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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:04:14 UTC
Update Date2021-09-14 15:20:35 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. L-Coprine has been detected, but not quantified in, a few different foods, such as common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make L-coprine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on L-Coprine.
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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point197 - 199 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility76.1 g/LALOGPS
logP10(-3) g/LALOGPS
logP10(-3.2) g/LChemAxon
logS10(-1.5) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.6631661259
DarkChem[M-H]-141.40931661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-Coprine,1TMS,#1C[Si](C)(C)OC(CCC(N)C(=O)O)=NC1(O)CC11876.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,1TMS,#2C[Si](C)(C)OC1(N=C(O)CCC(N)C(=O)O)CC11927.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,1TMS,#3C[Si](C)(C)OC(=O)C(N)CCC(O)=NC1(O)CC11877.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,1TMS,#4C[Si](C)(C)NC(CCC(O)=NC1(O)CC1)C(=O)O1965.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,2TMS,#1C[Si](C)(C)OC(=O)C(N)CCC(=NC1(O)CC1)O[Si](C)(C)C1871.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,2TMS,#2C[Si](C)(C)OC(CCC(N)C(=O)O)=NC1(O[Si](C)(C)C)CC11895.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,2TMS,#3C[Si](C)(C)NC(CCC(=NC1(O)CC1)O[Si](C)(C)C)C(=O)O1926.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,2TMS,#4C[Si](C)(C)OC(=O)C(N)CCC(O)=NC1(O[Si](C)(C)C)CC11895.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,2TMS,#5C[Si](C)(C)NC(CCC(O)=NC1(O[Si](C)(C)C)CC1)C(=O)O1999.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,2TMS,#6C[Si](C)(C)NC(CCC(O)=NC1(O)CC1)C(=O)O[Si](C)(C)C1925.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,2TMS,#7C[Si](C)(C)N(C(CCC(O)=NC1(O)CC1)C(=O)O)[Si](C)(C)C2122.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,3TMS,#1C[Si](C)(C)OC(=O)C(N)CCC(=NC1(O[Si](C)(C)C)CC1)O[Si](C)(C)C1895.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,3TMS,#2C[Si](C)(C)NC(CCC(=NC1(O)CC1)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1903.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,3TMS,#3C[Si](C)(C)NC(CCC(=NC1(O[Si](C)(C)C)CC1)O[Si](C)(C)C)C(=O)O1974.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,3TMS,#4C[Si](C)(C)OC(CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=NC1(O)CC12104.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,3TMS,#5C[Si](C)(C)NC(CCC(O)=NC1(O[Si](C)(C)C)CC1)C(=O)O[Si](C)(C)C1963.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,3TMS,#6C[Si](C)(C)OC1(N=C(O)CCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)CC12158.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,3TMS,#7C[Si](C)(C)OC(=O)C(CCC(O)=NC1(O)CC1)N([Si](C)(C)C)[Si](C)(C)C2077.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,1TBDMS,#1CC(C)(C)[Si](C)(C)OC(CCC(N)C(=O)O)=NC1(O)CC12085.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,1TBDMS,#2CC(C)(C)[Si](C)(C)OC1(N=C(O)CCC(N)C(=O)O)CC12151.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,1TBDMS,#3CC(C)(C)[Si](C)(C)OC(=O)C(N)CCC(O)=NC1(O)CC12094.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,1TBDMS,#4CC(C)(C)[Si](C)(C)NC(CCC(O)=NC1(O)CC1)C(=O)O2178.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,2TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)C(N)CCC(=NC1(O)CC1)O[Si](C)(C)C(C)(C)C2295.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,2TBDMS,#2CC(C)(C)[Si](C)(C)OC(CCC(N)C(=O)O)=NC1(O[Si](C)(C)C(C)(C)C)CC12337.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,2TBDMS,#3CC(C)(C)[Si](C)(C)NC(CCC(=NC1(O)CC1)O[Si](C)(C)C(C)(C)C)C(=O)O2389.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,2TBDMS,#4CC(C)(C)[Si](C)(C)OC(=O)C(N)CCC(O)=NC1(O[Si](C)(C)C(C)(C)C)CC12341.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,2TBDMS,#5CC(C)(C)[Si](C)(C)NC(CCC(O)=NC1(O[Si](C)(C)C(C)(C)C)CC1)C(=O)O2451.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,2TBDMS,#6CC(C)(C)[Si](C)(C)NC(CCC(O)=NC1(O)CC1)C(=O)O[Si](C)(C)C(C)(C)C2381.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,2TBDMS,#7CC(C)(C)[Si](C)(C)N(C(CCC(O)=NC1(O)CC1)C(=O)O)[Si](C)(C)C(C)(C)C2501.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,3TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)C(N)CCC(=NC1(O[Si](C)(C)C(C)(C)C)CC1)O[Si](C)(C)C(C)(C)C2535.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,3TBDMS,#2CC(C)(C)[Si](C)(C)NC(CCC(=NC1(O)CC1)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2549.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,3TBDMS,#3CC(C)(C)[Si](C)(C)NC(CCC(=NC1(O[Si](C)(C)C(C)(C)C)CC1)O[Si](C)(C)C(C)(C)C)C(=O)O2612.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,3TBDMS,#4CC(C)(C)[Si](C)(C)OC(CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1(O)CC12732.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,3TBDMS,#5CC(C)(C)[Si](C)(C)NC(CCC(O)=NC1(O[Si](C)(C)C(C)(C)C)CC1)C(=O)O[Si](C)(C)C(C)(C)C2590.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,3TBDMS,#6CC(C)(C)[Si](C)(C)OC1(N=C(O)CCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CC12777.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
L-Coprine,3TBDMS,#7CC(C)(C)[Si](C)(C)OC(=O)C(CCC(O)=NC1(O)CC1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2707.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - L-Coprine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9200000000-a122f01177e5d201af452017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Coprine GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-4329000000-a7dd2788543a604a77782017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Coprine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Coprine 10V, Positive-QTOFsplash10-0pi9-6930000000-743d2bc0563132ebf3ef2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Coprine 20V, Positive-QTOFsplash10-05fr-9500000000-f297023fb8752cf328e92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Coprine 40V, Positive-QTOFsplash10-0a4i-9000000000-d6652b0b83bf59e5acff2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Coprine 10V, Negative-QTOFsplash10-0ue9-2890000000-a0b201fc51831a763e832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Coprine 20V, Negative-QTOFsplash10-00di-9720000000-829295167ea340401a842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Coprine 40V, Negative-QTOFsplash10-00di-9000000000-56182246e2fa0629258e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Coprine 10V, Positive-QTOFsplash10-0zmi-9030000000-70eee36f93c8937a71182021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Coprine 20V, Positive-QTOFsplash10-000i-9000000000-f75ff566022137a86f842021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Coprine 40V, Positive-QTOFsplash10-052r-9000000000-a5328f3ba6c2d13c79bd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Coprine 10V, Negative-QTOFsplash10-0059-0910000000-b2a6bb3ff18352f8ed6b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Coprine 20V, Negative-QTOFsplash10-03di-2910000000-13c8f2b44f5609ea9be52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Coprine 40V, Negative-QTOFsplash10-0006-9100000000-7355fad45f5d3edf7cb52021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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
FooDB 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
MarkerDB IDNot Available
Good Scents 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.. .