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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:22 UTC

HMDB ID

HMDB0000992

Secondary Accession Numbers

HMDB00992

Metabolite Identification

Common Name

3-Succinoylpyridine

Description

3-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      15.843 -13.911   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      14.496 -14.680   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      15.843 -12.362   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.496 -11.614   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.172 -13.911   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.172 -12.372   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.170 -11.581   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      17.157 -10.041   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      18.510 -12.340   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.837 -11.559   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.177 -12.318   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      22.504 -11.537   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      21.190 -13.858   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    5                                                       
CONECT    3    1    4    7                                                  
CONECT    4    3    6                                                       
CONECT    5    2    6                                                       
CONECT    6    4    5                                                       
CONECT    7    8    9    3                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   12   13   10                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-oxo-4-(3-Pyridyl)-butanoic acid	ChEBI
4-oxo-4-(3-Pyridyl)-butyric acid	ChEBI
4-oxo-4-(Pyridin-3-yl)butyric acid	ChEBI
gamma-oxo-3-Pyridinebutanoic acid	ChEBI
gamma-oxo-3-Pyridinebutyric acid	ChEBI
4-oxo-4-(Pyridin-3-yl)butanoate	Kegg
4-oxo-4-(3-Pyridyl)-butanoate	Generator
4-oxo-4-(3-Pyridyl)-butyrate	Generator
4-oxo-4-(Pyridin-3-yl)butyrate	Generator
g-oxo-3-Pyridinebutanoate	Generator
g-oxo-3-Pyridinebutanoic acid	Generator
gamma-oxo-3-Pyridinebutanoate	Generator
Γ-oxo-3-pyridinebutanoate	Generator
Γ-oxo-3-pyridinebutanoic acid	Generator
g-oxo-3-Pyridinebutyrate	Generator
g-oxo-3-Pyridinebutyric acid	Generator
gamma-oxo-3-Pyridinebutyrate	Generator
Γ-oxo-3-pyridinebutyrate	Generator
Γ-oxo-3-pyridinebutyric acid	Generator
4-oxo-4-(Pyridin-3-yl)butanoic acid	Generator
4-OPC4a	HMDB
4-oxo-4-(3-Pyridyl)butanoic acid	HMDB
4-oxo-4-(3-Pyridyl)butyric acid	HMDB
3-Succinoylpyridine	ChEBI

Chemical Formula

C₉H₉NO₃

Average Molecular Weight

179.1727

Monoisotopic Molecular Weight

179.058243159

IUPAC Name

4-oxo-4-(pyridin-3-yl)butanoic acid

Traditional Name

3-succinoylpyridine

CAS Registry Number

4192-31-8

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 Key

JGSUNMCABQUBOY-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Gamma-keto acids and derivatives

Direct Parent

Gamma-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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:66951 )
pyridines (CHEBI:66951 )
aromatic ketone (CHEBI:66951 )

Ontology

Not Available

Endogenous (HMDB: HMDB0000992)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.78 g/L	ALOGPS
logP	0.08	ALOGPS
logP	-0.58	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.36	ChemAxon
pKa (Strongest Basic)	4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	67.26 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	45.2 m³·mol⁻¹	ChemAxon
Polarizability	17.56 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	140.823	31661259
DarkChem	[M-H]-	137.288	31661259
AllCCS	[M+H]+	138.383	32859911
AllCCS	[M-H]-	137.736	32859911
DeepCCS	[M+H]+	136.656	30932474
DeepCCS	[M-H]-	134.043	30932474
DeepCCS	[M-2H]-	169.95	30932474
DeepCCS	[M+Na]+	144.893	30932474
AllCCS	[M+H]+	138.4	32859911
AllCCS	[M+H-H2O]+	134.1	32859911
AllCCS	[M+NH4]+	142.4	32859911
AllCCS	[M+Na]+	143.5	32859911
AllCCS	[M-H]-	137.7	32859911
AllCCS	[M+Na-2H]-	138.5	32859911
AllCCS	[M+HCOO]-	139.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Succinoylpyridine	OC(=O)CCC(=O)C1=CC=CN=C1	2498.6	Standard polar	33892256
3-Succinoylpyridine	OC(=O)CCC(=O)C1=CC=CN=C1	1466.9	Standard non polar	33892256
3-Succinoylpyridine	OC(=O)CCC(=O)C1=CC=CN=C1	1676.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Succinoylpyridine,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCC(=O)C1=CC=CN=C1	1783.3	Semi standard non polar	33892256
3-Succinoylpyridine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC(=O)C1=CC=CN=C1	2024.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Succinoylpyridine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2900000000-cdf56b25edc68c2f1705	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Succinoylpyridine GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-6900000000-f05304f350bca5ab259e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Succinoylpyridine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Succinoylpyridine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Succinoylpyridine 10V, Positive-QTOF	splash10-03e9-0900000000-c0fd32804412d8d638a6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Succinoylpyridine 20V, Positive-QTOF	splash10-0a59-1900000000-29479745f7cd06d7f41a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Succinoylpyridine 40V, Positive-QTOF	splash10-0a4i-9500000000-80d81797aa4d0e346eb0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Succinoylpyridine 10V, Negative-QTOF	splash10-004i-0900000000-27835ce4d7a57894a3ae	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Succinoylpyridine 20V, Negative-QTOF	splash10-01t9-1900000000-415bf0948aaee59224d8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Succinoylpyridine 40V, Negative-QTOF	splash10-004i-9400000000-17dea7abdd8b5d22edaf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Succinoylpyridine 10V, Negative-QTOF	splash10-03fr-1900000000-fc1ca8393051783b0e09	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Succinoylpyridine 20V, Negative-QTOF	splash10-004i-9400000000-d342daf0e4a51d86b915	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Succinoylpyridine 40V, Negative-QTOF	splash10-004i-9100000000-80d7164d7b9aee9efbb5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Succinoylpyridine 10V, Positive-QTOF	splash10-001i-0900000000-b78cfbdca607c59cc236	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Succinoylpyridine 20V, Positive-QTOF	splash10-001i-2900000000-e70565ae7b1278e69ee3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Succinoylpyridine 40V, Positive-QTOF	splash10-0560-9300000000-f78cab9d8fda258d16c3	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022355

KNApSAcK ID

Not Available

Chemspider ID

424

KEGG Compound ID

C19569

BioCyc ID

CPD-14094

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5924

PubChem Compound

437

PDB ID

Not Available

ChEBI ID

66951

Food Biomarker Ontology

Not Available

VMH ID

M00917

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

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.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
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 ]

Showing metabocard for 3-Succinoylpyridine (HMDB0000992)

MOL for HMDB0000992 (3-Succinoylpyridine)

3D MOL for HMDB0000992 (3-Succinoylpyridine)

3D SDF for HMDB0000992 (3-Succinoylpyridine)

3D-SDF for HMDB0000992 (3-Succinoylpyridine)

PDB for HMDB0000992 (3-Succinoylpyridine)

3D PDB for HMDB0000992 (3-Succinoylpyridine)

SMILES for HMDB0000992 (3-Succinoylpyridine)

INCHI for HMDB0000992 (3-Succinoylpyridine)

Structure for HMDB0000992 (3-Succinoylpyridine)

3D Structure for HMDB0000992 (3-Succinoylpyridine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra