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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:12:50 UTC

Update Date

2021-09-26 22:56:44 UTC

HMDB ID

HMDB0247202

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5,5'-Dithiobis(2-nitrobenzoic acid)

Description

5,5'-Dithiobis(2-nitrobenzoic acid), also known as ellman's reagent or DTNB, belongs to the class of organic compounds known as nitrobenzoic acids and derivatives. Nitrobenzoic acids and derivatives are compounds containing a nitrobenzoic acid moiety, which consists of a benzene ring bearing both a carboxylic acid group and a nitro group on two different ring carbon atoms. Based on a literature review a small amount of articles have been published on 5,5'-Dithiobis(2-nitrobenzoic acid). This compound has been identified in human blood as reported by (PMID: 31557052 ). 5,5'-dithiobis(2-nitrobenzoic acid) is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5,5'-Dithiobis(2-nitrobenzoic 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


  Mrv1652309112102132D          

 26 27  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 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 S   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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  5  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  CHG  4  15   1  17  -1  24   1  26  -1
M  END

HMDB0247202
     RDKit          3D
5,5'-Dithiobis(2-nitrobenzoic acid)
 34 35  0  0  0  0  0  0  0  0999 V2000
   -2.8521    0.9298    1.9826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6347    0.8849    0.9804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7545    1.6411    1.0536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2935    0.0490   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1552   -0.7668   -0.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7963   -1.6187   -1.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3158   -2.6188   -0.8840 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6208   -2.1666    0.9601 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7788   -0.8195    0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3800    0.4819    0.8633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2950    1.4681    0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6288    1.2383    0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4717    2.3480    0.0710 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.1896    3.3578    0.8086 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5214    2.5149   -0.7488 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.9922   -0.0711    0.1088 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3464   -0.4508   -0.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3056    0.3043   -0.4100 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6514   -1.8205   -0.4159 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0580   -1.1098    0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5744   -1.6936   -2.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6837   -0.8989   -2.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0768   -0.0037   -1.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2426    0.7322   -1.5319 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.3908    1.8973   -1.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2900    0.1614   -2.2706 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.6215    1.3811    1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5718   -0.6821    0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505    0.7025    1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0074    2.5160    0.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8225   -2.4118    0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912   -2.1416    0.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2768   -2.3744   -2.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2811   -0.9600   -3.1490 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  2  0
  6 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 23  4  1  0
 20  9  1  0
  3 27  1  0
  5 28  1  0
 10 29  1  0
 11 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
 22 34  1  0
M  CHG  4  13   1  15  -1  24   1  26  -1
M  END


  Mrv1652309112102132D          

 26 27  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 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 S   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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  5  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  CHG  4  15   1  17  -1  24   1  26  -1
M  END
> <DATABASE_ID>
HMDB0247202

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=C(C=CC(SSC2=CC(C(O)=O)=C(C=C2)[N+]([O-])=O)=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H8N2O8S2/c17-13(18)9-5-7(1-3-11(9)15(21)22)25-26-8-2-4-12(16(23)24)10(6-8)14(19)20/h1-6H,(H,17,18)(H,19,20)

> <INCHI_KEY>
KIUMMUBSPKGMOY-UHFFFAOYSA-N

> <FORMULA>
C14H8N2O8S2

> <MOLECULAR_WEIGHT>
396.34

> <EXACT_MASS>
395.972207574

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
33.40417427538606

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(3-carboxy-4-nitrophenyl)disulfanyl]-2-nitrobenzoic acid

> <ALOGPS_LOGP>
2.69

> <JCHEM_LOGP>
3.768879145333333

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
1.7906280534118988

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1885673797849812

> <JCHEM_POLAR_SURFACE_AREA>
160.88

> <JCHEM_REFRACTIVITY>
89.61359999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.98e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ellman's reagent

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247202
     RDKit          3D
5,5'-Dithiobis(2-nitrobenzoic acid)
 34 35  0  0  0  0  0  0  0  0999 V2000
   -2.8521    0.9298    1.9826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6347    0.8849    0.9804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7545    1.6411    1.0536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2935    0.0490   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1552   -0.7668   -0.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7963   -1.6187   -1.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3158   -2.6188   -0.8840 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6208   -2.1666    0.9601 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7788   -0.8195    0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3800    0.4819    0.8633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2950    1.4681    0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6288    1.2383    0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4717    2.3480    0.0710 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.1896    3.3578    0.8086 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5214    2.5149   -0.7488 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.9922   -0.0711    0.1088 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3464   -0.4508   -0.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3056    0.3043   -0.4100 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6514   -1.8205   -0.4159 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0580   -1.1098    0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5744   -1.6936   -2.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6837   -0.8989   -2.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0768   -0.0037   -1.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2426    0.7322   -1.5319 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.3908    1.8973   -1.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2900    0.1614   -2.2706 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.6215    1.3811    1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5718   -0.6821    0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505    0.7025    1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0074    2.5160    0.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8225   -2.4118    0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912   -2.1416    0.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2768   -2.3744   -2.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2811   -0.9600   -3.1490 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  2  0
  6 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 23  4  1  0
 20  9  1  0
  3 27  1  0
  5 28  1  0
 10 29  1  0
 11 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
 22 34  1  0
M  CHG  4  13   1  15  -1  24   1  26  -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  S   UNK     0       2.667  -3.080   0.000  0.00  0.00           S+0
HETATM    8  S   UNK     0       1.334  -2.310   0.000  0.00  0.00           S+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+1
HETATM   16  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O-1
HETATM   18  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       2.667  -9.240   0.000  0.00  0.00           N+1
HETATM   25  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O-1
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   11   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    4   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    3   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

COMPND    HMDB0247202
HETATM    1  O1  UNL     1      -2.852   0.930   1.983  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.635   0.885   0.980  1.00  0.00           C  
HETATM    3  O2  UNL     1      -4.754   1.641   1.054  1.00  0.00           O  
HETATM    4  C2  UNL     1      -3.293   0.049  -0.145  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.155  -0.767  -0.062  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.796  -1.619  -1.052  1.00  0.00           C  
HETATM    7  S1  UNL     1      -0.316  -2.619  -0.884  1.00  0.00           S  
HETATM    8  S2  UNL     1       0.621  -2.167   0.960  1.00  0.00           S  
HETATM    9  C5  UNL     1       1.779  -0.819   0.699  1.00  0.00           C  
HETATM   10  C6  UNL     1       1.380   0.482   0.863  1.00  0.00           C  
HETATM   11  C7  UNL     1       2.295   1.468   0.646  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.629   1.238   0.262  1.00  0.00           C  
HETATM   13  N1  UNL     1       4.472   2.348   0.071  1.00  0.00           N1+
HETATM   14  O3  UNL     1       4.190   3.358   0.809  1.00  0.00           O  
HETATM   15  O4  UNL     1       5.521   2.515  -0.749  1.00  0.00           O1-
HETATM   16  C9  UNL     1       3.992  -0.071   0.109  1.00  0.00           C  
HETATM   17  C10 UNL     1       5.346  -0.451  -0.240  1.00  0.00           C  
HETATM   18  O5  UNL     1       6.306   0.304  -0.410  1.00  0.00           O  
HETATM   19  O6  UNL     1       5.651  -1.820  -0.416  1.00  0.00           O  
HETATM   20  C11 UNL     1       3.058  -1.110   0.329  1.00  0.00           C  
HETATM   21  C12 UNL     1      -2.574  -1.694  -2.187  1.00  0.00           C  
HETATM   22  C13 UNL     1      -3.684  -0.899  -2.272  1.00  0.00           C  
HETATM   23  C14 UNL     1      -4.077  -0.004  -1.257  1.00  0.00           C  
HETATM   24  N2  UNL     1      -5.243   0.732  -1.532  1.00  0.00           N1+
HETATM   25  O7  UNL     1      -5.391   1.897  -1.203  1.00  0.00           O  
HETATM   26  O8  UNL     1      -6.290   0.161  -2.271  1.00  0.00           O1-
HETATM   27  H1  UNL     1      -5.621   1.381   1.484  1.00  0.00           H  
HETATM   28  H2  UNL     1      -1.572  -0.682   0.845  1.00  0.00           H  
HETATM   29  H3  UNL     1       0.351   0.703   1.162  1.00  0.00           H  
HETATM   30  H4  UNL     1       2.007   2.516   0.768  1.00  0.00           H  
HETATM   31  H5  UNL     1       5.823  -2.412   0.364  1.00  0.00           H  
HETATM   32  H6  UNL     1       3.391  -2.142   0.194  1.00  0.00           H  
HETATM   33  H7  UNL     1      -2.277  -2.374  -2.959  1.00  0.00           H  
HETATM   34  H8  UNL     1      -4.281  -0.960  -3.149  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   27
CONECT    4    5    5   23
CONECT    5    6   28
CONECT    6    7   21   21
CONECT    7    8
CONECT    8    9
CONECT    9   10   10   20
CONECT   10   11   29
CONECT   11   12   12   30
CONECT   12   13   16
CONECT   13   14   14   15
CONECT   16   17   20   20
CONECT   17   18   18   19
CONECT   19   31
CONECT   20   32
CONECT   21   22   33
CONECT   22   23   23   34
CONECT   23   24
CONECT   24   25   25   26
END

HMDB0247202
     RDKit          3D
5,5'-Dithiobis(2-nitrobenzoic acid)
 34 35  0  0  0  0  0  0  0  0999 V2000
   -2.8521    0.9298    1.9826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6347    0.8849    0.9804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7545    1.6411    1.0536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2935    0.0490   -0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1552   -0.7668   -0.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7963   -1.6187   -1.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3158   -2.6188   -0.8840 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6208   -2.1666    0.9601 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7788   -0.8195    0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3800    0.4819    0.8633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2950    1.4681    0.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6288    1.2383    0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4717    2.3480    0.0710 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.1896    3.3578    0.8086 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5214    2.5149   -0.7488 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.9922   -0.0711    0.1088 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3464   -0.4508   -0.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3056    0.3043   -0.4100 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6514   -1.8205   -0.4159 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0580   -1.1098    0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5744   -1.6936   -2.1870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6837   -0.8989   -2.2717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0768   -0.0037   -1.2566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2426    0.7322   -1.5319 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.3908    1.8973   -1.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2900    0.1614   -2.2706 O   0  0  0  0  0  1  0  0  0  0  0  0
   -5.6215    1.3811    1.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5718   -0.6821    0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505    0.7025    1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0074    2.5160    0.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8225   -2.4118    0.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3912   -2.1416    0.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2768   -2.3744   -2.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2811   -0.9600   -3.1490 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  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  2  0
  6 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 23  4  1  0
 20  9  1  0
  3 27  1  0
  5 28  1  0
 10 29  1  0
 11 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
 22 34  1  0
M  CHG  4  13   1  15  -1  24   1  26  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,2'-Dinitro-5,5'-dithiodibenzoesaeure	ChEBI
2,2'-Dinitro-5,5'-dithiodibenzoic acid	ChEBI
3,3'-Dithiobis(6-nitrobenzoic acid)	ChEBI
5-(3-Carboxy-4-nitro-phenyl)disulfanyl-2-nitrobenzoic acid	ChEBI
Dithiobisnitrobenzoic acid	ChEBI
DTNB	ChEBI
Ellman's reagent	ChEBI
2,2'-Dinitro-5,5'-dithiodibenzoate	Generator
3,3'-Dithiobis(6-nitrobenzoate)	Generator
5-(3-Carboxy-4-nitro-phenyl)disulfanyl-2-nitrobenzoate	Generator
5-(3-Carboxy-4-nitro-phenyl)disulphanyl-2-nitrobenzoate	Generator
5-(3-Carboxy-4-nitro-phenyl)disulphanyl-2-nitrobenzoic acid	Generator
Dithiobisnitrobenzoate	Generator
5,5'-Dithiobis(2-nitrobenzoate)	Generator
5,5'-Dithiobis(nitrobenzoate)	HMDB
Acid, dithionitrobenzoic	HMDB
Dithionitrobenzoic acid	HMDB
Ellman reagent	HMDB
Ellmans reagent	HMDB
Reagent, ellman's	HMDB

Chemical Formula

C₁₄H₈N₂O₈S₂

Average Molecular Weight

396.34

Monoisotopic Molecular Weight

395.972207574

IUPAC Name

5-[(3-carboxy-4-nitrophenyl)disulfanyl]-2-nitrobenzoic acid

Traditional Name

ellman's reagent

CAS Registry Number

Not Available

SMILES

OC(=O)C1=C(C=CC(SSC2=CC(C(O)=O)=C(C=C2)[N+]([O-])=O)=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C14H8N2O8S2/c17-13(18)9-5-7(1-3-11(9)15(21)22)25-26-8-2-4-12(16(23)24)10(6-8)14(19)20/h1-6H,(H,17,18)(H,19,20)

InChI Key

KIUMMUBSPKGMOY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrobenzoic acids and derivatives. Nitrobenzoic acids and derivatives are compounds containing a nitrobenzoic acid moiety, which consists of a benzene ring bearing both a carboxylic acid group and a nitro group on two different ring carbon atoms.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Nitrobenzoic acids and derivatives

Alternative Parents

Substituents

Nitrobenzoate
M-sulfanylbenzoic acid
M-sulfanylbenzoic acid or derivatives
Benzoic acid
Nitrobenzene
Nitroaromatic compound
Benzoyl
Dicarboxylic acid or derivatives
Organic nitro compound
C-nitro compound
Organic disulfide
Carboxylic acid derivative
Carboxylic acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Sulfenyl compound
Organic oxoazanium
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organic disulfide (CHEBI:86228 )
nitrobenzoic acid (CHEBI:86228 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.69	ALOGPS
logP	3.77	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	1.19	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	160.88 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	89.61 m³·mol⁻¹	ChemAxon
Polarizability	33.4 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]+	169.108	30932474
DeepCCS	[M-H]-	165.848	30932474
DeepCCS	[M-2H]-	200.743	30932474
DeepCCS	[M+Na]+	176.91	30932474
AllCCS	[M+H]+	179.5	32859911
AllCCS	[M+H-H2O]+	176.9	32859911
AllCCS	[M+NH4]+	181.9	32859911
AllCCS	[M+Na]+	182.6	32859911
AllCCS	[M-H]-	166.6	32859911
AllCCS	[M+Na-2H]-	165.4	32859911
AllCCS	[M+HCOO]-	164.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,5'-Dithiobis(2-nitrobenzoic acid)	OC(=O)C1=C(C=CC(SSC2=CC(C(O)=O)=C(C=C2)[N+]([O-])=O)=C1)[N+]([O-])=O	5047.0	Standard polar	33892256
5,5'-Dithiobis(2-nitrobenzoic acid)	OC(=O)C1=C(C=CC(SSC2=CC(C(O)=O)=C(C=C2)[N+]([O-])=O)=C1)[N+]([O-])=O	2430.9	Standard non polar	33892256
5,5'-Dithiobis(2-nitrobenzoic acid)	OC(=O)C1=C(C=CC(SSC2=CC(C(O)=O)=C(C=C2)[N+]([O-])=O)=C1)[N+]([O-])=O	3569.2	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 - 5,5'-Dithiobis(2-nitrobenzoic acid) GC-MS (Non-derivatized) - 70eV, Positive	splash10-006t-9136000000-1a810a6e0f4b575d4546	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,5'-Dithiobis(2-nitrobenzoic acid) GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,5'-Dithiobis(2-nitrobenzoic acid) GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,5'-Dithiobis(2-nitrobenzoic acid) GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,5'-Dithiobis(2-nitrobenzoic acid) GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,5'-Dithiobis(2-nitrobenzoic acid) GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	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

6018

KEGG Compound ID

Not Available

BioCyc ID

DITHIO-NITROBENZOATE

BiGG ID

Not Available

Wikipedia Link

Ellman's_reagent

METLIN ID

Not Available

PubChem Compound

6254

PDB ID

Not Available

ChEBI ID

86228

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 5,5'-Dithiobis(2-nitrobenzoic acid) (HMDB0247202)

MOL for HMDB0247202 (5,5'-Dithiobis(2-nitrobenzoic acid))

3D MOL for HMDB0247202 (5,5'-Dithiobis(2-nitrobenzoic acid))

3D SDF for HMDB0247202 (5,5'-Dithiobis(2-nitrobenzoic acid))

3D-SDF for HMDB0247202 (5,5'-Dithiobis(2-nitrobenzoic acid))

PDB for HMDB0247202 (5,5'-Dithiobis(2-nitrobenzoic acid))

3D PDB for HMDB0247202 (5,5'-Dithiobis(2-nitrobenzoic acid))

SMILES for HMDB0247202 (5,5'-Dithiobis(2-nitrobenzoic acid))

INCHI for HMDB0247202 (5,5'-Dithiobis(2-nitrobenzoic acid))

Structure for HMDB0247202 (5,5'-Dithiobis(2-nitrobenzoic acid))

3D Structure for HMDB0247202 (5,5'-Dithiobis(2-nitrobenzoic acid))

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra