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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-05-18 14:04:01 UTC

Update Date

2023-02-21 17:18:01 UTC

HMDB ID

HMDB0013704

Secondary Accession Numbers

HMDB13704

Metabolite Identification

Common Name

6-Methylnicotinamide

Description

6-Methylnicotinamide belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group. 6-Methylnicotinamide 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 6-methylnicotinamide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 6-Methylnicotinamide.

Structure

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

14393052
  Mrv1652304062013002D          

 21 21  0  0  0  0            999 V2000
    3.0790    1.1880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.2870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.1880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6934    0.3423    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0357    0.3423    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3943   -0.0191    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071   -0.7178    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9058   -0.9050    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.2063    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -1.5428    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.2110    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.6995    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0  0  0  0
  2  4  1  0  0  0  0
  2 11  2  0  0  0  0
  3 10  1  0  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  5  7  1  0  0  0  0
  5 12  1  0  0  0  0
  5 13  1  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  7 14  1  0  0  0  0
  7 15  1  0  0  0  0
  7 16  1  0  0  0  0
  8  9  2  0  0  0  0
  8 17  1  0  0  0  0
  9 11  1  0  0  0  0
  9 18  1  0  0  0  0
 11 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013704

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]N([H])C(=O)C1=C(N=C([H])C([H])=C1[H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C8H10N2O/c1-2-7-6(8(9)11)4-3-5-10-7/h3-5H,2H2,1H3,(H2,9,11)

> <INCHI_KEY>
GOIWNSRZUNIIRY-UHFFFAOYSA-N

> <FORMULA>
C8H10N2O

> <MOLECULAR_WEIGHT>
150.1778

> <EXACT_MASS>
150.079312952

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
15.67045743820218

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-ethylpyridine-3-carboxamide

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
0.4381196993333334

> <ALOGPS_LOGS>
-0.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.750026909518901

> <JCHEM_PKA_STRONGEST_BASIC>
4.401992778185274

> <JCHEM_POLAR_SURFACE_AREA>
55.980000000000004

> <JCHEM_REFRACTIVITY>
42.197900000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.79e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-ethylpyridine-3-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 14393052                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  O   UNK     0       5.747   2.218   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       5.747  -2.402   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       8.415   2.218   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.747  -0.862   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414  -0.092   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081  -0.092   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.080  -0.862   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415  -0.862   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415  -2.402   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081   1.448   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -3.172   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       5.028   0.639   0.000  0.00  0.00           H+0
HETATM   13  H   UNK     0       3.800   0.639   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0       2.603  -0.036   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       2.253  -1.340   0.000  0.00  0.00           H+0
HETATM   16  H   UNK     0       3.557  -1.689   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       9.242  -0.385   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       9.242  -2.880   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       7.081  -4.127   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       8.415   3.172   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       9.242   1.740   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2    4   11                                                       
CONECT    3   10   20   21                                                  
CONECT    4    2    5    6                                                  
CONECT    5    4    7   12   13                                             
CONECT    6    4    8   10                                                  
CONECT    7    5   14   15   16                                             
CONECT    8    6    9   17                                                  
CONECT    9    8   11   18                                                  
CONECT   10    1    3    6                                                  
CONECT   11    2    9   19                                                  
CONECT   12    5                                                            
CONECT   13    5                                                            
CONECT   14    7                                                            
CONECT   15    7                                                            
CONECT   16    7                                                            
CONECT   17    8                                                            
CONECT   18    9                                                            
CONECT   19   11                                                            
CONECT   20    3                                                            
CONECT   21    3                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Ethylpyridine-3-carboximidate	HMDB

Chemical Formula

C₈H₁₀N₂O

Average Molecular Weight

150.1778

Monoisotopic Molecular Weight

150.079312952

IUPAC Name

2-ethylpyridine-3-carboxamide

Traditional Name

2-ethylpyridine-3-carboxamide

CAS Registry Number

6960-22-1

SMILES

[H]N([H])C(=O)C1=C(N=C([H])C([H])=C1[H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C8H10N2O/c1-2-7-6(8(9)11)4-3-5-10-7/h3-5H,2H2,1H3,(H2,9,11)

InChI Key

GOIWNSRZUNIIRY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Nicotinamides

Alternative Parents

Substituents

Nicotinamide
Heteroaromatic compound
Primary carboxylic acid amide
Carboxamide group
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 18439883)

Source

Endogenous

Endogenous (HMDB: HMDB0013704)

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

Not Available

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	27.9 g/L	ALOGPS
logP	0.48	ALOGPS
logP	0.44	ChemAxon
logS	-0.73	ALOGPS
pKa (Strongest Acidic)	13.75	ChemAxon
pKa (Strongest Basic)	4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.98 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.2 m³·mol⁻¹	ChemAxon
Polarizability	15.67 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]+	131.55	31661259
DarkChem	[M-H]-	131.037	31661259
DeepCCS	[M+H]+	142.736	30932474
DeepCCS	[M-H]-	140.285	30932474
DeepCCS	[M-2H]-	174.83	30932474
DeepCCS	[M+Na]+	150.547	30932474
AllCCS	[M+H]+	132.6	32859911
AllCCS	[M+H-H2O]+	128.3	32859911
AllCCS	[M+NH4]+	136.7	32859911
AllCCS	[M+Na]+	137.9	32859911
AllCCS	[M-H]-	130.7	32859911
AllCCS	[M+Na-2H]-	132.1	32859911
AllCCS	[M+HCOO]-	133.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.23 minutes	32390414
Predicted by Siyang on May 30, 2022	8.7579 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.31 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	143.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	556.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	287.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	87.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	50.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	276.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	254.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	208.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	598.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	38.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	764.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	167.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	205.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	459.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	349.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	152.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Methylnicotinamide	[H]N([H])C(=O)C1=C(N=C([H])C([H])=C1[H])C([H])([H])C([H])([H])[H]	1966.7	Standard polar	33892256
6-Methylnicotinamide	[H]N([H])C(=O)C1=C(N=C([H])C([H])=C1[H])C([H])([H])C([H])([H])[H]	1320.9	Standard non polar	33892256
6-Methylnicotinamide	[H]N([H])C(=O)C1=C(N=C([H])C([H])=C1[H])C([H])([H])C([H])([H])[H]	1192.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6-Methylnicotinamide,1TMS,isomer #1	CCC1=NC=CC=C1C(=O)N[Si](C)(C)C	1515.5	Semi standard non polar	33892256
6-Methylnicotinamide,1TMS,isomer #1	CCC1=NC=CC=C1C(=O)N[Si](C)(C)C	1566.6	Standard non polar	33892256
6-Methylnicotinamide,1TMS,isomer #1	CCC1=NC=CC=C1C(=O)N[Si](C)(C)C	1949.0	Standard polar	33892256
6-Methylnicotinamide,2TMS,isomer #1	CCC1=NC=CC=C1C(=O)N([Si](C)(C)C)[Si](C)(C)C	1561.3	Semi standard non polar	33892256
6-Methylnicotinamide,2TMS,isomer #1	CCC1=NC=CC=C1C(=O)N([Si](C)(C)C)[Si](C)(C)C	1644.9	Standard non polar	33892256
6-Methylnicotinamide,2TMS,isomer #1	CCC1=NC=CC=C1C(=O)N([Si](C)(C)C)[Si](C)(C)C	1910.4	Standard polar	33892256
6-Methylnicotinamide,1TBDMS,isomer #1	CCC1=NC=CC=C1C(=O)N[Si](C)(C)C(C)(C)C	1734.3	Semi standard non polar	33892256
6-Methylnicotinamide,1TBDMS,isomer #1	CCC1=NC=CC=C1C(=O)N[Si](C)(C)C(C)(C)C	1756.8	Standard non polar	33892256
6-Methylnicotinamide,1TBDMS,isomer #1	CCC1=NC=CC=C1C(=O)N[Si](C)(C)C(C)(C)C	2103.1	Standard polar	33892256
6-Methylnicotinamide,2TBDMS,isomer #1	CCC1=NC=CC=C1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2016.4	Semi standard non polar	33892256
6-Methylnicotinamide,2TBDMS,isomer #1	CCC1=NC=CC=C1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2036.8	Standard non polar	33892256
6-Methylnicotinamide,2TBDMS,isomer #1	CCC1=NC=CC=C1C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2123.9	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Available	Male	Normal	18439883	details

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

FDB111643

KNApSAcK ID

Not Available

Chemspider ID

10549642

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methylnicotinamide

METLIN ID

Not Available

PubChem Compound

14393052

PDB ID

Not Available

ChEBI ID

88954

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

Not Available

Showing metabocard for 6-Methylnicotinamide (HMDB0013704)

MOL for HMDB0013704 (6-Methylnicotinamide)

3D MOL for HMDB0013704 (6-Methylnicotinamide)

3D SDF for HMDB0013704 (6-Methylnicotinamide)

3D-SDF for HMDB0013704 (6-Methylnicotinamide)

PDB for HMDB0013704 (6-Methylnicotinamide)

3D PDB for HMDB0013704 (6-Methylnicotinamide)

SMILES for HMDB0013704 (6-Methylnicotinamide)

INCHI for HMDB0013704 (6-Methylnicotinamide)

Structure for HMDB0013704 (6-Methylnicotinamide)

3D Structure for HMDB0013704 (6-Methylnicotinamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized