3-Succinoylpyridine (CHEM035019)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:25:23 UTC
Update Date2016-11-09 01:21:14 UTC
Accession NumberCHEM035019
Identification
Common Name3-Succinoylpyridine
ClassSmall Molecule
DescriptionA monocarboxylic acid that is succinic acid in which the hydroxy group of one of the carboxy groups is replaced by a pyridin-3-yl group. A byproduct of tobacco-specific N-nitrosamines generated by cytochrome P-450 which catalyzes methylnitrosaminopyridylbutanone hydroxylation, this nicotine metabolite is commonly found in the urine of smokers.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-oxo-4-(3-Pyridyl)-butanoic acidChEBI
4-oxo-4-(3-Pyridyl)-butyric acidChEBI
4-oxo-4-(Pyridin-3-yl)butyric acidChEBI
gamma-oxo-3-Pyridinebutanoic acidChEBI
gamma-oxo-3-Pyridinebutyric acidChEBI
4-oxo-4-(Pyridin-3-yl)butanoateKegg
4-oxo-4-(3-Pyridyl)-butanoateGenerator
4-oxo-4-(3-Pyridyl)-butyrateGenerator
4-oxo-4-(Pyridin-3-yl)butyrateGenerator
g-oxo-3-PyridinebutanoateGenerator
g-oxo-3-Pyridinebutanoic acidGenerator
gamma-oxo-3-PyridinebutanoateGenerator
Γ-oxo-3-pyridinebutanoateGenerator
Γ-oxo-3-pyridinebutanoic acidGenerator
g-oxo-3-PyridinebutyrateGenerator
g-oxo-3-Pyridinebutyric acidGenerator
gamma-oxo-3-PyridinebutyrateGenerator
Γ-oxo-3-pyridinebutyrateGenerator
Γ-oxo-3-pyridinebutyric acidGenerator
4-oxo-4-(Pyridin-3-yl)butanoic acidGenerator
4-OPC4aHMDB
4-oxo-4-(3-Pyridyl)butanoic acidHMDB
4-oxo-4-(3-Pyridyl)butyric acidHMDB
3-SuccinoylpyridineChEBI
Chemical FormulaC9H9NO3
Average Molecular Mass179.173 g/mol
Monoisotopic Mass179.058 g/mol
CAS Registry Number4192-31-8
IUPAC Name4-oxo-4-(pyridin-3-yl)butanoic acid
Traditional Name3-succinoylpyridine
SMILESOC(=O)CCC(=O)C1=CC=CN=C1
InChI IdentifierInChI=1S/C9H9NO3/c11-8(3-4-9(12)13)7-2-1-5-10-6-7/h1-2,5-6H,3-4H2,(H,12,13)
InChI KeyJGSUNMCABQUBOY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassGamma-keto acids and derivatives
Direct ParentGamma-keto acids and derivatives
Alternative Parents
Substituents
  • Gamma-keto acid
  • Aryl ketone
  • Aryl alkyl ketone
  • Pyridine
  • Heteroaromatic compound
  • Ketone
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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 Solubility8.78 g/LALOGPS
logP0.08ALOGPS
logP-0.58ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.36ChemAxon
pKa (Strongest Basic)4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area67.26 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity45.2 m³·mol⁻¹ChemAxon
Polarizability17.56 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-0a4i-2900000000-cdf56b25edc68c2f1705Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-6900000000-f05304f350bca5ab259eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0900000000-c0fd32804412d8d638a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-1900000000-29479745f7cd06d7f41aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9500000000-80d81797aa4d0e346eb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-27835ce4d7a57894a3aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1900000000-415bf0948aaee59224d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9400000000-17dea7abdd8b5d22edafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-1900000000-fc1ca8393051783b0e09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9400000000-d342daf0e4a51d86b915Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-80d7164d7b9aee9efbb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-b78cfbdca607c59cc236Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2900000000-e70565ae7b1278e69ee3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0560-9300000000-f78cab9d8fda258d16c3Spectrum
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
1D NMR1H 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 IDHMDB0000992
FooDB IDFDB022355
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-14094
METLIN ID5924
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID424
ChEBI ID66951
PubChem Compound ID437
Kegg Compound IDC19569
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11368333
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=14581070
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17464070
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22267672
5. Schwartz, Sorell L.; McKennis, Herbert, Jr. The degradation of the pyrrolidine ring of (-)-nicotine in vitro. Formation of g-(3-pyridyl)-g-oxobutyric acid. Journal of Biological Chemistry (1963), 238 1807-12.
6. Felicia ND, Rekha GK, Murphy SE: Characterization of cytochrome P450 2A4 and 2A5-catalyzed 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism. Arch Biochem Biophys. 2000 Dec 15;384(2):418-24.
7. Baidoo EE, Clench MR, Smith RF, Tetler LW: Determination of nicotine and its metabolites in urine by solid-phase extraction and sample stacking capillary electrophoresis-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Nov 5;796(2):303-13.