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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:22 UTC
HMDB IDHMDB0000992
Secondary Accession Numbers
  • HMDB00992
Metabolite Identification
Common Name3-Succinoylpyridine
Description3-Succinoylpyridine, also known as 4-OPC4a, 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. 3-Succinoylpyridine 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 3-succinoylpyridine a potential biomarker for the consumption of these foods. 3-Succinoylpyridine 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 significant number of articles have been published on 3-Succinoylpyridine.
Structure
Data?1676999722
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 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.82331661259
DarkChem[M-H]-137.28831661259
AllCCS[M+H]+138.38332859911
AllCCS[M-H]-137.73632859911
DeepCCS[M+H]+136.65630932474
DeepCCS[M-H]-134.04330932474
DeepCCS[M-2H]-169.9530932474
DeepCCS[M+Na]+144.89330932474
AllCCS[M+H]+138.432859911
AllCCS[M+H-H2O]+134.132859911
AllCCS[M+NH4]+142.432859911
AllCCS[M+Na]+143.532859911
AllCCS[M-H]-137.732859911
AllCCS[M+Na-2H]-138.532859911
AllCCS[M+HCOO]-139.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-SuccinoylpyridineOC(=O)CCC(=O)C1=CC=CN=C12498.6Standard polar33892256
3-SuccinoylpyridineOC(=O)CCC(=O)C1=CC=CN=C11466.9Standard non polar33892256
3-SuccinoylpyridineOC(=O)CCC(=O)C1=CC=CN=C11676.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Succinoylpyridine,1TMS,isomer #1C[Si](C)(C)OC(=O)CCC(=O)C1=CC=CN=C11783.3Semi standard non polar33892256
3-Succinoylpyridine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCC(=O)C1=CC=CN=C12024.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Succinoylpyridine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-2900000000-cdf56b25edc68c2f17052017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Succinoylpyridine GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-6900000000-f05304f350bca5ab259e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Succinoylpyridine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Succinoylpyridine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Succinoylpyridine 10V, Positive-QTOFsplash10-03e9-0900000000-c0fd32804412d8d638a62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Succinoylpyridine 20V, Positive-QTOFsplash10-0a59-1900000000-29479745f7cd06d7f41a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Succinoylpyridine 40V, Positive-QTOFsplash10-0a4i-9500000000-80d81797aa4d0e346eb02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Succinoylpyridine 10V, Negative-QTOFsplash10-004i-0900000000-27835ce4d7a57894a3ae2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Succinoylpyridine 20V, Negative-QTOFsplash10-01t9-1900000000-415bf0948aaee59224d82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Succinoylpyridine 40V, Negative-QTOFsplash10-004i-9400000000-17dea7abdd8b5d22edaf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Succinoylpyridine 10V, Negative-QTOFsplash10-03fr-1900000000-fc1ca8393051783b0e092021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Succinoylpyridine 20V, Negative-QTOFsplash10-004i-9400000000-d342daf0e4a51d86b9152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Succinoylpyridine 40V, Negative-QTOFsplash10-004i-9100000000-80d7164d7b9aee9efbb52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Succinoylpyridine 10V, Positive-QTOFsplash10-001i-0900000000-b78cfbdca607c59cc2362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Succinoylpyridine 20V, Positive-QTOFsplash10-001i-2900000000-e70565ae7b1278e69ee32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Succinoylpyridine 40V, Positive-QTOFsplash10-0560-9300000000-f78cab9d8fda258d16c32021-09-22Wishart 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

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
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
FooDB 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
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]