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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:09:42 UTC

Update Date

2021-09-26 22:56:38 UTC

HMDB ID

HMDB0247149

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid

Description

4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid, also known as DABCYL, belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring. Based on a literature review very few articles have been published on 4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-[[4-(dimethylamino)phenyl]diazenyl]benzoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid 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

HMDB0247149
     RDKit          3D
4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid
 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.5198    0.6751   -1.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0411    0.0291    0.0587 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9076   -0.5047    1.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6189   -0.0531    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8689    0.9560    0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961    0.8835    0.9336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8751   -0.2657    0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5614   -0.3014    0.6260 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000   -0.0823   -0.3741 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7142   -0.0980   -0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4188   -1.2203   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8031   -1.2658   -0.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5330   -0.2074   -0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9914   -0.2623   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5868   -1.2913   -0.5424 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7487    0.8026    0.3286 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8448    0.9083    0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4574    0.9595    0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5696   -1.3017   -0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9375   -1.1690   -0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7281    1.2818   -1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8473   -0.0657   -1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3207    1.3730   -0.8502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9654   -0.3717    0.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6812   -0.0615    2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6732   -1.6085    1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4083    1.8386    1.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9301    1.6939    1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8521   -2.0692   -1.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3576   -2.1446   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3825    1.2406   -0.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4077    1.7652    0.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9334    1.8504    0.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0092   -2.1632   -0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4949   -1.9674   -0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  3
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
  7 19  1  0
 19 20  2  0
 20  4  1  0
 18 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
 11 29  1  0
 12 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END

  Mrv1652309112102092D          

 20 21  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   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
    1.4289   -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
    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   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.0750    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
 10  7  1  4  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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247149

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)C1=CC=C(C=C1)N=NC1=CC=C(C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H15N3O2/c1-18(2)14-9-7-13(8-10-14)17-16-12-5-3-11(4-6-12)15(19)20/h3-10H,1-2H3,(H,19,20)

> <INCHI_KEY>
WCKQPPQRFNHPRJ-UHFFFAOYSA-N

> <FORMULA>
C15H15N3O2

> <MOLECULAR_WEIGHT>
269.304

> <EXACT_MASS>
269.116426735

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.613707486831874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{2-[4-(dimethylamino)phenyl]diazen-1-yl}benzoic acid

> <ALOGPS_LOGP>
3.75

> <JCHEM_LOGP>
3.680579314027688

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.107987031262544

> <JCHEM_PKA_STRONGEST_BASIC>
3.42880705779309

> <JCHEM_POLAR_SURFACE_AREA>
65.26

> <JCHEM_REFRACTIVITY>
82.06179999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{2-[4-(dimethylamino)phenyl]diazen-1-yl}benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247149
     RDKit          3D
4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid
 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.5198    0.6751   -1.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0411    0.0291    0.0587 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9076   -0.5047    1.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6189   -0.0531    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8689    0.9560    0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961    0.8835    0.9336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8751   -0.2657    0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5614   -0.3014    0.6260 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000   -0.0823   -0.3741 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7142   -0.0980   -0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4188   -1.2203   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8031   -1.2658   -0.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5330   -0.2074   -0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9914   -0.2623   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5868   -1.2913   -0.5424 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7487    0.8026    0.3286 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8448    0.9083    0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4574    0.9595    0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5696   -1.3017   -0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9375   -1.1690   -0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7281    1.2818   -1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8473   -0.0657   -1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3207    1.3730   -0.8502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9654   -0.3717    0.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6812   -0.0615    2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6732   -1.6085    1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4083    1.8386    1.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9301    1.6939    1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8521   -2.0692   -1.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3576   -2.1446   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3825    1.2406   -0.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4077    1.7652    0.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9334    1.8504    0.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0092   -2.1632   -0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4949   -1.9674   -0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  3
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
  7 19  1  0
 19 20  2  0
 20  4  1  0
 18 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
 11 29  1  0
 12 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.667  -9.240   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       4.001 -10.010   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335 -16.940   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667 -16.940   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0247149
HETATM    1  C1  UNL     1      -5.520   0.675  -1.156  1.00  0.00           C  
HETATM    2  N1  UNL     1      -5.041   0.029   0.059  1.00  0.00           N  
HETATM    3  C2  UNL     1      -5.908  -0.505   1.062  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.619  -0.053   0.208  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.869   0.956   0.789  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.496   0.883   0.934  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.875  -0.266   0.464  1.00  0.00           C  
HETATM    8  N2  UNL     1       0.561  -0.301   0.626  1.00  0.00           N  
HETATM    9  N3  UNL     1       1.300  -0.082  -0.374  1.00  0.00           N  
HETATM   10  C7  UNL     1       2.714  -0.098  -0.301  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.419  -1.220  -0.729  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.803  -1.266  -0.676  1.00  0.00           C  
HETATM   13  C10 UNL     1       5.533  -0.207  -0.198  1.00  0.00           C  
HETATM   14  C11 UNL     1       6.991  -0.262  -0.148  1.00  0.00           C  
HETATM   15  O1  UNL     1       7.587  -1.291  -0.542  1.00  0.00           O  
HETATM   16  O2  UNL     1       7.749   0.803   0.329  1.00  0.00           O  
HETATM   17  C12 UNL     1       4.845   0.908   0.228  1.00  0.00           C  
HETATM   18  C13 UNL     1       3.457   0.960   0.177  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.570  -1.302  -0.122  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.938  -1.169  -0.238  1.00  0.00           C  
HETATM   21  H1  UNL     1      -4.728   1.282  -1.636  1.00  0.00           H  
HETATM   22  H2  UNL     1      -5.847  -0.066  -1.903  1.00  0.00           H  
HETATM   23  H3  UNL     1      -6.321   1.373  -0.850  1.00  0.00           H  
HETATM   24  H4  UNL     1      -6.965  -0.372   0.793  1.00  0.00           H  
HETATM   25  H5  UNL     1      -5.681  -0.061   2.042  1.00  0.00           H  
HETATM   26  H6  UNL     1      -5.673  -1.608   1.124  1.00  0.00           H  
HETATM   27  H7  UNL     1      -3.408   1.839   1.141  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.930   1.694   1.396  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.852  -2.069  -1.111  1.00  0.00           H  
HETATM   30  H10 UNL     1       5.358  -2.145  -1.011  1.00  0.00           H  
HETATM   31  H11 UNL     1       8.382   1.241  -0.355  1.00  0.00           H  
HETATM   32  H12 UNL     1       5.408   1.765   0.612  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.933   1.850   0.520  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.009  -2.163  -0.461  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.495  -1.967  -0.691  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4
CONECT    3   24   25   26
CONECT    4    5    5   20
CONECT    5    6   27
CONECT    6    7    7   28
CONECT    7    8   19
CONECT    8    9    9
CONECT    9   10
CONECT   10   11   11   18
CONECT   11   12   29
CONECT   12   13   13   30
CONECT   13   14   17
CONECT   14   15   15   16
CONECT   16   31
CONECT   17   18   18   32
CONECT   18   33
CONECT   19   20   20   34
CONECT   20   35
END

HMDB0247149
     RDKit          3D
4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid
 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.5198    0.6751   -1.1557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0411    0.0291    0.0587 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9076   -0.5047    1.0620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6189   -0.0531    0.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8689    0.9560    0.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961    0.8835    0.9336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8751   -0.2657    0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5614   -0.3014    0.6260 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000   -0.0823   -0.3741 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7142   -0.0980   -0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4188   -1.2203   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8031   -1.2658   -0.6755 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5330   -0.2074   -0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9914   -0.2623   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5868   -1.2913   -0.5424 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7487    0.8026    0.3286 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8448    0.9083    0.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4574    0.9595    0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5696   -1.3017   -0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9375   -1.1690   -0.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7281    1.2818   -1.6363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8473   -0.0657   -1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3207    1.3730   -0.8502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9654   -0.3717    0.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6812   -0.0615    2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6732   -1.6085    1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4083    1.8386    1.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9301    1.6939    1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8521   -2.0692   -1.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3576   -2.1446   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3825    1.2406   -0.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4077    1.7652    0.6124 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9334    1.8504    0.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0092   -2.1632   -0.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4949   -1.9674   -0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  3
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
  7 19  1  0
 19 20  2  0
 20  4  1  0
 18 10  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
 11 29  1  0
 12 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-[[4-(Dimethylamino)phenyl]diazenyl]benzoate	Generator
4-(4-Dimethylaminophenylazo)benzoic acid	HMDB
DABCYL	HMDB

Chemical Formula

C₁₅H₁₅N₃O₂

Average Molecular Weight

269.304

Monoisotopic Molecular Weight

269.116426735

IUPAC Name

4-{2-[4-(dimethylamino)phenyl]diazen-1-yl}benzoic acid

Traditional Name

4-{2-[4-(dimethylamino)phenyl]diazen-1-yl}benzoic acid

CAS Registry Number

Not Available

SMILES

CN(C)C1=CC=C(C=C1)N=NC1=CC=C(C=C1)C(O)=O

InChI Identifier

InChI=1S/C15H15N3O2/c1-18(2)14-9-7-13(8-10-14)17-16-12-5-3-11(4-6-12)15(19)20/h3-10H,1-2H3,(H,19,20)

InChI Key

WCKQPPQRFNHPRJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azobenzenes

Sub Class

Not Available

Direct Parent

Azobenzenes

Alternative Parents

Substituents

Azobenzene
Benzoic acid or derivatives
Benzoic acid
Benzoyl
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aniline or substituted anilines
Monocyclic benzene moiety
Benzenoid
Amino acid
Azo compound
Amino acid or derivatives
Tertiary amine
Carboxylic acid
Carboxylic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organooxygen compound
Organonitrogen compound
Amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
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	3.75	ALOGPS
logP	3.68	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.11	ChemAxon
pKa (Strongest Basic)	3.43	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	65.26 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.06 m³·mol⁻¹	ChemAxon
Polarizability	29.61 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]+	164.851	30932474
DeepCCS	[M-H]-	162.493	30932474
DeepCCS	[M-2H]-	195.379	30932474
DeepCCS	[M+Na]+	170.944	30932474
AllCCS	[M+H]+	163.2	32859911
AllCCS	[M+H-H2O]+	159.6	32859911
AllCCS	[M+NH4]+	166.5	32859911
AllCCS	[M+Na]+	167.5	32859911
AllCCS	[M-H]-	167.2	32859911
AllCCS	[M+Na-2H]-	166.6	32859911
AllCCS	[M+HCOO]-	166.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid	CN(C)C1=CC=C(C=C1)N=NC1=CC=C(C=C1)C(O)=O	3578.3	Standard polar	33892256
4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid	CN(C)C1=CC=C(C=C1)N=NC1=CC=C(C=C1)C(O)=O	2735.0	Standard non polar	33892256
4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid	CN(C)C1=CC=C(C=C1)N=NC1=CC=C(C=C1)C(O)=O	2809.1	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-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uxr-0590000000-ffa09f862edac78506e6	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid 10V, Positive-QTOF	splash10-00di-0390000000-9ebd1f354d41723933b5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid 20V, Positive-QTOF	splash10-00di-0590000000-001c6e79861cad432500	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid 40V, Positive-QTOF	splash10-0avl-3930000000-c54c14d646d618728b48	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid 10V, Negative-QTOF	splash10-00xr-0090000000-a60c4b6585655745ccc3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid 20V, Negative-QTOF	splash10-00xr-0090000000-e0562145c4c58dea08cb	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid 40V, Negative-QTOF	splash10-0a4i-0930000000-adc183b0b380935c2f24	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

21490039

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22650

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-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid (HMDB0247149)

MOL for HMDB0247149 (4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid)

3D MOL for HMDB0247149 (4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid)

3D SDF for HMDB0247149 (4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid)

3D-SDF for HMDB0247149 (4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid)

PDB for HMDB0247149 (4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid)

3D PDB for HMDB0247149 (4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid)

SMILES for HMDB0247149 (4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid)

INCHI for HMDB0247149 (4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid)

Structure for HMDB0247149 (4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid)

3D Structure for HMDB0247149 (4-[[4-(Dimethylamino)phenyl]diazenyl]benzoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra