Back to Compounds

Showing Compound Cotinine (FDB004716)

Record Information
Version1.0
Creation date2010-04-08 22:06:22 UTC
Update date2019-11-26 03:00:10 UTC
Primary IDFDB004716
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCotinine
DescriptionCotinine has an in vivo half life of approximately 20 hours, and is typically detectable for several days to up to one week after the use of tobacco. The level of cotinine in the blood is proportionate to the amount of exposure to tobacco smoke, so it is a valuable indicator of tobacco smoke exposure, including secondary (passive) smoke. People who smoke menthol cigarettes may retain cotinine in the blood for a longer period because menthol can compete with cotinine enzymatic metabolism. Genetic encoding of liver enzymes may also play a role, as African Americans routinely register higher blood cotinine levels than Caucasians. Several variable factors, such as menthol cigarette preference and puff size, suggest that the explanation for this difference may be more complex than gender or race.[citation needed]; Cotinine is a metabolite of nicotine. The word 'cotinine' is an anagram of 'nicotine'. It is used to measure the grade of tobacco smoking, but might also improve mental function.; Quantitatively, the most important metabolite of nicotine in most mammalian species is cotinine. In humans, about 70 to 80% of nicotine is converted to cotinine. This transformation involves two steps. The first is mediated by a cytochrome P450 system (mainly CYP2A6 and CYP2B6) to produce nicotine iminium ion. The second step is catalyzed by aldehyde oxidase (AOX). A number of cotinine metabolites have also been structurally characterized. Indeed, it appears that most of the reported urinary metabolites of nicotine are derived from cotinine. Cotinine is found in many foods, some of which are ceylon cinnamon, arrowhead, mountain yam, and rambutan.
CAS Number486-56-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Cotinine(15% OF the dose)HMDB
(-)-CotinineHMDB
(S)-(-)-CotinineHMDB
(S)-CotinineHMDB
CotininaHMDB
CotininumHMDB
S-(-)-CotinineHMDB
(-)-cotininebiospider
(s)-(-)-cotininebiospider
(S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinonebiospider
(s)-cotininebiospider
1-Methyl-5-(3-pyridinyl)-2-pyrrolidinonebiospider
1-methyl-5-pyridin-3-ylpyrrolidin-2-onebiospider
2-Pyrrolidinone, 1-methyl-5-(3-pyridinyl)-biospider
2-Pyrrolidinone, 1-methyl-5-(3-pyridinyl)-, (5S)-biospider
2-Pyrrolidinone, 1-methyl-5-(3-pyridinyl)-, (S)-biospider
2-Pyrrolidinone, 1-methyl-5-(3-pyridinyl)-, (S)- (9CI)biospider
Cotininebiospider
Cotinine [inn]biospider
S-(-)-cotininebiospider
Scotinebiospider
Predicted Properties
PropertyValueSource
Water Solubility117 g/LALOGPS
logP0.39ALOGPS
logP0.21ChemAxon
logS-0.18ALOGPS
pKa (Strongest Basic)4.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area33.2 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.28 m³·mol⁻¹ChemAxon
Polarizability18.57 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H12N2O
IUPAC name1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one
InChI IdentifierInChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3
InChI KeyUIKROCXWUNQSPJ-UHFFFAOYSA-N
Isomeric SMILESCN1C(CCC1=O)C1=CN=CC=C1
Average Molecular Weight176.2151
Monoisotopic Molecular Weight176.094963016
Classification
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
  • Pyrrolidone
  • 2-pyrrolidone
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Lactam
  • Carboxamide group
  • Carboxylic acid derivative
  • Azacycle
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point41 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP0.07LI,NY & GORROD,JW (1992)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-002b-9600000000-0cc3afdaebb529092e242014-09-20View Spectrum
GC-MSCotinine, non-derivatized, GC-MS Spectrumsplash10-0002-9500000000-f031a7d223ea527c7a80Spectrum
GC-MSCotinine, non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-61e8e1349a9d42866260Spectrum
GC-MSCotinine, non-derivatized, GC-MS Spectrumsplash10-0002-9500000000-f031a7d223ea527c7a80Spectrum
GC-MSCotinine, non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-61e8e1349a9d42866260Spectrum
Predicted GC-MSCotinine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0gdl-6900000000-7eb4053aab6127e95391Spectrum
Predicted GC-MSCotinine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCotinine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-2900000000-7f61a2f6f72860e4c6e12012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9100000000-3a5b30b90a390122b8682012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-b82772b6f28d39966cd12012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-0002-9500000000-e8a00bc1cf980c18ed062012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - CI-B (HITACHI M-60) , Positivesplash10-004i-0900000000-61e8e1349a9d428662602012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-16fb662f236943b7061e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-bb6734f53ed607f8551f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-3900000000-b7fe72bb7584aa19a7362017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-2900000000-bb9334268373122b4f812017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-bb6734f53ed607f8551f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-3900000000-617e9ef99f5ff220e7f92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-3900000000-1ad4398aa27830eabbbd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-3210604d5a8368e435a02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-785e2933ae8dc3d4b2972021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-4be8a9d2dee773690bd32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001j-9100000000-8081f3e6f95787810baa2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-a4a59884dbcf842f195a2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1900000000-0cfe8e8d340c82c8fd112015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9y-9500000000-e18e0cea3d758c6ff7682015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-6fcf3e50bea7e8c250082015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-dad0516bb0862355ae612015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05r4-9700000000-36486e0d1769fb592c7a2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-55ef895c84a338046aba2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1900000000-72acff4eea7467f916132021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9800000000-8b60e7a4fd9931166f142021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID395
ChEMBL IDCHEMBL664
KEGG Compound IDNot Available
Pubchem Compound ID408
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01046
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDCOTININE
BIGG IDNot Available
KNApSAcK IDC00034470
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCotinine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).