Cotinine N-oxide (CHEM021704)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:10:27 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021704
Identification
Common NameCotinine N-oxide
ClassSmall Molecule
DescriptionAn N-alkylpyrrolidine that is nicotine in which the methylene hydrogens at position 2 on the pyrrolidine ring have been replaced by an oxo group and the pyridine nitrogen converted into the corresponding N-oxide. A minor metabolite of nicotine.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-Cotinine N-oxideChEBI
(5S)-1-Methyl-5-(1-oxido-3-pyridinyl)-2-pyrrolidinoneChEBI
(S)-1-Methyl-5-(1-oxido-3-pyridinyl)-2-pyrrolidinoneChEBI
(S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone N-oxideChEBI
3-[(2S)-1-Methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olateChEBI
Cotinine-N-oxideChEBI
3-[(2S)-1-Methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olic acidGenerator
Cotinine-1-N-oxideMeSH, HMDB
Chemical FormulaC10H12N2O2
Average Molecular Mass192.215 g/mol
Monoisotopic Mass192.090 g/mol
CAS Registry Number36508-80-2
IUPAC Name3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate
Traditional Name3-[(2S)-1-methyl-5-oxopyrrolidin-2-yl]pyridin-1-ium-1-olate
SMILESCN1[C@@H](CCC1=O)C1=C[N+]([O-])=CC=C1
InChI IdentifierInChI=1S/C10H12N2O2/c1-11-9(4-5-10(11)13)8-3-2-6-12(14)7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1
InChI KeyCIPULDKLIIVIER-VIFPVBQESA-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
  • Alkaloid or derivatives
  • Pyridinium
  • Pyrrolidone
  • 2-pyrrolidone
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Lactam
  • Carboxamide group
  • Carboxylic acid derivative
  • Azacycle
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility11 g/LALOGPS
logP-0.66ALOGPS
logP-1ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)0.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area45.77 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity52.97 m³·mol⁻¹ChemAxon
Polarizability19.5 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007c-2900000000-b21511ca6ae8481af0e8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-c4eef2387e9f2b62d330Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-fef784f029be5b488c33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmj-4900000000-68e5ea5e4ec111232d7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-2aae58a0b3f0a1cfff7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1900000000-8a7a6a4c3590431d80baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-db8d337314f54fbc6087Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-18fc00c031adb8129b3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-18d8f25ee061190ca3b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-5900000000-e69e4e58d2b626f4e06bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-db2f5cc959f8b671bd15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-32cfe0677b371918de71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-2900000000-ffd6d9f4ac3b44e62d61Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001411
FooDB IDFDB022606
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-3185
METLIN ID6227
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID7991264
ChEBI ID89087
PubChem Compound ID9815514
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1478978
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15109883
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1521032
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15472033
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=16359169
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=17640086
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19065315
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=19466395
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=20097626
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=20301889
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=20822672
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=20980010
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=21452992
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=21719221
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23022114
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23318728
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23737496
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23983622
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=24755743
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=24968308
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=25013964
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=25304849
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=26721601
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=27480511
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=3443673
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=4625531
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=8294547
28. Riah, Omar; Dousset, Jean Claude; Courriere, Philippe; Baziard-Mouysset, Genevieve; Ecalle, Rene. Synthesis of cotinine and cotinine N-oxide. Evaluation of their interaction with nicotine in the insecticidal activity. Natural Product Letters (1997), 11(1), 37-45.
29. 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.
30. Jacob P 3rd, Shulgin AT, Yu L, Benowitz NL: Determination of the nicotine metabolite trans-3'-hydroxycotinine in urine of smokers using gas chromatography with nitrogen-selective detection or selected ion monitoring. J Chromatogr. 1992 Dec 2;583(2):145-54.
31. Xu X, Iba MM, Weisel CP: Simultaneous and sensitive measurement of anabasine, nicotine, and nicotine metabolites in human urine by liquid chromatography-tandem mass spectrometry. Clin Chem. 2004 Dec;50(12):2323-30. Epub 2004 Oct 7.
32. Brown KM, von Weymarn LB, Murphy SE: Identification of N-(hydroxymethyl) norcotinine as a major product of cytochrome P450 2A6, but not cytochrome P450 2A13-catalyzed cotinine metabolism. Chem Res Toxicol. 2005 Dec;18(12):1792-8.
33. Yildiz D: Nicotine, its metabolism and an overview of its biological effects. Toxicon. 2004 May;43(6):619-32.