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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 17:15:34 UTC

HMDB ID

HMDB0001267

Secondary Accession Numbers

HMDB01267

Metabolite Identification

Common Name

4-Oxo-4-(3-pyridyl)-butanamide

Description

4-Oxo-4-(3-pyridyl)-butanamide belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. 4-Oxo-4-(3-pyridyl)-butanamide 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 4-oxo-4-(3-pyridyl)-butanamide a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 4-Oxo-4-(3-pyridyl)-butanamide.

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      28.037 -37.109   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.807 -35.775   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.037 -34.441   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.497 -34.441   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      25.728 -35.775   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      26.497 -37.109   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.807 -33.107   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      30.347 -33.107   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      28.037 -31.775   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.497 -31.775   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.728 -30.441   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      26.497 -29.107   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0      24.188 -30.441   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    3    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
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-(3-Pyridyl)-4-oxobutyramide	HMDB, MeSH
POBAM	HMDB, MeSH
4-oxo-4-(Pyridin-3-yl)butanimidate	Generator, HMDB

Chemical Formula

C₉H₁₀N₂O₂

Average Molecular Weight

178.1879

Monoisotopic Molecular Weight

178.074227574

IUPAC Name

4-oxo-4-(pyridin-3-yl)butanamide

Traditional Name

4-oxo-4-(3-pyridyl)-butanamide

CAS Registry Number

Not Available

SMILES

NC(=O)CCC(=O)C1=CN=CC=C1

InChI Identifier

InChI=1S/C9H10N2O2/c10-9(13)4-3-8(12)7-2-1-5-11-6-7/h1-2,5-6H,3-4H2,(H2,10,13)

InChI Key

DJEKVKGYYASXCW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl alkyl ketones

Alternative Parents

Substituents

Aryl alkyl ketone
Fatty amide
Fatty acyl
Pyridine
Heteroaromatic compound
Carboxamide group
Primary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Organic oxide
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a small molecule (CPD-3190 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0001267)

Source

Endogenous

Endogenous (HMDB: HMDB0001267)

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)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

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)

Equine

Horse (FooDB: FOOD00378)

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	11.5 g/L	ALOGPS
logP	-0.45	ALOGPS
logP	-0.67	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	14.5	ChemAxon
pKa (Strongest Basic)	3.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	73.05 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	47.02 m³·mol⁻¹	ChemAxon
Polarizability	17.93 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]+	140.68	31661259
DarkChem	[M-H]-	137.144	31661259
AllCCS	[M+H]+	138.455	32859911
AllCCS	[M-H]-	138.494	32859911
DeepCCS	[M+H]+	138.263	30932474
DeepCCS	[M-H]-	135.666	30932474
DeepCCS	[M-2H]-	171.461	30932474
DeepCCS	[M+Na]+	146.442	30932474
AllCCS	[M+H]+	138.5	32859911
AllCCS	[M+H-H2O]+	134.2	32859911
AllCCS	[M+NH4]+	142.4	32859911
AllCCS	[M+Na]+	143.6	32859911
AllCCS	[M-H]-	138.5	32859911
AllCCS	[M+Na-2H]-	139.3	32859911
AllCCS	[M+HCOO]-	140.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Oxo-4-(3-pyridyl)-butanamide	NC(=O)CCC(=O)C1=CN=CC=C1	2543.3	Standard polar	33892256
4-Oxo-4-(3-pyridyl)-butanamide	NC(=O)CCC(=O)C1=CN=CC=C1	1781.1	Standard non polar	33892256
4-Oxo-4-(3-pyridyl)-butanamide	NC(=O)CCC(=O)C1=CN=CC=C1	1897.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Oxo-4-(3-pyridyl)-butanamide,1TMS,isomer #1	C[Si](C)(C)NC(=O)CCC(=O)C1=CC=CN=C1	1899.2	Semi standard non polar	33892256
4-Oxo-4-(3-pyridyl)-butanamide,1TMS,isomer #1	C[Si](C)(C)NC(=O)CCC(=O)C1=CC=CN=C1	1900.7	Standard non polar	33892256
4-Oxo-4-(3-pyridyl)-butanamide,1TMS,isomer #1	C[Si](C)(C)NC(=O)CCC(=O)C1=CC=CN=C1	2442.7	Standard polar	33892256
4-Oxo-4-(3-pyridyl)-butanamide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)CCC(=O)C1=CC=CN=C1)[Si](C)(C)C	1971.3	Semi standard non polar	33892256
4-Oxo-4-(3-pyridyl)-butanamide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)CCC(=O)C1=CC=CN=C1)[Si](C)(C)C	2037.2	Standard non polar	33892256
4-Oxo-4-(3-pyridyl)-butanamide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)CCC(=O)C1=CC=CN=C1)[Si](C)(C)C	2369.1	Standard polar	33892256
4-Oxo-4-(3-pyridyl)-butanamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CCC(=O)C1=CC=CN=C1	2136.4	Semi standard non polar	33892256
4-Oxo-4-(3-pyridyl)-butanamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CCC(=O)C1=CC=CN=C1	2123.8	Standard non polar	33892256
4-Oxo-4-(3-pyridyl)-butanamide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CCC(=O)C1=CC=CN=C1	2545.8	Standard polar	33892256
4-Oxo-4-(3-pyridyl)-butanamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)CCC(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C	2418.8	Semi standard non polar	33892256
4-Oxo-4-(3-pyridyl)-butanamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)CCC(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C	2493.7	Standard non polar	33892256
4-Oxo-4-(3-pyridyl)-butanamide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)CCC(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C	2511.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Oxo-4-(3-pyridyl)-butanamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-4900000000-fca086f20b800603ae03	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Oxo-4-(3-pyridyl)-butanamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - 4-Oxo-4-(3-pyridyl)-butanamide 10V, Positive-QTOF	splash10-03fr-0900000000-01a52ea89a85a2079640	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-4-(3-pyridyl)-butanamide 20V, Positive-QTOF	splash10-0bt9-1900000000-b1e5ab7bb6c0dafba12e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-4-(3-pyridyl)-butanamide 40V, Positive-QTOF	splash10-0a4i-9500000000-bced671069cb9f33d2c8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-4-(3-pyridyl)-butanamide 10V, Negative-QTOF	splash10-004i-0900000000-8e5b87f8c01e7c9f1712	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-4-(3-pyridyl)-butanamide 20V, Negative-QTOF	splash10-004i-3900000000-6ead6a151969f35cfe77	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-4-(3-pyridyl)-butanamide 40V, Negative-QTOF	splash10-0006-9000000000-c66af7319e42c761ee8b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-4-(3-pyridyl)-butanamide 10V, Negative-QTOF	splash10-004i-0900000000-86fad4d7edf0e4479130	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-4-(3-pyridyl)-butanamide 20V, Negative-QTOF	splash10-004i-9300000000-b00d85a32d37d06c85f2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-4-(3-pyridyl)-butanamide 40V, Negative-QTOF	splash10-004l-9100000000-1a65c0089597eefe4bfd	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-4-(3-pyridyl)-butanamide 10V, Positive-QTOF	splash10-004i-0900000000-70f72c44c2c8183d817a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-4-(3-pyridyl)-butanamide 20V, Positive-QTOF	splash10-01q9-1900000000-e8383d9449509ffdc21d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Oxo-4-(3-pyridyl)-butanamide 40V, Positive-QTOF	splash10-0563-9400000000-acc23fcc3bf2de0b7f65	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

Cytoplasm

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

FDB022521

KNApSAcK ID

Not Available

Chemspider ID

422

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6122

PubChem Compound

435

PDB ID

Not Available

ChEBI ID

166502

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Eldirdiri N, Ulgen M, Jacob P 3rd, Gorrod JW: The in vitro metabolism of norcotinine and related biotransformation products by microsomal preparations. Eur J Drug Metab Pharmacokinet. 1997 Oct-Dec;22(4):385-90. [PubMed:9512938 ]
BOWMAN ER, McKENNIS H Jr: Studies on the metabolism of (-)-cotinine in the human. J Pharmacol Exp Ther. 1962 Mar;135:306-11. [PubMed:13872096 ]

Showing metabocard for 4-Oxo-4-(3-pyridyl)-butanamide (HMDB0001267)

MOL for HMDB0001267 (4-Oxo-4-(3-pyridyl)-butanamide)

3D MOL for HMDB0001267 (4-Oxo-4-(3-pyridyl)-butanamide)

3D SDF for HMDB0001267 (4-Oxo-4-(3-pyridyl)-butanamide)

3D-SDF for HMDB0001267 (4-Oxo-4-(3-pyridyl)-butanamide)

PDB for HMDB0001267 (4-Oxo-4-(3-pyridyl)-butanamide)

3D PDB for HMDB0001267 (4-Oxo-4-(3-pyridyl)-butanamide)

SMILES for HMDB0001267 (4-Oxo-4-(3-pyridyl)-butanamide)

INCHI for HMDB0001267 (4-Oxo-4-(3-pyridyl)-butanamide)

Structure for HMDB0001267 (4-Oxo-4-(3-pyridyl)-butanamide)

3D Structure for HMDB0001267 (4-Oxo-4-(3-pyridyl)-butanamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra