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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:35 UTC
Update Date2019-07-23 06:09:11 UTC
HMDB IDHMDB0031642
Secondary Accession Numbers
  • HMDB31642
Metabolite Identification
Common NameN-Nitroso-pyrrolidine
DescriptionN-Nitroso-pyrrolidine belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. N-Nitroso-pyrrolidine is a strong basic compound (based on its pKa). Outside of the human body, N-Nitroso-pyrrolidine has been detected, but not quantified in, several different foods, such as green bell peppers, orange bell peppers, pepper (c. annuum), red bell peppers, and yellow bell peppers. This could make N-nitroso-pyrrolidine a potential biomarker for the consumption of these foods. N-Nitroso-pyrrolidine is a potentially toxic compound.
Structure
Data?1563862151
Synonyms
ValueSource
1-NitrosopyrrolidineHMDB
1-Nitroso-pyrrolidineHMDB
N-Nitroso-1-pyrrolidinamineHMDB
Nitroso-pyrrolidineHMDB
NitrosopyrrolidineHMDB
Tetrahydro-N-nitroso-pyrroleHMDB
N-NitrosopyrrolidineHMDB
N NitrosopyrrolidineHMDB
Chemical FormulaC4H8N2O
Average Molecular Weight100.1191
Monoisotopic Molecular Weight100.063662888
IUPAC Name1-nitrosopyrrolidine
Traditional NameN-nitrosopyrrolidine
CAS Registry Number930-55-2
SMILES
O=NN1CCCC1
InChI Identifier
InChI=1S/C4H8N2O/c7-5-6-3-1-2-4-6/h1-4H2
InChI KeyWNYADZVDBIBLJJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrrolidines. Pyrrolidines are compounds containing a pyrrolidine ring, which is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassNot Available
Direct ParentPyrrolidines
Alternative Parents
Substituents
  • Pyrrolidine
  • Organic n-nitroso compound
  • Organic nitroso compound
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Industrial process:

Role

Environmental role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility52.9 g/LALOGPS
logP-0.07ALOGPS
logP0.44ChemAxon
logS-0.28ALOGPS
pKa (Strongest Basic)3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.67 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.59 m³·mol⁻¹ChemAxon
Polarizability10.02 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0g2c-9000000000-25d8797fa4ff751a2d70Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-1900000000-85f43e28b348aeb93404Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-1900000000-85f43e28b348aeb93404Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-1900000000-85f43e28b348aeb93404Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-3900000000-79fa9d8de9566bec999eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0zfr-7900000000-0a674ea8d4b2d3f65b02Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0pb9-9500000000-98bb6cb1fe4c3f9a5bc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-954c68340e2ec5c96773Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-9400000000-b485c8519f27b43bd31eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-c7530b5d976c4a448753Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-4f72e350127fc271c203Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-9000000000-370f605a1fa54cb29bffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9000000000-e5d77a59e81129df0a5cSpectrum
MSMass Spectrum (Electron Ionization)splash10-0f6x-9300000000-c9950fc76ef0705da573Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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 IDFDB008291
KNApSAcK IDNot Available
Chemspider ID13002
KEGG Compound IDC19285
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13591
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tatematsu K, Koide A, Morimura K, Fukushima S, Mori Y: The enhancing effect of ethanol on the mutagenic activation of N-nitrosomethylbenzylamine by cytochrome P450 2A in the rat oesophagus. Mutagenesis. 2013 Mar;28(2):161-9. doi: 10.1093/mutage/ges066. Epub 2013 Jan 15. [PubMed:23325793 ]
  2. Li L, Wang P, Xu X, Zhou G: Influence of various cooking methods on the concentrations of volatile N-nitrosamines and biogenic amines in dry-cured sausages. J Food Sci. 2012 May;77(5):C560-5. doi: 10.1111/j.1750-3841.2012.02667.x. [PubMed:23163937 ]
  3. Pozzi R, Bocchini P, Pinelli F, Galletti GC: Determination of nitrosamines in water by gas chromatography/chemical ionization/selective ion trapping mass spectrometry. J Chromatogr A. 2011 Apr 8;1218(14):1808-14. doi: 10.1016/j.chroma.2011.02.009. Epub 2011 Feb 13. [PubMed:21377686 ]
  4. Authors unspecified: N-Nitrosamines (15 listings): N-Nitrosopyrrolidine. Rep Carcinog. 2011;12:323-4. [PubMed:21860516 ]
  5. Wagner ED, Hsu KM, Lagunas A, Mitch WA, Plewa MJ: Comparative genotoxicity of nitrosamine drinking water disinfection byproducts in Salmonella and mammalian cells. Mutat Res. 2012 Jan 24;741(1-2):109-15. doi: 10.1016/j.mrgentox.2011.11.006. Epub 2011 Nov 18. [PubMed:22108029 ]
  6. Hecht SS, Upadhyaya P, Wang M: Evolution of research on the DNA adduct chemistry of N-nitrosopyrrolidine and related aldehydes. Chem Res Toxicol. 2011 Jun 20;24(6):781-90. doi: 10.1021/tx200064a. Epub 2011 Apr 21. [PubMed:21480629 ]
  7. Tezel U, Padhye LP, Huang CH, Pavlostathis SG: Biotransformation of nitrosamines and precursor secondary amines under methanogenic conditions. Environ Sci Technol. 2011 Oct 1;45(19):8290-7. doi: 10.1021/es2005557. Epub 2011 Sep 2. [PubMed:21863807 ]
  8. Ma F, Wan Y, Yuan G, Meng L, Dong Z, Hu J: Occurrence and source of nitrosamines and secondary amines in groundwater and its adjacent Jialu River basin, China. Environ Sci Technol. 2012 Mar 20;46(6):3236-43. doi: 10.1021/es204520b. Epub 2012 Mar 1. [PubMed:22352424 ]
  9. Engemann A, Focke C, Humpf HU: Intestinal formation of N-nitroso compounds in the pig cecum model. J Agric Food Chem. 2013 Jan 30;61(4):998-1005. doi: 10.1021/jf305040e. Epub 2013 Jan 22. [PubMed:23297847 ]
  10. McDonald JA, Harden NB, Nghiem LD, Khan SJ: Analysis of N-nitrosamines in water by isotope dilution gas chromatography-electron ionisation tandem mass spectrometry. Talanta. 2012 Sep 15;99:146-54. doi: 10.1016/j.talanta.2012.05.032. Epub 2012 May 25. [PubMed:22967534 ]
  11. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .