NP-MRD: Showing NP-Card for 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NP0000222)

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Record Information

Version

1.0

Created at

2009-01-29 12:50:38 UTC

Updated at

2021-06-30 02:06:18 UTC

NP-MRD ID

NP0000222

Secondary Accession Numbers

None

Natural Product 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>
NP0000222

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

207.2291 Da

Monoisotopic Mass

207.10078 Da

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=CC=CN=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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, simulated)	Varshavi.d26			2021-08-10	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0011603

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]
Zhang L, Qu Z, Song A, Yang J, Yu J, Zhang W, Zhuang C: Garlic oil blocks tobacco carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced lung tumorigenesis by inducing phase II drug-metabolizing enzymes. Food Chem Toxicol. 2021 Sep 23;157:112581. doi: 10.1016/j.fct.2021.112581. [PubMed:34562529 ]
Jin SW, Im JS, Park JH, Kim HG, Lee GH, Kim SJ, Kwack SJ, Kim KB, Chung KH, Lee BM, Kacew S, Jeong HG, Kim HS: Effects of tobacco compound 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) on the expression of epigenetically regulated genes in lung carcinogenesis. J Toxicol Environ Health A. 2021 Aug 29:1-16. doi: 10.1080/15287394.2021.1965059. [PubMed:34459362 ]
Hu SC, Min S, Kang HK, Yang DJ, Lewis SM, Davis KJ, Patton RE, Bryant MS, Sepehr E, Trbojevich R, Pearce MG, Bishop ME, Heflich RH, Maisha MP, Felton R, Chemerynski S, Yee SB, Coraggio M, Rosenfeldt H, Yeager RP, Howard PC, Tang Y: 14-Day Nose-Only Inhalation Toxicity and Haber's Rule Study of NNK in Sprague-Dawley Rats. Toxicol Sci. 2021 Sep 28;183(2):319-337. doi: 10.1093/toxsci/kfab094. [PubMed:34329464 ]

Showing NP-Card for 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NP0000222)

MOL for NP0000222 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone )

3D MOL for NP0000222 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone )

3D SDF for NP0000222 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone )

3D-SDF for NP0000222 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone )

PDB for NP0000222 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone )

3D PDB for NP0000222 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone )

SMILES for NP0000222 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone )

INCHI for NP0000222 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone )

Structure for NP0000222 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone )

3D Structure for NP0000222 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone )