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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:49:21 UTC
Update Date2023-02-21 17:29:04 UTC
HMDB IDHMDB0041946
Secondary Accession Numbers
  • HMDB41946
Metabolite Identification
Common NameN-Nitrosoproline
DescriptionN-Nitrosoproline, also known as NO-pro, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Nitrosoproline has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make N-nitrosoproline a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N-Nitrosoproline.
Structure
Data?1677000544
Synonyms
ValueSource
1-Nitroso-L-prolineHMDB
1-Nitrosoproline (acd/name 4.0)HMDB
N-Nitroso-L-prolineHMDB
Nitroso-L-prolineHMDB
NitrosoprolineHMDB
NO-ProHMDB
NPROHMDB
Nitrosoproline, (cis)-isomerHMDB
Nitrosoproline, (trans)-isomerHMDB
Nitrosoproline, 14C-labeled CPDHMDB
Nitrosoproline, (D,L)-isomerHMDB
Nitrosoproline, (D)-isomerHMDB
1-Nitrosopyrrolidine-2-carboxylateHMDB
N-NitrosoprolineMeSH
Chemical FormulaC5H8N2O3
Average Molecular Weight144.1286
Monoisotopic Molecular Weight144.053492132
IUPAC Name1-nitrosopyrrolidine-2-carboxylic acid
Traditional Namenitrosoproline
CAS Registry Number7519-36-0
SMILES
OC(=O)C1CCCN1N=O
InChI Identifier
InChI=1S/C5H8N2O3/c8-5(9)4-2-1-3-7(4)6-10/h4H,1-3H2,(H,8,9)
InChI KeyWLKPHJWEIIAIFW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline 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 ParentProline and derivatives
Alternative Parents
Substituents
  • Proline or derivatives
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine
  • Organic n-nitroso compound
  • Organic nitroso compound
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility43.1 g/LALOGPS
logP-0.19ALOGPS
logP0.013ChemAxon
logS-0.52ALOGPS
pKa (Strongest Acidic)3.73ChemAxon
pKa (Strongest Basic)2.78ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.97 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity33.42 m³·mol⁻¹ChemAxon
Polarizability12.92 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+130.27131661259
DarkChem[M-H]-125.52131661259
DeepCCS[M+H]+125.64630932474
DeepCCS[M-H]-123.40730932474
DeepCCS[M-2H]-159.64730932474
DeepCCS[M+Na]+134.4330932474
AllCCS[M+H]+131.132859911
AllCCS[M+H-H2O]+126.632859911
AllCCS[M+NH4]+135.332859911
AllCCS[M+Na]+136.532859911
AllCCS[M-H]-125.832859911
AllCCS[M+Na-2H]-127.532859911
AllCCS[M+HCOO]-129.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-NitrosoprolineOC(=O)C1CCCN1N=O2101.5Standard polar33892256
N-NitrosoprolineOC(=O)C1CCCN1N=O1401.5Standard non polar33892256
N-NitrosoprolineOC(=O)C1CCCN1N=O1544.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Nitrosoproline,1TMS,isomer #1C[Si](C)(C)OC(=O)C1CCCN1N=O1502.5Semi standard non polar33892256
N-Nitrosoproline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1CCCN1N=O1758.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Nitrosoproline GC-MS (Non-derivatized) - 70eV, Positivesplash10-002g-9100000000-4c76df1934b69fd8cee42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Nitrosoproline GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9200000000-8d02dc80048c159067cf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Nitrosoproline 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 - N-Nitrosoproline 10V, Positive-QTOFsplash10-0002-1900000000-88da6af2dfad7ef72d202016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosoproline 20V, Positive-QTOFsplash10-0002-5900000000-e3af96f067eaf91cdba92016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosoproline 40V, Positive-QTOFsplash10-0006-9000000000-5783b4e9c7f80712ef652016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosoproline 10V, Negative-QTOFsplash10-0007-5900000000-cd35a3d360022913a5612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosoproline 20V, Negative-QTOFsplash10-002b-9400000000-19d3f92911b61a6615052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosoproline 40V, Negative-QTOFsplash10-0aor-9100000000-ff5802d4b6e78532625b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosoproline 10V, Negative-QTOFsplash10-0006-2900000000-5af2e2f6d4ae9ed5123b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosoproline 20V, Negative-QTOFsplash10-014j-9100000000-aa63d528a3a61240fea92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosoproline 40V, Negative-QTOFsplash10-0002-9000000000-0a69d5519333a983f48d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosoproline 10V, Positive-QTOFsplash10-002b-8900000000-d143893f34ed790c2c2f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosoproline 20V, Positive-QTOFsplash10-0002-9300000000-d7a035b4e5efd70d97b32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Nitrosoproline 40V, Positive-QTOFsplash10-0a4i-9000000000-4b5ecbdedb2bdc511c552021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB111682
KNApSAcK IDNot Available
Chemspider ID22565
KEGG Compound IDC19485
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNitrosoproline
METLIN IDNot Available
PubChem Compound24141
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 ReferencesNot Available