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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

HMDB0001004

Secondary Accession Numbers

HMDB01004

Metabolite Identification

Common Name

Oxoamide

Description

Oxoamide 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. Oxoamide 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 oxoamide a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Oxoamide.

Structure

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

HMDB01004.mol
  Mrv0541 02231218522D          

 14 14  0  0  0  0            999 V2000
    1.4292    1.0307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    1.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292    0.2061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    2.2689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    2.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292   -2.2689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292   -1.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146   -2.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7146   -1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  4  2  0  0  0  0
  5  6  1  0  0  0  0
  5  2  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 10 11  1  0  0  0  0
 10  2  1  0  0  0  0
 11  4  1  0  0  0  0
  4 12  1  0  0  0  0
  8 12  2  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001004

> <DATABASE_NAME>
hmdb

> <SMILES>
CNC(=O)CCC(=O)C1=CN=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2O2/c1-11-10(14)5-4-9(13)8-3-2-6-12-7-8/h2-3,6-7H,4-5H2,1H3,(H,11,14)

> <INCHI_KEY>
WOOSCPWOYYLIHS-UHFFFAOYSA-N

> <FORMULA>
C10H12N2O2

> <MOLECULAR_WEIGHT>
192.2145

> <EXACT_MASS>
192.089877638

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
19.71044168108861

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-methyl-4-oxo-4-(pyridin-3-yl)butanamide

> <ALOGPS_LOGP>
0.01

> <JCHEM_LOGP>
-0.4451828933333335

> <ALOGPS_LOGS>
-1.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.647565446054486

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.40984783152761

> <JCHEM_PKA_STRONGEST_BASIC>
3.8074177835320424

> <JCHEM_POLAR_SURFACE_AREA>
59.06

> <JCHEM_REFRACTIVITY>
51.9161

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-methyl-4-oxo-4-(pyridin-3-yl)butanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB01004.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       2.668   1.924   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   2.693   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.668   0.385   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.334  -0.385   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.334   4.235   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.668   5.005   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -2.668  -4.235   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -2.668  -2.693   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -5.005   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.924   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -1.924   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -2.693   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -4.235   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    5   10                                                  
CONECT    3    4                                                            
CONECT    4    3   11   12                                                  
CONECT    5    6    2                                                       
CONECT    6    5                                                            
CONECT    7    8    9                                                       
CONECT    8    7   12                                                       
CONECT    9    7   14                                                       
CONECT   10   11    2                                                       
CONECT   11   10    4                                                       
CONECT   12    4    8   13                                                  
CONECT   13   12   14                                                       
CONECT   14    9   13                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
gamma-(3-Pyridyl)-gamma-oxo-N-methylbutyramide	MeSH
4-(3-Pyridyl)-4-oxo-N-methylbutyramide	HMDB
4-oxo-4-(3-Pyridyl)-N-methylbutanamide	HMDB
N-Methyl-gamma-oxo-3-pyridinebutanamide	HMDB
N-Methyl-4-oxo-4-(pyridin-3-yl)butanimidate	Generator, HMDB
Oxoamide	MeSH

Chemical Formula

C₁₀H₁₂N₂O₂

Average Molecular Weight

192.2145

Monoisotopic Molecular Weight

192.089877638

IUPAC Name

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

Traditional Name

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

CAS Registry Number

713-05-3

SMILES

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

InChI Identifier

InChI=1S/C10H12N2O2/c1-11-10(14)5-4-9(13)8-3-2-6-12-7-8/h2-3,6-7H,4-5H2,1H3,(H,11,14)

InChI Key

WOOSCPWOYYLIHS-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
N-acyl-amine
Pyridine
Fatty acyl
Heteroaromatic compound
Secondary carboxylic acid amide
Carboxamide group
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic nitrogen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a small molecule (CPD-3191 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0001004)

Source

Endogenous

Endogenous (HMDB: HMDB0001004)

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	0.0043 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.69	LI,NY & GORROD,JW (1992)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.45 g/L	ALOGPS
logP	0.01	ALOGPS
logP	-0.45	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	14.41	ChemAxon
pKa (Strongest Basic)	3.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	51.92 m³·mol⁻¹	ChemAxon
Polarizability	19.71 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]+	145.465	31661259
DarkChem	[M-H]-	141.667	31661259
AllCCS	[M+H]+	142.665	32859911
AllCCS	[M-H]-	144.351	32859911
DeepCCS	[M+H]+	140.863	30932474
DeepCCS	[M-H]-	138.304	30932474
DeepCCS	[M-2H]-	173.918	30932474
DeepCCS	[M+Na]+	149.288	30932474
AllCCS	[M+H]+	142.7	32859911
AllCCS	[M+H-H2O]+	138.5	32859911
AllCCS	[M+NH4]+	146.5	32859911
AllCCS	[M+Na]+	147.6	32859911
AllCCS	[M-H]-	144.4	32859911
AllCCS	[M+Na-2H]-	145.1	32859911
AllCCS	[M+HCOO]-	145.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oxoamide	CNC(=O)CCC(=O)C1=CN=CC=C1	2726.2	Standard polar	33892256
Oxoamide	CNC(=O)CCC(=O)C1=CN=CC=C1	1907.6	Standard non polar	33892256
Oxoamide	CNC(=O)CCC(=O)C1=CN=CC=C1	1946.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Oxoamide,1TMS,isomer #1	CN(C(=O)CCC(=O)C1=CC=CN=C1)[Si](C)(C)C	1904.1	Semi standard non polar	33892256
Oxoamide,1TMS,isomer #1	CN(C(=O)CCC(=O)C1=CC=CN=C1)[Si](C)(C)C	1960.0	Standard non polar	33892256
Oxoamide,1TMS,isomer #1	CN(C(=O)CCC(=O)C1=CC=CN=C1)[Si](C)(C)C	2400.1	Standard polar	33892256
Oxoamide,1TBDMS,isomer #1	CN(C(=O)CCC(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C	2132.5	Semi standard non polar	33892256
Oxoamide,1TBDMS,isomer #1	CN(C(=O)CCC(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C	2194.1	Standard non polar	33892256
Oxoamide,1TBDMS,isomer #1	CN(C(=O)CCC(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C	2518.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Oxoamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-4900000000-b4127a0f5559e0c1ec06	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxoamide 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 - Oxoamide 10V, Positive-QTOF	splash10-03dl-0900000000-e774a91f322b671f415a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxoamide 20V, Positive-QTOF	splash10-0a4i-2900000000-e5a5a9ae896687f43c25	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxoamide 40V, Positive-QTOF	splash10-0a4i-9700000000-4bb4da8a151d7770a636	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxoamide 10V, Negative-QTOF	splash10-0006-0900000000-f2612c39399a985683ff	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxoamide 20V, Negative-QTOF	splash10-01r6-3900000000-7f95fbc3d468a8d11e87	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxoamide 40V, Negative-QTOF	splash10-056u-9300000000-9cebd2b0f8a67a81dda9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxoamide 10V, Negative-QTOF	splash10-0006-0900000000-b12a30a94a0bd68c8be3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxoamide 20V, Negative-QTOF	splash10-00bc-9200000000-3d98bed4b61fbe2e42a1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxoamide 40V, Negative-QTOF	splash10-002f-9100000000-f798930c8874ff9f603e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxoamide 10V, Positive-QTOF	splash10-0006-0900000000-28e5a41c5b9b22fade09	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxoamide 20V, Positive-QTOF	splash10-001i-2900000000-d37a2ff651bf32777825	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxoamide 40V, Positive-QTOF	splash10-053r-9300000000-7028e1d53509091e52e9	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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 (predicted from logP)

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

FDB022363

KNApSAcK ID

Not Available

Chemspider ID

423

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5934

PubChem Compound

436

PDB ID

Not Available

ChEBI ID

166504

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1381801

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Oxoamide (HMDB0001004)

MOL for HMDB0001004 (Oxoamide)

3D MOL for HMDB0001004 (Oxoamide)

3D SDF for HMDB0001004 (Oxoamide)

3D-SDF for HMDB0001004 (Oxoamide)

PDB for HMDB0001004 (Oxoamide)

3D PDB for HMDB0001004 (Oxoamide)

SMILES for HMDB0001004 (Oxoamide)

INCHI for HMDB0001004 (Oxoamide)

Structure for HMDB0001004 (Oxoamide)

3D Structure for HMDB0001004 (Oxoamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra