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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:38:59 UTC

Update Date

2021-09-26 22:52:16 UTC

HMDB ID

HMDB0244493

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol

Description

4-(2-amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond. Based on a literature review very few articles have been published on 4-(2-amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-(2-amino-1-methyl-1h-imidazo[4,5-b]pyridin-6-yl)phenol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0244493
     RDKit          3D
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol
 30 32  0  0  0  0  0  0  0  0999 V2000
    3.1090   -1.9059   -0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9869   -0.4733    0.1794 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0275    0.3866    0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4183    0.0788    0.2587 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4812    1.6008    0.4436 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1195    1.5341    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1750    2.4860    0.5481 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1147    2.1417    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4611    0.8173    0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8821    0.4102    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2488   -0.6737   -0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5906   -1.0702   -0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5686   -0.3973    0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8789   -0.8432    0.0629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1953    0.6942    0.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8645    1.0796    0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4874   -0.1753    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8256    0.1983    0.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8141   -2.4810    0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5017   -2.2715   -0.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1697   -2.1732   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7325   -0.8273    0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1406    0.7091   -0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271    2.8725    0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980   -1.2096   -1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8895   -1.9243   -1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5375   -0.5199   -0.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9724    1.2150    1.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5652    1.9291    1.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2052   -1.2078    0.0775 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
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  2  0
 18  2  1  0
 18  6  1  0
 16 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  8 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

1HP
  Mrv0541 02241213042D          

 18 20  0  0  0  0            999 V2000
   -0.3099    0.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0244    0.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8090    0.2931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0639   -0.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2939    0.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1189    0.9606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8090    1.6280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0244    1.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3099    1.7856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4046    1.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4046    0.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1191    0.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1191   -0.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8335   -1.1019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5480   -0.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -1.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5480    0.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8335    0.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  5  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  7  5  2  0  0  0  0
  8  2  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 10 11  1  0  0  0  0
 11  1  2  0  0  0  0
 12 11  1  0  0  0  0
 12 18  2  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
 14 15  1  0  0  0  0
 15 17  2  0  0  0  0
 16 15  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244493

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(N)=NC2=C1C=C(C=N2)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H12N4O/c1-17-11-6-9(7-15-12(11)16-13(17)14)8-2-4-10(18)5-3-8/h2-7,18H,1H3,(H2,14,15,16)

> <INCHI_KEY>
UGJXOCBVCWTJFP-UHFFFAOYSA-N

> <FORMULA>
C13H12N4O

> <MOLECULAR_WEIGHT>
240.2606

> <EXACT_MASS>
240.101111026

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.713539128089366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{2-amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl}phenol

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
1.7894962833333325

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.761768132642294

> <JCHEM_PKA_STRONGEST_BASIC>
5.459341812419169

> <JCHEM_POLAR_SURFACE_AREA>
76.96000000000001

> <JCHEM_REFRACTIVITY>
70.57190000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{2-amino-1-methylimidazo[4,5-b]pyridin-6-yl}phenol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244493
     RDKit          3D
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol
 30 32  0  0  0  0  0  0  0  0999 V2000
    3.1090   -1.9059   -0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9869   -0.4733    0.1794 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0275    0.3866    0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4183    0.0788    0.2587 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4812    1.6008    0.4436 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1195    1.5341    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1750    2.4860    0.5481 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1147    2.1417    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4611    0.8173    0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8821    0.4102    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2488   -0.6737   -0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5906   -1.0702   -0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5686   -0.3973    0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8789   -0.8432    0.0629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1953    0.6942    0.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8645    1.0796    0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4874   -0.1753    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8256    0.1983    0.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8141   -2.4810    0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5017   -2.2715   -0.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1697   -2.1732   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7325   -0.8273    0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1406    0.7091   -0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271    2.8725    0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980   -1.2096   -1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8895   -1.9243   -1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5375   -0.5199   -0.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9724    1.2150    1.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5652    1.9291    1.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2052   -1.2078    0.0775 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
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  2  0
 18  2  1  0
 18  6  1  0
 16 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  8 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1HP                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.578   0.253   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.912   1.023   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -3.377   0.547   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -3.853  -0.917   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.282   1.793   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -5.822   1.793   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      -3.377   3.039   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.912   2.563   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.578   3.333   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.755   2.563   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.755   1.023   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.089   0.253   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.089  -1.287   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.423  -2.057   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.756  -1.287   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.090  -2.057   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.756   0.253   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.423   1.023   0.000  0.00  0.00           C+0
CONECT    1    2   11                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    5    4                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    2    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    1   12                                                  
CONECT   12   11   18   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   17   16                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   12   17                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0244493
HETATM    1  C1  UNL     1       3.109  -1.906  -0.001  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.987  -0.473   0.179  1.00  0.00           N  
HETATM    3  C2  UNL     1       4.027   0.387   0.292  1.00  0.00           C  
HETATM    4  N2  UNL     1       5.418   0.079   0.259  1.00  0.00           N  
HETATM    5  N3  UNL     1       3.481   1.601   0.444  1.00  0.00           N  
HETATM    6  C3  UNL     1       2.120   1.534   0.430  1.00  0.00           C  
HETATM    7  N4  UNL     1       1.175   2.486   0.548  1.00  0.00           N  
HETATM    8  C4  UNL     1      -0.115   2.142   0.501  1.00  0.00           C  
HETATM    9  C5  UNL     1      -0.461   0.817   0.332  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.882   0.410   0.281  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.249  -0.674  -0.484  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.591  -1.070  -0.538  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.569  -0.397   0.161  1.00  0.00           C  
HETATM   14  O1  UNL     1      -5.879  -0.843   0.063  1.00  0.00           O  
HETATM   15  C10 UNL     1      -4.195   0.694   0.930  1.00  0.00           C  
HETATM   16  C11 UNL     1      -2.865   1.080   0.978  1.00  0.00           C  
HETATM   17  C12 UNL     1       0.487  -0.175   0.209  1.00  0.00           C  
HETATM   18  C13 UNL     1       1.826   0.198   0.260  1.00  0.00           C  
HETATM   19  H1  UNL     1       2.814  -2.481   0.895  1.00  0.00           H  
HETATM   20  H2  UNL     1       2.502  -2.271  -0.876  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.170  -2.173  -0.266  1.00  0.00           H  
HETATM   22  H4  UNL     1       5.733  -0.827   0.661  1.00  0.00           H  
HETATM   23  H5  UNL     1       6.141   0.709  -0.145  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.927   2.873   0.591  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.498  -1.210  -1.037  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.889  -1.924  -1.139  1.00  0.00           H  
HETATM   27  H9  UNL     1      -6.538  -0.520  -0.635  1.00  0.00           H  
HETATM   28  H10 UNL     1      -4.972   1.215   1.475  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.565   1.929   1.574  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.205  -1.208   0.078  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   18
CONECT    3    4    5    5
CONECT    4   22   23
CONECT    5    6
CONECT    6    7    7   18
CONECT    7    8
CONECT    8    9    9   24
CONECT    9   10   17
CONECT   10   11   11   16
CONECT   11   12   25
CONECT   12   13   13   26
CONECT   13   14   15
CONECT   14   27
CONECT   15   16   16   28
CONECT   16   29
CONECT   17   18   18   30
END

HMDB0244493
     RDKit          3D
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol
 30 32  0  0  0  0  0  0  0  0999 V2000
    3.1090   -1.9059   -0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9869   -0.4733    0.1794 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0275    0.3866    0.2920 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4183    0.0788    0.2587 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4812    1.6008    0.4436 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1195    1.5341    0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1750    2.4860    0.5481 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1147    2.1417    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4611    0.8173    0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8821    0.4102    0.2805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2488   -0.6737   -0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5906   -1.0702   -0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5686   -0.3973    0.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8789   -0.8432    0.0629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1953    0.6942    0.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8645    1.0796    0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4874   -0.1753    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8256    0.1983    0.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8141   -2.4810    0.8946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5017   -2.2715   -0.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1697   -2.1732   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7325   -0.8273    0.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1406    0.7091   -0.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271    2.8725    0.5905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980   -1.2096   -1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8895   -1.9243   -1.1392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5375   -0.5199   -0.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9724    1.2150    1.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5652    1.9291    1.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2052   -1.2078    0.0775 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
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  2  0
 18  2  1  0
 18  6  1  0
 16 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  4 23  1  0
  8 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-amino-1-Methyl-6-(4-hydroxyphenyl)imidazo(4,5-b)pyridine	MeSH
4'-OH-PhIP	MeSH

Chemical Formula

C₁₃H₁₂N₄O

Average Molecular Weight

240.2606

Monoisotopic Molecular Weight

240.101111026

IUPAC Name

4-{2-amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl}phenol

Traditional Name

4-{2-amino-1-methylimidazo[4,5-b]pyridin-6-yl}phenol

CAS Registry Number

Not Available

SMILES

CN1C(N)=NC2=C1C=C(C=N2)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C13H12N4O/c1-17-11-6-9(7-15-12(11)16-13(17)14)8-2-4-10(18)5-3-8/h2-7,18H,1H3,(H2,14,15,16)

InChI Key

UGJXOCBVCWTJFP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Phenylpyridines

Direct Parent

Phenylpyridines

Alternative Parents

Substituents

3-phenylpyridine
Imidazopyridine
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aminoimidazole
Monocyclic benzene moiety
N-substituted imidazole
Benzenoid
Azole
Imidazole
Heteroaromatic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Amine
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	2.15	ALOGPS
logP	1.79	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	9.76	ChemAxon
pKa (Strongest Basic)	5.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	76.96 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.57 m³·mol⁻¹	ChemAxon
Polarizability	25.71 Å³	ChemAxon
Number of Rings	3	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
DeepCCS	[M+H]+	159.829	30932474
DeepCCS	[M-H]-	157.433	30932474
DeepCCS	[M-2H]-	190.438	30932474
DeepCCS	[M+Na]+	165.77	30932474
AllCCS	[M+H]+	155.4	32859911
AllCCS	[M+H-H2O]+	151.4	32859911
AllCCS	[M+NH4]+	159.2	32859911
AllCCS	[M+Na]+	160.3	32859911
AllCCS	[M-H]-	158.7	32859911
AllCCS	[M+Na-2H]-	158.2	32859911
AllCCS	[M+HCOO]-	157.8	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.	3.28 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7863 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.02 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	892.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	264.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	123.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	159.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	98.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	301.7 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	303.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	139.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	667.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	71.7 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	699.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	181.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	226.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	580.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	375.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	116.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol	CN1C(N)=NC2=C1C=C(C=N2)C1=CC=C(O)C=C1	3611.5	Standard polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol	CN1C(N)=NC2=C1C=C(C=N2)C1=CC=C(O)C=C1	2478.0	Standard non polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol	CN1C(N)=NC2=C1C=C(C=N2)C1=CC=C(O)C=C1	3022.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,2TMS,isomer #1	CN1C(N[Si](C)(C)C)=NC2=NC=C(C3=CC=C(O[Si](C)(C)C)C=C3)C=C21	2808.9	Semi standard non polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,2TMS,isomer #1	CN1C(N[Si](C)(C)C)=NC2=NC=C(C3=CC=C(O[Si](C)(C)C)C=C3)C=C21	2775.3	Standard non polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,2TMS,isomer #1	CN1C(N[Si](C)(C)C)=NC2=NC=C(C3=CC=C(O[Si](C)(C)C)C=C3)C=C21	3396.0	Standard polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,2TMS,isomer #2	CN1C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=NC=C(C3=CC=C(O)C=C3)C=C21	2919.1	Semi standard non polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,2TMS,isomer #2	CN1C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=NC=C(C3=CC=C(O)C=C3)C=C21	2978.1	Standard non polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,2TMS,isomer #2	CN1C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=NC=C(C3=CC=C(O)C=C3)C=C21	3456.3	Standard polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,3TMS,isomer #1	CN1C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=NC=C(C3=CC=C(O[Si](C)(C)C)C=C3)C=C21	2769.0	Semi standard non polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,3TMS,isomer #1	CN1C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=NC=C(C3=CC=C(O[Si](C)(C)C)C=C3)C=C21	2907.4	Standard non polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,3TMS,isomer #1	CN1C(N([Si](C)(C)C)[Si](C)(C)C)=NC2=NC=C(C3=CC=C(O[Si](C)(C)C)C=C3)C=C21	3146.4	Standard polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,2TBDMS,isomer #1	CN1C(N[Si](C)(C)C(C)(C)C)=NC2=NC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C=C21	3290.8	Semi standard non polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,2TBDMS,isomer #1	CN1C(N[Si](C)(C)C(C)(C)C)=NC2=NC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C=C21	3216.0	Standard non polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,2TBDMS,isomer #1	CN1C(N[Si](C)(C)C(C)(C)C)=NC2=NC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C=C21	3510.3	Standard polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,2TBDMS,isomer #2	CN1C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=NC=C(C3=CC=C(O)C=C3)C=C21	3314.2	Semi standard non polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,2TBDMS,isomer #2	CN1C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=NC=C(C3=CC=C(O)C=C3)C=C21	3404.2	Standard non polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,2TBDMS,isomer #2	CN1C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=NC=C(C3=CC=C(O)C=C3)C=C21	3474.2	Standard polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,3TBDMS,isomer #1	CN1C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=NC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C=C21	3369.7	Semi standard non polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,3TBDMS,isomer #1	CN1C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=NC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C=C21	3533.7	Standard non polar	33892256
4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol,3TBDMS,isomer #1	CN1C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=NC=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C=C21	3363.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dm-0590000000-8d9f8e7acc7c834dc612	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol 10V, Positive-QTOF	splash10-0006-0090000000-6747669f89723bf2c745	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol 20V, Positive-QTOF	splash10-0006-0190000000-ad24df9502c200cc886f	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol 40V, Positive-QTOF	splash10-03ld-1920000000-6dbc8a7a4a6c99f5291d	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol 10V, Negative-QTOF	splash10-000i-0090000000-5adb5f3f947f87e713b7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol 20V, Negative-QTOF	splash10-000i-0090000000-5e35693d72f5b36904d3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol 40V, Negative-QTOF	splash10-00dl-6490000000-9b1092b1cae20f85c050	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol 10V, Positive-QTOF	splash10-0006-0090000000-e3081d3cffd1c3b2456a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol 20V, Positive-QTOF	splash10-0006-0090000000-08183779d970f57ebcc1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol 40V, Positive-QTOF	splash10-03dj-0950000000-5c2b9d087bb84ef7c247	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol 10V, Negative-QTOF	splash10-000i-0090000000-58b9d530d708b3eee227	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol 20V, Negative-QTOF	splash10-000i-0290000000-eff5a240ac4e4e019680	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol 40V, Negative-QTOF	splash10-001i-0940000000-9f807402a3415fa1dd83	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06898

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

20129462

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol (HMDB0244493)

MOL for HMDB0244493 (4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol)

3D MOL for HMDB0244493 (4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol)

3D SDF for HMDB0244493 (4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol)

3D-SDF for HMDB0244493 (4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol)

PDB for HMDB0244493 (4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol)

3D PDB for HMDB0244493 (4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol)

SMILES for HMDB0244493 (4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol)

INCHI for HMDB0244493 (4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol)

Structure for HMDB0244493 (4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol)

3D Structure for HMDB0244493 (4-(2-Amino-1-methyl-1H-imidazo[4,5-b]pyridin-6-yl)phenol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra