Record Information
Version1.0
Creation date2010-04-08 22:10:15 UTC
Update date2019-11-26 03:07:10 UTC
Primary IDFDB012597
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. L-Coprine is a very strong basic compound (based on its pKa). 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.
CAS Number58919-61-2
Structure
Thumb
Synonyms
SynonymSource
CoprineHMDB
N(5)-(1-Hydroxycyclopropyl)-L-glutamineHMDB
N-(1-Hydroxycyclopropyl)-L-glutamineHMDB
2-Amino-4-[(1-hydroxycyclopropyl)-C-hydroxycarbonimidoyl]butanoateGenerator
Coprine; L-formdb_source
L-Glutamine, N-(1-hydroxycyclopropyl)-biospider
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC8H14N2O4
IUPAC name2-amino-4-[(1-hydroxycyclopropyl)-C-hydroxycarbonimidoyl]butanoic acid
InChI IdentifierInChI=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
Isomeric SMILESNC(CCC(O)=NC1(O)CC1)C(O)=O
Average Molecular Weight202.2078
Monoisotopic Molecular Weight202.095356946
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 47.52%; H 6.98%; N 13.85%; O 31.65%DFC
Melting PointMp 197-199°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +7.6 (c, 4.1 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9200000000-a122f01177e5d201af45JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-4329000000-a7dd2788543a604a7778JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pi9-6930000000-743d2bc0563132ebf3efJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-9500000000-f297023fb8752cf328e9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-d6652b0b83bf59e5acffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-2890000000-a0b201fc51831a763e83JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9720000000-829295167ea340401a84JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-56182246e2fa0629258eJSpectraViewer
ChemSpider ID3677218
ChEMBL IDNot Available
KEGG Compound IDC08271
Pubchem Compound ID4479242
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34266
CRC / DFC (Dictionary of Food Compounds) IDBCZ97-Z:HJF56-B
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00001349
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference