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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:10:23 UTC

Update Date

2021-09-26 22:55:00 UTC

HMDB ID

HMDB0246136

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide

Description

N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide, also known as 4-nitro-alpha-acetylamino-beta-hydroxypropiophenone, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Based on a literature review very few articles have been published on N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-[1-(hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide 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

HMDB0246136
     RDKit          3D
N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide
 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.4300    2.2329    0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2316    1.5040   -0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7565    1.8503   -1.4056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6265    0.4837    0.4830 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -0.1649   -0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8680   -1.6116   -0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8214   -2.3169   -0.8163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3075   -0.0658    0.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5491    0.1075    2.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0814   -0.1604    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4723   -0.2795   -0.8520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8078   -0.3639   -1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8212   -0.3292   -0.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1936   -0.3941   -0.6924 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.0655   -0.3034    0.1955 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6196   -0.5373   -1.9824 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.4352   -0.2101    1.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -0.1278    1.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3677    2.2480    1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3812    1.7662   -0.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4337    3.2865   -0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0013    0.1929    1.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1886    0.2793   -1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7446   -1.5676   -0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1567   -2.0036    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1872   -2.5482   -0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125   -0.2940   -1.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1122   -0.4573   -2.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2353   -0.1817    1.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8077   -0.0338    2.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
 18 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
 11 27  1  0
 12 28  1  0
 17 29  1  0
 18 30  1  0
M  CHG  2  14   1  16  -1
M  END

  Mrv1652309112101102D          

 18 18  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  CHG  2  16   1  18  -1
M  END
> <DATABASE_ID>
HMDB0246136

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NC(CO)C(=O)C1=CC=C(C=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O5/c1-7(15)12-10(6-14)11(16)8-2-4-9(5-3-8)13(17)18/h2-5,10,14H,6H2,1H3,(H,12,15)

> <INCHI_KEY>
MXTCOGZRSFDQTK-UHFFFAOYSA-N

> <FORMULA>
C11H12N2O5

> <MOLECULAR_WEIGHT>
252.226

> <EXACT_MASS>
252.074621494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.582025302113216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[3-hydroxy-1-(4-nitrophenyl)-1-oxopropan-2-yl]acetamide

> <ALOGPS_LOGP>
0.41

> <JCHEM_LOGP>
-0.11255143999999993

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.782537640473606

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.452639405550553

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9773764285142659

> <JCHEM_POLAR_SURFACE_AREA>
109.54000000000002

> <JCHEM_REFRACTIVITY>
61.62240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[3-hydroxy-1-(4-nitrophenyl)-1-oxopropan-2-yl]acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246136
     RDKit          3D
N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide
 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.4300    2.2329    0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2316    1.5040   -0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7565    1.8503   -1.4056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6265    0.4837    0.4830 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -0.1649   -0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8680   -1.6116   -0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8214   -2.3169   -0.8163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3075   -0.0658    0.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5491    0.1075    2.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0814   -0.1604    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4723   -0.2795   -0.8520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8078   -0.3639   -1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8212   -0.3292   -0.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1936   -0.3941   -0.6924 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.0655   -0.3034    0.1955 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6196   -0.5373   -1.9824 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.4352   -0.2101    1.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -0.1278    1.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3677    2.2480    1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3812    1.7662   -0.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4337    3.2865   -0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0013    0.1929    1.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1886    0.2793   -1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7446   -1.5676   -0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1567   -2.0036    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1872   -2.5482   -0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125   -0.2940   -1.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1122   -0.4573   -2.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2353   -0.1817    1.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8077   -0.0338    2.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
 18 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
 11 27  1  0
 12 28  1  0
 17 29  1  0
 18 30  1  0
M  CHG  2  14   1  16  -1
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       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       2.667  -4.620   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      10.669  -7.700   0.000  0.00  0.00           N+1
HETATM   17  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0246136
HETATM    1  C1  UNL     1      -4.430   2.233   0.174  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.232   1.504  -0.274  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.757   1.850  -1.406  1.00  0.00           O  
HETATM    4  N1  UNL     1      -2.627   0.484   0.483  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.429  -0.165  -0.073  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.868  -1.612  -0.285  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.821  -2.317  -0.816  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.308  -0.066   0.888  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.549   0.107   2.105  1.00  0.00           O  
HETATM   10  C6  UNL     1       1.081  -0.160   0.460  1.00  0.00           C  
HETATM   11  C7  UNL     1       1.472  -0.280  -0.852  1.00  0.00           C  
HETATM   12  C8  UNL     1       2.808  -0.364  -1.246  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.821  -0.329  -0.312  1.00  0.00           C  
HETATM   14  N2  UNL     1       5.194  -0.394  -0.692  1.00  0.00           N1+
HETATM   15  O4  UNL     1       6.065  -0.303   0.196  1.00  0.00           O  
HETATM   16  O5  UNL     1       5.620  -0.537  -1.982  1.00  0.00           O1-
HETATM   17  C10 UNL     1       3.435  -0.210   1.005  1.00  0.00           C  
HETATM   18  C11 UNL     1       2.117  -0.128   1.392  1.00  0.00           C  
HETATM   19  H1  UNL     1      -4.368   2.248   1.299  1.00  0.00           H  
HETATM   20  H2  UNL     1      -5.381   1.766  -0.154  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.434   3.286  -0.210  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.001   0.193   1.397  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.189   0.279  -1.042  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.745  -1.568  -0.939  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.157  -2.004   0.725  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.187  -2.548  -0.119  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.712  -0.294  -1.632  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.112  -0.457  -2.275  1.00  0.00           H  
HETATM   29  H11 UNL     1       4.235  -0.182   1.747  1.00  0.00           H  
HETATM   30  H12 UNL     1       1.808  -0.034   2.438  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    4
CONECT    4    5   22
CONECT    5    6    8   23
CONECT    6    7   24   25
CONECT    7   26
CONECT    8    9    9   10
CONECT   10   11   11   18
CONECT   11   12   27
CONECT   12   13   13   28
CONECT   13   14   17
CONECT   14   15   15   16
CONECT   17   18   18   29
CONECT   18   30
END

HMDB0246136
     RDKit          3D
N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide
 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.4300    2.2329    0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2316    1.5040   -0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7565    1.8503   -1.4056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6265    0.4837    0.4830 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4290   -0.1649   -0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8680   -1.6116   -0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8214   -2.3169   -0.8163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3075   -0.0658    0.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5491    0.1075    2.1055 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0814   -0.1604    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4723   -0.2795   -0.8520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8078   -0.3639   -1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8212   -0.3292   -0.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1936   -0.3941   -0.6924 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.0655   -0.3034    0.1955 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6196   -0.5373   -1.9824 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.4352   -0.2101    1.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -0.1278    1.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3677    2.2480    1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3812    1.7662   -0.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4337    3.2865   -0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0013    0.1929    1.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1886    0.2793   -1.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7446   -1.5676   -0.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1567   -2.0036    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1872   -2.5482   -0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125   -0.2940   -1.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1122   -0.4573   -2.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2353   -0.1817    1.7473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8077   -0.0338    2.4377 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
 18 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
 11 27  1  0
 12 28  1  0
 17 29  1  0
 18 30  1  0
M  CHG  2  14   1  16  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Nitro-alpha-acetylamino-beta-hydroxypropiophenone	HMDB
p-Nitro-alpha-acetylamino-beta-hydroxypropiophenone	HMDB

Chemical Formula

C₁₁H₁₂N₂O₅

Average Molecular Weight

252.226

Monoisotopic Molecular Weight

252.074621494

IUPAC Name

N-[3-hydroxy-1-(4-nitrophenyl)-1-oxopropan-2-yl]acetamide

Traditional Name

N-[3-hydroxy-1-(4-nitrophenyl)-1-oxopropan-2-yl]acetamide

CAS Registry Number

Not Available

SMILES

CC(=O)NC(CO)C(=O)C1=CC=C(C=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C11H12N2O5/c1-7(15)12-10(6-14)11(16)8-2-4-9(5-3-8)13(17)18/h2-5,10,14H,6H2,1H3,(H,12,15)

InChI Key

MXTCOGZRSFDQTK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Nitrobenzene
Nitroaromatic compound
Benzoyl
Aryl alkyl ketone
Monocyclic benzene moiety
Beta-hydroxy ketone
Benzenoid
Acetamide
Carboxamide group
Organic nitro compound
C-nitro compound
Secondary carboxylic acid amide
Carboxylic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Primary alcohol
Organic oxide
Organic zwitterion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	0.41	ALOGPS
logP	-0.11	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	11.45	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.54 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	61.62 m³·mol⁻¹	ChemAxon
Polarizability	23.58 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
DeepCCS	[M+H]+	155.782	30932474
DeepCCS	[M-H]-	152.522	30932474
DeepCCS	[M-2H]-	187.782	30932474
DeepCCS	[M+Na]+	164.034	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide	CC(=O)NC(CO)C(=O)C1=CC=C(C=C1)[N+]([O-])=O	3331.3	Standard polar	33892256
N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide	CC(=O)NC(CO)C(=O)C1=CC=C(C=C1)[N+]([O-])=O	2290.6	Standard non polar	33892256
N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide	CC(=O)NC(CO)C(=O)C1=CC=C(C=C1)[N+]([O-])=O	2345.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide,2TMS,isomer #1	CC(=O)N(C(CO[Si](C)(C)C)C(=O)C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C	2264.3	Semi standard non polar	33892256
N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide,2TMS,isomer #1	CC(=O)N(C(CO[Si](C)(C)C)C(=O)C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C	2375.6	Standard non polar	33892256
N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide,2TMS,isomer #1	CC(=O)N(C(CO[Si](C)(C)C)C(=O)C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C	2812.3	Standard polar	33892256
N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide,2TBDMS,isomer #1	CC(=O)N(C(CO[Si](C)(C)C(C)(C)C)C(=O)C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C	2811.2	Semi standard non polar	33892256
N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide,2TBDMS,isomer #1	CC(=O)N(C(CO[Si](C)(C)C(C)(C)C)C(=O)C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C	2813.6	Standard non polar	33892256
N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide,2TBDMS,isomer #1	CC(=O)N(C(CO[Si](C)(C)C(C)(C)C)C(=O)C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C	2948.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-9750000000-f92a9fb5eff71e3355f8	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	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

58622

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65112

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 N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide (HMDB0246136)

MOL for HMDB0246136 (N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide)

3D MOL for HMDB0246136 (N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide)

3D SDF for HMDB0246136 (N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide)

3D-SDF for HMDB0246136 (N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide)

PDB for HMDB0246136 (N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide)

3D PDB for HMDB0246136 (N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide)

SMILES for HMDB0246136 (N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide)

INCHI for HMDB0246136 (N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide)

Structure for HMDB0246136 (N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide)

3D Structure for HMDB0246136 (N-[1-(Hydroxymethyl)-2-(4-nitrophenyl)-2-oxoethyl]acetamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

NMR Spectra