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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9)transporters (3) Show 12 proteins XML

enzymes (9)transporters (3) Show 12 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:47 UTC

HMDB ID

HMDB0014933

Secondary Accession Numbers

HMDB14933

Metabolite Identification

Common Name

Sulfasalazine

Description

Sulfasalazine is only found in individuals that have used or taken this drug. It is a drug that is used in the management of inflammatory bowel diseases. Its activity is generally considered to lie in its metabolic breakdown product, 5-aminosalicylic acid (see mesalamine) released in the colon. (From Martindale, The Extra Pharmacopoeia, 30th ed, p907)The mode of action of Sulfasalazine or its metabolites, 5-aminosalicylic acid (5-ASA) and sulfapyridine (SP), is still under investigation, but may be related to the anti-inflammatory and/or immunomodulatory properties that have been observed in animal and in vitro models, to its affinity for connective tissue, and/or to the relatively high concentration it reaches in serous fluids, the liver and intestinal walls, as demonstrated in autoradiographic studies in animals. In ulcerative colitis, clinical studies utilizing rectal administration of Sulfasalazine, SP and 5-ASA have indicated that the major therapeutic action may reside in the 5-ASA moiety. The relative contribution of the parent drug and the major metabolites in rheumatoid arthritis is unknown.

Structure

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

 
  Mrv0541 02231215002D          
 
 28 30  0  0  0  0            999 V2000
   17.7326   -9.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4412   -8.8604    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.7326  -10.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0204   -8.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1571   -9.2768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7290   -8.2760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1790   -8.2760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0204  -10.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3118   -9.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8693   -8.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3118  -10.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8620   -8.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5815   -9.2695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5959  -10.5076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5742   -7.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2937   -8.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7705  -10.0730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2901   -8.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9633  -10.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9633  -11.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1562  -10.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1562  -11.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3452  -10.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3490  -11.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1562  -12.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5381  -11.9468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9670  -13.3455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3490  -13.3455    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  1  0  0  0  0
  2  6  2  0  0  0  0
  2  7  2  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  2  0  0  0  0
 11 14  1  0  0  0  0
 12 15  2  0  0  0  0
 13 16  1  0  0  0  0
 14 17  2  0  0  0  0
 15 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  2  0  0  0  0
  9 11  2  0  0  0  0
 16 18  2  0  0  0  0
 23 24  2  0  0  0  0
M  END

HMDB0014933
     RDKit          3D
Sulfasalazine
 42 44  0  0  0  0  0  0  0  0999 V2000
    7.5335    2.7469   -0.1408 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2970    2.6888    0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6055    3.8222    0.3782 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6020    1.4247   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2341    1.3093   -0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5573    0.1286   -0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234    0.0726   -0.0463 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6588   -1.0019    0.3866 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2924   -1.2711    0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2608   -1.2196    1.8968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5948   -1.4880    2.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4314   -1.8209    1.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1234   -2.1687    1.2775 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.2521   -2.8293    2.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6168   -3.1858    0.2681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0697   -0.7384    1.2230 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1579    0.1034    0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9354    1.2377    0.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9942    2.0207   -1.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2810    1.6533   -2.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4990    0.5042   -2.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4763   -0.2202   -1.0299 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8656   -1.8689   -0.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5097   -1.5971   -0.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575   -0.9993   -0.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6106   -0.9041   -0.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2881    0.2751   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6580    0.3122   -0.7403 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9144    4.7692    0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6784    2.2099    0.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3537   -0.9617    2.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701   -1.4586    3.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6120   -0.4594    2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4820    1.4892    0.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5963    2.9209   -1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3268    2.2775   -3.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9433    0.2445   -3.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4439   -2.1227   -1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1033   -1.6479   -1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6784   -1.9051   -0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1335   -1.8252   -1.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1690   -0.5171   -1.0080 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
 13 14  2  0
 13 15  2  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 12 23  1  0
 23 24  2  0
  6 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27  4  1  0
 24  9  1  0
 22 17  1  0
  3 29  1  0
  5 30  1  0
 10 31  1  0
 11 32  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 23 38  1  0
 24 39  1  0
 25 40  1  0
 26 41  1  0
 28 42  1  0
M  END

 
  Mrv0541 02231215002D          
 
 28 30  0  0  0  0            999 V2000
   17.7326   -9.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4412   -8.8604    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.7326  -10.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0204   -8.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1571   -9.2768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7290   -8.2760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1790   -8.2760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0204  -10.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3118   -9.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8693   -8.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3118  -10.0986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8620   -8.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5815   -9.2695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5959  -10.5076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5742   -7.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2937   -8.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7705  -10.0730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2901   -8.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9633  -10.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9633  -11.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1562  -10.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1562  -11.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3452  -10.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3490  -11.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1562  -12.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5381  -11.9468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9670  -13.3455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3490  -13.3455    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  1  0  0  0  0
  2  6  2  0  0  0  0
  2  7  2  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  2  0  0  0  0
 11 14  1  0  0  0  0
 12 15  2  0  0  0  0
 13 16  1  0  0  0  0
 14 17  2  0  0  0  0
 15 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  2  0  0  0  0
  9 11  2  0  0  0  0
 16 18  2  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014933

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H14N4O5S/c23-16-9-6-13(11-15(16)18(24)25)21-20-12-4-7-14(8-5-12)28(26,27)22-17-3-1-2-10-19-17/h1-11,23H,(H,19,22)(H,24,25)/b21-20+

> <INCHI_KEY>
NCEXYHBECQHGNR-QZQOTICOSA-N

> <FORMULA>
C18H14N4O5S

> <MOLECULAR_WEIGHT>
398.393

> <EXACT_MASS>
398.068490268

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
39.685937133860094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-5-[(E)-2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl]benzoic acid

> <ALOGPS_LOGP>
2.92

> <JCHEM_LOGP>
3.937434786830155

> <ALOGPS_LOGS>
-3.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.746071734284534

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.297738885179465

> <JCHEM_PKA_STRONGEST_BASIC>
2.4018806904923524

> <JCHEM_POLAR_SURFACE_AREA>
141.31

> <JCHEM_REFRACTIVITY>
104.60289999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfasalazine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014933
     RDKit          3D
Sulfasalazine
 42 44  0  0  0  0  0  0  0  0999 V2000
    7.5335    2.7469   -0.1408 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2970    2.6888    0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6055    3.8222    0.3782 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6020    1.4247   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2341    1.3093   -0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5573    0.1286   -0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234    0.0726   -0.0463 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6588   -1.0019    0.3866 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2924   -1.2711    0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2608   -1.2196    1.8968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5948   -1.4880    2.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4314   -1.8209    1.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1234   -2.1687    1.2775 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.2521   -2.8293    2.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6168   -3.1858    0.2681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0697   -0.7384    1.2230 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1579    0.1034    0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9354    1.2377    0.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9942    2.0207   -1.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2810    1.6533   -2.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4990    0.5042   -2.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4763   -0.2202   -1.0299 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8656   -1.8689   -0.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5097   -1.5971   -0.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575   -0.9993   -0.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6106   -0.9041   -0.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2881    0.2751   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6580    0.3122   -0.7403 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9144    4.7692    0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6784    2.2099    0.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3537   -0.9617    2.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701   -1.4586    3.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6120   -0.4594    2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4820    1.4892    0.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5963    2.9209   -1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3268    2.2775   -3.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9433    0.2445   -3.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4439   -2.1227   -1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1033   -1.6479   -1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6784   -1.9051   -0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1335   -1.8252   -1.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1690   -0.5171   -1.0080 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
 13 14  2  0
 13 15  2  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 12 23  1  0
 23 24  2  0
  6 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27  4  1  0
 24  9  1  0
 22 17  1  0
  3 29  1  0
  5 30  1  0
 10 31  1  0
 11 32  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 23 38  1  0
 24 39  1  0
 25 40  1  0
 26 41  1  0
 28 42  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      33.101 -17.317   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0      34.424 -16.539   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      33.101 -18.851   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.771 -16.539   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      35.760 -17.317   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0      33.094 -15.449   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      35.801 -15.449   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      31.771 -19.614   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.449 -17.317   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      37.089 -16.539   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.449 -18.851   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      37.076 -15.005   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      38.419 -17.303   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      29.112 -19.614   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      38.405 -14.235   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      39.748 -16.533   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      27.572 -18.803   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      39.742 -14.999   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      26.065 -19.676   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.065 -21.421   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.558 -18.803   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.558 -22.294   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      23.044 -19.676   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.051 -21.421   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      24.558 -24.039   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      21.538 -22.301   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      26.072 -24.912   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      23.051 -24.912   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6    7                                             
CONECT    3    1    8                                                       
CONECT    4    1    9                                                       
CONECT    5    2   10                                                       
CONECT    6    2                                                            
CONECT    7    2                                                            
CONECT    8    3   11                                                       
CONECT    9    4   11                                                       
CONECT   10    5   12   13                                                  
CONECT   11    8   14    9                                                  
CONECT   12   10   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   17                                                       
CONECT   15   12   18                                                       
CONECT   16   13   18                                                       
CONECT   17   14   19                                                       
CONECT   18   15   16                                                       
CONECT   19   17   20   21                                                  
CONECT   20   19   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   24   25                                                  
CONECT   23   21   24                                                       
CONECT   24   22   26   23                                                  
CONECT   25   22   27   28                                                  
CONECT   26   24                                                            
CONECT   27   25                                                            
CONECT   28   25                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

COMPND    HMDB0014933
HETATM    1  O1  UNL     1       7.533   2.747  -0.141  1.00  0.00           O  
HETATM    2  C1  UNL     1       6.297   2.689   0.013  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.605   3.822   0.378  1.00  0.00           O  
HETATM    4  C2  UNL     1       5.602   1.425  -0.195  1.00  0.00           C  
HETATM    5  C3  UNL     1       4.234   1.309  -0.037  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.557   0.129  -0.228  1.00  0.00           C  
HETATM    7  N1  UNL     1       2.123   0.073  -0.046  1.00  0.00           N  
HETATM    8  N2  UNL     1       1.659  -1.002   0.387  1.00  0.00           N  
HETATM    9  C5  UNL     1       0.292  -1.271   0.636  1.00  0.00           C  
HETATM   10  C6  UNL     1      -0.261  -1.220   1.897  1.00  0.00           C  
HETATM   11  C7  UNL     1      -1.595  -1.488   2.099  1.00  0.00           C  
HETATM   12  C8  UNL     1      -2.431  -1.821   1.036  1.00  0.00           C  
HETATM   13  S1  UNL     1      -4.123  -2.169   1.277  1.00  0.00           S  
HETATM   14  O3  UNL     1      -4.252  -2.829   2.625  1.00  0.00           O  
HETATM   15  O4  UNL     1      -4.617  -3.186   0.268  1.00  0.00           O  
HETATM   16  N3  UNL     1      -5.070  -0.738   1.223  1.00  0.00           N  
HETATM   17  C9  UNL     1      -5.158   0.103   0.074  1.00  0.00           C  
HETATM   18  C10 UNL     1      -5.935   1.238   0.098  1.00  0.00           C  
HETATM   19  C11 UNL     1      -5.994   2.021  -1.027  1.00  0.00           C  
HETATM   20  C12 UNL     1      -5.281   1.653  -2.135  1.00  0.00           C  
HETATM   21  C13 UNL     1      -4.499   0.504  -2.145  1.00  0.00           C  
HETATM   22  N4  UNL     1      -4.476  -0.220  -1.030  1.00  0.00           N  
HETATM   23  C14 UNL     1      -1.866  -1.869  -0.219  1.00  0.00           C  
HETATM   24  C15 UNL     1      -0.510  -1.597  -0.432  1.00  0.00           C  
HETATM   25  C16 UNL     1       4.257  -0.999  -0.592  1.00  0.00           C  
HETATM   26  C17 UNL     1       5.611  -0.904  -0.753  1.00  0.00           C  
HETATM   27  C18 UNL     1       6.288   0.275  -0.563  1.00  0.00           C  
HETATM   28  O5  UNL     1       7.658   0.312  -0.740  1.00  0.00           O  
HETATM   29  H1  UNL     1       5.914   4.769   0.174  1.00  0.00           H  
HETATM   30  H2  UNL     1       3.678   2.210   0.254  1.00  0.00           H  
HETATM   31  H3  UNL     1       0.354  -0.962   2.775  1.00  0.00           H  
HETATM   32  H4  UNL     1      -2.070  -1.459   3.076  1.00  0.00           H  
HETATM   33  H5  UNL     1      -5.612  -0.459   2.065  1.00  0.00           H  
HETATM   34  H6  UNL     1      -6.482   1.489   0.996  1.00  0.00           H  
HETATM   35  H7  UNL     1      -6.596   2.921  -1.044  1.00  0.00           H  
HETATM   36  H8  UNL     1      -5.327   2.278  -3.034  1.00  0.00           H  
HETATM   37  H9  UNL     1      -3.943   0.244  -3.052  1.00  0.00           H  
HETATM   38  H10 UNL     1      -2.444  -2.123  -1.105  1.00  0.00           H  
HETATM   39  H11 UNL     1      -0.103  -1.648  -1.452  1.00  0.00           H  
HETATM   40  H12 UNL     1       3.678  -1.905  -0.731  1.00  0.00           H  
HETATM   41  H13 UNL     1       6.133  -1.825  -1.045  1.00  0.00           H  
HETATM   42  H14 UNL     1       8.169  -0.517  -1.008  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   29
CONECT    4    5    5   27
CONECT    5    6   30
CONECT    6    7   25   25
CONECT    7    8    8
CONECT    8    9
CONECT    9   10   10   24
CONECT   10   11   31
CONECT   11   12   12   32
CONECT   12   13   23
CONECT   13   14   14   15   15
CONECT   13   16
CONECT   16   17   33
CONECT   17   18   18   22
CONECT   18   19   34
CONECT   19   20   20   35
CONECT   20   21   36
CONECT   21   22   22   37
CONECT   23   24   24   38
CONECT   24   39
CONECT   25   26   40
CONECT   26   27   27   41
CONECT   27   28
CONECT   28   42
END

HMDB0014933
     RDKit          3D
Sulfasalazine
 42 44  0  0  0  0  0  0  0  0999 V2000
    7.5335    2.7469   -0.1408 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2970    2.6888    0.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6055    3.8222    0.3782 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6020    1.4247   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2341    1.3093   -0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5573    0.1286   -0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234    0.0726   -0.0463 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6588   -1.0019    0.3866 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2924   -1.2711    0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2608   -1.2196    1.8968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5948   -1.4880    2.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4314   -1.8209    1.0364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1234   -2.1687    1.2775 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.2521   -2.8293    2.6253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6168   -3.1858    0.2681 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0697   -0.7384    1.2230 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1579    0.1034    0.0741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9354    1.2377    0.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9942    2.0207   -1.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2810    1.6533   -2.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4990    0.5042   -2.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4763   -0.2202   -1.0299 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8656   -1.8689   -0.2186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5097   -1.5971   -0.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2575   -0.9993   -0.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6106   -0.9041   -0.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2881    0.2751   -0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6580    0.3122   -0.7403 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9144    4.7692    0.1738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6784    2.2099    0.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3537   -0.9617    2.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0701   -1.4586    3.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6120   -0.4594    2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4820    1.4892    0.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5963    2.9209   -1.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3268    2.2775   -3.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9433    0.2445   -3.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4439   -2.1227   -1.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1033   -1.6479   -1.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6784   -1.9051   -0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1335   -1.8252   -1.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1690   -0.5171   -1.0080 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
 13 14  2  0
 13 15  2  0
 13 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 12 23  1  0
 23 24  2  0
  6 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27  4  1  0
 24  9  1  0
 22 17  1  0
  3 29  1  0
  5 30  1  0
 10 31  1  0
 11 32  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
 23 38  1  0
 24 39  1  0
 25 40  1  0
 26 41  1  0
 28 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)benzoic acid	ChEBI
2-Hydroxy-5-[4-(pyridin-2-ylsulfamoyl)-phenylazo]-benzoic acid	ChEBI
4-(Pyridyl-2-amidosulfonyl)-3'-carboxy-4'-hydroxyazobenzene	ChEBI
5-((p-(2-Pyridylsulfamoyl)phenyl)azo)salicylic acid	ChEBI
5-(4-(2-Pyridylsulfamoyl)phenylazo)-2-hydroxybenzoic acid	ChEBI
5-(p-(2-Pyridylsulfamyl)phenylazo)salicylic acid	ChEBI
Azulfidine	ChEBI
Salazosulfapiridina	ChEBI
Salazosulfapyridine	ChEBI
Salazosulfapyridinum	ChEBI
Salicylazosulfapyridine	ChEBI
Sulfasalazina	ChEBI
Sulfasalazinum	ChEBI
2-Hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)benzoate	Generator
2-Hydroxy-5-((4-((2-pyridinylamino)sulphonyl)phenyl)azo)benzoate	Generator
2-Hydroxy-5-((4-((2-pyridinylamino)sulphonyl)phenyl)azo)benzoic acid	Generator
2-Hydroxy-5-[4-(pyridin-2-ylsulfamoyl)-phenylazo]-benzoate	Generator
2-Hydroxy-5-[4-(pyridin-2-ylsulphamoyl)-phenylazo]-benzoate	Generator
2-Hydroxy-5-[4-(pyridin-2-ylsulphamoyl)-phenylazo]-benzoic acid	Generator
4-(Pyridyl-2-amidosulphonyl)-3'-carboxy-4'-hydroxyazobenzene	Generator
5-((p-(2-Pyridylsulfamoyl)phenyl)azo)salicylate	Generator
5-((p-(2-Pyridylsulphamoyl)phenyl)azo)salicylate	Generator
5-((p-(2-Pyridylsulphamoyl)phenyl)azo)salicylic acid	Generator
5-(4-(2-Pyridylsulfamoyl)phenylazo)-2-hydroxybenzoate	Generator
5-(4-(2-Pyridylsulphamoyl)phenylazo)-2-hydroxybenzoate	Generator
5-(4-(2-Pyridylsulphamoyl)phenylazo)-2-hydroxybenzoic acid	Generator
5-(p-(2-Pyridylsulfamyl)phenylazo)salicylate	Generator
5-(p-(2-Pyridylsulphamyl)phenylazo)salicylate	Generator
5-(p-(2-Pyridylsulphamyl)phenylazo)salicylic acid	Generator
Salazosulphapiridina	Generator
Salazosulphapyridine	Generator
Salazosulphapyridinum	Generator
Salicylazosulphapyridine	Generator
Sulphasalazina	Generator
Sulphasalazinum	Generator
Sulphasalazine	Generator
Sulfasalazin	HMDB

Chemical Formula

C₁₈H₁₄N₄O₅S

Average Molecular Weight

398.393

Monoisotopic Molecular Weight

398.068490268

IUPAC Name

2-hydroxy-5-[(E)-2-{4-[(pyridin-2-yl)sulfamoyl]phenyl}diazen-1-yl]benzoic acid

Traditional Name

sulfasalazine

CAS Registry Number

599-79-1

SMILES

OC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=C1

InChI Identifier

InChI=1S/C18H14N4O5S/c23-16-9-6-13(11-15(16)18(24)25)21-20-12-4-7-14(8-5-12)28(26,27)22-17-3-1-2-10-19-17/h1-11,23H,(H,19,22)(H,24,25)/b21-20+

InChI Key

NCEXYHBECQHGNR-QZQOTICOSA-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
Benzenesulfonamide
Hydroxybenzoic acid
Salicylic acid or derivatives
Salicylic acid
Benzoic acid or derivatives
Benzoic acid
Benzenesulfonyl group
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Pyridine
Imidolactam
Benzenoid
Organosulfonic acid amide
Heteroaromatic compound
Vinylogous acid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Aminosulfonyl compound
Sulfonyl
Azo compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:9334 )
azobenzenes (CHEBI:9334 )
pyridines (CHEBI:9334 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014933)
Membrane (HMDB: HMDB0014933)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

non-steroidal anti-inflammatory drug (HMDB: HMDB0014933)
gastrointestinal drug (HMDB: HMDB0014933)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

antiinfective agent (HMDB: HMDB0014933)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	220 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.046 g/L	Not Available
LogP	2.5	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	199.7	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.046 g/L	ALOGPS
logP	2.92	ALOGPS
logP	3.94	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	2.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	141.31 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.6 m³·mol⁻¹	ChemAxon
Polarizability	39.69 Å³	ChemAxon
Number of Rings	3	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]+	189.898	30932474
DeepCCS	[M-H]-	187.54	30932474
DeepCCS	[M-2H]-	221.606	30932474
DeepCCS	[M+Na]+	196.726	30932474
AllCCS	[M+H]+	190.6	32859911
AllCCS	[M+H-H2O]+	187.9	32859911
AllCCS	[M+NH4]+	193.0	32859911
AllCCS	[M+Na]+	193.7	32859911
AllCCS	[M-H]-	184.9	32859911
AllCCS	[M+Na-2H]-	184.4	32859911
AllCCS	[M+HCOO]-	184.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sulfasalazine	OC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=C1	5322.1	Standard polar	33892256
Sulfasalazine	OC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=C1	3909.5	Standard non polar	33892256
Sulfasalazine	OC(=O)C1=CC(=CC=C1O)\N=N\C1=CC=C(C=C1)S(=O)(=O)NC1=NC=CC=C1	3676.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sulfasalazine,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(S(=O)(=O)NC3=CC=CC=N3)C=C2)=CC=C1O	3835.0	Semi standard non polar	33892256
Sulfasalazine,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(S(=O)(=O)NC3=CC=CC=N3)C=C2)C=C1C(=O)O	3893.4	Semi standard non polar	33892256
Sulfasalazine,1TMS,isomer #3	C[Si](C)(C)N(C1=CC=CC=N1)S(=O)(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1	3724.4	Semi standard non polar	33892256
Sulfasalazine,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(S(=O)(=O)NC3=CC=CC=N3)C=C2)=CC=C1O[Si](C)(C)C	3830.3	Semi standard non polar	33892256
Sulfasalazine,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(S(=O)(=O)N(C3=CC=CC=N3)[Si](C)(C)C)C=C2)=CC=C1O	3514.6	Semi standard non polar	33892256
Sulfasalazine,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(S(=O)(=O)N(C3=CC=CC=N3)[Si](C)(C)C)C=C2)C=C1C(=O)O	3651.8	Semi standard non polar	33892256
Sulfasalazine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(S(=O)(=O)N(C3=CC=CC=N3)[Si](C)(C)C)C=C2)=CC=C1O[Si](C)(C)C	3558.3	Semi standard non polar	33892256
Sulfasalazine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(S(=O)(=O)N(C3=CC=CC=N3)[Si](C)(C)C)C=C2)=CC=C1O[Si](C)(C)C	3559.3	Standard non polar	33892256
Sulfasalazine,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(S(=O)(=O)N(C3=CC=CC=N3)[Si](C)(C)C)C=C2)=CC=C1O[Si](C)(C)C	4698.6	Standard polar	33892256
Sulfasalazine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(S(=O)(=O)NC3=CC=CC=N3)C=C2)=CC=C1O	4091.3	Semi standard non polar	33892256
Sulfasalazine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(S(=O)(=O)NC3=CC=CC=N3)C=C2)C=C1C(=O)O	4199.8	Semi standard non polar	33892256
Sulfasalazine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C1=CC=CC=N1)S(=O)(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1	3998.1	Semi standard non polar	33892256
Sulfasalazine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(S(=O)(=O)NC3=CC=CC=N3)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C	4264.7	Semi standard non polar	33892256
Sulfasalazine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(S(=O)(=O)N(C3=CC=CC=N3)[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O	3982.9	Semi standard non polar	33892256
Sulfasalazine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(S(=O)(=O)N(C3=CC=CC=N3)[Si](C)(C)C(C)(C)C)C=C2)C=C1C(=O)O	4103.2	Semi standard non polar	33892256
Sulfasalazine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(S(=O)(=O)N(C3=CC=CC=N3)[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C	4154.9	Semi standard non polar	33892256
Sulfasalazine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(S(=O)(=O)N(C3=CC=CC=N3)[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C	4229.9	Standard non polar	33892256
Sulfasalazine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(S(=O)(=O)N(C3=CC=CC=N3)[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C	4783.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfasalazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6w-6695000000-47b5c3a0d5190268e477	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfasalazine GC-MS (2 TMS) - 70eV, Positive	splash10-00di-2549110000-cce76e754cd947c9bdf8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sulfasalazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sulfasalazine , positive-QTOF	splash10-0002-0239100000-5bf223e6e250eb77105a	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfasalazine 10V, Positive-QTOF	splash10-0002-0009000000-9e5b613387b866753d70	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfasalazine 20V, Positive-QTOF	splash10-0a4j-2019000000-5dbdcf5699c56f6a59d8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfasalazine 40V, Positive-QTOF	splash10-002b-9240000000-6268787fab73d296c1d8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfasalazine 10V, Negative-QTOF	splash10-0f6t-0009000000-5eea07137968cfa96d18	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfasalazine 20V, Negative-QTOF	splash10-0udi-0009000000-642c65b2544ce824decc	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfasalazine 40V, Negative-QTOF	splash10-0k97-9663000000-5acc71d633a9ef82ea98	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfasalazine 10V, Positive-QTOF	splash10-001i-0009000000-a266ecec49bba90668ba	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfasalazine 20V, Positive-QTOF	splash10-005a-2089000000-ad13a0c69c0256eb5505	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfasalazine 40V, Positive-QTOF	splash10-0092-3936000000-d0a391d2c705ca56748e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfasalazine 10V, Negative-QTOF	splash10-0002-0009000000-cf36a51de9de200e8014	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfasalazine 20V, Negative-QTOF	splash10-0002-2917000000-1f1274dcd32e5287cfb7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sulfasalazine 40V, Negative-QTOF	splash10-0002-1900000000-16464eaa00e58b69be2d	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

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 DB00795	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00795	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00795

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10605946

KEGG Compound ID

C07316

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sulfasalazine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

9334

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)

Download (PDF)

General References

Not Available

Only showing the first 10 proteins. There are 12 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Acetyl-CoA acetyltransferase, mitochondrial

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Plays a major role in ketone body metabolism.
Gene Name:: ACAT1
Uniprot ID:: P24752
Molecular weight:: 45199.2

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Faison LD, White HL: Sulfasalazine inhibits lyso-PAF: acetyl-COA acetyltransferase. Prostaglandins. 1992 Sep;44(3):245-9. [PubMed:1357724 ]

Enzyme Details

2. Arachidonate 5-lipoxygenase

General function:: Involved in metal ion binding
Specific function:: Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:: ALOX5
Uniprot ID:: P09917
Molecular weight:: 77982.595

References

Nielsen OH, Bukhave K, Elmgreen J, Ahnfelt-Ronne I: Inhibition of 5-lipoxygenase pathway of arachidonic acid metabolism in human neutrophils by sulfasalazine and 5-aminosalicylic acid. Dig Dis Sci. 1987 Jun;32(6):577-82. [PubMed:2882965 ]
Allgayer H, Eisenburg J, Paumgartner G: Soybean lipoxygenase inhibition: studies with the sulphasalazine metabolites N-acetylaminosalicylic acid, 5-aminosalicylic acid and sulphapyridine. Eur J Clin Pharmacol. 1984;26(4):449-51. [PubMed:6428914 ]
Sircar JC, Schwender CF, Carethers ME: Inhibition of soybean lipoxygenase by sulfasalazine and 5-aminosalicylic acid: a possible mode of action in ulcerative colitis. Biochem Pharmacol. 1983 Jan 1;32(1):170-2. [PubMed:6131674 ]

Enzyme Details

3. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

References

Mifflin RC, Saada JI, Di Mari JF, Valentich JD, Adegboyega PA, Powell DW: Aspirin-mediated COX-2 transcript stabilization via sustained p38 activation in human intestinal myofibroblasts. Mol Pharmacol. 2004 Feb;65(2):470-8. [PubMed:14742690 ]
Generini S, Fiori G, Matucci Cerinic M: Therapy of spondylarthropathy in inflammatory bowel disease. Clin Exp Rheumatol. 2002 Nov-Dec;20(6 Suppl 28):S88-94. [PubMed:12463455 ]
Distrutti E, Sediari L, Mencarelli A, Renga B, Orlandi S, Russo G, Caliendo G, Santagada V, Cirino G, Wallace JL, Fiorucci S: 5-Amino-2-hydroxybenzoic acid 4-(5-thioxo-5H-[1,2]dithiol-3yl)-phenyl ester (ATB-429), a hydrogen sulfide-releasing derivative of mesalamine, exerts antinociceptive effects in a model of postinflammatory hypersensitivity. J Pharmacol Exp Ther. 2006 Oct;319(1):447-58. Epub 2006 Jul 19. [PubMed:16855178 ]
Cipolla G, Crema F, Sacco S, Moro E, de Ponti F, Frigo G: Nonsteroidal anti-inflammatory drugs and inflammatory bowel disease: current perspectives. Pharmacol Res. 2002 Jul;46(1):1-6. [PubMed:12208114 ]
Pruzanski W, Stefanski E, Vadas P, Ramamurthy NS: Inhibition of extracellular release of proinflammatory secretory phospholipase A2 (sPLA2) by sulfasalazine: a novel mechanism of anti-inflammatory activity. Biochem Pharmacol. 1997 Jun 15;53(12):1901-7. [PubMed:9256165 ]

Enzyme Details

4. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Allgayer H: Review article: mechanisms of action of mesalazine in preventing colorectal carcinoma in inflammatory bowel disease. Aliment Pharmacol Ther. 2003 Sep;18 Suppl 2:10-4. [PubMed:12950415 ]

Enzyme Details

5. Inhibitor of nuclear factor kappa-B kinase subunit beta

General function:: Involved in protein kinase activity
Specific function:: Acts as part of the IKK complex in the conventional pathway of NF-kappa-B activation and phosphorylates inhibitors of NF-kappa-B thus leading to the dissociation of the inhibitor/NF- kappa-B complex and ultimately the degradation of the inhibitor. Also phosphorylates NCOA3
Gene Name:: IKBKB
Uniprot ID:: O14920
Molecular weight:: 86563.2

References

Weber CK, Liptay S, Wirth T, Adler G, Schmid RM: Suppression of NF-kappaB activity by sulfasalazine is mediated by direct inhibition of IkappaB kinases alpha and beta. Gastroenterology. 2000 Nov;119(5):1209-18. [PubMed:11054378 ]
Allgayer H: Review article: mechanisms of action of mesalazine in preventing colorectal carcinoma in inflammatory bowel disease. Aliment Pharmacol Ther. 2003 Sep;18 Suppl 2:10-4. [PubMed:12950415 ]

Enzyme Details

6. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

7. Inhibitor of nuclear factor kappa-B kinase subunit alpha

General function:: Involved in protein kinase activity
Specific function:: Acts as part of the IKK complex in the conventional pathway of NF-kappa-B activation and phosphorylates inhibitors of NF-kappa-B thus leading to the dissociation of the inhibitor/NF- kappa-B complex and ultimately the degradation of the inhibitor. As part of the non-canonical pathway of NF-kappa-B activation, the MAP3K14-activated CHUK/IKKA homodimer phosphorylates NFKB2/p100 associated with RelB, inducing its proteolytic processing to NFKB2/p52 and the formation of NF-kappa-B RelB-p52 complexes. Also phosphorylates NCOA3. Phosphorylates 'Ser-10' of histone H3 at NF- kappa-B-regulated promoters during inflammatory responses triggered by cytokines
Gene Name:: CHUK
Uniprot ID:: O15111
Molecular weight:: 84652.9

References

Weber CK, Liptay S, Wirth T, Adler G, Schmid RM: Suppression of NF-kappaB activity by sulfasalazine is mediated by direct inhibition of IkappaB kinases alpha and beta. Gastroenterology. 2000 Nov;119(5):1209-18. [PubMed:11054378 ]
Allgayer H: Review article: mechanisms of action of mesalazine in preventing colorectal carcinoma in inflammatory bowel disease. Aliment Pharmacol Ther. 2003 Sep;18 Suppl 2:10-4. [PubMed:12950415 ]

Enzyme Details

8. Peroxisome proliferator-activated receptor gamma

General function:: Involved in DNA binding
Specific function:: Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the receptor binds to a promoter element in the gene for acyl-CoA oxidase and activates its transcription. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis
Gene Name:: PPARG
Uniprot ID:: P37231
Molecular weight:: 57619.6

References

Rousseaux C, Lefebvre B, Dubuquoy L, Lefebvre P, Romano O, Auwerx J, Metzger D, Wahli W, Desvergne B, Naccari GC, Chavatte P, Farce A, Bulois P, Cortot A, Colombel JF, Desreumaux P: Intestinal antiinflammatory effect of 5-aminosalicylic acid is dependent on peroxisome proliferator-activated receptor-gamma. J Exp Med. 2005 Apr 18;201(8):1205-15. Epub 2005 Apr 11. [PubMed:15824083 ]
Schwab M, Reynders V, Loitsch S, Shastri YM, Steinhilber D, Schroder O, Stein J: PPARgamma is involved in mesalazine-mediated induction of apoptosis and inhibition of cell growth in colon cancer cells. Carcinogenesis. 2008 Jul;29(7):1407-14. doi: 10.1093/carcin/bgn118. Epub 2008 Jun 9. [PubMed:18544567 ]
Linard C, Gremy O, Benderitter M: Reduction of peroxisome proliferation-activated receptor gamma expression by gamma-irradiation as a mechanism contributing to inflammatory response in rat colon: modulation by the 5-aminosalicylic acid agonist. J Pharmacol Exp Ther. 2008 Mar;324(3):911-20. Epub 2007 Dec 12. [PubMed:18077625 ]
Desreumaux P, Ghosh S: Review article: mode of action and delivery of 5-aminosalicylic acid - new evidence. Aliment Pharmacol Ther. 2006 Sep;24 Suppl 1:2-9. [PubMed:16939423 ]

Enzyme Details

9. Cystine/glutamate transporter

General function:: Involved in transport
Specific function:: Sodium-independent, high-affinity exchange of anionic amino acids with high specificity for anionic form of cystine and glutamate.
Gene Name:: SLC7A11
Uniprot ID:: Q9UPY5
Molecular weight:: 55422.44

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Gout PW, Buckley AR, Simms CR, Bruchovsky N: Sulfasalazine, a potent suppressor of lymphoma growth by inhibition of the x(c)- cystine transporter: a new action for an old drug. Leukemia. 2001 Oct;15(10):1633-40. [PubMed:11587223 ]

Transporters

Enzyme Details

1. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Dahan A, Amidon GL: Small intestinal efflux mediated by MRP2 and BCRP shifts sulfasalazine intestinal permeability from high to low, enabling its colonic targeting. Am J Physiol Gastrointest Liver Physiol. 2009 Aug;297(2):G371-7. doi: 10.1152/ajpgi.00102.2009. Epub 2009 Jun 18. [PubMed:19541926 ]

Enzyme Details

2. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

Karlsson JE, Heddle C, Rozkov A, Rotticci-Mulder J, Tuvesson O, Hilgendorf C, Andersson TB: High-activity p-glycoprotein, multidrug resistance protein 2, and breast cancer resistance protein membrane vesicles prepared from transiently transfected human embryonic kidney 293-epstein-barr virus nuclear antigen cells. Drug Metab Dispos. 2010 Apr;38(4):705-14. doi: 10.1124/dmd.109.028886. Epub 2010 Jan 13. [PubMed:20071452 ]
Shukla S, Zaher H, Hartz A, Bauer B, Ware JA, Ambudkar SV: Curcumin inhibits the activity of ABCG2/BCRP1, a multidrug resistance-linked ABC drug transporter in mice. Pharm Res. 2009 Feb;26(2):480-7. doi: 10.1007/s11095-008-9735-8. Epub 2008 Oct 9. [PubMed:18841445 ]
Dahan A, Amidon GL: Small intestinal efflux mediated by MRP2 and BCRP shifts sulfasalazine intestinal permeability from high to low, enabling its colonic targeting. Am J Physiol Gastrointest Liver Physiol. 2009 Aug;297(2):G371-7. doi: 10.1152/ajpgi.00102.2009. Epub 2009 Jun 18. [PubMed:19541926 ]

Enzyme Details

3. Proton-coupled folate transporter

General function:: Involved in transmembrane transport
Specific function:: Has been shown to act both as an intestinal proton- coupled high-affinity folate transporter and as an intestinal heme transporter which mediates heme uptake from the gut lumen into duodenal epithelial cells. The iron is then released from heme and may be transported into the bloodstream. Dietary heme iron is an important nutritional source of iron. Shows a higher affinity for folate than heme
Gene Name:: SLC46A1
Uniprot ID:: Q96NT5
Molecular weight:: 49770.0

References

Nakai Y, Inoue K, Abe N, Hatakeyama M, Ohta KY, Otagiri M, Hayashi Y, Yuasa H: Functional characterization of human proton-coupled folate transporter/heme carrier protein 1 heterologously expressed in mammalian cells as a folate transporter. J Pharmacol Exp Ther. 2007 Aug;322(2):469-76. Epub 2007 May 2. [PubMed:17475902 ]

Only showing the first 10 proteins. There are 12 proteins in total.

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Showing metabocard for Sulfasalazine (HMDB0014933)

MOL for HMDB0014933 (Sulfasalazine)

3D MOL for HMDB0014933 (Sulfasalazine)

3D SDF for HMDB0014933 (Sulfasalazine)

3D-SDF for HMDB0014933 (Sulfasalazine)

PDB for HMDB0014933 (Sulfasalazine)

3D PDB for HMDB0014933 (Sulfasalazine)

SMILES for HMDB0014933 (Sulfasalazine)

INCHI for HMDB0014933 (Sulfasalazine)

Structure for HMDB0014933 (Sulfasalazine)

3D Structure for HMDB0014933 (Sulfasalazine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Transporters

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