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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:33:14 UTC

Update Date

2021-09-26 22:55:41 UTC

HMDB ID

HMDB0246537

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Nitrophenyl 4-guanidinobenzoate

Description

4-Nitrophenyl 4-guanidinobenzoate belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). Based on a literature review a significant number of articles have been published on 4-Nitrophenyl 4-guanidinobenzoate. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-nitrophenyl 4-guanidinobenzoate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Nitrophenyl 4-guanidinobenzoate 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

HMDB0246537
     RDKit          3D
4-Nitrophenyl 4-guanidinobenzoate
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.3215    0.1071    1.1262 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2580   -0.9090    2.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4145   -1.2594    2.8417 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1494   -1.5019    2.3106 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9731   -1.1606    1.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9748   -1.0385    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8267   -0.7060   -0.4934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6254   -0.4802    0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5705   -0.1289   -0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5395   -0.0203   -1.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8050    0.1077   -0.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9311    0.4415   -0.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1989    1.7757   -0.9739 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3099    2.1909   -1.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1681    1.2465   -2.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3118    1.6232   -2.9750 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.6064    2.8159   -3.2020 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1554    0.6718   -3.4917 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.9167   -0.0881   -2.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7941   -0.4911   -1.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6187   -0.6008    1.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733   -0.9352    2.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7158    0.9377    1.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9735    0.0131    0.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7716   -0.6412    3.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9165   -2.1454    2.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9208   -1.2153   -0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8244   -0.6080   -1.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5609    2.5597   -0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4777    3.2497   -1.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5823   -0.8279   -2.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5767   -1.5244   -1.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3101   -0.4301    2.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7571   -1.0285    3.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  2  0
  8 21  1  0
 21 22  2  0
 22  5  1  0
 20 12  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  6 27  1  0
  7 28  1  0
 13 29  1  0
 14 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
 22 34  1  0
M  CHG  2  16   1  18  -1
M  END


  Mrv1652309112101332D          

 22 23  0  0  0  0            999 V2000
    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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    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
    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 O   0  0  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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  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
 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
  3 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
M  CHG  2  16   1  18  -1
M  END
> <DATABASE_ID>
HMDB0246537

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(N)=NC1=CC=C(C=C1)C(=O)OC1=CC=C(C=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H12N4O4/c15-14(16)17-10-3-1-9(2-4-10)13(19)22-12-7-5-11(6-8-12)18(20)21/h1-8H,(H4,15,16,17)

> <INCHI_KEY>
CFOQGBUQTOGYKI-UHFFFAOYSA-N

> <FORMULA>
C14H12N4O4

> <MOLECULAR_WEIGHT>
300.274

> <EXACT_MASS>
300.085854882

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.686920921440837

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-nitrophenyl 4-[(diaminomethylidene)amino]benzoate

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
2.180344308333333

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.757028152310012

> <JCHEM_POLAR_SURFACE_AREA>
133.84

> <JCHEM_REFRACTIVITY>
80.25580000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-nitrophenyl 4-[(diaminomethylidene)amino]benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246537
     RDKit          3D
4-Nitrophenyl 4-guanidinobenzoate
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.3215    0.1071    1.1262 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2580   -0.9090    2.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4145   -1.2594    2.8417 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1494   -1.5019    2.3106 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9731   -1.1606    1.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9748   -1.0385    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8267   -0.7060   -0.4934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6254   -0.4802    0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5705   -0.1289   -0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5395   -0.0203   -1.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8050    0.1077   -0.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9311    0.4415   -0.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1989    1.7757   -0.9739 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3099    2.1909   -1.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1681    1.2465   -2.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3118    1.6232   -2.9750 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.6064    2.8159   -3.2020 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1554    0.6718   -3.4917 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.9167   -0.0881   -2.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7941   -0.4911   -1.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6187   -0.6008    1.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733   -0.9352    2.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7158    0.9377    1.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9735    0.0131    0.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7716   -0.6412    3.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9165   -2.1454    2.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9208   -1.2153   -0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8244   -0.6080   -1.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5609    2.5597   -0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4777    3.2497   -1.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5823   -0.8279   -2.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5767   -1.5244   -1.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3101   -0.4301    2.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7571   -1.0285    3.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  2  0
  8 21  1  0
 21 22  2  0
 22  5  1  0
 20 12  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  6 27  1  0
  7 28  1  0
 13 29  1  0
 14 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
 22 34  1  0
M  CHG  2  16   1  18  -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       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+1
HETATM   17  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O-1
HETATM   19  N   UNK     0       2.667  -9.240   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       1.334 -11.550   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       0.000  -9.240   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   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                                                            
CONECT   19    3   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0246537
HETATM    1  N1  UNL     1      -5.322   0.107   1.126  1.00  0.00           N  
HETATM    2  C1  UNL     1      -5.258  -0.909   2.104  1.00  0.00           C  
HETATM    3  N2  UNL     1      -6.414  -1.259   2.842  1.00  0.00           N  
HETATM    4  N3  UNL     1      -4.149  -1.502   2.311  1.00  0.00           N  
HETATM    5  C2  UNL     1      -2.973  -1.161   1.576  1.00  0.00           C  
HETATM    6  C3  UNL     1      -2.975  -1.039   0.202  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.827  -0.706  -0.493  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.625  -0.480   0.148  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.570  -0.129  -0.613  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.540  -0.020  -1.874  1.00  0.00           O  
HETATM   11  O2  UNL     1       1.805   0.108  -0.025  1.00  0.00           O  
HETATM   12  C7  UNL     1       2.931   0.442  -0.759  1.00  0.00           C  
HETATM   13  C8  UNL     1       3.199   1.776  -0.974  1.00  0.00           C  
HETATM   14  C9  UNL     1       4.310   2.191  -1.702  1.00  0.00           C  
HETATM   15  C10 UNL     1       5.168   1.246  -2.224  1.00  0.00           C  
HETATM   16  N4  UNL     1       6.312   1.623  -2.975  1.00  0.00           N1+
HETATM   17  O3  UNL     1       6.606   2.816  -3.202  1.00  0.00           O  
HETATM   18  O4  UNL     1       7.155   0.672  -3.492  1.00  0.00           O1-
HETATM   19  C11 UNL     1       4.917  -0.088  -2.020  1.00  0.00           C  
HETATM   20  C12 UNL     1       3.794  -0.491  -1.285  1.00  0.00           C  
HETATM   21  C13 UNL     1      -0.619  -0.601   1.518  1.00  0.00           C  
HETATM   22  C14 UNL     1      -1.773  -0.935   2.217  1.00  0.00           C  
HETATM   23  H1  UNL     1      -4.716   0.938   1.208  1.00  0.00           H  
HETATM   24  H2  UNL     1      -5.973   0.013   0.335  1.00  0.00           H  
HETATM   25  H3  UNL     1      -6.772  -0.641   3.576  1.00  0.00           H  
HETATM   26  H4  UNL     1      -6.917  -2.145   2.649  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.921  -1.215  -0.320  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.824  -0.608  -1.587  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.561   2.560  -0.589  1.00  0.00           H  
HETATM   30  H8  UNL     1       4.478   3.250  -1.842  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.582  -0.828  -2.423  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.577  -1.524  -1.112  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.310  -0.430   2.045  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.757  -1.029   3.310  1.00  0.00           H  
CONECT    1    2   23   24
CONECT    2    3    4    4
CONECT    3   25   26
CONECT    4    5
CONECT    5    6    6   22
CONECT    6    7   27
CONECT    7    8    8   28
CONECT    8    9   21
CONECT    9   10   10   11
CONECT   11   12
CONECT   12   13   13   20
CONECT   13   14   29
CONECT   14   15   15   30
CONECT   15   16   19
CONECT   16   17   17   18
CONECT   19   20   20   31
CONECT   20   32
CONECT   21   22   22   33
CONECT   22   34
END

HMDB0246537
     RDKit          3D
4-Nitrophenyl 4-guanidinobenzoate
 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.3215    0.1071    1.1262 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2580   -0.9090    2.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4145   -1.2594    2.8417 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1494   -1.5019    2.3106 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9731   -1.1606    1.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9748   -1.0385    0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8267   -0.7060   -0.4934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6254   -0.4802    0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5705   -0.1289   -0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5395   -0.0203   -1.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8050    0.1077   -0.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9311    0.4415   -0.7593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1989    1.7757   -0.9739 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3099    2.1909   -1.7016 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1681    1.2465   -2.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3118    1.6232   -2.9750 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.6064    2.8159   -3.2020 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1554    0.6718   -3.4917 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.9167   -0.0881   -2.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7941   -0.4911   -1.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6187   -0.6008    1.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7733   -0.9352    2.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7158    0.9377    1.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9735    0.0131    0.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7716   -0.6412    3.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9165   -2.1454    2.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9208   -1.2153   -0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8244   -0.6080   -1.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5609    2.5597   -0.5891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4777    3.2497   -1.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5823   -0.8279   -2.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5767   -1.5244   -1.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3101   -0.4301    2.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7571   -1.0285    3.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  2  0
  8 21  1  0
 21 22  2  0
 22  5  1  0
 20 12  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  6 27  1  0
  7 28  1  0
 13 29  1  0
 14 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
 22 34  1  0
M  CHG  2  16   1  18  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Nitrophenyl 4-guanidinobenzoic acid	Generator
4-Nitrophenyl 4-carbamimidamidobenzoic acid	HMDB
4-Nitrophenyl 4'-guanidinobenzoate	HMDB
4-Nitrophenyl 4'-guanidinobenzoate, hydrochloride	HMDB
4-Nitrophenyl p'-guanidinobenzoate	HMDB
p-Nitrophenyl p'-guanidinobenzoate	HMDB
Para-nitrophenyl p'-guanidinobenzoate	HMDB

Chemical Formula

C₁₄H₁₂N₄O₄

Average Molecular Weight

300.274

Monoisotopic Molecular Weight

300.085854882

IUPAC Name

4-nitrophenyl 4-[(diaminomethylidene)amino]benzoate

Traditional Name

4-nitrophenyl 4-[(diaminomethylidene)amino]benzoate

CAS Registry Number

Not Available

SMILES

NC(N)=NC1=CC=C(C=C1)C(=O)OC1=CC=C(C=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C14H12N4O4/c15-14(16)17-10-3-1-9(2-4-10)13(19)22-12-7-5-11(6-8-12)18(20)21/h1-8H,(H4,15,16,17)

InChI Key

CFOQGBUQTOGYKI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depside backbone
Guanidinobenzoic acid or derivatives
Benzoate ester
Phenol ester
Benzoic acid or derivatives
Nitrobenzene
Phenoxy compound
Nitroaromatic compound
Benzoyl
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Guanidine
Organic nitro compound
C-nitro compound
Organic oxoazanium
Organic 1,3-dipolar compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
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	1.67	ALOGPS
logP	2.18	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	8.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	133.84 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.26 m³·mol⁻¹	ChemAxon
Polarizability	29.69 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]+	161.21	30932474
DeepCCS	[M-H]-	158.852	30932474
DeepCCS	[M-2H]-	192.129	30932474
DeepCCS	[M+Na]+	168.216	30932474
AllCCS	[M+H]+	166.3	32859911
AllCCS	[M+H-H2O]+	162.9	32859911
AllCCS	[M+NH4]+	169.4	32859911
AllCCS	[M+Na]+	170.2	32859911
AllCCS	[M-H]-	169.2	32859911
AllCCS	[M+Na-2H]-	168.5	32859911
AllCCS	[M+HCOO]-	167.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.0044 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.32 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	769.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	259.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	108.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	58.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	292.8 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	337.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	605.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	723.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	229.0 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	799.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	191.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	262.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	492.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	513.5 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	237.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Nitrophenyl 4-guanidinobenzoate	NC(N)=NC1=CC=C(C=C1)C(=O)OC1=CC=C(C=C1)[N+]([O-])=O	3863.7	Standard polar	33892256
4-Nitrophenyl 4-guanidinobenzoate	NC(N)=NC1=CC=C(C=C1)C(=O)OC1=CC=C(C=C1)[N+]([O-])=O	2827.0	Standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate	NC(N)=NC1=CC=C(C=C1)C(=O)OC1=CC=C(C=C1)[N+]([O-])=O	3107.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Nitrophenyl 4-guanidinobenzoate,1TMS,isomer #1	C[Si](C)(C)NC(N)=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1	3200.7	Semi standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,1TMS,isomer #1	C[Si](C)(C)NC(N)=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1	2961.6	Standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,1TMS,isomer #1	C[Si](C)(C)NC(N)=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1	4729.6	Standard polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,2TMS,isomer #1	C[Si](C)(C)NC(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N[Si](C)(C)C	3315.4	Semi standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,2TMS,isomer #1	C[Si](C)(C)NC(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N[Si](C)(C)C	2966.4	Standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,2TMS,isomer #1	C[Si](C)(C)NC(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N[Si](C)(C)C	4455.6	Standard polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,2TMS,isomer #2	C[Si](C)(C)N(C(N)=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)[Si](C)(C)C	3213.4	Semi standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,2TMS,isomer #2	C[Si](C)(C)N(C(N)=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)[Si](C)(C)C	3033.9	Standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,2TMS,isomer #2	C[Si](C)(C)N(C(N)=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)[Si](C)(C)C	4536.3	Standard polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,3TMS,isomer #1	C[Si](C)(C)NC(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N([Si](C)(C)C)[Si](C)(C)C	3225.4	Semi standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,3TMS,isomer #1	C[Si](C)(C)NC(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N([Si](C)(C)C)[Si](C)(C)C	3003.9	Standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,3TMS,isomer #1	C[Si](C)(C)NC(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N([Si](C)(C)C)[Si](C)(C)C	4027.0	Standard polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,4TMS,isomer #1	C[Si](C)(C)N(C(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	3199.8	Semi standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,4TMS,isomer #1	C[Si](C)(C)N(C(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	3022.8	Standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,4TMS,isomer #1	C[Si](C)(C)N(C(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	3638.2	Standard polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(N)=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1	3449.8	Semi standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(N)=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1	3142.4	Standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(N)=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1	4680.5	Standard polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N[Si](C)(C)C(C)(C)C	3814.3	Semi standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N[Si](C)(C)C(C)(C)C	3342.4	Standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N[Si](C)(C)C(C)(C)C	4236.2	Standard polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)[Si](C)(C)C(C)(C)C	3714.1	Semi standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)[Si](C)(C)C(C)(C)C	3432.8	Standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(N)=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)[Si](C)(C)C(C)(C)C	4473.3	Standard polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3906.9	Semi standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3616.7	Standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3964.2	Standard polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	4080.9	Semi standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3814.0	Standard non polar	33892256
4-Nitrophenyl 4-guanidinobenzoate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=NC1=CC=C(C(=O)OC2=CC=C([N+](=O)[O-])C=C2)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3724.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl 4-guanidinobenzoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-03k9-5900000000-32828ee763cabb303d41	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrophenyl 4-guanidinobenzoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28527

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

30744

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 4-guanidinobenzoate (HMDB0246537)

MOL for HMDB0246537 (4-Nitrophenyl 4-guanidinobenzoate)

3D MOL for HMDB0246537 (4-Nitrophenyl 4-guanidinobenzoate)

3D SDF for HMDB0246537 (4-Nitrophenyl 4-guanidinobenzoate)

3D-SDF for HMDB0246537 (4-Nitrophenyl 4-guanidinobenzoate)

PDB for HMDB0246537 (4-Nitrophenyl 4-guanidinobenzoate)

3D PDB for HMDB0246537 (4-Nitrophenyl 4-guanidinobenzoate)

SMILES for HMDB0246537 (4-Nitrophenyl 4-guanidinobenzoate)

INCHI for HMDB0246537 (4-Nitrophenyl 4-guanidinobenzoate)

Structure for HMDB0246537 (4-Nitrophenyl 4-guanidinobenzoate)

3D Structure for HMDB0246537 (4-Nitrophenyl 4-guanidinobenzoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra