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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015149

Secondary Accession Numbers

HMDB15149

Metabolite Identification

Common Name

Balsalazide

Description

Balsalazide is an anti-inflammatory drug used in the treatment of Inflammatory Bowel Disease. It is sold under the name 'Colazal' in the US and 'Colazide' in the UK. The chemical name is (E)-5-[[-4-(2-carboxyethyl) aminocarbonyl] phenyl]azo] -2-hydroxybenzoic acid. It is usually administered as the disodium salt. Balsalazide releases mesalazine, also known as 5-aminosalicylic acid, or 5-ASA, in the large intestine. Its advantage over that drug in the treatment of Ulcerative colitis is believed to be the delivery of the active agent past the small intestine to the large intestine, the active site of ulcerative colitis.

Structure

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


  Mrv0541 04191212162D          

 26 27  0  0  0  0            999 V2000
    7.2023  -23.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4877  -23.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2036  -20.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3457  -23.1029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3457  -22.2779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2023  -24.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0615  -20.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167  -23.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4891  -21.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3471  -21.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4877  -22.2778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2036  -19.8028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6312  -23.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7760  -21.0403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9181  -21.0404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167  -24.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4891  -21.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7747  -20.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0602  -21.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7732  -23.5153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6325  -20.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0615  -19.8028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6312  -24.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0602  -21.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7747  -22.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4877  -24.7529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  9  1  0  0  0  0
  4 13  1  0  0  0  0
  5  4  2  0  0  0  0
  6  1  1  0  0  0  0
  7 10  1  0  0  0  0
  8  1  2  0  0  0  0
  9 17  2  0  0  0  0
 10 21  1  0  0  0  0
 11  2  2  0  0  0  0
 12  3  2  0  0  0  0
 13  8  1  0  0  0  0
 14  7  1  0  0  0  0
 15  3  1  0  0  0  0
 16  6  2  0  0  0  0
 17 25  1  0  0  0  0
 18 24  2  0  0  0  0
 19  5  1  0  0  0  0
 20  2  1  0  0  0  0
 21 15  1  0  0  0  0
 22  7  2  0  0  0  0
 23 13  2  0  0  0  0
 24 19  1  0  0  0  0
 25 19  2  0  0  0  0
 26  6  1  0  0  0  0
 16 23  1  0  0  0  0
 18  9  1  0  0  0  0
M  END

HMDB0015149
     RDKit          3D
Balsalazide
 41 42  0  0  0  0  0  0  0  0999 V2000
    6.8734    1.6387   -0.5325 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2268    0.8990    0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9268    1.5962    1.4387 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0214   -0.5174    0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0194   -1.2681   -0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6335   -1.0563    0.0458 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7800    0.0222   -0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1367    1.1330   -0.5378 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3370   -0.1011    0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115    1.0309    0.5656 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2579    0.9071    0.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3775   -0.3118    0.8470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7502   -0.4965    1.1494 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7375   -0.2998    0.6510 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9341   -0.0707    0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0927    0.0578   -1.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3078    0.2893   -1.9070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4575    0.4115   -1.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6919    0.6435   -1.7078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3333    0.2892    0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5475    0.4174    1.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4490    0.3092    2.2745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7970    0.6517    0.4881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1221    0.0580    0.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3613   -1.4241    0.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7124   -1.3156    0.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7854    2.0362    1.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9091   -0.7951    1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0353   -1.0144    0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2279   -2.3747   -0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1795   -1.0946   -1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0923   -1.9460    0.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1311    1.9789    0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3036    1.7921    1.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2046   -0.0351   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4093    0.3853   -2.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8187    0.7369   -2.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0686    1.5252    0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9936   -0.0424    1.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0769   -2.4111    0.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2146   -2.2345   -0.0631 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  2  0
 12 25  1  0
 25 26  2  0
 26  9  1  0
 24 15  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 17 36  1  0
 19 37  1  0
 23 38  1  0
 24 39  1  0
 25 40  1  0
 26 41  1  0
M  END


  Mrv0541 04191212162D          

 26 27  0  0  0  0            999 V2000
    7.2023  -23.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4877  -23.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2036  -20.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3457  -23.1029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3457  -22.2779    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2023  -24.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0615  -20.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167  -23.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4891  -21.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3471  -21.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4877  -22.2778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2036  -19.8028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6312  -23.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7760  -21.0403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9181  -21.0404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9167  -24.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4891  -21.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7747  -20.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0602  -21.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7732  -23.5153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6325  -20.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0615  -19.8028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6312  -24.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0602  -21.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7747  -22.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4877  -24.7529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  9  1  0  0  0  0
  4 13  1  0  0  0  0
  5  4  2  0  0  0  0
  6  1  1  0  0  0  0
  7 10  1  0  0  0  0
  8  1  2  0  0  0  0
  9 17  2  0  0  0  0
 10 21  1  0  0  0  0
 11  2  2  0  0  0  0
 12  3  2  0  0  0  0
 13  8  1  0  0  0  0
 14  7  1  0  0  0  0
 15  3  1  0  0  0  0
 16  6  2  0  0  0  0
 17 25  1  0  0  0  0
 18 24  2  0  0  0  0
 19  5  1  0  0  0  0
 20  2  1  0  0  0  0
 21 15  1  0  0  0  0
 22  7  2  0  0  0  0
 23 13  2  0  0  0  0
 24 19  1  0  0  0  0
 25 19  2  0  0  0  0
 26  6  1  0  0  0  0
 16 23  1  0  0  0  0
 18  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015149

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H15N3O6/c21-14-6-5-12(9-13(14)17(25)26)20-19-11-3-1-10(2-4-11)16(24)18-8-7-15(22)23/h1-6,9,21H,7-8H2,(H,18,24)(H,22,23)(H,25,26)/b20-19+

> <INCHI_KEY>
IPOKCKJONYRRHP-FMQUCBEESA-N

> <FORMULA>
C17H15N3O6

> <MOLECULAR_WEIGHT>
357.3175

> <EXACT_MASS>
357.096085227

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
35.98486676626132

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(E)-2-{4-[(2-carboxyethyl)carbamoyl]phenyl}diazen-1-yl]-2-hydroxybenzoic acid

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
3.172469480333333

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.7323069558352695

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0649272543262662

> <JCHEM_PKA_STRONGEST_BASIC>
-0.03339614995957785

> <JCHEM_POLAR_SURFACE_AREA>
148.65

> <JCHEM_REFRACTIVITY>
94.37320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
balsalazide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015149
     RDKit          3D
Balsalazide
 41 42  0  0  0  0  0  0  0  0999 V2000
    6.8734    1.6387   -0.5325 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2268    0.8990    0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9268    1.5962    1.4387 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0214   -0.5174    0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0194   -1.2681   -0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6335   -1.0563    0.0458 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7800    0.0222   -0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1367    1.1330   -0.5378 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3370   -0.1011    0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115    1.0309    0.5656 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2579    0.9071    0.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3775   -0.3118    0.8470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7502   -0.4965    1.1494 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7375   -0.2998    0.6510 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9341   -0.0707    0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0927    0.0578   -1.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3078    0.2893   -1.9070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4575    0.4115   -1.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6919    0.6435   -1.7078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3333    0.2892    0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5475    0.4174    1.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4490    0.3092    2.2745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7970    0.6517    0.4881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1221    0.0580    0.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3613   -1.4241    0.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7124   -1.3156    0.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7854    2.0362    1.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9091   -0.7951    1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0353   -1.0144    0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2279   -2.3747   -0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1795   -1.0946   -1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0923   -1.9460    0.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1311    1.9789    0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3036    1.7921    1.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2046   -0.0351   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4093    0.3853   -2.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8187    0.7369   -2.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0686    1.5252    0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9936   -0.0424    1.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0769   -2.4111    0.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2146   -2.2345   -0.0631 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  2  0
 12 25  1  0
 25 26  2  0
 26  9  1  0
 24 15  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 17 36  1  0
 19 37  1  0
 23 38  1  0
 24 39  1  0
 25 40  1  0
 26 41  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      13.444 -43.895   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.110 -43.125   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.780 -38.505   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      17.445 -43.125   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      17.445 -41.585   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      13.444 -45.435   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.115 -38.505   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.778 -43.125   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.446 -39.275   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.781 -39.275   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.110 -41.585   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      22.780 -36.965   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      16.112 -43.895   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      29.449 -39.275   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      24.114 -39.275   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      14.778 -46.205   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.446 -40.815   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.113 -38.505   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.779 -40.815   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.777 -43.895   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      25.447 -38.505   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      28.115 -36.965   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      16.112 -45.435   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.779 -39.275   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.113 -41.585   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.110 -46.205   0.000  0.00  0.00           O+0
CONECT    1    2    6    8                                                  
CONECT    2    1   11   20                                                  
CONECT    3    9   12   15                                                  
CONECT    4   13    5                                                       
CONECT    5    4   19                                                       
CONECT    6    1   16   26                                                  
CONECT    7   10   14   22                                                  
CONECT    8    1   13                                                       
CONECT    9    3   17   18                                                  
CONECT   10    7   21                                                       
CONECT   11    2                                                            
CONECT   12    3                                                            
CONECT   13    4    8   23                                                  
CONECT   14    7                                                            
CONECT   15    3   21                                                       
CONECT   16    6   23                                                       
CONECT   17    9   25                                                       
CONECT   18   24    9                                                       
CONECT   19    5   24   25                                                  
CONECT   20    2                                                            
CONECT   21   10   15                                                       
CONECT   22    7                                                            
CONECT   23   13   16                                                       
CONECT   24   18   19                                                       
CONECT   25   17   19                                                       
CONECT   26    6                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

COMPND    HMDB0015149
HETATM    1  O1  UNL     1       6.873   1.639  -0.533  1.00  0.00           O  
HETATM    2  C1  UNL     1       7.227   0.899   0.410  1.00  0.00           C  
HETATM    3  O2  UNL     1       7.927   1.596   1.439  1.00  0.00           O  
HETATM    4  C2  UNL     1       7.021  -0.517   0.578  1.00  0.00           C  
HETATM    5  C3  UNL     1       6.019  -1.268  -0.172  1.00  0.00           C  
HETATM    6  N1  UNL     1       4.634  -1.056   0.046  1.00  0.00           N  
HETATM    7  C4  UNL     1       3.780   0.022  -0.115  1.00  0.00           C  
HETATM    8  O3  UNL     1       4.137   1.133  -0.538  1.00  0.00           O  
HETATM    9  C5  UNL     1       2.337  -0.101   0.226  1.00  0.00           C  
HETATM   10  C6  UNL     1       1.612   1.031   0.566  1.00  0.00           C  
HETATM   11  C7  UNL     1       0.258   0.907   0.872  1.00  0.00           C  
HETATM   12  C8  UNL     1      -0.378  -0.312   0.847  1.00  0.00           C  
HETATM   13  N2  UNL     1      -1.750  -0.496   1.149  1.00  0.00           N  
HETATM   14  N3  UNL     1      -2.737  -0.300   0.651  1.00  0.00           N  
HETATM   15  C9  UNL     1      -3.934  -0.071   0.067  1.00  0.00           C  
HETATM   16  C10 UNL     1      -4.093   0.058  -1.326  1.00  0.00           C  
HETATM   17  C11 UNL     1      -5.308   0.289  -1.907  1.00  0.00           C  
HETATM   18  C12 UNL     1      -6.458   0.412  -1.160  1.00  0.00           C  
HETATM   19  O4  UNL     1      -7.692   0.644  -1.708  1.00  0.00           O  
HETATM   20  C13 UNL     1      -6.333   0.289   0.223  1.00  0.00           C  
HETATM   21  C14 UNL     1      -7.548   0.417   1.028  1.00  0.00           C  
HETATM   22  O5  UNL     1      -7.449   0.309   2.274  1.00  0.00           O  
HETATM   23  O6  UNL     1      -8.797   0.652   0.488  1.00  0.00           O  
HETATM   24  C15 UNL     1      -5.122   0.058   0.807  1.00  0.00           C  
HETATM   25  C16 UNL     1       0.361  -1.424   0.507  1.00  0.00           C  
HETATM   26  C17 UNL     1       1.712  -1.316   0.199  1.00  0.00           C  
HETATM   27  H1  UNL     1       8.785   2.036   1.168  1.00  0.00           H  
HETATM   28  H2  UNL     1       6.909  -0.795   1.680  1.00  0.00           H  
HETATM   29  H3  UNL     1       8.035  -1.014   0.352  1.00  0.00           H  
HETATM   30  H4  UNL     1       6.228  -2.375  -0.076  1.00  0.00           H  
HETATM   31  H5  UNL     1       6.180  -1.095  -1.291  1.00  0.00           H  
HETATM   32  H6  UNL     1       4.092  -1.946   0.446  1.00  0.00           H  
HETATM   33  H7  UNL     1       2.131   1.979   0.579  1.00  0.00           H  
HETATM   34  H8  UNL     1      -0.304   1.792   1.136  1.00  0.00           H  
HETATM   35  H9  UNL     1      -3.205  -0.035  -1.926  1.00  0.00           H  
HETATM   36  H10 UNL     1      -5.409   0.385  -2.984  1.00  0.00           H  
HETATM   37  H11 UNL     1      -7.819   0.737  -2.698  1.00  0.00           H  
HETATM   38  H12 UNL     1      -9.069   1.525   0.047  1.00  0.00           H  
HETATM   39  H13 UNL     1      -4.994  -0.042   1.887  1.00  0.00           H  
HETATM   40  H14 UNL     1      -0.077  -2.411   0.468  1.00  0.00           H  
HETATM   41  H15 UNL     1       2.215  -2.235  -0.063  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   32
CONECT    7    8    8    9
CONECT    9   10   10   26
CONECT   10   11   33
CONECT   11   12   12   34
CONECT   12   13   25
CONECT   13   14   14
CONECT   14   15
CONECT   15   16   16   24
CONECT   16   17   35
CONECT   17   18   18   36
CONECT   18   19   20
CONECT   19   37
CONECT   20   21   24   24
CONECT   21   22   22   23
CONECT   23   38
CONECT   24   39
CONECT   25   26   26   40
CONECT   26   41
END

HMDB0015149
     RDKit          3D
Balsalazide
 41 42  0  0  0  0  0  0  0  0999 V2000
    6.8734    1.6387   -0.5325 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2268    0.8990    0.4099 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9268    1.5962    1.4387 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0214   -0.5174    0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0194   -1.2681   -0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6335   -1.0563    0.0458 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7800    0.0222   -0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1367    1.1330   -0.5378 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3370   -0.1011    0.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115    1.0309    0.5656 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2579    0.9071    0.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3775   -0.3118    0.8470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7502   -0.4965    1.1494 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7375   -0.2998    0.6510 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9341   -0.0707    0.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0927    0.0578   -1.3255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3078    0.2893   -1.9070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4575    0.4115   -1.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6919    0.6435   -1.7078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3333    0.2892    0.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5475    0.4174    1.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4490    0.3092    2.2745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7970    0.6517    0.4881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1221    0.0580    0.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3613   -1.4241    0.5072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7124   -1.3156    0.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7854    2.0362    1.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9091   -0.7951    1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0353   -1.0144    0.3515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2279   -2.3747   -0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1795   -1.0946   -1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0923   -1.9460    0.4460 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1311    1.9789    0.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3036    1.7921    1.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2046   -0.0351   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4093    0.3853   -2.9837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8187    0.7369   -2.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0686    1.5252    0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9936   -0.0424    1.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0769   -2.4111    0.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2146   -2.2345   -0.0631 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  2  0
 12 25  1  0
 25 26  2  0
 26  9  1  0
 24 15  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
 10 33  1  0
 11 34  1  0
 16 35  1  0
 17 36  1  0
 19 37  1  0
 23 38  1  0
 24 39  1  0
 25 40  1  0
 26 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-5-((4-(((2-Carboxyethyl)amino)carbonyl)phenyl)azo)-2-hydroxybenzoic acid	ChEBI
(e)-5-({p-[(2-carboxyethyl)carbamoyl]phenyl}azo)-2-salicylic acid	ChEBI
3-(2-{4-[(2-carboxyethyl)carbamoyl]phenyl}hydrazinylidene)-6-oxocyclohexa-1,4-diene-1-carboxylic acid	ChEBI
5-[4-(2-Carboxy-ethylcarbamoyl)-phenylazo]-2-hydroxy-benzoic acid	ChEBI
Balsalazida	ChEBI
Balsalazido	ChEBI
Balsalazidum	ChEBI
(e)-5-((4-(((2-Carboxyethyl)amino)carbonyl)phenyl)azo)-2-hydroxybenzoate	Generator
(e)-5-({p-[(2-carboxyethyl)carbamoyl]phenyl}azo)-2-salicylate	Generator
3-(2-{4-[(2-carboxyethyl)carbamoyl]phenyl}hydrazinylidene)-6-oxocyclohexa-1,4-diene-1-carboxylate	Generator
5-[4-(2-Carboxy-ethylcarbamoyl)-phenylazo]-2-hydroxy-benzoate	Generator
Balsalazide disodium	HMDB

Chemical Formula

C₁₇H₁₅N₃O₆

Average Molecular Weight

357.3175

Monoisotopic Molecular Weight

357.096085227

IUPAC Name

5-[(E)-2-{4-[(2-carboxyethyl)carbamoyl]phenyl}diazen-1-yl]-2-hydroxybenzoic acid

Traditional Name

balsalazide

CAS Registry Number

80573-04-2

SMILES

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

InChI Identifier

InChI=1S/C17H15N3O6/c21-14-6-5-12(9-13(14)17(25)26)20-19-11-3-1-10(2-4-11)16(24)18-8-7-15(22)23/h1-6,9,21H,7-8H2,(H,18,24)(H,22,23)(H,25,26)/b20-19+

InChI Key

IPOKCKJONYRRHP-FMQUCBEESA-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
Beta amino acid or derivatives
Hydroxybenzoic acid
Salicylic acid or derivatives
Salicylic acid
Benzoic acid
Benzoic acid or derivatives
Benzamide
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Vinylogous acid
Azo compound
Secondary carboxylic acid amide
Carboxamide group
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Carboxylic acid
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monohydroxybenzoic acid (CHEBI:267413 )

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: HMDB0015149)
Membrane (HMDB: HMDB0015149)

Source

Exogenous

Exogenous (HMDB: HMDB0015149)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Non-steroidal anti-inflammatory drug (HMDB: HMDB0015149)
Gastrointestinal drug (HMDB: HMDB0015149)
Anti-ulcer drug (HMDB: HMDB0015149)
Prodrug (HMDB: HMDB0015149)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.062 g/L	Not Available
LogP	1.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.062 g/L	ALOGPS
logP	3.37	ALOGPS
logP	3.17	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.06	ChemAxon
pKa (Strongest Basic)	-0.033	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	148.65 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	94.37 m³·mol⁻¹	ChemAxon
Polarizability	35.98 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]+	184.084	30932474
DeepCCS	[M-H]-	181.726	30932474
DeepCCS	[M-2H]-	215.677	30932474
DeepCCS	[M+Na]+	190.905	30932474
AllCCS	[M+H]+	179.7	32859911
AllCCS	[M+H-H2O]+	176.9	32859911
AllCCS	[M+NH4]+	182.2	32859911
AllCCS	[M+Na]+	182.9	32859911
AllCCS	[M-H]-	181.3	32859911
AllCCS	[M+Na-2H]-	180.9	32859911
AllCCS	[M+HCOO]-	180.7	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.	4.16 minutes	32390414
Predicted by Siyang on May 30, 2022	10.8975 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.26 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	143.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1498.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	209.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	92.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	152.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	57.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	310.1 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	409.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	141.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	658.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	364.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1369.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	248.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	308.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	454.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	174.6 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	306.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Balsalazide	OC(=O)CCNC(=O)C1=CC=C(C=C1)\N=N\C1=CC=C(O)C(=C1)C(O)=O	4846.3	Standard polar	33892256
Balsalazide	OC(=O)CCNC(=O)C1=CC=C(C=C1)\N=N\C1=CC=C(O)C(=C1)C(O)=O	3152.1	Standard non polar	33892256
Balsalazide	OC(=O)CCNC(=O)C1=CC=C(C=C1)\N=N\C1=CC=C(O)C(=C1)C(O)=O	3669.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Balsalazide,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCNC(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1	3884.3	Semi standard non polar	33892256
Balsalazide,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(C(=O)NCCC(=O)O)C=C2)C=C1C(=O)O	3899.9	Semi standard non polar	33892256
Balsalazide,1TMS,isomer #3	C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(C(=O)NCCC(=O)O)C=C2)=CC=C1O	3881.6	Semi standard non polar	33892256
Balsalazide,1TMS,isomer #4	C[Si](C)(C)N(CCC(=O)O)C(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1	3808.7	Semi standard non polar	33892256
Balsalazide,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCNC(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O)=C2)C=C1	3847.9	Semi standard non polar	33892256
Balsalazide,2TMS,isomer #2	C[Si](C)(C)OC(=O)CCNC(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O[Si](C)(C)C)=C2)C=C1	3797.0	Semi standard non polar	33892256
Balsalazide,2TMS,isomer #3	C[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1)[Si](C)(C)C	3613.8	Semi standard non polar	33892256
Balsalazide,2TMS,isomer #4	C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(C(=O)NCCC(=O)O)C=C2)=CC=C1O[Si](C)(C)C	3859.9	Semi standard non polar	33892256
Balsalazide,2TMS,isomer #5	C[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(C(=O)N(CCC(=O)O)[Si](C)(C)C)C=C2)C=C1C(=O)O	3725.8	Semi standard non polar	33892256
Balsalazide,2TMS,isomer #6	C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(C(=O)N(CCC(=O)O)[Si](C)(C)C)C=C2)=CC=C1O	3621.1	Semi standard non polar	33892256
Balsalazide,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCNC(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2)C=C1	3783.5	Semi standard non polar	33892256
Balsalazide,3TMS,isomer #2	C[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O)=C2)C=C1)[Si](C)(C)C	3598.4	Semi standard non polar	33892256
Balsalazide,3TMS,isomer #3	C[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O[Si](C)(C)C)=C2)C=C1)[Si](C)(C)C	3532.0	Semi standard non polar	33892256
Balsalazide,3TMS,isomer #4	C[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(C(=O)N(CCC(=O)O)[Si](C)(C)C)C=C2)=CC=C1O[Si](C)(C)C	3613.3	Semi standard non polar	33892256
Balsalazide,4TMS,isomer #1	C[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2)C=C1)[Si](C)(C)C	3577.8	Semi standard non polar	33892256
Balsalazide,4TMS,isomer #1	C[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2)C=C1)[Si](C)(C)C	3449.0	Standard non polar	33892256
Balsalazide,4TMS,isomer #1	C[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C)C(C(=O)O[Si](C)(C)C)=C2)C=C1)[Si](C)(C)C	4085.5	Standard polar	33892256
Balsalazide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCNC(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1	4158.0	Semi standard non polar	33892256
Balsalazide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(C(=O)NCCC(=O)O)C=C2)C=C1C(=O)O	4198.2	Semi standard non polar	33892256
Balsalazide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(C(=O)NCCC(=O)O)C=C2)=CC=C1O	4172.3	Semi standard non polar	33892256
Balsalazide,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CCC(=O)O)C(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1	4093.1	Semi standard non polar	33892256
Balsalazide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCNC(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C2)C=C1	4357.5	Semi standard non polar	33892256
Balsalazide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCNC(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2)C=C1	4286.3	Semi standard non polar	33892256
Balsalazide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O)=C2)C=C1)[Si](C)(C)C(C)(C)C	4172.8	Semi standard non polar	33892256
Balsalazide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(C(=O)NCCC(=O)O)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C	4327.4	Semi standard non polar	33892256
Balsalazide,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(/N=N/C2=CC=C(C(=O)N(CCC(=O)O)[Si](C)(C)C(C)(C)C)C=C2)C=C1C(=O)O	4238.4	Semi standard non polar	33892256
Balsalazide,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(C(=O)N(CCC(=O)O)[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O	4146.9	Semi standard non polar	33892256
Balsalazide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCNC(=O)C1=CC=C(/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)C=C1	4412.4	Semi standard non polar	33892256
Balsalazide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(C(=O)O)=C2)C=C1)[Si](C)(C)C(C)(C)C	4325.9	Semi standard non polar	33892256
Balsalazide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/N=N/C2=CC=C(O)C(C(=O)O[Si](C)(C)C(C)(C)C)=C2)C=C1)[Si](C)(C)C(C)(C)C	4220.1	Semi standard non polar	33892256
Balsalazide,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(/N=N/C2=CC=C(C(=O)N(CCC(=O)O)[Si](C)(C)C(C)(C)C)C=C2)=CC=C1O[Si](C)(C)C(C)(C)C	4271.8	Semi standard non polar	33892256
Balsalazide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/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)C=C1)[Si](C)(C)C(C)(C)C	4361.2	Semi standard non polar	33892256
Balsalazide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/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)C=C1)[Si](C)(C)C(C)(C)C	4104.3	Standard non polar	33892256
Balsalazide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCN(C(=O)C1=CC=C(/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)C=C1)[Si](C)(C)C(C)(C)C	4264.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Balsalazide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ldi-1393000000-af92622c6ce32e802a99	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Balsalazide GC-MS (3 TMS) - 70eV, Positive	splash10-052f-2239460000-dd6d65f067d80197bd6e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Balsalazide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Balsalazide 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 - Balsalazide 10V, Positive-QTOF	splash10-05mo-1359000000-5ac19318b9222056db99	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Balsalazide 20V, Positive-QTOF	splash10-01b9-4194000000-a389ca20ea5f71b14f1b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Balsalazide 40V, Positive-QTOF	splash10-00or-9460000000-058a3d277554ae6ad3a0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Balsalazide 10V, Negative-QTOF	splash10-0r00-0859000000-0815df00a696a3bf2ef9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Balsalazide 20V, Negative-QTOF	splash10-0cdl-1596000000-f30b936242fc2a51a3bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Balsalazide 40V, Negative-QTOF	splash10-0a4i-1920000000-ab19fc8210a3b9bf159a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Balsalazide 10V, Positive-QTOF	splash10-014i-0090000000-938e67d0a29d75e91560	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Balsalazide 20V, Positive-QTOF	splash10-0297-0094000000-71c0a9165a9dbb26d8ed	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Balsalazide 40V, Positive-QTOF	splash10-0fvi-0590000000-6f84da2d9032ab43467d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Balsalazide 10V, Negative-QTOF	splash10-0a4i-0019000000-5cde35cdf9191a2d0721	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Balsalazide 20V, Negative-QTOF	splash10-001l-0092000000-e9ef5ce26a4f3979c212	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Balsalazide 40V, Negative-QTOF	splash10-0006-2290000000-1ff988f1dc562e4db92f	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 DB01014	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01014	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

DB01014

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10662422

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Balsalazide

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

267413

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

Wiggins JB, Rajapakse R: Balsalazide: a novel 5-aminosalicylate prodrug for the treatment of active ulcerative colitis. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1279-84. doi: 10.1517/17425250903206996. [PubMed:19743890 ]
Ragunath K, Williams JG: Review article: balsalazide therapy in ulcerative colitis. Aliment Pharmacol Ther. 2001 Oct;15(10):1549-54. [PubMed:11563993 ]

Enzymes

Enzyme Details

1. 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

Wiggins JB, Rajapakse R: Balsalazide: a novel 5-aminosalicylate prodrug for the treatment of active ulcerative colitis. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1279-84. doi: 10.1517/17425250903206996. [PubMed:19743890 ]
Rask-Madsen J, Bukhave K, Laursen LS, Lauritsen K: 5-Lipoxygenase inhibitors for the treatment of inflammatory bowel disease. Agents Actions. 1992;Spec No:C37-46. [PubMed:1359745 ]

Enzyme Details

2. 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

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 ]
Wiggins JB, Rajapakse R: Balsalazide: a novel 5-aminosalicylate prodrug for the treatment of active ulcerative colitis. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1279-84. doi: 10.1517/17425250903206996. [PubMed:19743890 ]
Stolfi C, Fina D, Caruso R, Caprioli F, Sarra M, Fantini MC, Rizzo A, Pallone F, Monteleone G: Cyclooxygenase-2-dependent and -independent inhibition of proliferation of colon cancer cells by 5-aminosalicylic acid. Biochem Pharmacol. 2008 Feb 1;75(3):668-76. Epub 2007 Sep 29. [PubMed:17981262 ]
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

3. 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

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 ]
Wiggins JB, Rajapakse R: Balsalazide: a novel 5-aminosalicylate prodrug for the treatment of active ulcerative colitis. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1279-84. doi: 10.1517/17425250903206996. [PubMed:19743890 ]
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 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

4. 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

Tursi A: Balsalazide in treating colonic diseases. Expert Opin Drug Metab Toxicol. 2009 Dec;5(12):1555-63. doi: 10.1517/17425250903228842. [PubMed:19708827 ]
Iacucci M, de Silva S, Ghosh S: Mesalazine in inflammatory bowel disease: a trendy topic once again? Can J Gastroenterol. 2010 Feb;24(2):127-33. [PubMed:20151072 ]
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 ]
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 ]

Showing metabocard for Balsalazide (HMDB0015149)

MOL for HMDB0015149 (Balsalazide)

3D MOL for HMDB0015149 (Balsalazide)

3D SDF for HMDB0015149 (Balsalazide)

3D-SDF for HMDB0015149 (Balsalazide)

PDB for HMDB0015149 (Balsalazide)

3D PDB for HMDB0015149 (Balsalazide)

SMILES for HMDB0015149 (Balsalazide)

INCHI for HMDB0015149 (Balsalazide)

Structure for HMDB0015149 (Balsalazide)

3D Structure for HMDB0015149 (Balsalazide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References