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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015380

Secondary Accession Numbers

HMDB15380

Metabolite Identification

Common Name

Olsalazine

Description

Olsalazine, also known as dipentum or olsalazine sodium, 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. It is sold under the name Dipentum. Olsalazine is a drug which is used for the treatment of inflammatory bowel disease and ulcerative colitis. Olsalazine gained Food and Drug Administration (FDA) approval in 1990. Olsalazine is an extremely weak basic (essentially neutral) compound (based on its pKa). Like balsalazide, olsalazine is believed to deliver mesalazine, or 5-aminosalicylic acid (5-ASA), past the small intestine, directly to the large intestine, which is the active site of disease in ulcerative colitis. The chemical name is 3,3' -azobis (6-hydroxybenzoate)salicylic acid. The drug is supplied by UCB Pharma. Olsalazine is an anti-inflammatory drug used in the treatment of inflammatory bowel disease such as ulcerative colitis. It is sold as the disodium salt. The Australian biotech company Giaconda has developed a combination therapy for treating constipation-predominant irritable bowel syndrome that uses olsalazine and the anti-gout drug colchicine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0015380
     RDKit          3D
Olsalazine
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.8968   -2.6272   -1.1321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5194   -1.6840   -0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8910   -1.7629   -0.4409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8094   -0.4815   -0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4338   -0.3597   -0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7544    0.7714    0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488    0.8541   -0.1336 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4326   -0.1281   -0.0320 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432    0.0394   -0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042    0.8517   -1.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6477    1.0310   -1.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5341    0.3798   -0.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9026    0.5087   -0.7812 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872   -0.4449    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0485   -1.1130    1.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2743   -0.9616    1.0805 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6087   -1.9261    2.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7274   -0.6093    0.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794    1.7969    0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8537    1.7152    0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5166    0.5776    0.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9059    0.4374    0.5384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3383   -1.9692    0.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9109   -1.2115   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5540    1.3293   -1.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0073    1.6671   -2.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2405    1.1014   -1.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8082   -2.9316    2.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3931   -1.2605    1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9220    2.6869    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4234    2.5157    1.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4096    1.2076    0.9581 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  2  0
  6 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  4  1  0
 18  9  1  0
  3 23  1  0
  5 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
 22 32  1  0
M  END

 
  Mrv0541 02231215212D          
 
 22 23  0  0  0  0            999 V2000
   15.8430  -10.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8224  -11.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1295   -9.8043    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5668   -9.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5291  -11.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4194  -10.2159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2734  -10.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2941  -11.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5497  -12.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7025   -9.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9595  -11.5056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2151  -12.7233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7847  -12.6891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7025   -8.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9924  -10.2159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9924   -8.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2755   -9.8077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2755   -8.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9924   -7.7426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5585   -8.5659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2789   -7.3310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7059   -7.3344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
  9 13  2  0  0  0  0
 10 14  1  0  0  0  0
 10 15  2  0  0  0  0
 14 16  2  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  2  0  0  0  0
  7  8  2  0  0  0  0
 17 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015380

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(O)C(=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H10N2O6/c17-11-3-1-7(5-9(11)13(19)20)15-16-8-2-4-12(18)10(6-8)14(21)22/h1-6,17-18H,(H,19,20)(H,21,22)/b16-15+

> <INCHI_KEY>
QQBDLJCYGRGAKP-FOCLMDBBSA-N

> <FORMULA>
C14H10N2O6

> <MOLECULAR_WEIGHT>
302.239

> <EXACT_MASS>
302.053886062

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
28.607371805346208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(E)-2-(3-carboxy-4-hydroxyphenyl)diazen-1-yl]-2-hydroxybenzoic acid

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
4.387174662

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.5288097153094884

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.926955922273939

> <JCHEM_PKA_STRONGEST_BASIC>
-0.018819112142214878

> <JCHEM_POLAR_SURFACE_AREA>
139.78

> <JCHEM_REFRACTIVITY>
78.85119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
olsalazine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015380
     RDKit          3D
Olsalazine
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.8968   -2.6272   -1.1321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5194   -1.6840   -0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8910   -1.7629   -0.4409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8094   -0.4815   -0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4338   -0.3597   -0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7544    0.7714    0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488    0.8541   -0.1336 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4326   -0.1281   -0.0320 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432    0.0394   -0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042    0.8517   -1.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6477    1.0310   -1.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5341    0.3798   -0.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9026    0.5087   -0.7812 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872   -0.4449    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0485   -1.1130    1.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2743   -0.9616    1.0805 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6087   -1.9261    2.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7274   -0.6093    0.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794    1.7969    0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8537    1.7152    0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5166    0.5776    0.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9059    0.4374    0.5384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3383   -1.9692    0.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9109   -1.2115   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5540    1.3293   -1.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0073    1.6671   -2.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2405    1.1014   -1.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8082   -2.9316    2.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3931   -1.2605    1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9220    2.6869    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4234    2.5157    1.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4096    1.2076    0.9581 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  2  0
  6 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  4  1  0
 18  9  1  0
  3 23  1  0
  5 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
 22 32  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      29.574 -19.070   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.535 -20.613   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      28.242 -18.301   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      30.925 -18.340   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.854 -21.413   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      26.916 -19.070   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      32.244 -19.134   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.282 -20.670   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.893 -22.956   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.578 -18.308   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      33.524 -21.477   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      32.135 -23.750   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      29.465 -23.686   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      25.578 -16.765   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.252 -19.070   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.252 -15.990   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.914 -18.308   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.914 -16.765   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.252 -14.453   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      21.576 -15.990   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      22.921 -13.685   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      25.584 -13.691   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7                                                       
CONECT    5    2    8    9                                                  
CONECT    6    3   10                                                       
CONECT    7    4    8                                                       
CONECT    8    5   11    7                                                  
CONECT    9    5   12   13                                                  
CONECT   10    6   14   15                                                  
CONECT   11    8                                                            
CONECT   12    9                                                            
CONECT   13    9                                                            
CONECT   14   10   16                                                       
CONECT   15   10   17                                                       
CONECT   16   14   18   19                                                  
CONECT   17   15   18                                                       
CONECT   18   16   20   17                                                  
CONECT   19   16   21   22                                                  
CONECT   20   18                                                            
CONECT   21   19                                                            
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0015380
HETATM    1  O1  UNL     1      -3.897  -2.627  -1.132  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.519  -1.684  -0.617  1.00  0.00           C  
HETATM    3  O2  UNL     1      -5.891  -1.763  -0.441  1.00  0.00           O  
HETATM    4  C2  UNL     1      -3.809  -0.482  -0.193  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.434  -0.360  -0.351  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.754   0.771   0.047  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.349   0.854  -0.134  1.00  0.00           N  
HETATM    8  N2  UNL     1       0.433  -0.128  -0.032  1.00  0.00           N  
HETATM    9  C5  UNL     1       1.843   0.039  -0.229  1.00  0.00           C  
HETATM   10  C6  UNL     1       2.304   0.852  -1.251  1.00  0.00           C  
HETATM   11  C7  UNL     1       3.648   1.031  -1.464  1.00  0.00           C  
HETATM   12  C8  UNL     1       4.534   0.380  -0.632  1.00  0.00           C  
HETATM   13  O3  UNL     1       5.903   0.509  -0.781  1.00  0.00           O  
HETATM   14  C9  UNL     1       4.087  -0.445   0.405  1.00  0.00           C  
HETATM   15  C10 UNL     1       5.048  -1.113   1.259  1.00  0.00           C  
HETATM   16  O4  UNL     1       6.274  -0.962   1.081  1.00  0.00           O  
HETATM   17  O5  UNL     1       4.609  -1.926   2.282  1.00  0.00           O  
HETATM   18  C11 UNL     1       2.727  -0.609   0.599  1.00  0.00           C  
HETATM   19  C12 UNL     1      -2.479   1.797   0.614  1.00  0.00           C  
HETATM   20  C13 UNL     1      -3.854   1.715   0.789  1.00  0.00           C  
HETATM   21  C14 UNL     1      -4.517   0.578   0.386  1.00  0.00           C  
HETATM   22  O6  UNL     1      -5.906   0.437   0.538  1.00  0.00           O  
HETATM   23  H1  UNL     1      -6.338  -1.969   0.446  1.00  0.00           H  
HETATM   24  H2  UNL     1      -1.911  -1.211  -0.810  1.00  0.00           H  
HETATM   25  H3  UNL     1       1.554   1.329  -1.862  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.007   1.667  -2.264  1.00  0.00           H  
HETATM   27  H5  UNL     1       6.240   1.101  -1.527  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.808  -2.932   2.168  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.393  -1.261   1.419  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.922   2.687   0.923  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.423   2.516   1.233  1.00  0.00           H  
HETATM   32  H10 UNL     1      -6.410   1.208   0.958  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   23
CONECT    4    5    5   21
CONECT    5    6   24
CONECT    6    7   19   19
CONECT    7    8    8
CONECT    8    9
CONECT    9   10   10   18
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   13   14
CONECT   13   27
CONECT   14   15   18   18
CONECT   15   16   16   17
CONECT   17   28
CONECT   18   29
CONECT   19   20   30
CONECT   20   21   21   31
CONECT   21   22
CONECT   22   32
END

HMDB0015380
     RDKit          3D
Olsalazine
 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.8968   -2.6272   -1.1321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5194   -1.6840   -0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8910   -1.7629   -0.4409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8094   -0.4815   -0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4338   -0.3597   -0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7544    0.7714    0.0465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3488    0.8541   -0.1336 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4326   -0.1281   -0.0320 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8432    0.0394   -0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042    0.8517   -1.2510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6477    1.0310   -1.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5341    0.3798   -0.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9026    0.5087   -0.7812 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872   -0.4449    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0485   -1.1130    1.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2743   -0.9616    1.0805 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6087   -1.9261    2.2823 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7274   -0.6093    0.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794    1.7969    0.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8537    1.7152    0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5166    0.5776    0.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9059    0.4374    0.5384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3383   -1.9692    0.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9109   -1.2115   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5540    1.3293   -1.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0073    1.6671   -2.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2405    1.1014   -1.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8082   -2.9316    2.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3931   -1.2605    1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9220    2.6869    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4234    2.5157    1.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4096    1.2076    0.9581 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  2  0
  6 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  4  1  0
 18  9  1  0
  3 23  1  0
  5 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
 17 28  1  0
 18 29  1  0
 19 30  1  0
 20 31  1  0
 22 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Dipentum	HMDB
Olsalazine sodium	HMDB

Chemical Formula

C₁₄H₁₀N₂O₆

Average Molecular Weight

302.239

Monoisotopic Molecular Weight

302.053886062

IUPAC Name

5-[(E)-2-(3-carboxy-4-hydroxyphenyl)diazen-1-yl]-2-hydroxybenzoic acid

Traditional Name

olsalazine

CAS Registry Number

15722-48-2

SMILES

OC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(O)C(=C1)C(O)=O

InChI Identifier

InChI=1S/C14H10N2O6/c17-11-3-1-7(5-9(11)13(19)20)15-16-8-2-4-12(18)10(6-8)14(21)22/h1-6,17-18H,(H,19,20)(H,21,22)/b16-15+

InChI Key

QQBDLJCYGRGAKP-FOCLMDBBSA-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
Hydroxybenzoic acid
Salicylic acid or derivatives
Salicylic acid
Benzoic acid or derivatives
Benzoic acid
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Vinylogous acid
Azo compound
Organic 1,3-dipolar compound
Carboxylic acid
Carboxylic acid derivative
Propargyl-type 1,3-dipolar organic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015380)
Extracellular (HMDB: HMDB0015380)

Source

Exogenous

Exogenous (HMDB: HMDB0015380)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	240 °C (decomposition)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.078 g/L	Not Available
LogP	2.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.078 g/L	ALOGPS
logP	2.77	ALOGPS
logP	4.39	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	2.93	ChemAxon
pKa (Strongest Basic)	-0.019	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	139.78 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.85 m³·mol⁻¹	ChemAxon
Polarizability	28.61 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]+	164.723	30932474
DeepCCS	[M-H]-	162.365	30932474
DeepCCS	[M-2H]-	195.379	30932474
DeepCCS	[M+Na]+	170.816	30932474
AllCCS	[M+H]+	166.6	32859911
AllCCS	[M+H-H2O]+	163.2	32859911
AllCCS	[M+NH4]+	169.7	32859911
AllCCS	[M+Na]+	170.6	32859911
AllCCS	[M-H]-	165.5	32859911
AllCCS	[M+Na-2H]-	164.8	32859911
AllCCS	[M+HCOO]-	164.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.04 minutes	32390414
Predicted by Siyang on May 30, 2022	11.3893 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.01 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	55.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1718.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	259.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	89.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	85.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	442.9 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	498.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	117.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	743.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	360.2 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	1460.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	271.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	374.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	600.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	151.6 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	299.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Olsalazine	OC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(O)C(=C1)C(O)=O	4221.6	Standard polar	33892256
Olsalazine	OC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(O)C(=C1)C(O)=O	2893.7	Standard non polar	33892256
Olsalazine	OC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(O)C(=C1)C(O)=O	2911.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Olsalazine,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O)C(C(=O)O)=C2)=CC=C1O	3202.1	Semi standard non polar	33892256
Olsalazine,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1C(=O)O	3186.3	Semi standard non polar	33892256
Olsalazine,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O)=C2)=CC=C1O	3078.7	Semi standard non polar	33892256
Olsalazine,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O)C(C(=O)O[Si](C)(C)C)=C2)=CC=C1O	3053.3	Semi standard non polar	33892256
Olsalazine,2TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O)C(C(=O)O)=C2)=CC=C1O[Si](C)(C)C	3080.9	Semi standard non polar	33892256
Olsalazine,2TMS,isomer #4	C[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O)=C2)C=C1C(=O)O	3081.7	Semi standard non polar	33892256
Olsalazine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2)=CC=C1O	3016.8	Semi standard non polar	33892256
Olsalazine,3TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O)=C2)=CC=C1O[Si](C)(C)C	3041.2	Semi standard non polar	33892256
Olsalazine,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2)=CC=C1O[Si](C)(C)C	3061.9	Semi standard non polar	33892256
Olsalazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O)C(C(=O)O)=C2)=CC=C1O	3476.5	Semi standard non polar	33892256
Olsalazine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1C(=O)O	3502.5	Semi standard non polar	33892256
Olsalazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C2)=CC=C1O	3608.3	Semi standard non polar	33892256
Olsalazine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2)=CC=C1O	3546.2	Semi standard non polar	33892256
Olsalazine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O)C(C(=O)O)=C2)=CC=C1O[Si](C)(C)C(C)(C)C	3602.1	Semi standard non polar	33892256
Olsalazine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C2)C=C1C(=O)O	3638.2	Semi standard non polar	33892256
Olsalazine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2)=CC=C1O	3690.6	Semi standard non polar	33892256
Olsalazine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C2)=CC=C1O[Si](C)(C)C(C)(C)C	3790.9	Semi standard non polar	33892256
Olsalazine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2)=CC=C1O[Si](C)(C)C(C)(C)C	3864.1	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 - Olsalazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-1941000000-280432522076c6c2ecde	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Olsalazine GC-MS (4 TMS) - 70eV, Positive	splash10-007k-3091060000-9240a61a4df477ec469a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Olsalazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Olsalazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Olsalazine 10V, Positive-QTOF	splash10-0udi-0169000000-eec3ced209a0cbb0db94	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Olsalazine 20V, Positive-QTOF	splash10-0pbi-0192000000-1871f32f63f256924151	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Olsalazine 40V, Positive-QTOF	splash10-0zi0-4940000000-5242870d6e92c5770375	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Olsalazine 10V, Negative-QTOF	splash10-0udi-0269000000-d99f02b963a55874115d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Olsalazine 20V, Negative-QTOF	splash10-0r00-0291000000-d498e8b80c9d6157a43e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Olsalazine 40V, Negative-QTOF	splash10-0a4i-0920000000-9308cf8b2a3270fdbe45	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Olsalazine 10V, Positive-QTOF	splash10-000i-0091000000-0407edb727a6dc86736b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Olsalazine 20V, Positive-QTOF	splash10-00kr-0290000000-15f46b8ccd52040f0d87	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Olsalazine 40V, Positive-QTOF	splash10-0c33-0690000000-835682abfe82b09946d9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Olsalazine 10V, Negative-QTOF	splash10-0udi-0019000000-6f1fdd414a31404ce61f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Olsalazine 20V, Negative-QTOF	splash10-08fr-0091000000-8f61d29ce7524211d111	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Olsalazine 40V, Negative-QTOF	splash10-03di-0090000000-4e4e69e7208a4f9deb46	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01250	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01250	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01250

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10642377

KEGG Compound ID

C07323

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Olsalazine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

101369

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

Not Available

Enzymes

Enzyme Details

1. Thiopurine S-methyltransferase

General function:: Involved in thiopurine S-methyltransferase activity
Specific function:: Catalyzes the S-methylation of thiopurine drugs such as 6-mercaptopurine.
Gene Name:: TPMT
Uniprot ID:: P51580
Molecular weight:: 28180.09

References

Lewis LD, Benin A, Szumlanski CL, Otterness DM, Lennard L, Weinshilboum RM, Nierenberg DW: Olsalazine and 6-mercaptopurine-related bone marrow suppression: a possible drug-drug interaction. Clin Pharmacol Ther. 1997 Oct;62(4):464-75. [PubMed:9357398 ]
Lennard L: TPMT in the treatment of Crohn's disease with azathioprine. Gut. 2002 Aug;51(2):143-6. [PubMed:12117866 ]
Lennard L: Clinical implications of thiopurine methyltransferase--optimization of drug dosage and potential drug interactions. Ther Drug Monit. 1998 Oct;20(5):527-31. [PubMed:9780130 ]
Shipkova M, Niedmann PD, Armstrong VW, Oellerich M, Wieland E: Determination of thiopurine methyltransferase activity in isolated human erythrocytes does not reflect putative in vivo enzyme inhibition by sulfasalazine. Clin Chem. 2004 Feb;50(2):438-41. [PubMed:14752016 ]

Enzyme Details

2. Interferon gamma

General function:: Involved in cytokine activity
Specific function:: Produced by lymphocytes activated by specific antigens or mitogens. IFN-gamma, in addition to having antiviral activity, has important immunoregulatory functions. It is a potent activator of macrophages, it has antiproliferative effects on transformed cells and it can potentiate the antiviral and antitumor effects of the type I interferons
Gene Name:: IFNG
Uniprot ID:: P01579
Molecular weight:: 19348.2

References

Egan LJ, Sandborn WJ: Inhibition of nuclear factor kappaB by sulfasalazine: a new target for inflammatory bowel disease therapy? Gastroenterology. 1998 Nov;115(5):1295-6. [PubMed:9797390 ]
Ito R, Shin-Ya M, Kishida T, Urano A, Takada R, Sakagami J, Imanishi J, Kita M, Ueda Y, Iwakura Y, Kataoka K, Okanoue T, Mazda O: Interferon-gamma is causatively involved in experimental inflammatory bowel disease in mice. Clin Exp Immunol. 2006 Nov;146(2):330-8. [PubMed:17034586 ]

Showing metabocard for Olsalazine (HMDB0015380)

MOL for HMDB0015380 (Olsalazine)

3D MOL for HMDB0015380 (Olsalazine)

3D SDF for HMDB0015380 (Olsalazine)

3D-SDF for HMDB0015380 (Olsalazine)

PDB for HMDB0015380 (Olsalazine)

3D PDB for HMDB0015380 (Olsalazine)

SMILES for HMDB0015380 (Olsalazine)

INCHI for HMDB0015380 (Olsalazine)

Structure for HMDB0015380 (Olsalazine)

3D Structure for HMDB0015380 (Olsalazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References