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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-01-29 12:50:38 UTC

Update Date

2023-02-21 17:17:29 UTC

HMDB ID

HMDB0011603

Secondary Accession Numbers

HMDB11603

Metabolite Identification

Common Name

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone

Description

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (also known as NNK) is a potent tobacco-specific nitrosamine derived from nicotine. It plays a key role in human tobacco-related cancers (PMID:24830349 ). NNK is found in cured tobacco and is also produced during its burning or combustion in cigarettes. NNK is abundantly present in cigarette smoke (20-280 ng/cigarette). Electronic cigarettes (e-cigarettes) do not convert nicotine to NNK due to their lower operating temperatures. NNK is a procarcinogen. This means it must be activated by cytochrome P450 enzymes (CYP2A6 and CYP2B6) to become a carcinogen (PMID:24830349 ). NNK can also be activated by myeloperoxidase (MPO) and epoxide hydrolase (EPHX1). All activation processes lead to the formation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol from NNK, which is called NNAL (PMID:24830349 ). NNAL can be detoxified via glucuronidation via glucuronidases. Once NNK is activated to NNAL, this compound initiates a cascade of signalling pathways (for example ERK1/2, NF‚âà√≠‚Äö√†¬¥B, PI3K/Akt, MAPK, FasL, K-ras), resulting in uncontrolled cellular proliferation and tumorigenesis. NNK is known as a mutagen and can cause point mutations that affect cell growth proliferation and differentiation. NNK also targets the SULT1A1, TGF-beta, and angiotensin II genes. NNK plays a key role in gene silencing, gene modification, and carcinogenesis. NNK has been implicated in tumour promotion by activating nicotinic acetylcholine receptors (nAChRs) and ‚âà√≠‚Äö√¢¬ß-adrenergic receptors (‚âà√≠‚Äö√¢¬ß-AdrRs), leading to downstream activation of parallel signal transduction pathways that facilitate tumour progression (PMID:24830349 ). Antioxidants such as EGCG (from green tea) inhibit lung tumorigenesis by NNK.

Structure

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

HMDB0011603
     RDKit          3D
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone
 28 28  0  0  0  0  0  0  0  0999 V2000
    4.3895   -0.4625   -1.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558   -0.4931   -0.3273 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2533    0.6133   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0140    0.4870    0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0949   -0.6300    0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0579   -0.5824    0.9930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9285   -1.0285    2.1520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3269   -0.0398    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5435    0.4867   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8081    0.9903   -0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8407    0.9715   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5969    0.4540    1.1175 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4226   -0.0313    1.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8946   -1.5910    0.4926 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2264   -2.7376    0.0596 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7643   -1.4772   -1.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1880    0.0581   -2.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1437    0.1424   -0.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0131    0.8996   -1.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8353    1.5162   -0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3169    0.3409    1.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4609    1.4677    0.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1911   -0.5820   -1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6425   -1.6020    0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7460    0.5264   -1.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9205    1.3899   -1.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8000    1.3719   -0.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2104   -0.4586    2.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  2 14  1  0
 14 15  2  0
 13  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
M  END


  Mrv1652302242018342D          

 15 15  0  0  0  0            999 V2000
   25.0071  -14.9725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0071  -15.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7215  -16.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4361  -15.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1505  -16.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8650  -15.7975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8650  -14.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5794  -16.2101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2939  -15.7975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2926  -16.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2926  -17.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5782  -17.4476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8637  -17.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8637  -16.2101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5782  -15.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
 10 15  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0011603

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(CCCC(=O)C1=CN=CC=C1)N=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H13N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8H,3,5,7H2,1H3

> <INCHI_KEY>
FLAQQSHRLBFIEZ-UHFFFAOYSA-N

> <FORMULA>
C10H13N3O2

> <MOLECULAR_WEIGHT>
207.2291

> <EXACT_MASS>
207.100776675

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.119555418078534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butan-1-one

> <ALOGPS_LOGP>
0.33

> <JCHEM_LOGP>
0.5788376940000002

> <ALOGPS_LOGS>
-2.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.4709973788

> <JCHEM_PKA_STRONGEST_BASIC>
3.955183166091193

> <JCHEM_POLAR_SURFACE_AREA>
62.63

> <JCHEM_REFRACTIVITY>
57.249700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nnk (carcinogen)

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011603
     RDKit          3D
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone
 28 28  0  0  0  0  0  0  0  0999 V2000
    4.3895   -0.4625   -1.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558   -0.4931   -0.3273 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2533    0.6133   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0140    0.4870    0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0949   -0.6300    0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0579   -0.5824    0.9930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9285   -1.0285    2.1520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3269   -0.0398    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5435    0.4867   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8081    0.9903   -0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8407    0.9715   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5969    0.4540    1.1175 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4226   -0.0313    1.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8946   -1.5910    0.4926 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2264   -2.7376    0.0596 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7643   -1.4772   -1.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1880    0.0581   -2.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1437    0.1424   -0.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0131    0.8996   -1.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8353    1.5162   -0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3169    0.3409    1.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4609    1.4677    0.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1911   -0.5820   -1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6425   -1.6020    0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7460    0.5264   -1.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9205    1.3899   -1.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8000    1.3719   -0.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2104   -0.4586    2.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  2 14  1  0
 14 15  2  0
 13  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
M  END

HEADER    PROTEIN                                 24-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-20         0                                  
HETATM    1  O   UNK     0      46.680 -27.949   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      46.680 -29.489   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      48.013 -30.259   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      49.347 -29.489   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      50.681 -30.259   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      52.015 -29.489   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      52.015 -27.949   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      53.348 -30.259   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      54.682 -29.489   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      45.346 -30.259   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      45.346 -31.799   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      44.013 -32.569   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      42.679 -31.799   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      42.679 -30.259   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      44.013 -29.489   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8                                                            
CONECT   10    2   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   10   14                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0011603
HETATM    1  C1  UNL     1       4.389  -0.462  -1.145  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.156  -0.493  -0.327  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.253   0.613  -0.375  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.014   0.487   0.442  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.095  -0.630   0.081  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.058  -0.582   0.993  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.928  -1.028   2.152  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.327  -0.040   0.590  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.544   0.487  -0.661  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.808   0.990  -0.989  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.841   0.971  -0.089  1.00  0.00           C  
HETATM   12  N2  UNL     1      -4.597   0.454   1.118  1.00  0.00           N  
HETATM   13  C10 UNL     1      -3.423  -0.031   1.470  1.00  0.00           C  
HETATM   14  N3  UNL     1       2.895  -1.591   0.493  1.00  0.00           N  
HETATM   15  O2  UNL     1       3.226  -2.738   0.060  1.00  0.00           O  
HETATM   16  H1  UNL     1       4.764  -1.477  -1.273  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.188   0.058  -2.094  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.144   0.142  -0.589  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.013   0.900  -1.447  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.835   1.516  -0.005  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.317   0.341   1.507  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.461   1.468   0.404  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.191  -0.582  -1.012  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.643  -1.602   0.155  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.746   0.526  -1.410  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.920   1.390  -1.981  1.00  0.00           H  
HETATM   27  H12 UNL     1      -5.800   1.372  -0.387  1.00  0.00           H  
HETATM   28  H13 UNL     1      -3.210  -0.459   2.456  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   14
CONECT    3    4   19   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7    7    8
CONECT    8    9    9   13
CONECT    9   10   25
CONECT   10   11   11   26
CONECT   11   12   27
CONECT   12   13   13
CONECT   13   28
CONECT   14   15   15
END

HMDB0011603
     RDKit          3D
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone
 28 28  0  0  0  0  0  0  0  0999 V2000
    4.3895   -0.4625   -1.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1558   -0.4931   -0.3273 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2533    0.6133   -0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0140    0.4870    0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0949   -0.6300    0.0805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0579   -0.5824    0.9930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9285   -1.0285    2.1520 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3269   -0.0398    0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5435    0.4867   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8081    0.9903   -0.9892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8407    0.9715   -0.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5969    0.4540    1.1175 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4226   -0.0313    1.4699 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8946   -1.5910    0.4926 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2264   -2.7376    0.0596 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7643   -1.4772   -1.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1880    0.0581   -2.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1437    0.1424   -0.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0131    0.8996   -1.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8353    1.5162   -0.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3169    0.3409    1.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4609    1.4677    0.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1911   -0.5820   -1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6425   -1.6020    0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7460    0.5264   -1.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9205    1.3899   -1.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8000    1.3719   -0.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2104   -0.4586    2.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  2 14  1  0
 14 15  2  0
 13  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(N-Methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone	ChEBI
NNK	ChEBI
NNK (Carcinogen)	ChEBI
4-(Methylnitrosoamino)-1-(3-pyridyl)-1-butanone	HMDB
4'-(Nitrosomethylamino)-1-(3-pyridyl)-1-butanone	HMDB
NNK CPD	HMDB
4-(N-Nitrosomethylamino)-1-(3-pyridyl)-1-butanone	HMDB
4-(Methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone	HMDB
4-(Methylintrosamino)-1-(3-pyridyl)-1-butanone	HMDB
4-(Methylnitrosoamino)-1-(3-pyridinyl)-1-butanone	HMDB
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone	ChEBI

Chemical Formula

C₁₀H₁₃N₃O₂

Average Molecular Weight

207.2291

Monoisotopic Molecular Weight

207.100776675

IUPAC Name

4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butan-1-one

Traditional Name

nnk (carcinogen)

CAS Registry Number

64091-91-4

SMILES

CN(CCCC(=O)C1=CN=CC=C1)N=O

InChI Identifier

InChI=1S/C10H13N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8H,3,5,7H2,1H3

InChI Key

FLAQQSHRLBFIEZ-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
Pyridine
Heteroaromatic compound
Organic n-nitroso compound
Organic nitroso compound
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyridines (CHEBI:32692 )
nitrosamine (CHEBI:32692 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0011603)

Organ

Liver (HMDB: HMDB0011603)
Kidney (HMDB: HMDB0011603)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0011603)

Cellular substructure

Cytoplasm (HMDB: HMDB0011603)

Source

Endogenous

Endogenous (HMDB: HMDB0011603)

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

Biological role

Drug metabolite (HMDB: HMDB0011603)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	64 °C	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	1.09 g/L	ALOGPS
logP	0.33	ALOGPS
logP	0.58	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	15.47	ChemAxon
pKa (Strongest Basic)	3.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	62.63 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	57.25 m³·mol⁻¹	ChemAxon
Polarizability	21.12 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	148.947	31661259
DarkChem	[M-H]-	144.433	31661259
DeepCCS	[M+H]+	142.703	30932474
DeepCCS	[M-H]-	140.002	30932474
DeepCCS	[M-2H]-	176.092	30932474
DeepCCS	[M+Na]+	151.631	30932474
AllCCS	[M+H]+	146.1	32859911
AllCCS	[M+H-H2O]+	142.1	32859911
AllCCS	[M+NH4]+	149.8	32859911
AllCCS	[M+Na]+	150.9	32859911
AllCCS	[M-H]-	148.8	32859911
AllCCS	[M+Na-2H]-	149.4	32859911
AllCCS	[M+HCOO]-	150.1	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.	3.21 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9111 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.19 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1459.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	276.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	134.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	75.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	312.1 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	371.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	98.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	909.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	199.9 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	1233.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	272.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	233.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	436.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	315.4 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	117.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone	CN(CCCC(=O)C1=CN=CC=C1)N=O	2486.9	Standard polar	33892256
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone	CN(CCCC(=O)C1=CN=CC=C1)N=O	1851.3	Standard non polar	33892256
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone	CN(CCCC(=O)C1=CN=CC=C1)N=O	1933.9	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 - 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-9800000000-57c49f29c9d7332bea22	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone 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-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone 10V, Positive-QTOF	splash10-0a4i-1980000000-6eed182d10c9a03751b7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone 20V, Positive-QTOF	splash10-0002-3910000000-5fed6b71985ed1afcab4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone 40V, Positive-QTOF	splash10-001m-9600000000-1c5f7245d666beff11f2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone 10V, Negative-QTOF	splash10-0a4i-3390000000-e76106f4b8f69d27d9aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone 20V, Negative-QTOF	splash10-0a70-9840000000-3d022ffc7f1a61b3d6d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone 40V, Negative-QTOF	splash10-056r-9100000000-1782fbf95a7044f769a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone 10V, Positive-QTOF	splash10-0002-0920000000-1d8ea81c64d584ea02d1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone 20V, Positive-QTOF	splash10-0002-1900000000-63e35eaa2366ca02b75d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone 40V, Positive-QTOF	splash10-001i-7900000000-5f96473ea00e041d2dcc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone 10V, Negative-QTOF	splash10-0a4i-0090000000-482b470c4a0ac6884d93	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone 20V, Negative-QTOF	splash10-0a6r-9820000000-35e475a0c732f383cc12	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone 40V, Negative-QTOF	splash10-00or-9300000000-37d4b4467865dbb44ac7	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	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+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

FDB028314

KNApSAcK ID

Not Available

Chemspider ID

43038

KEGG Compound ID

C16453

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

NNK

METLIN ID

Not Available

PubChem Compound

47289

PDB ID

Not Available

ChEBI ID

32692

Food Biomarker Ontology

Not Available

VMH ID

M00932

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Smith TJ, Guo Z, Guengerich FP, Yang CS: Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) by human cytochrome P450 1A2 and its inhibition by phenethyl isothiocyanate. Carcinogenesis. 1996 Apr;17(4):809-13. [PubMed:8625495 ]
Xue J, Yang S, Seng S: Mechanisms of Cancer Induction by Tobacco-Specific NNK and NNN. Cancers (Basel). 2014 May 14;6(2):1138-56. doi: 10.3390/cancers6021138. [PubMed:24830349 ]

Enzymes

Enzyme Details

1. Carbonyl reductase [NADPH] 1

General function:: Involved in oxidoreductase activity
Specific function:: NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:: CBR1
Uniprot ID:: P16152
Molecular weight:: 30374.73

Reactions

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone + NADPH + Hydrogen Ion → 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + NADP	details

Enzyme Details

2. Carbonyl reductase [NADPH] 3

General function:: Involved in oxidoreductase activity
Specific function:: Has low NADPH-dependent oxidoreductase activity towards 4-benzoylpyridine and menadione (in vitro).
Gene Name:: CBR3
Uniprot ID:: O75828
Molecular weight:: 30849.97

Reactions

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone + NADPH + Hydrogen Ion → 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + NADP	details

Enzyme Details

3. Corticosteroid 11-beta-dehydrogenase isozyme 1

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the reaction runs only in one direction, from 7-ketocholesterol to 7-beta-hydroxycholesterol (By similarity).
Gene Name:: HSD11B1
Uniprot ID:: P28845
Molecular weight:: 32400.665

Reactions

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone + NADPH + Hydrogen Ion → 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + NADP	details

Showing metabocard for 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (HMDB0011603)

MOL for HMDB0011603 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone)

3D MOL for HMDB0011603 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone)

3D SDF for HMDB0011603 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone)

3D-SDF for HMDB0011603 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone)

PDB for HMDB0011603 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone)

3D PDB for HMDB0011603 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone)

SMILES for HMDB0011603 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone)

INCHI for HMDB0011603 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone)

Structure for HMDB0011603 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone)

3D Structure for HMDB0011603 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions