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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:49:04 UTC
Update Date2023-02-21 17:29:04 UTC
HMDB IDHMDB0041940
Secondary Accession Numbers
  • HMDB41940
Metabolite Identification
Common NameN'-nitrosonornicotine
DescriptionN'-nitrosonornicotine, also known as NNN, belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring. N'-nitrosonornicotine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. N'-nitrosonornicotine is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Based on a literature review very few articles have been published on N'-nitrosonornicotine.
Structure
Data?1677000543
Synonyms
ValueSource
NNNKegg
N-NitrosonornicotineHMDB
NitrosonornicotineHMDB
N-Nitrosonor-nicotineHMDB
N'-nitrosonornicotine, (+-)-isomerHMDB
N'-nitrosonornicotine, (S)-isomerHMDB
Chemical FormulaC9H11N3O
Average Molecular Weight177.2031
Monoisotopic Molecular Weight177.090211989
IUPAC Name3-(1-nitrosopyrrolidin-2-yl)pyridine
Traditional Namenitrosonornicotine
CAS Registry Number16543-55-8
SMILES
O=NN1CCCC1C1=CN=CC=C1
InChI Identifier
InChI=1S/C9H11N3O/c13-11-12-6-2-4-9(12)8-3-1-5-10-7-8/h1,3,5,7,9H,2,4,6H2
InChI KeyXKABJYQDMJTNGQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyrrolidinylpyridines
Direct ParentPyrrolidinylpyridines
Alternative Parents
Substituents
  • Pyrrolidinylpyridine
  • Heteroaromatic compound
  • Pyrrolidine
  • Organic n-nitroso compound
  • Organic nitroso compound
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point47 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.19 g/LALOGPS
logP0.71ALOGPS
logP1.01ChemAxon
logS-1.7ALOGPS
pKa (Strongest Basic)4.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area45.56 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.72 m³·mol⁻¹ChemAxon
Polarizability18.13 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.91831661259
DarkChem[M-H]-134.60131661259
DeepCCS[M+H]+138.91630932474
DeepCCS[M-H]-135.67730932474
DeepCCS[M-2H]-172.80230932474
DeepCCS[M+Na]+148.3430932474
AllCCS[M+H]+139.032859911
AllCCS[M+H-H2O]+134.532859911
AllCCS[M+NH4]+143.232859911
AllCCS[M+Na]+144.432859911
AllCCS[M-H]-140.432859911
AllCCS[M+Na-2H]-140.932859911
AllCCS[M+HCOO]-141.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N'-nitrosonornicotineO=NN1CCCC1C1=CN=CC=C12272.9Standard polar33892256
N'-nitrosonornicotineO=NN1CCCC1C1=CN=CC=C11641.9Standard non polar33892256
N'-nitrosonornicotineO=NN1CCCC1C1=CN=CC=C11786.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N'-nitrosonornicotine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-6900000000-fd2ef6c01a4b17ce52732017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N'-nitrosonornicotine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N'-nitrosonornicotine 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'-nitrosonornicotine 10V, Positive-QTOFsplash10-004i-0900000000-12f56e19de9cbe3985652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosonornicotine 20V, Positive-QTOFsplash10-002b-0900000000-91649128a892cc839eb62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosonornicotine 40V, Positive-QTOFsplash10-00kf-9700000000-873fd2c47c2d68c835942016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosonornicotine 10V, Negative-QTOFsplash10-004i-0900000000-c12c118d1c7651944f812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosonornicotine 20V, Negative-QTOFsplash10-0a6r-2900000000-e35c2cff64ce3c329c362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosonornicotine 40V, Negative-QTOFsplash10-056r-9700000000-fae379e939e02b8283372016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosonornicotine 10V, Positive-QTOFsplash10-004i-0900000000-5e75feafb4c32781d4782021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosonornicotine 20V, Positive-QTOFsplash10-004i-0900000000-ec7ff1c81f701ccb3c4b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosonornicotine 40V, Positive-QTOFsplash10-0036-9500000000-34ad449443dff74d1f2f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosonornicotine 10V, Negative-QTOFsplash10-004i-2900000000-0f48d5bc2f759fd6c2bb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosonornicotine 20V, Negative-QTOFsplash10-004i-3900000000-794ade8a28d915dff3712021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosonornicotine 40V, Negative-QTOFsplash10-002e-9400000000-6c58cf9f856143d2092f2021-09-22Wishart 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+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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID25973
KEGG Compound IDC16452
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkN-Nitrosonornicotine
METLIN IDNot Available
PubChem Compound27919
PDB IDNot Available
ChEBI ID80502
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