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Showing metabocard for 3-Methylpyridine (HMDB0061887)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:56:38 UTC
Update Date2023-02-21 17:30:33 UTC
HMDB IDHMDB0061887
Secondary Accession Numbers
  • HMDB61887
Metabolite Identification
Common Name3-Methylpyridine
Description3-Methylpyridine, also known as beta-picoline or 3-mepy, belongs to the class of organic compounds known as methylpyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a methyl group. 3-Methylpyridine is a very strong basic compound (based on its pKa). A methylpyridine that is pyridine substituted by a methyl group at position 3. Outside of the human body, 3-Methylpyridine has been detected, but not quantified in, sweet oranges and tea. This could make 3-methylpyridine a potential biomarker for the consumption of these foods.
Structure
Data?1677000633
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0061887 (3-Methylpyridine)


  Mrv1652304272018142D          

  7  7  0  0  0  0            999 V2000
   -0.8250   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  2  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
Download

3D MOL for HMDB0061887 (3-Methylpyridine)

HMDB0061887
     RDKit          3D
3-Methylpyridine
 14 14  0  0  0  0  0  0  0  0999 V2000
   -2.0289    0.4087   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5906    0.0144   -0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3848    0.9748    0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    0.5822    0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974   -0.7435    0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1046   -1.6398    0.0128 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865   -1.3040   -0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6762   -0.4838    0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2432    0.7551   -1.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2815    1.2082    0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0654    2.0007    0.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4744    1.3440    0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1385   -1.0522    0.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9721   -2.0649   -0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  7 14  1  0
M  END
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3D SDF for HMDB0061887 (3-Methylpyridine)


  Mrv1652304272018142D          

  7  7  0  0  0  0            999 V2000
   -0.8250   -1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  2  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061887

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CN=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H7N/c1-6-3-2-4-7-5-6/h2-5H,1H3

> <INCHI_KEY>
ITQTTZVARXURQS-UHFFFAOYSA-N

> <FORMULA>
C6H7N

> <MOLECULAR_WEIGHT>
93.1265

> <EXACT_MASS>
93.057849229

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
10.31154883866584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methylpyridine

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
1.2689947783333335

> <ALOGPS_LOGS>
0.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
5.627866775155743

> <JCHEM_POLAR_SURFACE_AREA>
12.89

> <JCHEM_REFRACTIVITY>
28.942299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.97e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methylpyridine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0061887 (3-Methylpyridine)

HMDB0061887
     RDKit          3D
3-Methylpyridine
 14 14  0  0  0  0  0  0  0  0999 V2000
   -2.0289    0.4087   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5906    0.0144   -0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3848    0.9748    0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    0.5822    0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974   -0.7435    0.1689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1046   -1.6398    0.0128 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865   -1.3040   -0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6762   -0.4838    0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2432    0.7551   -1.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2815    1.2082    0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0654    2.0007    0.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4744    1.3440    0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1385   -1.0522    0.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9721   -2.0649   -0.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  5 13  1  0
  7 14  1  0
M  END
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PDB for HMDB0061887 (3-Methylpyridine)

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0      -1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.770   1.334   0.000  0.00  0.00           N+0
CONECT    1    6                                                            
CONECT    2    3    4                                                       
CONECT    3    2    6                                                       
CONECT    4    2    7                                                       
CONECT    5    6    7                                                       
CONECT    6    1    3    5                                                  
CONECT    7    4    5                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END
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3D PDB for HMDB0061887 (3-Methylpyridine)

COMPND    HMDB0061887
HETATM    1  C1  UNL     1      -2.029   0.409  -0.184  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.591   0.014  -0.060  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.385   0.975   0.098  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.714   0.582   0.210  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.097  -0.743   0.169  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.105  -1.640   0.013  1.00  0.00           N  
HETATM    7  C6  UNL     1      -0.187  -1.304  -0.099  1.00  0.00           C  
HETATM    8  H1  UNL     1      -2.676  -0.484   0.010  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.243   0.755  -1.219  1.00  0.00           H  
HETATM   10  H3  UNL     1      -2.282   1.208   0.570  1.00  0.00           H  
HETATM   11  H4  UNL     1       0.065   2.001   0.127  1.00  0.00           H  
HETATM   12  H5  UNL     1       2.474   1.344   0.334  1.00  0.00           H  
HETATM   13  H6  UNL     1       3.139  -1.052   0.257  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.972  -2.065  -0.226  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    3    7
CONECT    3    4   11
CONECT    4    5    5   12
CONECT    5    6   13
CONECT    6    7    7
CONECT    7   14
END
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SMILES for HMDB0061887 (3-Methylpyridine)

CC1=CN=CC=C1
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INCHI for HMDB0061887 (3-Methylpyridine)

InChI=1S/C6H7N/c1-6-3-2-4-7-5-6/h2-5H,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
3-MepyChEBI
3-PicolineChEBI
beta-PicolineChEBI
m-MethylpyridineChEBI
m-PicolineChEBI
b-PicolineGenerator
Β-picolineGenerator
Chemical FormulaC6H7N
Average Molecular Weight93.1265
Monoisotopic Molecular Weight93.057849229
IUPAC Name3-methylpyridine
Traditional Name3-methylpyridine
CAS Registry Number108-99-6
SMILES
CC1=CN=CC=C1
InChI Identifier
InChI=1S/C6H7N/c1-6-3-2-4-7-5-6/h2-5H,1H3
InChI KeyITQTTZVARXURQS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methylpyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a methyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassMethylpyridines
Direct ParentMethylpyridines
Alternative Parents
Substituents
  • Methylpyridine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateNot Available
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 Solubility197 g/LALOGPS
logP1.11ALOGPS
logP1.27ChemAxon
logS0.33ALOGPS
pKa (Strongest Basic)5.63ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.89 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.94 m³·mol⁻¹ChemAxon
Polarizability10.31 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+116.43131661259
DarkChem[M-H]-112.56231661259
DeepCCS[M+H]+120.35730932474
DeepCCS[M-H]-117.87430932474
DeepCCS[M-2H]-154.04230932474
DeepCCS[M+Na]+128.7630932474
AllCCS[M+H]+115.132859911
AllCCS[M+H-H2O]+109.832859911
AllCCS[M+NH4]+120.032859911
AllCCS[M+Na]+121.432859911
AllCCS[M-H]-117.932859911
AllCCS[M+Na-2H]-120.932859911
AllCCS[M+HCOO]-124.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-MethylpyridineCC1=CC=CN=C11296.9Standard polar33892256
3-MethylpyridineCC1=CC=CN=C1847.7Standard non polar33892256
3-MethylpyridineCC1=CC=CN=C1866.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Methylpyridine EI-B (Non-derivatized)splash10-00kf-9000000000-5fb57b3d6b75f2db13ce2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methylpyridine EI-B (Non-derivatized)splash10-0006-9000000000-66864d74d8303f94af132017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methylpyridine EI-B (Non-derivatized)splash10-0006-9000000000-6547e160a6da43a20e112017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methylpyridine EI-B (Non-derivatized)splash10-00kf-9000000000-759c5b98b6c617c91a182017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methylpyridine EI-B (Non-derivatized)splash10-0006-9000000000-f5d09461ea2a38433f8f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methylpyridine EI-B (Non-derivatized)splash10-00kf-9000000000-5fb57b3d6b75f2db13ce2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methylpyridine EI-B (Non-derivatized)splash10-0006-9000000000-66864d74d8303f94af132018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methylpyridine EI-B (Non-derivatized)splash10-0006-9000000000-6547e160a6da43a20e112018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methylpyridine EI-B (Non-derivatized)splash10-00kf-9000000000-759c5b98b6c617c91a182018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Methylpyridine EI-B (Non-derivatized)splash10-0006-9000000000-f5d09461ea2a38433f8f2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylpyridine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-f6fe3e5eff0b70caf9df2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methylpyridine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylpyridine 30V, Positive-QTOFsplash10-002f-9000000000-cd9c86e8e1509d8691ac2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylpyridine 10V, Positive-QTOFsplash10-0006-9000000000-dca4dbfeb3fd9d6723712021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylpyridine 0V, Positive-QTOFsplash10-0006-9000000000-a779bb95300133cc49692021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylpyridine 10V, Positive-QTOFsplash10-0006-9000000000-3ec3829581db715ed2a42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylpyridine 0V, Positive-QTOFsplash10-0006-9000000000-c71db157914608ef8bef2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Methylpyridine 30V, Positive-QTOFsplash10-002f-9000000000-09247933683d0520b05f2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylpyridine 10V, Positive-QTOFsplash10-0006-9000000000-e1e55a4a73fed66115402015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylpyridine 20V, Positive-QTOFsplash10-0006-9000000000-2bd650731ad9e55181092015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylpyridine 40V, Positive-QTOFsplash10-014i-9000000000-55acc7495020901c24ef2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylpyridine 10V, Negative-QTOFsplash10-0006-9000000000-5d5495ca47309e6ea21c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylpyridine 20V, Negative-QTOFsplash10-0006-9000000000-d85c0691680bf01565ed2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylpyridine 40V, Negative-QTOFsplash10-00kf-9000000000-487e134234972a5ca7c02015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylpyridine 10V, Positive-QTOFsplash10-0006-9000000000-dd74f41efa97537d70c42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylpyridine 20V, Positive-QTOFsplash10-00kf-9000000000-d1804d757cfdefdbc8272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylpyridine 40V, Positive-QTOFsplash10-0gb9-9000000000-437c0b398a6831a28ccd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylpyridine 10V, Negative-QTOFsplash10-0006-9000000000-eef4c1f804c025cbb9782021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylpyridine 20V, Negative-QTOFsplash10-0006-9000000000-eef4c1f804c025cbb9782021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methylpyridine 40V, Negative-QTOFsplash10-00kf-9000000000-6bcf220724a1cffc08052021-09-22Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01996
Phenol Explorer Compound IDNot Available
FooDB IDFDB004416
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Methylpyridine
METLIN IDNot Available
PubChem Compound7970
PDB IDNot Available
ChEBI ID39922
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Veena Kushwaha, Singh RP, Katyal M: Metal complexation with 2-hydroxy-6-methylpyridine-3-carboxylic acid. Talanta. 1973 Apr;20(4):431-2. [PubMed:18961302 ]
  2. Wikipedia [Link]
  3. Bernard Gupton, 'Process for making 3-amino-2-chloro-4-methylpyridine.' U.S. Patent US20020052507, issued May 02, 2002. [Link]
  4. Helmut Beschke, Hans Schaefer, Gerd Schreyer, Wilhelm Alfons Schuler, Wolfgang Weigert, 'Catalyst for the production of pyridine and 3-methylpyridine.' U.S. Patent US3960766, issued February, 1971. [Link]
  5. Helmut Beschke, Franz-Ludwig Dahm, Heinz Friedrich, Gerd Schreyer, 'Process for the recovery of pyridine and 3-methylpyridine.' U.S. Patent US4237299, issued October, 1979. [Link]
  6. Dev D. Suresh, Robert DiCosimo, Richard Loiseau, Maria S. Friedrich, Hsiao-Chiung Szabo, 'Preparation of 3-methylpyridine from 2-methylglutaronitrile.' U.S. Patent US5066809, issued June, 1985. [Link]