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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (21) Show 21 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2012-09-13 11:40:19 UTC

Update Date

2023-02-21 17:28:58 UTC

HMDB ID

HMDB0041809

Secondary Accession Numbers

HMDB41809

Metabolite Identification

Common Name

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

Description

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol, also known as NNAL or mnapb CPD, belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms. 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol.

Structure

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

HMDB0041809
     RDKit          3D
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol
 30 30  0  0  0  0  0  0  0  0999 V2000
    3.5745   -0.7126   -0.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1714    0.4925    0.3446 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720    0.6784    1.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7009    0.7329    0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4231   -0.5011   -0.4832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8793   -0.4429   -1.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9537   -1.6901   -1.9198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0501   -0.2604   -0.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7330    0.9330   -0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8450    1.1272    0.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2792    0.1203    1.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5978   -1.0409    1.2716 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139   -1.2396    0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0860    1.5560    0.2722 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1511    1.4310    0.9034 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9514   -1.5408    0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6335   -0.9200   -0.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5961   -0.6057   -1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9087   -0.1901    1.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0859    1.6111    1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1093    0.9286    1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092    1.6552   -0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2181   -0.5554   -1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4779   -1.4225    0.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8075    0.3191   -2.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8756   -2.3563   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4507    1.7623   -1.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3957    2.0750    0.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1497    0.2641    1.9329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0190   -2.2083    0.5193 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  1  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
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
M  END


  Mrv0541 09131211402D          

 15 15  0  0  0  0            999 V2000
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  9  4  1  0  0  0  0
  9  8  2  0  0  0  0
 10  5  1  0  0  0  0
 10  9  1  0  0  0  0
 11  6  2  0  0  0  0
 11  8  1  0  0  0  0
 13  1  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 15 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041809

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H15N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8,10,14H,3,5,7H2,1H3

> <INCHI_KEY>
OGRXKBUCZFFSTL-UHFFFAOYSA-N

> <FORMULA>
C10H15N3O2

> <MOLECULAR_WEIGHT>
209.245

> <EXACT_MASS>
209.116426739

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
22.109084716177335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
0.4924019806666664

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.228965705038775

> <JCHEM_PKA_STRONGEST_BASIC>
4.726184857514163

> <JCHEM_POLAR_SURFACE_AREA>
65.78999999999999

> <JCHEM_REFRACTIVITY>
57.978699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.64e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041809
     RDKit          3D
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol
 30 30  0  0  0  0  0  0  0  0999 V2000
    3.5745   -0.7126   -0.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1714    0.4925    0.3446 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720    0.6784    1.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7009    0.7329    0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4231   -0.5011   -0.4832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8793   -0.4429   -1.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9537   -1.6901   -1.9198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0501   -0.2604   -0.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7330    0.9330   -0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8450    1.1272    0.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2792    0.1203    1.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5978   -1.0409    1.2716 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139   -1.2396    0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0860    1.5560    0.2722 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1511    1.4310    0.9034 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9514   -1.5408    0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6335   -0.9200   -0.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5961   -0.6057   -1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9087   -0.1901    1.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0859    1.6111    1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1093    0.9286    1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092    1.6552   -0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2181   -0.5554   -1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4779   -1.4225    0.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8075    0.3191   -2.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8756   -2.3563   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4507    1.7623   -1.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3957    2.0750    0.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1497    0.2641    1.9329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0190   -2.2083    0.5193 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  1  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
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       9.336  -2.310   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       8.002  -1.540   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.669  -1.540   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2    4    6                                                       
CONECT    3    5    7                                                       
CONECT    4    2    9                                                       
CONECT    5    3   10                                                       
CONECT    6    2   11                                                       
CONECT    7    3   13                                                       
CONECT    8    9   11                                                       
CONECT    9    4    8   10                                                  
CONECT   10    5    9   14                                                  
CONECT   11    6    8                                                       
CONECT   12   13   15                                                       
CONECT   13    1    7   12                                                  
CONECT   14   10                                                            
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0041809
HETATM    1  C1  UNL     1       3.575  -0.713  -0.362  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.171   0.493   0.345  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.972   0.678   1.077  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.701   0.733   0.305  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.423  -0.501  -0.483  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.879  -0.443  -1.254  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.954  -1.690  -1.920  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.050  -0.260  -0.374  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.733   0.933  -0.374  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.845   1.127   0.451  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.279   0.120   1.285  1.00  0.00           C  
HETATM   12  N2  UNL     1      -3.598  -1.041   1.272  1.00  0.00           N  
HETATM   13  C10 UNL     1      -2.514  -1.240   0.471  1.00  0.00           C  
HETATM   14  N3  UNL     1       4.086   1.556   0.272  1.00  0.00           N  
HETATM   15  O2  UNL     1       5.151   1.431   0.903  1.00  0.00           O  
HETATM   16  H1  UNL     1       2.951  -1.541   0.021  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.634  -0.920  -0.060  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.596  -0.606  -1.452  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.909  -0.190   1.804  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.086   1.611   1.705  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.109   0.929   1.073  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.709   1.655  -0.308  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.218  -0.555  -1.281  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.478  -1.422   0.085  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.807   0.319  -2.035  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.876  -2.356  -1.187  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.451   1.762  -1.001  1.00  0.00           H  
HETATM   28  H13 UNL     1      -4.396   2.075   0.455  1.00  0.00           H  
HETATM   29  H14 UNL     1      -5.150   0.264   1.933  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.019  -2.208   0.519  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    8   25
CONECT    7   26
CONECT    8    9    9   13
CONECT    9   10   27
CONECT   10   11   11   28
CONECT   11   12   29
CONECT   12   13   13
CONECT   13   30
CONECT   14   15   15
END

HMDB0041809
     RDKit          3D
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol
 30 30  0  0  0  0  0  0  0  0999 V2000
    3.5745   -0.7126   -0.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1714    0.4925    0.3446 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9720    0.6784    1.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7009    0.7329    0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4231   -0.5011   -0.4832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8793   -0.4429   -1.2541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9537   -1.6901   -1.9198 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0501   -0.2604   -0.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7330    0.9330   -0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8450    1.1272    0.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2792    0.1203    1.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5978   -1.0409    1.2716 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5139   -1.2396    0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0860    1.5560    0.2722 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1511    1.4310    0.9034 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9514   -1.5408    0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6335   -0.9200   -0.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5961   -0.6057   -1.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9087   -0.1901    1.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0859    1.6111    1.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1093    0.9286    1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092    1.6552   -0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2181   -0.5554   -1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4779   -1.4225    0.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8075    0.3191   -2.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8756   -2.3563   -1.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4507    1.7623   -1.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3957    2.0750    0.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1497    0.2641    1.9329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0190   -2.2083    0.5193 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  1  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
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butan-1-ol	ChEBI
4-(Methylnitrosoamino)-1-(3-pyridyl)-1-butanol	ChEBI
4-[Methyl(nitroso)amino]-1-(3-pyridyl)-1-butanol	ChEBI
4-[Methyl(nitroso)amino]-1-(pyridin-3-yl)butan-1-ol	ChEBI
NNAL	ChEBI
NNAL CPD	HMDB
4-(Methylnitrosoamino)-1--(3-pyridyl)-1-butanol	HMDB
4-(N-Methyl-N-nitrosamino)-1-(3-pyridyl)butan-1-ol	HMDB
MNAPB CPD	HMDB

Chemical Formula

C₁₀H₁₅N₃O₂

Average Molecular Weight

209.245

Monoisotopic Molecular Weight

209.116426739

IUPAC Name

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

Traditional Name

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

CAS Registry Number

76014-81-8

SMILES

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

InChI Identifier

InChI=1S/C10H15N3O2/c1-13(12-15)7-3-5-10(14)9-4-2-6-11-8-9/h2,4,6,8,10,14H,3,5,7H2,1H3

InChI Key

OGRXKBUCZFFSTL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Not Available

Direct Parent

Pyridines and derivatives

Alternative Parents

Substituents

Pyridine
Heteroaromatic compound
Secondary alcohol
Organic n-nitroso compound
Azacycle
Organic nitroso compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Aromatic alcohol
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyridines (CHEBI:82569 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0041809)

Organ

Liver (HMDB: HMDB0041809)
Kidney (HMDB: HMDB0041809)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0041809)

Cellular substructure

Cytoplasm (HMDB: HMDB0041809)
Extracellular (HMDB: HMDB0041809)

Source

Endogenous

Endogenous (HMDB: HMDB0041809)

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	2.64 g/L	ALOGPS
logP	0.48	ALOGPS
logP	0.49	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	14.23	ChemAxon
pKa (Strongest Basic)	4.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	65.79 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	57.98 m³·mol⁻¹	ChemAxon
Polarizability	22.11 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]+	149.164	31661259
DarkChem	[M-H]-	142.456	31661259
DeepCCS	[M+H]+	144.557	30932474
DeepCCS	[M-H]-	141.023	30932474
DeepCCS	[M-2H]-	178.04	30932474
DeepCCS	[M+Na]+	153.623	30932474
AllCCS	[M+H]+	147.8	32859911
AllCCS	[M+H-H2O]+	143.9	32859911
AllCCS	[M+NH4]+	151.5	32859911
AllCCS	[M+Na]+	152.5	32859911
AllCCS	[M-H]-	149.8	32859911
AllCCS	[M+Na-2H]-	150.5	32859911
AllCCS	[M+HCOO]-	151.3	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.	2.52 minutes	32390414
Predicted by Siyang on May 30, 2022	9.3074 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.56 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1174.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	231.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	120.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	158.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	49.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	253.6 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	326.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	117.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	656.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	40.5 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	1089.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	183.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	189.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	432.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	293.7 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	85.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol	CN(CCCC(O)C1=CN=CC=C1)N=O	2507.7	Standard polar	33892256
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol	CN(CCCC(O)C1=CN=CC=C1)N=O	1852.1	Standard non polar	33892256
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol	CN(CCCC(O)C1=CN=CC=C1)N=O	2023.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol,1TMS,isomer #1	CN(CCCC(O[Si](C)(C)C)C1=CC=CN=C1)N=O	1921.8	Semi standard non polar	33892256
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol,1TBDMS,isomer #1	CN(CCCC(O[Si](C)(C)C(C)(C)C)C1=CC=CN=C1)N=O	2162.7	Semi standard non polar	33892256

Spectra

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
Urine	Detected and Quantified	0.00000616 (0.00000454-0.00000762) umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	National Health a...	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

94646

KEGG Compound ID

C19574

BioCyc ID

CPD-21235

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

104856

PDB ID

Not Available

ChEBI ID

82569

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

Only showing the first 10 proteins. There are 21 proteins in total.

Show all enzymes and transporters

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. UDP-glucuronosyltransferase 2B28

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:: UGT2B28
Uniprot ID:: Q9BY64
Molecular weight:: 38742.9

Reactions

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol glucuronide + Uridine 5'-diphosphate	details
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

4. UDP-glucuronosyltransferase 2B4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:: UGT2B4
Uniprot ID:: P06133
Molecular weight:: 60512.035

Reactions

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol glucuronide + Uridine 5'-diphosphate	details
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

5. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

Reactions

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol glucuronide + Uridine 5'-diphosphate	details
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

6. UDP-glucuronosyltransferase 2B10

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT2B10
Uniprot ID:: P36537
Molecular weight:: 60773.485

Reactions

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol glucuronide + Uridine 5'-diphosphate	details
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

7. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

Reactions

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol glucuronide + Uridine 5'-diphosphate	details
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

8. UDP-glucuronosyltransferase 2B15

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:: UGT2B15
Uniprot ID:: P54855
Molecular weight:: 61035.815

Reactions

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol glucuronide + Uridine 5'-diphosphate	details
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

9. UDP-glucuronosyltransferase 2A1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:: UGT2A1
Uniprot ID:: Q9Y4X1
Molecular weight:: 60771.605

Reactions

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol glucuronide + Uridine 5'-diphosphate	details
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

10. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol glucuronide + Uridine 5'-diphosphate	details
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol + Uridine diphosphate glucuronic acid → NNAL-N-glucuronide + Uridine 5'-diphosphate	details

Only showing the first 10 proteins. There are 21 proteins in total.

Show all enzymes and transporters

Showing metabocard for 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol (HMDB0041809)

MOL for HMDB0041809 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol)

3D MOL for HMDB0041809 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol)

3D SDF for HMDB0041809 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol)

3D-SDF for HMDB0041809 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol)

PDB for HMDB0041809 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol)

3D PDB for HMDB0041809 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol)

SMILES for HMDB0041809 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol)

INCHI for HMDB0041809 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol)

Structure for HMDB0041809 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol)

3D Structure for HMDB0041809 (4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions

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