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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:43:26 UTC

Update Date

2021-09-26 23:09:44 UTC

HMDB ID

HMDB0255150

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Hydroxy phip

Description

N-hydroxy-PhIP, also known as N-OH-phip, 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. N-hydroxy-PhIP 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 N-hydroxy-PhIP. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-hydroxy phip is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-Hydroxy phip 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

HMDB0255150
     RDKit          3D
N-Hydroxy phip
 30 32  0  0  0  0  0  0  0  0999 V2000
    2.7607   -1.7594   -0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667   -0.4281   -0.0759 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5288    0.4101    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9443    0.1942    0.2930 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6390    0.5707   -0.7980 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9466    1.5270    0.8012 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6044    1.4042    0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5893    2.2452    1.0234 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6868    1.8959    0.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9927    0.6554    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3605    0.2806    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3332    1.2028   -0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6518    0.8296   -0.4752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0166   -0.4889   -0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0595   -1.4231   -0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7551   -1.0313    0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0649   -0.1953   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3828    0.1663    0.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6709   -2.4750    0.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9662   -1.9554   -1.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7869   -1.7872   -1.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4653   -0.2448    1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5733    0.2653   -0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877    2.5647    1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1184    2.2590   -0.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4187    1.5749   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0548   -0.8079   -0.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3498   -2.4790   -0.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0431   -1.8101    0.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1614   -1.1607   -0.5078 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
  3  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  2  0
 18  2  1  0
 18  7  1  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  9 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END


  Mrv1652309112116432D          

 18 20  0  0  0  0            999 V2000
   -0.3984   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -1.4124    0.0000 O   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  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  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
  9 14  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255150

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(NO)=NC2=C1C=C(C=N2)C1=CC=CC=C1

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

> <INCHI_KEY>
DCVWQAGUQFBCTF-UHFFFAOYSA-N

> <FORMULA>
C13H12N4O

> <MOLECULAR_WEIGHT>
240.266

> <EXACT_MASS>
240.101111022

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
25.804492453727168

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
2.4302574676666664

> <ALOGPS_LOGS>
-2.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.46018898761124

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.468578055269713

> <JCHEM_PKA_STRONGEST_BASIC>
3.1475258087997062

> <JCHEM_POLAR_SURFACE_AREA>
62.97

> <JCHEM_REFRACTIVITY>
70.87780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-{1-methyl-6-phenylimidazo[4,5-b]pyridin-2-yl}hydroxylamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255150
     RDKit          3D
N-Hydroxy phip
 30 32  0  0  0  0  0  0  0  0999 V2000
    2.7607   -1.7594   -0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667   -0.4281   -0.0759 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5288    0.4101    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9443    0.1942    0.2930 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6390    0.5707   -0.7980 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9466    1.5270    0.8012 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6044    1.4042    0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5893    2.2452    1.0234 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6868    1.8959    0.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9927    0.6554    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3605    0.2806    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3332    1.2028   -0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6518    0.8296   -0.4752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0166   -0.4889   -0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0595   -1.4231   -0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7551   -1.0313    0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0649   -0.1953   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3828    0.1663    0.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6709   -2.4750    0.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9662   -1.9554   -1.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7869   -1.7872   -1.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4653   -0.2448    1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5733    0.2653   -0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877    2.5647    1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1184    2.2590   -0.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4187    1.5749   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0548   -0.8079   -0.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3498   -2.4790   -0.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0431   -1.8101    0.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1614   -1.1607   -0.5078 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
  3  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  2  0
 18  2  1  0
 18  7  1  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  9 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.530   0.237   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.531  -2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.865  -2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.865  -4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.531  -5.153   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.198  -4.383   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -2.713  -1.303   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      -3.483  -2.637   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15    4   16                                                       
CONECT   16   15    2   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0255150
HETATM    1  C1  UNL     1       2.761  -1.759  -0.655  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.567  -0.428  -0.076  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.529   0.410   0.332  1.00  0.00           C  
HETATM    4  N2  UNL     1       4.944   0.194   0.293  1.00  0.00           N  
HETATM    5  O1  UNL     1       5.639   0.571  -0.798  1.00  0.00           O  
HETATM    6  N3  UNL     1       2.947   1.527   0.801  1.00  0.00           N  
HETATM    7  C3  UNL     1       1.604   1.404   0.693  1.00  0.00           C  
HETATM    8  N4  UNL     1       0.589   2.245   1.023  1.00  0.00           N  
HETATM    9  C4  UNL     1      -0.687   1.896   0.818  1.00  0.00           C  
HETATM   10  C5  UNL     1      -0.993   0.655   0.259  1.00  0.00           C  
HETATM   11  C6  UNL     1      -2.360   0.281   0.040  1.00  0.00           C  
HETATM   12  C7  UNL     1      -3.333   1.203  -0.265  1.00  0.00           C  
HETATM   13  C8  UNL     1      -4.652   0.830  -0.475  1.00  0.00           C  
HETATM   14  C9  UNL     1      -5.017  -0.489  -0.382  1.00  0.00           C  
HETATM   15  C10 UNL     1      -4.060  -1.423  -0.080  1.00  0.00           C  
HETATM   16  C11 UNL     1      -2.755  -1.031   0.126  1.00  0.00           C  
HETATM   17  C12 UNL     1       0.065  -0.195  -0.073  1.00  0.00           C  
HETATM   18  C13 UNL     1       1.383   0.166   0.139  1.00  0.00           C  
HETATM   19  H1  UNL     1       2.671  -2.475   0.189  1.00  0.00           H  
HETATM   20  H2  UNL     1       1.966  -1.955  -1.387  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.787  -1.787  -1.093  1.00  0.00           H  
HETATM   22  H4  UNL     1       5.465  -0.245   1.077  1.00  0.00           H  
HETATM   23  H5  UNL     1       6.573   0.265  -0.755  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.488   2.565   1.081  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.118   2.259  -0.355  1.00  0.00           H  
HETATM   26  H8  UNL     1      -5.419   1.575  -0.717  1.00  0.00           H  
HETATM   27  H9  UNL     1      -6.055  -0.808  -0.544  1.00  0.00           H  
HETATM   28  H10 UNL     1      -4.350  -2.479  -0.005  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.043  -1.810   0.362  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.161  -1.161  -0.508  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   18
CONECT    3    4    6    6
CONECT    4    5   22
CONECT    5   23
CONECT    6    7
CONECT    7    8    8   18
CONECT    8    9
CONECT    9   10   10   24
CONECT   10   11   17
CONECT   11   12   12   16
CONECT   12   13   25
CONECT   13   14   14   26
CONECT   14   15   27
CONECT   15   16   16   28
CONECT   16   29
CONECT   17   18   18   30
END

HMDB0255150
     RDKit          3D
N-Hydroxy phip
 30 32  0  0  0  0  0  0  0  0999 V2000
    2.7607   -1.7594   -0.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667   -0.4281   -0.0759 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5288    0.4101    0.3320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9443    0.1942    0.2930 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6390    0.5707   -0.7980 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9466    1.5270    0.8012 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6044    1.4042    0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5893    2.2452    1.0234 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6868    1.8959    0.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9927    0.6554    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3605    0.2806    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3332    1.2028   -0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6518    0.8296   -0.4752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0166   -0.4889   -0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0595   -1.4231   -0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7551   -1.0313    0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0649   -0.1953   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3828    0.1663    0.1389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6709   -2.4750    0.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9662   -1.9554   -1.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7869   -1.7872   -1.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4653   -0.2448    1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5733    0.2653   -0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4877    2.5647    1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1184    2.2590   -0.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4187    1.5749   -0.7173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0548   -0.8079   -0.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3498   -2.4790   -0.0053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0431   -1.8101    0.3617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1614   -1.1607   -0.5078 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
  3  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 10 17  1  0
 17 18  2  0
 18  2  1  0
 18  7  1  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  9 24  1  0
 12 25  1  0
 13 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-Hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine	ChEBI
2-Hydroxyamino-phip	ChEBI
N-OH-PhIP	ChEBI
2-Hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine	MeSH
N-Hydroxy-phip	MeSH

Chemical Formula

C₁₃H₁₂N₄O

Average Molecular Weight

240.266

Monoisotopic Molecular Weight

240.101111022

IUPAC Name

N-{1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-yl}hydroxylamine

Traditional Name

N-{1-methyl-6-phenylimidazo[4,5-b]pyridin-2-yl}hydroxylamine

CAS Registry Number

Not Available

SMILES

CN1C(NO)=NC2=C1C=C(C=N2)C1=CC=CC=C1

InChI Identifier

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

InChI Key

DCVWQAGUQFBCTF-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
Arylhydroxamate
Monocyclic benzene moiety
N-substituted imidazole
Benzenoid
Azole
Imidazole
Heteroaromatic compound
Azacycle
N-organohydroxylamine
Organic oxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
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)

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	2.1	ALOGPS
logP	2.43	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	14.47	ChemAxon
pKa (Strongest Basic)	3.15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.97 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.88 m³·mol⁻¹	ChemAxon
Polarizability	25.8 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]+	153.76	30932474
DeepCCS	[M-H]-	151.365	30932474
DeepCCS	[M-2H]-	184.394	30932474
DeepCCS	[M+Na]+	159.691	30932474
AllCCS	[M+H]+	155.6	32859911
AllCCS	[M+H-H2O]+	151.5	32859911
AllCCS	[M+NH4]+	159.3	32859911
AllCCS	[M+Na]+	160.4	32859911
AllCCS	[M-H]-	158.7	32859911
AllCCS	[M+Na-2H]-	158.2	32859911
AllCCS	[M+HCOO]-	157.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Hydroxy phip	CN1C(NO)=NC2=C1C=C(C=N2)C1=CC=CC=C1	3663.1	Standard polar	33892256
N-Hydroxy phip	CN1C(NO)=NC2=C1C=C(C=N2)C1=CC=CC=C1	2426.6	Standard non polar	33892256
N-Hydroxy phip	CN1C(NO)=NC2=C1C=C(C=N2)C1=CC=CC=C1	2698.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Hydroxy phip,1TMS,isomer #1	CN1C(N(O)[Si](C)(C)C)=NC2=NC=C(C3=CC=CC=C3)C=C21	2475.8	Semi standard non polar	33892256
N-Hydroxy phip,1TMS,isomer #1	CN1C(N(O)[Si](C)(C)C)=NC2=NC=C(C3=CC=CC=C3)C=C21	2538.7	Standard non polar	33892256
N-Hydroxy phip,1TMS,isomer #1	CN1C(N(O)[Si](C)(C)C)=NC2=NC=C(C3=CC=CC=C3)C=C21	3367.9	Standard polar	33892256
N-Hydroxy phip,1TBDMS,isomer #1	CN1C(N(O)[Si](C)(C)C(C)(C)C)=NC2=NC=C(C3=CC=CC=C3)C=C21	2702.1	Semi standard non polar	33892256
N-Hydroxy phip,1TBDMS,isomer #1	CN1C(N(O)[Si](C)(C)C(C)(C)C)=NC2=NC=C(C3=CC=CC=C3)C=C21	2711.1	Standard non polar	33892256
N-Hydroxy phip,1TBDMS,isomer #1	CN1C(N(O)[Si](C)(C)C(C)(C)C)=NC2=NC=C(C3=CC=CC=C3)C=C21	3418.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Hydroxy phip GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0970000000-19e9d50e10945276572a	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Hydroxy phip GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

94711

KEGG Compound ID

C20286

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

104954

PDB ID

Not Available

ChEBI ID

133920

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 N-Hydroxy phip (HMDB0255150)

MOL for HMDB0255150 (N-Hydroxy phip)

3D MOL for HMDB0255150 (N-Hydroxy phip)

3D SDF for HMDB0255150 (N-Hydroxy phip)

3D-SDF for HMDB0255150 (N-Hydroxy phip)

PDB for HMDB0255150 (N-Hydroxy phip)

3D PDB for HMDB0255150 (N-Hydroxy phip)

SMILES for HMDB0255150 (N-Hydroxy phip)

INCHI for HMDB0255150 (N-Hydroxy phip)

Structure for HMDB0255150 (N-Hydroxy phip)

3D Structure for HMDB0255150 (N-Hydroxy phip)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra