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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:49:01 UTC
Update Date2023-02-21 17:29:03 UTC
HMDB IDHMDB0041939
Secondary Accession Numbers
  • HMDB41939
Metabolite Identification
Common NameN'-nitrosoanabasine
DescriptionN'-Nitrosoanabasine (NAB) is a minor tobacco alkaloid that is derived from the tertiary amine known as anabasine (PMID: 3286030 ). It belongs to a group of nitrosamines called tobacco-specific nitrosamines (TSNAs). It is thought that during tobacco processing, minor alkaloids such as NAB originate from bacterial action or oxidation (PMID: 29751076 ). Nitrosamines are chemically stable compounds under physiological conditions, but they are known as causative factors for cancers of the lung, pancreas, esophagus, and oral cavity (PMID: 29751076 ). Activation of TSNAs through α-hydroxylation leads to binding of TSNA to DNA and other cellular macromolecules. This results in biological actions such as carcinogenicity, mutagenicity, embryopathy and other teratogenic actions (PMID: 4997817 ). N'-nitrosoanabasine is only found in individuals who smoke or who are exposed to tobacco smoke.
Structure
Data?1677000543
Synonyms
ValueSource
3-(1-Nitroso-2-piperidinyl)-pyridineKegg
N'-nitrosoanabasine, (+-)-isomerHMDB
N'-nitrosoanabasine, (S)-isomerHMDB
Chemical FormulaC10H13N3O
Average Molecular Weight191.2297
Monoisotopic Molecular Weight191.105862053
IUPAC Name3-(1-nitrosopiperidin-2-yl)pyridine
Traditional Name3-(1-nitrosopiperidin-2-yl)pyridine
CAS Registry Number1133-64-8
SMILES
O=NN1CCCCC1C1=CN=CC=C1
InChI Identifier
InChI=1S/C10H13N3O/c14-12-13-7-2-1-5-10(13)9-4-3-6-11-8-9/h3-4,6,8,10H,1-2,5,7H2
InChI KeyBXYPVKMROLGXJI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Alkaloid or derivatives
  • 1-nitrosopiperidine
  • Piperidine
  • Pyridine
  • Heteroaromatic compound
  • Organic n-nitroso compound
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitroso compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
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 Solubility2.08 g/LALOGPS
logP1.02ALOGPS
logP1.46ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)4.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area45.56 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.32 m³·mol⁻¹ChemAxon
Polarizability20.04 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]+142.70831661259
DarkChem[M-H]-137.97131661259
DeepCCS[M+H]+142.95530932474
DeepCCS[M-H]-140.23430932474
DeepCCS[M-2H]-176.6630932474
DeepCCS[M+Na]+152.19830932474
AllCCS[M+H]+142.832859911
AllCCS[M+H-H2O]+138.432859911
AllCCS[M+NH4]+146.932859911
AllCCS[M+Na]+148.132859911
AllCCS[M-H]-145.432859911
AllCCS[M+Na-2H]-145.732859911
AllCCS[M+HCOO]-146.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N'-nitrosoanabasineO=NN1CCCCC1C1=CN=CC=C12296.4Standard polar33892256
N'-nitrosoanabasineO=NN1CCCCC1C1=CN=CC=C11841.8Standard non polar33892256
N'-nitrosoanabasineO=NN1CCCCC1C1=CN=CC=C11838.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N'-nitrosoanabasine GC-MS (Non-derivatized) - 70eV, Positivesplash10-03xr-1900000000-dd8105864573fc0047272017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N'-nitrosoanabasine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N'-nitrosoanabasine 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'-nitrosoanabasine 10V, Positive-QTOFsplash10-0006-0900000000-013977f2c6fda88acd252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosoanabasine 20V, Positive-QTOFsplash10-01qc-0900000000-9179722f24c850b6c4302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosoanabasine 40V, Positive-QTOFsplash10-0pc0-8900000000-0c2cea4a2db968797ec22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosoanabasine 10V, Negative-QTOFsplash10-0006-0900000000-560c30f02c22be3af4b72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosoanabasine 20V, Negative-QTOFsplash10-00dl-1900000000-718e27224fb00b1ad8ab2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosoanabasine 40V, Negative-QTOFsplash10-056r-9700000000-aa32cd08fe30d1e5d2f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosoanabasine 10V, Negative-QTOFsplash10-006x-1900000000-04b6843c996a27751dc12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosoanabasine 20V, Negative-QTOFsplash10-054x-2900000000-98ffe6b8797db154283d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosoanabasine 40V, Negative-QTOFsplash10-004i-9600000000-357f471b7aa5832862f12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosoanabasine 10V, Positive-QTOFsplash10-0006-0900000000-d5f59b970051e63a9dab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosoanabasine 20V, Positive-QTOFsplash10-0006-1900000000-18eddd1a2e9cdaa3bac92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N'-nitrosoanabasine 40V, Positive-QTOFsplash10-06uu-9700000000-963b14a1bc1d3f6878f52021-09-22Wishart 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 ID13696
KEGG Compound IDC19477
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14335
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. Hecht SS, Hoffmann D: Tobacco-specific nitrosamines, an important group of carcinogens in tobacco and tobacco smoke. Carcinogenesis. 1988 Jun;9(6):875-84. doi: 10.1093/carcin/9.6.875. [PubMed:3286030 ]
  2. Konstantinou E, Fotopoulou F, Drosos A, Dimakopoulou N, Zagoriti Z, Niarchos A, Makrynioti D, Kouretas D, Farsalinos K, Lagoumintzis G, Poulas K: Tobacco-specific nitrosamines: A literature review. Food Chem Toxicol. 2018 Aug;118:198-203. doi: 10.1016/j.fct.2018.05.008. Epub 2018 May 8. [PubMed:29751076 ]
  3. Magee PN: Toxicity of nitrosamines: their possible human health hazards. Food Cosmet Toxicol. 1971 Apr;9(2):207-18. doi: 10.1016/0015-6264(71)90306-3. [PubMed:4997817 ]