower activity towards all-trans-retinal. Has highest activity with benzaldehyde and decanal (in vitro). Has a preference for NAD, but shows considerable activity with NADP (in vitro).
Gene Name:
ALDH8A1
Uniprot ID:
Q9H2A2
Molecular Weight:
53400.88 Da
References
  1. Wikipedia. Disulfiram. Last Updated 14 June 2009. [Link]
Target Details
7. Aldehyde dehydrogenase, dimeric NADP-preferring
General Function:
Benzaldehyde dehydrogenase (nad+) activity
Specific Function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular Weight:
50394.57 Da
References
  1. Wikipedia. Disulfiram. Last Updated 14 June 2009. [Link]
Target Details
8. Aldehyde dehydrogenase, mitochondrial
General Function:
Electron carrier activity
Specific Function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular Weight:
56380.93 Da
References
  1. Wikipedia. Disulfiram. Last Updated 14 June 2009. [Link]