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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:38:05 UTC

Update Date

2021-09-26 22:54:07 UTC

HMDB ID

HMDB0245573

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Nitrophenyl beta-D-xyloside

Description

2-(4-nitrophenoxy)oxane-3,4,5-triol, also known as 4-nitrophenyl beta-D-xyloside or PNP xyloside, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Based on a literature review very few articles have been published on 2-(4-nitrophenoxy)oxane-3,4,5-triol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-nitrophenyl beta-d-xyloside is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Nitrophenyl beta-D-xyloside 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

HMDB0245573
     RDKit          3D
4-Nitrophenyl beta-D-xyloside
 32 33  0  0  0  0  0  0  0  0999 V2000
   -6.3166   -0.8366    0.6240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6621   -0.1125   -0.1298 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.2721    0.6551   -1.0737 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.2559   -0.0734   -0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5594   -0.8172    0.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063   -0.7924    1.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4301    0.0208    0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0761   -0.0070    0.3697 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8381    0.7169   -0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167    1.6243    0.4682 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3125    0.9429    1.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4562    0.3297    0.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4840   -0.1142    1.4033 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8534   -0.7777   -0.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8342   -1.3299   -1.0485 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8203   -0.1482   -1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0872   -1.1427   -1.7637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1042    0.7708   -0.7432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4837    0.7255   -0.8445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1565   -1.4453    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6885   -1.3971    1.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3348    1.3344   -1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6330    1.5991    2.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6775    0.0898    1.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7794    1.1207   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0736    0.6560    1.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3951   -1.5306    0.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6214   -1.5953   -0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253    0.4677   -1.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7265   -1.6871   -2.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827    1.4196   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9752    1.3339   -1.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  7 18  1  0
 18 19  2  0
 19  4  1  0
 16  9  1  0
  5 20  1  0
  6 21  1  0
  9 22  1  0
 11 23  1  0
 11 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
 18 31  1  0
 19 32  1  0
M  CHG  2   2   1   3  -1
M  END


  Mrv1652309112100382D          

 19 20  0  0  0  0            999 V2000
    2.8579   -2.4750    0.0000 C   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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 N   0  3  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
    5.0013    2.0625    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 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
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  4 17  1  0  0  0  0
  3 18  1  0  0  0  0
  2 19  1  0  0  0  0
M  CHG  2  14   1  16  -1
M  END
> <DATABASE_ID>
HMDB0245573

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1COC(OC2=CC=C(C=C2)[N+]([O-])=O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H13NO7/c13-8-5-18-11(10(15)9(8)14)19-7-3-1-6(2-4-7)12(16)17/h1-4,8-11,13-15H,5H2

> <INCHI_KEY>
MLJYKRYCCUGBBV-UHFFFAOYSA-N

> <FORMULA>
C11H13NO7

> <MOLECULAR_WEIGHT>
271.225

> <EXACT_MASS>
271.069201763

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.62586765438715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-nitrophenoxy)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.20

> <JCHEM_LOGP>
-0.028068467666666482

> <ALOGPS_LOGS>
-1.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.399754499442324

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.235021157776165

> <JCHEM_PKA_STRONGEST_BASIC>
-3.526598503638537

> <JCHEM_POLAR_SURFACE_AREA>
122.29

> <JCHEM_REFRACTIVITY>
60.54130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-nitrophenoxy)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0245573
     RDKit          3D
4-Nitrophenyl beta-D-xyloside
 32 33  0  0  0  0  0  0  0  0999 V2000
   -6.3166   -0.8366    0.6240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6621   -0.1125   -0.1298 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.2721    0.6551   -1.0737 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.2559   -0.0734   -0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5594   -0.8172    0.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063   -0.7924    1.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4301    0.0208    0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0761   -0.0070    0.3697 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8381    0.7169   -0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167    1.6243    0.4682 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3125    0.9429    1.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4562    0.3297    0.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4840   -0.1142    1.4033 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8534   -0.7777   -0.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8342   -1.3299   -1.0485 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8203   -0.1482   -1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0872   -1.1427   -1.7637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1042    0.7708   -0.7432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4837    0.7255   -0.8445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1565   -1.4453    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6885   -1.3971    1.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3348    1.3344   -1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6330    1.5991    2.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6775    0.0898    1.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7794    1.1207   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0736    0.6560    1.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3951   -1.5306    0.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6214   -1.5953   -0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253    0.4677   -1.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7265   -1.6871   -2.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827    1.4196   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9752    1.3339   -1.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  7 18  1  0
 18 19  2  0
 19  4  1  0
 16  9  1  0
  5 20  1  0
  6 21  1  0
  9 22  1  0
 11 23  1  0
 11 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
 18 31  1  0
 19 32  1  0
M  CHG  2   2   1   3  -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       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   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  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       9.336   2.310   0.000  0.00  0.00           N+1
HETATM   15  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O-1
HETATM   17  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    4                                                            
CONECT   18    3                                                            
CONECT   19    2                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0245573
HETATM    1  O1  UNL     1      -6.317  -0.837   0.624  1.00  0.00           O  
HETATM    2  N1  UNL     1      -5.662  -0.113  -0.130  1.00  0.00           N1+
HETATM    3  O2  UNL     1      -6.272   0.655  -1.074  1.00  0.00           O1-
HETATM    4  C1  UNL     1      -4.256  -0.073  -0.018  1.00  0.00           C  
HETATM    5  C2  UNL     1      -3.559  -0.817   0.908  1.00  0.00           C  
HETATM    6  C3  UNL     1      -2.206  -0.792   1.030  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.430   0.021   0.188  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.076  -0.007   0.370  1.00  0.00           O  
HETATM    9  C5  UNL     1       0.838   0.717  -0.355  1.00  0.00           C  
HETATM   10  O4  UNL     1       1.517   1.624   0.468  1.00  0.00           O  
HETATM   11  C6  UNL     1       2.313   0.943   1.392  1.00  0.00           C  
HETATM   12  C7  UNL     1       3.456   0.330   0.609  1.00  0.00           C  
HETATM   13  O5  UNL     1       4.484  -0.114   1.403  1.00  0.00           O  
HETATM   14  C8  UNL     1       2.853  -0.778  -0.242  1.00  0.00           C  
HETATM   15  O6  UNL     1       3.834  -1.330  -1.049  1.00  0.00           O  
HETATM   16  C9  UNL     1       1.820  -0.148  -1.128  1.00  0.00           C  
HETATM   17  O7  UNL     1       1.087  -1.143  -1.764  1.00  0.00           O  
HETATM   18  C10 UNL     1      -2.104   0.771  -0.743  1.00  0.00           C  
HETATM   19  C11 UNL     1      -3.484   0.726  -0.845  1.00  0.00           C  
HETATM   20  H1  UNL     1      -4.156  -1.445   1.558  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.689  -1.397   1.777  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.335   1.334  -1.116  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.633   1.599   2.199  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.678   0.090   1.761  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.779   1.121  -0.129  1.00  0.00           H  
HETATM   26  H7  UNL     1       5.074   0.656   1.600  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.395  -1.531   0.443  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.621  -1.595  -0.526  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.325   0.468  -1.890  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.727  -1.687  -2.303  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.583   1.420  -1.426  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.975   1.334  -1.593  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5    5   19
CONECT    5    6   20
CONECT    6    7    7   21
CONECT    7    8   18
CONECT    8    9
CONECT    9   10   16   22
CONECT   10   11
CONECT   11   12   23   24
CONECT   12   13   14   25
CONECT   13   26
CONECT   14   15   16   27
CONECT   15   28
CONECT   16   17   29
CONECT   17   30
CONECT   18   19   19   31
CONECT   19   32
END

HMDB0245573
     RDKit          3D
4-Nitrophenyl beta-D-xyloside
 32 33  0  0  0  0  0  0  0  0999 V2000
   -6.3166   -0.8366    0.6240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6621   -0.1125   -0.1298 N   0  0  0  0  0  4  0  0  0  0  0  0
   -6.2721    0.6551   -1.0737 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.2559   -0.0734   -0.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5594   -0.8172    0.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063   -0.7924    1.0297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4301    0.0208    0.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0761   -0.0070    0.3697 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8381    0.7169   -0.3552 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5167    1.6243    0.4682 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3125    0.9429    1.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4562    0.3297    0.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4840   -0.1142    1.4033 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8534   -0.7777   -0.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8342   -1.3299   -1.0485 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8203   -0.1482   -1.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0872   -1.1427   -1.7637 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1042    0.7708   -0.7432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4837    0.7255   -0.8445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1565   -1.4453    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6885   -1.3971    1.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3348    1.3344   -1.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6330    1.5991    2.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6775    0.0898    1.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7794    1.1207   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0736    0.6560    1.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3951   -1.5306    0.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6214   -1.5953   -0.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253    0.4677   -1.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7265   -1.6871   -2.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827    1.4196   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9752    1.3339   -1.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  7 18  1  0
 18 19  2  0
 19  4  1  0
 16  9  1  0
  5 20  1  0
  6 21  1  0
  9 22  1  0
 11 23  1  0
 11 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
 18 31  1  0
 19 32  1  0
M  CHG  2   2   1   3  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Nitrophenyl beta-D-xyloside	MeSH
4-Nitrophenyl beta-D-xyloside, (alpha-D)-isomer	MeSH
4-Nitrophenyl-alpha-D-xylopyranoside	MeSH
PNP Xyloside	MeSH
PNPX	MeSH
p-Nitrophenyl beta-D-xylopyranoside	MeSH
p-Nitrophenyl beta-D-xyloside	MeSH
p-Nitrophenylxyloside	MeSH
Para-nitrophenyl beta-D-xyloside	MeSH
4-Nitrophenyl b-D-xyloside	Generator
4-Nitrophenyl β-D-xyloside	Generator

Chemical Formula

C₁₁H₁₃NO₇

Average Molecular Weight

271.225

Monoisotopic Molecular Weight

271.069201763

IUPAC Name

2-(4-nitrophenoxy)oxane-3,4,5-triol

Traditional Name

2-(4-nitrophenoxy)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OC1COC(OC2=CC=C(C=C2)[N+]([O-])=O)C(O)C1O

InChI Identifier

InChI=1S/C11H13NO7/c13-8-5-18-11(10(15)9(8)14)19-7-3-1-6(2-4-7)12(16)17/h1-4,8-11,13-15H,5H2

InChI Key

MLJYKRYCCUGBBV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
O-glycosyl compound
Pentose monosaccharide
Nitrobenzene
Phenoxy compound
Nitroaromatic compound
Phenol ether
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
C-nitro compound
Organic nitro compound
Secondary alcohol
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Acetal
Organic oxoazanium
Oxacycle
Organoheterocyclic compound
Polyol
Organopnictogen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Organic salt
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

a xyloside (CPD-13210 )
a <i>p</i>-nitrophenyl-modified glycoside (CPD-13210 )
a pyranoside (CPD-13210 )

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	-0.2	ALOGPS
logP	-0.028	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	12.24	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.54 m³·mol⁻¹	ChemAxon
Polarizability	24.63 Å³	ChemAxon
Number of Rings	2	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]+	164.331	30932474
DeepCCS	[M-H]-	161.973	30932474
DeepCCS	[M-2H]-	195.202	30932474
DeepCCS	[M+Na]+	170.972	30932474
AllCCS	[M+H]+	161.9	32859911
AllCCS	[M+H-H2O]+	158.3	32859911
AllCCS	[M+NH4]+	165.2	32859911
AllCCS	[M+Na]+	166.2	32859911
AllCCS	[M-H]-	159.0	32859911
AllCCS	[M+Na-2H]-	158.8	32859911
AllCCS	[M+HCOO]-	158.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Nitrophenyl beta-D-xyloside	OC1COC(OC2=CC=C(C=C2)[N+]([O-])=O)C(O)C1O	3484.3	Standard polar	33892256
4-Nitrophenyl beta-D-xyloside	OC1COC(OC2=CC=C(C=C2)[N+]([O-])=O)C(O)C1O	2541.1	Standard non polar	33892256
4-Nitrophenyl beta-D-xyloside	OC1COC(OC2=CC=C(C=C2)[N+]([O-])=O)C(O)C1O	2475.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl beta-D-xyloside GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udr-9880000000-426ea41593179d31eec6	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl beta-D-xyloside GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl beta-D-xyloside GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl beta-D-xyloside GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl beta-D-xyloside GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl beta-D-xyloside GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl beta-D-xyloside GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl beta-D-xyloside GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl beta-D-xyloside GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl beta-D-xyloside GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl beta-D-xyloside GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl beta-D-xyloside GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl beta-D-xyloside GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl beta-D-xyloside GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl beta-D-xyloside GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl beta-D-xyloside GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

301789

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

340484

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-Nitrophenyl beta-D-xyloside (HMDB0245573)

MOL for HMDB0245573 (4-Nitrophenyl beta-D-xyloside)

3D MOL for HMDB0245573 (4-Nitrophenyl beta-D-xyloside)

3D SDF for HMDB0245573 (4-Nitrophenyl beta-D-xyloside)

3D-SDF for HMDB0245573 (4-Nitrophenyl beta-D-xyloside)

PDB for HMDB0245573 (4-Nitrophenyl beta-D-xyloside)

3D PDB for HMDB0245573 (4-Nitrophenyl beta-D-xyloside)

SMILES for HMDB0245573 (4-Nitrophenyl beta-D-xyloside)

INCHI for HMDB0245573 (4-Nitrophenyl beta-D-xyloside)

Structure for HMDB0245573 (4-Nitrophenyl beta-D-xyloside)

3D Structure for HMDB0245573 (4-Nitrophenyl beta-D-xyloside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

NMR Spectra