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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-12 00:26:03 UTC

Update Date

2021-09-26 23:18:21 UTC

HMDB ID

HMDB0260294

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Bis(4-nitrophenyl) hydrogen phosphate

Description

bis(4-nitrophenyl) hydrogen phosphate, also known as bis-4-nitrophenyl phosphoric acid, belongs to the class of organic compounds known as aryl phosphodiesters. These are aryl phosphates in which the phosphate is esterified at exactly two positions. bis(4-nitrophenyl) hydrogen phosphate exists in all living organisms, ranging from bacteria to humans. Based on a literature review very few articles have been published on bis(4-nitrophenyl) hydrogen phosphate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Bis(4-nitrophenyl) hydrogen phosphate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Bis(4-nitrophenyl) hydrogen phosphate 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

HMDB0260294
     RDKit          3D
Bis(4-nitrophenyl) hydrogen phosphate
 32 33  0  0  0  0  0  0  0  0999 V2000
    7.3466   -0.1795    0.2593 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4963   -0.2123   -0.6686 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.9371   -0.5417   -1.9081 O   0  0  0  0  0  1  0  0  0  0  0  0
    5.1241    0.0859   -0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6946    0.4210    0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3659    0.6994    1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4911    0.6454   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1532    0.9365    0.2313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0074   -0.2144    0.6693 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.7466    0.3236    1.8905 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6693   -1.6911    1.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951   -0.4034   -0.6509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4449   -0.2278   -0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0080    1.0112   -0.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3741    1.2198   -0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1464    0.1463   -0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5461    0.3269    0.0653 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.2707   -0.6360    0.3828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1519    1.5468   -0.0939 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.5835   -1.1231    0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2256   -1.2999   -0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9188    0.3126   -1.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2485    0.0339   -1.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3907    0.4607    1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9741    0.9699    2.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1638   -2.4259    0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3865    1.8458   -0.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8038    2.1921   -0.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1779   -1.9697    0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8338   -2.2958    0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2255    0.2735   -2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6027   -0.2306   -2.4633 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  2  0
  9 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  2  0
  7 22  1  0
 22 23  2  0
 23  4  1  0
 21 13  1  0
  5 24  1  0
  6 25  1  0
 11 26  1  0
 14 27  1  0
 15 28  1  0
 20 29  1  0
 21 30  1  0
 22 31  1  0
 23 32  1  0
M  CHG  4   2   1   3  -1  17   1  19  -1
M  END

B4N
  Mrv0541 02241213252D          

 23 24  0  0  0  0            999 V2000
    2.1483    0.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8627   -0.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8627   -0.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5772   -1.3286    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.5772   -2.1536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -0.9161    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1483   -1.3286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -0.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -0.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7193    0.3214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0049   -0.0911    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4076    0.6234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4174   -0.8055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7096   -0.5036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4241   -0.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1386   -0.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8530   -0.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8530    0.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5675    1.1464    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -4.2820    0.7339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5675    1.9714    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.1386    1.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4241    0.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  2  0  0  0  0
  4  5  2  0  0  0  0
  4  6  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  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 23  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 22  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 22 23  2  0  0  0  0
M  CHG  4   4   1   6  -1  19   1  21  -1
M  END
> <DATABASE_ID>
HMDB0260294

> <DATABASE_NAME>
hmdb

> <SMILES>
OP(=O)(OC1=CC=C(C=C1)[N+]([O-])=O)OC1=CC=C(C=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H9N2O8P/c15-13(16)9-1-5-11(6-2-9)21-23(19,20)22-12-7-3-10(4-8-12)14(17)18/h1-8H,(H,19,20)

> <INCHI_KEY>
MHSVUSZEHNVFKW-UHFFFAOYSA-N

> <FORMULA>
C12H9N2O8P

> <MOLECULAR_WEIGHT>
340.1822

> <EXACT_MASS>
340.009651786

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
27.790813001532662

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
bis(4-nitrophenoxy)phosphinic acid

> <ALOGPS_LOGP>
2.08

> <JCHEM_LOGP>
2.931702898666667

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8498227521612964

> <JCHEM_POLAR_SURFACE_AREA>
147.39999999999998

> <JCHEM_REFRACTIVITY>
77.8211

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bis(p-nitrophenyl)phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0260294
     RDKit          3D
Bis(4-nitrophenyl) hydrogen phosphate
 32 33  0  0  0  0  0  0  0  0999 V2000
    7.3466   -0.1795    0.2593 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4963   -0.2123   -0.6686 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.9371   -0.5417   -1.9081 O   0  0  0  0  0  1  0  0  0  0  0  0
    5.1241    0.0859   -0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6946    0.4210    0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3659    0.6994    1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4911    0.6454   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1532    0.9365    0.2313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0074   -0.2144    0.6693 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.7466    0.3236    1.8905 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6693   -1.6911    1.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951   -0.4034   -0.6509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4449   -0.2278   -0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0080    1.0112   -0.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3741    1.2198   -0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1464    0.1463   -0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5461    0.3269    0.0653 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.2707   -0.6360    0.3828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1519    1.5468   -0.0939 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.5835   -1.1231    0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2256   -1.2999   -0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9188    0.3126   -1.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2485    0.0339   -1.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3907    0.4607    1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9741    0.9699    2.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1638   -2.4259    0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3865    1.8458   -0.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8038    2.1921   -0.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1779   -1.9697    0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8338   -2.2958    0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2255    0.2735   -2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6027   -0.2306   -2.4633 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  2  0
  9 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  2  0
  7 22  1  0
 22 23  2  0
 23  4  1  0
 21 13  1  0
  5 24  1  0
  6 25  1  0
 11 26  1  0
 14 27  1  0
 15 28  1  0
 20 29  1  0
 21 30  1  0
 22 31  1  0
 23 32  1  0
M  CHG  4   2   1   3  -1  17   1  19  -1
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: B4N                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.010   0.600   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.344  -0.170   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.344  -1.710   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       6.677  -2.480   0.000  0.00  0.00           N+1
HETATM    5  O   UNK     0       6.677  -4.020   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       8.011  -1.710   0.000  0.00  0.00           O-1
HETATM    7  C   UNK     0       4.010  -2.480   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.676  -1.710   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.676  -0.170   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.343   0.600   0.000  0.00  0.00           O+0
HETATM   11  P   UNK     0       0.009  -0.170   0.000  0.00  0.00           P+0
HETATM   12  O   UNK     0      -0.761   1.164   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.779  -1.504   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.325  -0.940   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.658  -0.170   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.992  -0.940   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.326  -0.170   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.326   1.370   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -6.659   2.140   0.000  0.00  0.00           N+1
HETATM   20  O   UNK     0      -7.993   1.370   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.659   3.680   0.000  0.00  0.00           O-1
HETATM   22  C   UNK     0      -3.992   2.140   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.658   1.370   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8                                                       
CONECT    8    7    9                                                       
CONECT    9    1    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23                                                       
CONECT   23   15   22                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0260294
HETATM    1  O1  UNL     1       7.347  -0.180   0.259  1.00  0.00           O  
HETATM    2  N1  UNL     1       6.496  -0.212  -0.669  1.00  0.00           N1+
HETATM    3  O2  UNL     1       6.937  -0.542  -1.908  1.00  0.00           O1-
HETATM    4  C1  UNL     1       5.124   0.086  -0.422  1.00  0.00           C  
HETATM    5  C2  UNL     1       4.695   0.421   0.857  1.00  0.00           C  
HETATM    6  C3  UNL     1       3.366   0.699   1.044  1.00  0.00           C  
HETATM    7  C4  UNL     1       2.491   0.645  -0.011  1.00  0.00           C  
HETATM    8  O3  UNL     1       1.153   0.937   0.231  1.00  0.00           O  
HETATM    9  P1  UNL     1      -0.007  -0.214   0.669  1.00  0.00           P  
HETATM   10  O4  UNL     1      -0.747   0.324   1.891  1.00  0.00           O  
HETATM   11  O5  UNL     1       0.669  -1.691   1.123  1.00  0.00           O  
HETATM   12  O6  UNL     1      -1.095  -0.403  -0.651  1.00  0.00           O  
HETATM   13  C5  UNL     1      -2.445  -0.228  -0.472  1.00  0.00           C  
HETATM   14  C6  UNL     1      -3.008   1.011  -0.642  1.00  0.00           C  
HETATM   15  C7  UNL     1      -4.374   1.220  -0.468  1.00  0.00           C  
HETATM   16  C8  UNL     1      -5.146   0.146  -0.120  1.00  0.00           C  
HETATM   17  N2  UNL     1      -6.546   0.327   0.065  1.00  0.00           N1+
HETATM   18  O7  UNL     1      -7.271  -0.636   0.383  1.00  0.00           O  
HETATM   19  O8  UNL     1      -7.152   1.547  -0.094  1.00  0.00           O1-
HETATM   20  C9  UNL     1      -4.584  -1.123   0.056  1.00  0.00           C  
HETATM   21  C10 UNL     1      -3.226  -1.300  -0.123  1.00  0.00           C  
HETATM   22  C11 UNL     1       2.919   0.313  -1.279  1.00  0.00           C  
HETATM   23  C12 UNL     1       4.249   0.034  -1.468  1.00  0.00           C  
HETATM   24  H1  UNL     1       5.391   0.461   1.680  1.00  0.00           H  
HETATM   25  H2  UNL     1       2.974   0.970   2.035  1.00  0.00           H  
HETATM   26  H3  UNL     1       0.164  -2.426   0.668  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.386   1.846  -0.917  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.804   2.192  -0.604  1.00  0.00           H  
HETATM   29  H6  UNL     1      -5.178  -1.970   0.329  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.834  -2.296   0.023  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.225   0.274  -2.098  1.00  0.00           H  
HETATM   32  H9  UNL     1       4.603  -0.231  -2.463  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5    5   23
CONECT    5    6   24
CONECT    6    7    7   25
CONECT    7    8   22
CONECT    8    9
CONECT    9   10   10   11   12
CONECT   11   26
CONECT   12   13
CONECT   13   14   14   21
CONECT   14   15   27
CONECT   15   16   16   28
CONECT   16   17   20
CONECT   17   18   18   19
CONECT   20   21   21   29
CONECT   21   30
CONECT   22   23   23   31
CONECT   23   32
END

HMDB0260294
     RDKit          3D
Bis(4-nitrophenyl) hydrogen phosphate
 32 33  0  0  0  0  0  0  0  0999 V2000
    7.3466   -0.1795    0.2593 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4963   -0.2123   -0.6686 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.9371   -0.5417   -1.9081 O   0  0  0  0  0  1  0  0  0  0  0  0
    5.1241    0.0859   -0.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6946    0.4210    0.8566 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3659    0.6994    1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4911    0.6454   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1532    0.9365    0.2313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0074   -0.2144    0.6693 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.7466    0.3236    1.8905 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6693   -1.6911    1.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0951   -0.4034   -0.6509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4449   -0.2278   -0.4725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0080    1.0112   -0.6425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3741    1.2198   -0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1464    0.1463   -0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5461    0.3269    0.0653 N   0  0  0  0  0  4  0  0  0  0  0  0
   -7.2707   -0.6360    0.3828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1519    1.5468   -0.0939 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.5835   -1.1231    0.0564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2256   -1.2999   -0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9188    0.3126   -1.2795 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2485    0.0339   -1.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3907    0.4607    1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9741    0.9699    2.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1638   -2.4259    0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3865    1.8458   -0.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8038    2.1921   -0.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1779   -1.9697    0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8338   -2.2958    0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2255    0.2735   -2.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6027   -0.2306   -2.4633 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  2  0
  9 11  1  0
  9 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  2  0
  7 22  1  0
 22 23  2  0
 23  4  1  0
 21 13  1  0
  5 24  1  0
  6 25  1  0
 11 26  1  0
 14 27  1  0
 15 28  1  0
 20 29  1  0
 21 30  1  0
 22 31  1  0
 23 32  1  0
M  CHG  4   2   1   3  -1  17   1  19  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Bis-4-nitrophenyl phosphate	Kegg
Bis-4-nitrophenyl phosphoric acid	Generator
Bis(4-nitrophenyl) hydrogen phosphoric acid	Generator
BNPP-4	MeSH
BPNPP	MeSH
Bis(4-nitrophenyl)phosphate, sodium salt	MeSH
Bis(P-nitrophenyl)phosphate	MeSH
Bis(para-nitrophenol)phosphate	MeSH
Bis(4-nitrophenyl)phosphate, calcium salt	MeSH
Bis-P-nitrophenyl phosphate	MeSH
Bis(4-nitrophenyl)phosphoric acid	Generator
Bis(4-nitrophenoxy)phosphinate	Generator
Bis(4-nitrophenyl)phosphate	MeSH

Chemical Formula

C₁₂H₉N₂O₈P

Average Molecular Weight

340.1822

Monoisotopic Molecular Weight

340.009651786

IUPAC Name

bis(4-nitrophenoxy)phosphinic acid

Traditional Name

bis(p-nitrophenyl)phosphate

CAS Registry Number

Not Available

SMILES

OP(=O)(OC1=CC=C(C=C1)[N+]([O-])=O)OC1=CC=C(C=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C12H9N2O8P/c15-13(16)9-1-5-11(6-2-9)21-23(19,20)22-12-7-3-10(4-8-12)14(17)18/h1-8H,(H,19,20)

InChI Key

MHSVUSZEHNVFKW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl phosphodiesters. These are aryl phosphates in which the phosphate is esterified at exactly two positions.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Aryl phosphodiesters

Alternative Parents

Substituents

Aryl phosphodiester
Nitrobenzene
Phenoxy compound
Nitroaromatic compound
Monocyclic benzene moiety
Benzenoid
C-nitro compound
Organic nitro compound
Organic oxoazanium
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

aryl phosphate (CHEBI:3122 )

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	2.08	ALOGPS
logP	2.93	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	0.85	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	147.4 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	77.82 m³·mol⁻¹	ChemAxon
Polarizability	27.79 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
AllCCS	[M+H]+	171.347	32859911
AllCCS	[M+H-H2O]+	168.215	32859911
AllCCS	[M+Na]+	175.076	32859911
AllCCS	[M+NH4]+	174.245	32859911
AllCCS	[M-H]-	165.636	32859911
AllCCS	[M+Na-2H]-	164.557	32859911
AllCCS	[M+HCOO]-	163.5	32859911
DeepCCS	[M+H]+	159.629	30932474
DeepCCS	[M-H]-	157.271	30932474
DeepCCS	[M-2H]-	190.155	30932474
DeepCCS	[M+Na]+	165.722	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.2 minutes	32390414
Predicted by Siyang on May 30, 2022	12.4834 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.52 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1752.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	345.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	160.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	199.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	115.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	478.4 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	509.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	131.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1061.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	491.4 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	1065.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	394.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	359.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	403.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	329.9 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	179.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bis(4-nitrophenyl) hydrogen phosphate	OP(=O)(OC1=CC=C(C=C1)[N+]([O-])=O)OC1=CC=C(C=C1)[N+]([O-])=O	4186.2	Standard polar	33892256
Bis(4-nitrophenyl) hydrogen phosphate	OP(=O)(OC1=CC=C(C=C1)[N+]([O-])=O)OC1=CC=C(C=C1)[N+]([O-])=O	2776.5	Standard non polar	33892256
Bis(4-nitrophenyl) hydrogen phosphate	OP(=O)(OC1=CC=C(C=C1)[N+]([O-])=O)OC1=CC=C(C=C1)[N+]([O-])=O	2808.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bis(4-nitrophenyl) hydrogen phosphate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(OC1=CC=C([N+](=O)[O-])C=C1)OC1=CC=C([N+](=O)[O-])C=C1	2975.4	Semi standard non polar	33892256
Bis(4-nitrophenyl) hydrogen phosphate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(OC1=CC=C([N+](=O)[O-])C=C1)OC1=CC=C([N+](=O)[O-])C=C1	2810.8	Standard non polar	33892256
Bis(4-nitrophenyl) hydrogen phosphate,1TMS,isomer #1	C[Si](C)(C)OP(=O)(OC1=CC=C([N+](=O)[O-])C=C1)OC1=CC=C([N+](=O)[O-])C=C1	3689.3	Standard polar	33892256
Bis(4-nitrophenyl) hydrogen phosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=C([N+](=O)[O-])C=C1)OC1=CC=C([N+](=O)[O-])C=C1	3259.4	Semi standard non polar	33892256
Bis(4-nitrophenyl) hydrogen phosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=C([N+](=O)[O-])C=C1)OC1=CC=C([N+](=O)[O-])C=C1	3018.0	Standard non polar	33892256
Bis(4-nitrophenyl) hydrogen phosphate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OP(=O)(OC1=CC=C([N+](=O)[O-])C=C1)OC1=CC=C([N+](=O)[O-])C=C1	3797.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bis(4-nitrophenyl) hydrogen phosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-6948000000-b1eb4254e6f068873bb6	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bis(4-nitrophenyl) hydrogen phosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bis(4-nitrophenyl) hydrogen phosphate LC-ESI-QQ , negative-QTOF	splash10-000i-0009000000-d5f9f89f73732a9439d2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bis(4-nitrophenyl) hydrogen phosphate LC-ESI-QQ , negative-QTOF	splash10-000i-0009000000-7961acf93ea4ca39ae8e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bis(4-nitrophenyl) hydrogen phosphate LC-ESI-QQ , negative-QTOF	splash10-000i-1908000000-b360365d152403c9df04	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bis(4-nitrophenyl) hydrogen phosphate LC-ESI-QQ , negative-QTOF	splash10-000i-1900000000-55ea0d8e2b91ac0f9310	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bis(4-nitrophenyl) hydrogen phosphate LC-ESI-QQ , negative-QTOF	splash10-000i-1900000000-11552e3273cc2d043659	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(4-nitrophenyl) hydrogen phosphate 10V, Positive-QTOF	splash10-0006-0009000000-3a64c7a736d6ab5c4e00	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(4-nitrophenyl) hydrogen phosphate 20V, Positive-QTOF	splash10-006x-0009000000-6b858e883fffc2fe4bfe	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(4-nitrophenyl) hydrogen phosphate 40V, Positive-QTOF	splash10-01q9-1922000000-8ae9ba3ffaf40e75b3c7	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(4-nitrophenyl) hydrogen phosphate 10V, Negative-QTOF	splash10-000i-0019000000-177d806f34a8a9444b68	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(4-nitrophenyl) hydrogen phosphate 20V, Negative-QTOF	splash10-000i-0109000000-e647b50bdeeb94c24a57	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(4-nitrophenyl) hydrogen phosphate 40V, Negative-QTOF	splash10-01u0-9120000000-fd0a7139424f44d04b5b	2017-07-26	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

DB07418

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

250

KEGG Compound ID

C03779

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 Bis(4-nitrophenyl) hydrogen phosphate (HMDB0260294)

MOL for HMDB0260294 (Bis(4-nitrophenyl) hydrogen phosphate)

3D MOL for HMDB0260294 (Bis(4-nitrophenyl) hydrogen phosphate)

3D SDF for HMDB0260294 (Bis(4-nitrophenyl) hydrogen phosphate)

3D-SDF for HMDB0260294 (Bis(4-nitrophenyl) hydrogen phosphate)

PDB for HMDB0260294 (Bis(4-nitrophenyl) hydrogen phosphate)

3D PDB for HMDB0260294 (Bis(4-nitrophenyl) hydrogen phosphate)

SMILES for HMDB0260294 (Bis(4-nitrophenyl) hydrogen phosphate)

INCHI for HMDB0260294 (Bis(4-nitrophenyl) hydrogen phosphate)

Structure for HMDB0260294 (Bis(4-nitrophenyl) hydrogen phosphate)

3D Structure for HMDB0260294 (Bis(4-nitrophenyl) hydrogen phosphate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra