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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:39 UTC
HMDB IDHMDB0000992
Secondary Accession Numbers
  • HMDB00992
Metabolite Identification
Common Name3-Succinoylpyridine
Description3-succinoylpyridine is the byproduct of tobacco-specific N-nitrosamines generated by the enzyme cytochrome P 450 which catalyzes methylnitrosaminopyridylbutanone hydroxylation. (PMID: 11368333 ). This nicotine metabolite is commonly found in the urine of smokers. (PMID: 14581070 ).
Structure
Data?1563860679
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)butyric acidHMDB
4-oxo-4-(3-Pyridyl)butanoic acidHMDB
3-SuccinoylpyridineChEBI
Chemical FormulaC9H9NO3
Average Molecular Weight179.1727
Monoisotopic Molecular Weight179.058243159
IUPAC Name4-oxo-4-(pyridin-3-yl)butanoic acid
Traditional Name3-succinoylpyridine
CAS Registry Number4192-31-8
SMILES
OC(=O)CCC(=O)C1=CC=CN=C1
InChI Identifier
InChI=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
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 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
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
FoodDB IDFDB022355
KNApSAcK IDNot Available
Chemspider ID424
KEGG Compound IDC19569
BioCyc IDCPD-14094
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5924
PubChem Compound437
PDB IDNot Available
ChEBI ID66951
Food Biomarker OntologyNot Available
VMH IDM00917
References
Synthesis ReferenceSchwartz, 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:11368333 ]
  2. 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. [PubMed:14581070 ]