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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:45:46 UTC
HMDB IDHMDB0001297
Secondary Accession Numbers
  • HMDB01297
Metabolite Identification
Common NameNorcotinine
DescriptionNorcotinine belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms. In humans, norcotinine is involved in the nicotine metabolism pathway. Norcotinine 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 norcotinine a potential biomarker for the consumption of these foods. Norcotinine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on Norcotinine.
Structure
Data?1582752190
Synonyms
ValueSource
(RS)-NorcotinineHMDB
5-(3-Pyridinyl)-2-pyrrolidinoneHMDB
DemethylcotinineHMDB
Norcotinine, (+-)-isomerMeSH, HMDB
Norcotinine, (R)-isomerMeSH, HMDB
Norcotinine, (S)-isomerMeSH, HMDB
Chemical FormulaC9H10N2O
Average Molecular Weight162.1885
Monoisotopic Molecular Weight162.079312952
IUPAC Name5-(pyridin-3-yl)pyrrolidin-2-one
Traditional Name5-pyridin-3-ylpyrrolidin-2-one
CAS Registry Number17114-40-8
SMILES
O=C1CCC(N1)C1=CN=CC=C1
InChI Identifier
InChI=1S/C9H10N2O/c12-9-4-3-8(11-9)7-2-1-5-10-6-7/h1-2,5-6,8H,3-4H2,(H,11,12)
InChI KeyFXFANIORDKRCCA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassNot Available
Direct ParentPyridines and derivatives
Alternative Parents
Substituents
  • Pyridine
  • Heteroaromatic compound
  • Cyclic carboximidic acid
  • Pyrroline
  • Lactim
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
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 Solubility12.9 g/LALOGPS
logP10(0.13) g/LALOGPS
logP10(-0.013) g/LChemAxon
logS10(-1.1) g/LALOGPS
pKa (Strongest Acidic)13.76ChemAxon
pKa (Strongest Basic)4.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.38 m³·mol⁻¹ChemAxon
Polarizability16.72 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]+137.25831661259
DarkChem[M-H]-132.7131661259
AllCCS[M+H]+135.46432859911
AllCCS[M-H]-136.37432859911
DeepCCS[M+H]+135.01430932474
DeepCCS[M-H]-132.14230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NorcotinineO=C1CCC(N1)C1=CN=CC=C12481.8Standard polar33892256
NorcotinineO=C1CCC(N1)C1=CN=CC=C11568.0Standard non polar33892256
NorcotinineO=C1CCC(N1)C1=CN=CC=C11842.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Norcotinine,1TMS,isomer #1C[Si](C)(C)N1C(=O)CCC1C1=CC=CN=C11677.3Semi standard non polar33892256
Norcotinine,1TMS,isomer #1C[Si](C)(C)N1C(=O)CCC1C1=CC=CN=C11687.4Standard non polar33892256
Norcotinine,1TMS,isomer #1C[Si](C)(C)N1C(=O)CCC1C1=CC=CN=C12184.0Standard polar33892256
Norcotinine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CCC1C1=CC=CN=C11930.2Semi standard non polar33892256
Norcotinine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CCC1C1=CC=CN=C11942.6Standard non polar33892256
Norcotinine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C(=O)CCC1C1=CC=CN=C12340.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Norcotinine GC-MS (Non-derivatized) - 70eV, Positivesplash10-06rx-6900000000-7167061e9fe9558a04562017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norcotinine 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 - Norcotinine 10V, Positive-QTOFsplash10-03di-0900000000-6b212cf317cd02f3fb272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcotinine 20V, Positive-QTOFsplash10-03dj-1900000000-47e1891277a98c78b7d82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcotinine 40V, Positive-QTOFsplash10-0v0u-9400000000-a2be02f0fbf0884511202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcotinine 10V, Negative-QTOFsplash10-03di-0900000000-f03246b316270169b0042016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcotinine 20V, Negative-QTOFsplash10-03di-1900000000-9816a6273230e64c8a152016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcotinine 40V, Negative-QTOFsplash10-0006-9400000000-94d564ccce13bc3f27932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcotinine 10V, Negative-QTOFsplash10-03di-0900000000-68b80ae98d7436c26dac2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcotinine 20V, Negative-QTOFsplash10-03di-3900000000-dc0d7910e90353c87b8a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcotinine 40V, Negative-QTOFsplash10-002f-9300000000-c6cdc7817919d9ca67b22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcotinine 10V, Positive-QTOFsplash10-03di-0900000000-d99f4e50b73cef46d2992021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcotinine 20V, Positive-QTOFsplash10-03di-1900000000-2a1c38a43f8c2aa321792021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norcotinine 40V, Positive-QTOFsplash10-00mo-9100000000-60ef78843c02c161575c2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.051 +/- 0.017 uMAdult (>18 years old)BothSmoking details
Associated Disorders and Diseases
Disease References
Smoking
  1. Zuccaro P, Altieri I, Rosa M, Passa AR, Pichini S, Ricciarello G, Pacifici R: Determination of nicotine and four metabolites in the serum of smokers by high-performance liquid chromatography with ultraviolet detection. J Chromatogr. 1993 Nov 24;621(2):257-61. [PubMed:8294547 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022540
KNApSAcK IDNot Available
Chemspider ID400
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6142
PubChem Compound413
PDB IDNot Available
ChEBI ID89406
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceDewey, Lovell J. Metabolites of nicotine and a synthesis of nornicotine. Journal of the American Chemical Society (1958), 80 1634-6.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zuccaro P, Altieri I, Rosa M, Passa AR, Pichini S, Ricciarello G, Pacifici R: Determination of nicotine and four metabolites in the serum of smokers by high-performance liquid chromatography with ultraviolet detection. J Chromatogr. 1993 Nov 24;621(2):257-61. [PubMed:8294547 ]
  2. Kyerematen GA, Morgan ML, Chattopadhyay B, deBethizy JD, Vesell ES: Disposition of nicotine and eight metabolites in smokers and nonsmokers: identification in smokers of two metabolites that are longer lived than cotinine. Clin Pharmacol Ther. 1990 Dec;48(6):641-51. [PubMed:2249376 ]
  3. McManus KT, deBethizy JD, Garteiz DA, Kyerematen GA, Vesell ES: A new quantitative thermospray LC-MS method for nicotine and its metabolites in biological fluids. J Chromatogr Sci. 1990 Oct;28(10):510-6. [PubMed:2246349 ]
  4. Kim I, Huestis MA: A validated method for the determination of nicotine, cotinine, trans-3'-hydroxycotinine, and norcotinine in human plasma using solid-phase extraction and liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry. J Mass Spectrom. 2006 Jun;41(6):815-21. [PubMed:16705667 ]