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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (1) Show 5 proteins XML

enzymes (4)transporters (1) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:35 UTC

HMDB ID

HMDB0014359

Secondary Accession Numbers

HMDB14359

Metabolite Identification

Common Name

Torasemide

Description

Torasemide, also known as demadex or luprac, belongs to the class of organic compounds known as pyridinesulfonamides. These are heterocyclic compounds containing a pyridine ring substituted by one or more sulfonamide groups. Torasemide is a strong basic compound (based on its pKa). torasemide can be converted into torasemide through the action of the enzyme solute carrier family 22 member 6. In humans, torasemide is involved in torsemide action pathway. An N-sulfonylurea obtained by formal condensation of pyridine-3-sulfonic acid with the free amino group of N-isopropylurea.

Structure

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

HMDB0014359
     RDKit          3D
Torasemide
 44 45  0  0  0  0  0  0  0  0999 V2000
   -5.1608    1.8814   -0.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503    0.7644   -0.9560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4311    0.1761   -2.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5923   -0.8452   -2.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5798   -1.2737   -1.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3648   -0.6937   -0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2947   -1.1455    0.3139 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4027   -1.3542    1.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6234   -1.3203    2.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7071   -1.5671    3.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5919   -1.8406    4.3648 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3849   -1.8795    3.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517   -1.6406    2.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2934   -1.6944    1.6682 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.2597   -2.7579    0.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3744   -2.1603    2.6164 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072   -0.2397    0.9613 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0362   -0.1789    0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7905   -1.1920    0.1336 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5183    1.0213   -0.3414 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7522    1.1162   -1.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7052    2.0176   -0.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6281    1.6566   -2.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2275    0.3193   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7247    2.4529    0.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3707    2.4631   -1.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1267    1.3857   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2445    0.5260   -2.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7639   -1.2922   -3.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136   -2.0687   -2.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -1.3230   -0.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5496   -1.1271    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6732   -1.5394    4.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820   -2.1062    4.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2170    0.6046    1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9063    1.8842   -0.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2001    0.0912   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2251    1.3830    0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1376    2.8329    0.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5019    2.4198   -0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7377    2.7687   -2.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6761    1.3582   -2.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4817    1.2744   -3.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1106    0.8425    0.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  2  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
  6 24  2  0
 24  2  1  0
 13  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 17 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 22 39  1  0
 22 40  1  0
 23 41  1  0
 23 42  1  0
 23 43  1  0
 24 44  1  0
M  END

214
  Mrv0541 02231214312D          

 24 25  0  0  0  0            999 V2000
    5.9363   -0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1114   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7612   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3650    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6507    1.6498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5075   -1.2374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9363    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6507   -2.4748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3650    2.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9363   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2218   -1.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7930   -1.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3650    2.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0794    1.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6507    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6507   -1.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2218   -2.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642   -1.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7930   -2.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9363   -2.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642   -2.4748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787   -2.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  2  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  0  0  0  0
  4 15  2  0  0  0  0
  5  9  1  0  0  0  0
  5 15  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 15  1  0  0  0  0
  8 16  2  0  0  0  0
  8 21  1  0  0  0  0
  9 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 11  2  0  0  0  0
 10 16  1  0  0  0  0
 11 17  1  0  0  0  0
 12 18  1  0  0  0  0
 12 20  2  0  0  0  0
 17 21  2  0  0  0  0
 18 19  2  0  0  0  0
 19 22  1  0  0  0  0
 19 24  1  0  0  0  0
 20 23  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014359

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)NC(=O)NS(=O)(=O)C1=C(NC2=CC=CC(C)=C2)C=CN=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N4O3S/c1-11(2)18-16(21)20-24(22,23)15-10-17-8-7-14(15)19-13-6-4-5-12(3)9-13/h4-11H,1-3H3,(H,17,19)(H2,18,20,21)

> <INCHI_KEY>
NGBFQHCMQULJNZ-UHFFFAOYSA-N

> <FORMULA>
C16H20N4O3S

> <MOLECULAR_WEIGHT>
348.42

> <EXACT_MASS>
348.125611216

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
36.1517443045435

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-({4-[(3-methylphenyl)amino]pyridin-3-yl}sulfonyl)-3-(propan-2-yl)urea

> <ALOGPS_LOGP>
1.76

> <JCHEM_LOGP>
1.8639035948569933

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.738516496384207

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.922537313388586

> <JCHEM_PKA_STRONGEST_BASIC>
4.19782418417848

> <JCHEM_POLAR_SURFACE_AREA>
100.19

> <JCHEM_REFRACTIVITY>
91.8931

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
torsemide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014359
     RDKit          3D
Torasemide
 44 45  0  0  0  0  0  0  0  0999 V2000
   -5.1608    1.8814   -0.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503    0.7644   -0.9560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4311    0.1761   -2.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5923   -0.8452   -2.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5798   -1.2737   -1.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3648   -0.6937   -0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2947   -1.1455    0.3139 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4027   -1.3542    1.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6234   -1.3203    2.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7071   -1.5671    3.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5919   -1.8406    4.3648 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3849   -1.8795    3.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517   -1.6406    2.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2934   -1.6944    1.6682 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.2597   -2.7579    0.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3744   -2.1603    2.6164 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072   -0.2397    0.9613 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0362   -0.1789    0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7905   -1.1920    0.1336 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5183    1.0213   -0.3414 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7522    1.1162   -1.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7052    2.0176   -0.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6281    1.6566   -2.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2275    0.3193   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7247    2.4529    0.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3707    2.4631   -1.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1267    1.3857   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2445    0.5260   -2.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7639   -1.2922   -3.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136   -2.0687   -2.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -1.3230   -0.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5496   -1.1271    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6732   -1.5394    4.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820   -2.1062    4.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2170    0.6046    1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9063    1.8842   -0.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2001    0.0912   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2251    1.3830    0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1376    2.8329    0.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5019    2.4198   -0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7377    2.7687   -2.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6761    1.3582   -2.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4817    1.2744   -3.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1106    0.8425    0.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  2  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
  6 24  2  0
 24  2  1  0
 13  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 17 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 22 39  1  0
 22 40  1  0
 23 41  1  0
 23 42  1  0
 23 43  1  0
 24 44  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 214                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      11.081  -0.770   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       9.541  -0.770   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.621  -0.770   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.748   0.770   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      12.415   3.080   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       8.414  -2.310   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      11.081   0.770   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      12.415  -4.620   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      13.748   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.081  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.747  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.080  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.748   5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.082   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.415   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.415  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.747  -4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.747  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.413  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.080  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.081  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.413  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.747  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.080  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2    3    7   10                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   15                                                            
CONECT    5    9   15                                                       
CONECT    6   11   12                                                       
CONECT    7    1   15                                                       
CONECT    8   16   21                                                       
CONECT    9    5   13   14                                                  
CONECT   10    1   11   16                                                  
CONECT   11    6   10   17                                                  
CONECT   12    6   18   20                                                  
CONECT   13    9                                                            
CONECT   14    9                                                            
CONECT   15    4    5    7                                                  
CONECT   16    8   10                                                       
CONECT   17   11   21                                                       
CONECT   18   12   19                                                       
CONECT   19   18   22   24                                                  
CONECT   20   12   23                                                       
CONECT   21    8   17                                                       
CONECT   22   19   23                                                       
CONECT   23   20   22                                                       
CONECT   24   19                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0014359
HETATM    1  C1  UNL     1      -5.161   1.881  -0.519  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.250   0.764  -0.956  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.431   0.176  -2.175  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.592  -0.845  -2.564  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.580  -1.274  -1.736  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.365  -0.694  -0.477  1.00  0.00           C  
HETATM    7  N1  UNL     1      -1.295  -1.145   0.314  1.00  0.00           N  
HETATM    8  C7  UNL     1      -1.403  -1.354   1.683  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.623  -1.320   2.335  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.707  -1.567   3.690  1.00  0.00           C  
HETATM   11  N2  UNL     1      -1.592  -1.841   4.365  1.00  0.00           N  
HETATM   12  C10 UNL     1      -0.385  -1.880   3.743  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.252  -1.641   2.399  1.00  0.00           C  
HETATM   14  S1  UNL     1       1.293  -1.694   1.668  1.00  0.00           S  
HETATM   15  O1  UNL     1       1.260  -2.758   0.576  1.00  0.00           O  
HETATM   16  O2  UNL     1       2.374  -2.160   2.616  1.00  0.00           O  
HETATM   17  N3  UNL     1       1.807  -0.240   0.961  1.00  0.00           N  
HETATM   18  C12 UNL     1       3.036  -0.179   0.264  1.00  0.00           C  
HETATM   19  O3  UNL     1       3.790  -1.192   0.134  1.00  0.00           O  
HETATM   20  N4  UNL     1       3.518   1.021  -0.341  1.00  0.00           N  
HETATM   21  C13 UNL     1       4.752   1.116  -1.050  1.00  0.00           C  
HETATM   22  C14 UNL     1       5.705   2.018  -0.274  1.00  0.00           C  
HETATM   23  C15 UNL     1       4.628   1.657  -2.452  1.00  0.00           C  
HETATM   24  C16 UNL     1      -3.228   0.319  -0.140  1.00  0.00           C  
HETATM   25  H1  UNL     1      -4.725   2.453   0.305  1.00  0.00           H  
HETATM   26  H2  UNL     1      -5.371   2.463  -1.429  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.127   1.386  -0.224  1.00  0.00           H  
HETATM   28  H4  UNL     1      -5.245   0.526  -2.829  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.764  -1.292  -3.543  1.00  0.00           H  
HETATM   30  H6  UNL     1      -1.914  -2.069  -2.019  1.00  0.00           H  
HETATM   31  H7  UNL     1      -0.390  -1.323  -0.177  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.550  -1.127   1.833  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.673  -1.539   4.208  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.482  -2.106   4.337  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.217   0.605   1.042  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.906   1.884  -0.246  1.00  0.00           H  
HETATM   37  H13 UNL     1       5.200   0.091  -1.077  1.00  0.00           H  
HETATM   38  H14 UNL     1       6.225   1.383   0.497  1.00  0.00           H  
HETATM   39  H15 UNL     1       5.138   2.833   0.194  1.00  0.00           H  
HETATM   40  H16 UNL     1       6.502   2.420  -0.921  1.00  0.00           H  
HETATM   41  H17 UNL     1       4.738   2.769  -2.437  1.00  0.00           H  
HETATM   42  H18 UNL     1       3.676   1.358  -2.896  1.00  0.00           H  
HETATM   43  H19 UNL     1       5.482   1.274  -3.043  1.00  0.00           H  
HETATM   44  H20 UNL     1      -3.111   0.843   0.813  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3   24
CONECT    3    4   28
CONECT    4    5    5   29
CONECT    5    6   30
CONECT    6    7   24   24
CONECT    7    8   31
CONECT    8    9    9   13
CONECT    9   10   32
CONECT   10   11   11   33
CONECT   11   12
CONECT   12   13   13   34
CONECT   13   14
CONECT   14   15   15   16   16
CONECT   14   17
CONECT   17   18   35
CONECT   18   19   19   20
CONECT   20   21   36
CONECT   21   22   23   37
CONECT   22   38   39   40
CONECT   23   41   42   43
CONECT   24   44
END

HMDB0014359
     RDKit          3D
Torasemide
 44 45  0  0  0  0  0  0  0  0999 V2000
   -5.1608    1.8814   -0.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2503    0.7644   -0.9560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4311    0.1761   -2.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5923   -0.8452   -2.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5798   -1.2737   -1.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3648   -0.6937   -0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2947   -1.1455    0.3139 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4027   -1.3542    1.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6234   -1.3203    2.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7071   -1.5671    3.6904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5919   -1.8406    4.3648 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3849   -1.8795    3.7435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2517   -1.6406    2.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2934   -1.6944    1.6682 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.2597   -2.7579    0.5757 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3744   -2.1603    2.6164 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072   -0.2397    0.9613 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0362   -0.1789    0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7905   -1.1920    0.1336 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5183    1.0213   -0.3414 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7522    1.1162   -1.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7052    2.0176   -0.2737 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6281    1.6566   -2.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2275    0.3193   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7247    2.4529    0.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3707    2.4631   -1.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1267    1.3857   -0.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2445    0.5260   -2.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7639   -1.2922   -3.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136   -2.0687   -2.0188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903   -1.3230   -0.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5496   -1.1271    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6732   -1.5394    4.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820   -2.1062    4.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2170    0.6046    1.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9063    1.8842   -0.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2001    0.0912   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2251    1.3830    0.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1376    2.8329    0.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5019    2.4198   -0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7377    2.7687   -2.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6761    1.3582   -2.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4817    1.2744   -3.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1106    0.8425    0.8127 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  2  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
  6 24  2  0
 24  2  1  0
 13  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 17 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 22 39  1  0
 22 40  1  0
 23 41  1  0
 23 42  1  0
 23 43  1  0
 24 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Isopropyl-3-((4-m-toluidino-3-pyridyl)sulfonyl)urea	ChEBI
Demadex	ChEBI
Luprac	ChEBI
N-(((1-Methylethyl)amino)carbonyl)-4-((3-methylphenyl)amino)-3-pyridinesulfonamide	ChEBI
Torasemida	ChEBI
Torasemidum	ChEBI
Torsemide	ChEBI
1-Isopropyl-3-((4-m-toluidino-3-pyridyl)sulphonyl)urea	Generator
N-(((1-Methylethyl)amino)carbonyl)-4-((3-methylphenyl)amino)-3-pyridinesulphonamide	Generator
1-Isopropyl-3-((4-(3-methylphenylamino)pyridine)-3-sulfonyl)urea	HMDB

Chemical Formula

C₁₆H₂₀N₄O₃S

Average Molecular Weight

348.42

Monoisotopic Molecular Weight

348.125611216

IUPAC Name

1-({4-[(3-methylphenyl)amino]pyridin-3-yl}sulfonyl)-3-(propan-2-yl)urea

Traditional Name

torsemide

CAS Registry Number

56211-40-6

SMILES

CC(C)NC(=O)NS(=O)(=O)C1=C(NC2=CC=CC(C)=C2)C=CN=C1

InChI Identifier

InChI=1S/C16H20N4O3S/c1-11(2)18-16(21)20-24(22,23)15-10-17-8-7-14(15)19-13-6-4-5-12(3)9-13/h4-11H,1-3H3,(H,17,19)(H2,18,20,21)

InChI Key

NGBFQHCMQULJNZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridinesulfonamides. These are heterocyclic compounds containing a pyridine ring substituted by one or more sulfonamide groups.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinesulfonamides

Direct Parent

Pyridinesulfonamides

Alternative Parents

Substituents

Pyridine-3-sulfonamide
Dihydropyridine
Toluene
Sulfonylurea
Monocyclic benzene moiety
Hydropyridine
Benzenoid
Secondary ketimine
Heteroaromatic compound
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Carboximidic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

secondary amino compound (CHEBI:9637 )
aminopyridine (CHEBI:9637 )
N-sulfonylurea (CHEBI:9637 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014359)
Membrane (HMDB: HMDB0014359)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Torsemide Action Pathway (PathBank: SMP0000118)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	164 - 164 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.06 g/L	Not Available
LogP	2.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.06 g/L	ALOGPS
logP	1.76	ALOGPS
logP	1.86	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	5.92	ChemAxon
pKa (Strongest Basic)	4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.19 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.89 m³·mol⁻¹	ChemAxon
Polarizability	36.15 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
DarkChem	[M+H]+	180.491	31661259
DarkChem	[M-H]-	181.927	31661259
DeepCCS	[M+H]+	185.016	30932474
DeepCCS	[M-H]-	182.658	30932474
DeepCCS	[M-2H]-	216.843	30932474
DeepCCS	[M+Na]+	192.157	30932474
AllCCS	[M+H]+	182.0	32859911
AllCCS	[M+H-H2O]+	179.1	32859911
AllCCS	[M+NH4]+	184.7	32859911
AllCCS	[M+Na]+	185.5	32859911
AllCCS	[M-H]-	179.4	32859911
AllCCS	[M+Na-2H]-	179.5	32859911
AllCCS	[M+HCOO]-	179.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Torasemide	CC(C)NC(=O)NS(=O)(=O)C1=C(NC2=CC=CC(C)=C2)C=CN=C1	4140.2	Standard polar	33892256
Torasemide	CC(C)NC(=O)NS(=O)(=O)C1=C(NC2=CC=CC(C)=C2)C=CN=C1	2522.9	Standard non polar	33892256
Torasemide	CC(C)NC(=O)NS(=O)(=O)C1=C(NC2=CC=CC(C)=C2)C=CN=C1	2985.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Torasemide,1TMS,isomer #1	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)NC(=O)N(C(C)C)[Si](C)(C)C)=C1	2953.6	Semi standard non polar	33892256
Torasemide,1TMS,isomer #1	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)NC(=O)N(C(C)C)[Si](C)(C)C)=C1	2892.4	Standard non polar	33892256
Torasemide,1TMS,isomer #1	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)NC(=O)N(C(C)C)[Si](C)(C)C)=C1	4339.3	Standard polar	33892256
Torasemide,1TMS,isomer #2	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)N(C(=O)NC(C)C)[Si](C)(C)C)=C1	2932.3	Semi standard non polar	33892256
Torasemide,1TMS,isomer #2	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)N(C(=O)NC(C)C)[Si](C)(C)C)=C1	2812.9	Standard non polar	33892256
Torasemide,1TMS,isomer #2	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)N(C(=O)NC(C)C)[Si](C)(C)C)=C1	4353.9	Standard polar	33892256
Torasemide,1TMS,isomer #3	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)NC(=O)NC(C)C)[Si](C)(C)C)=C1	2847.2	Semi standard non polar	33892256
Torasemide,1TMS,isomer #3	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)NC(=O)NC(C)C)[Si](C)(C)C)=C1	2817.8	Standard non polar	33892256
Torasemide,1TMS,isomer #3	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)NC(=O)NC(C)C)[Si](C)(C)C)=C1	4066.5	Standard polar	33892256
Torasemide,2TMS,isomer #1	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)NC(=O)N(C(C)C)[Si](C)(C)C)[Si](C)(C)C)=C1	2776.7	Semi standard non polar	33892256
Torasemide,2TMS,isomer #1	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)NC(=O)N(C(C)C)[Si](C)(C)C)[Si](C)(C)C)=C1	3001.4	Standard non polar	33892256
Torasemide,2TMS,isomer #1	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)NC(=O)N(C(C)C)[Si](C)(C)C)[Si](C)(C)C)=C1	3774.2	Standard polar	33892256
Torasemide,2TMS,isomer #2	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)N(C(=O)N(C(C)C)[Si](C)(C)C)[Si](C)(C)C)=C1	2899.1	Semi standard non polar	33892256
Torasemide,2TMS,isomer #2	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)N(C(=O)N(C(C)C)[Si](C)(C)C)[Si](C)(C)C)=C1	3071.2	Standard non polar	33892256
Torasemide,2TMS,isomer #2	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)N(C(=O)N(C(C)C)[Si](C)(C)C)[Si](C)(C)C)=C1	3993.8	Standard polar	33892256
Torasemide,2TMS,isomer #3	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)N(C(=O)NC(C)C)[Si](C)(C)C)[Si](C)(C)C)=C1	2746.3	Semi standard non polar	33892256
Torasemide,2TMS,isomer #3	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)N(C(=O)NC(C)C)[Si](C)(C)C)[Si](C)(C)C)=C1	2965.8	Standard non polar	33892256
Torasemide,2TMS,isomer #3	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)N(C(=O)NC(C)C)[Si](C)(C)C)[Si](C)(C)C)=C1	3912.5	Standard polar	33892256
Torasemide,3TMS,isomer #1	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)N(C(=O)N(C(C)C)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=C1	2774.6	Semi standard non polar	33892256
Torasemide,3TMS,isomer #1	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)N(C(=O)N(C(C)C)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=C1	3236.3	Standard non polar	33892256
Torasemide,3TMS,isomer #1	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)N(C(=O)N(C(C)C)[Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=C1	3580.2	Standard polar	33892256
Torasemide,1TBDMS,isomer #1	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)NC(=O)N(C(C)C)[Si](C)(C)C(C)(C)C)=C1	3204.2	Semi standard non polar	33892256
Torasemide,1TBDMS,isomer #1	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)NC(=O)N(C(C)C)[Si](C)(C)C(C)(C)C)=C1	3129.3	Standard non polar	33892256
Torasemide,1TBDMS,isomer #1	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)NC(=O)N(C(C)C)[Si](C)(C)C(C)(C)C)=C1	4308.6	Standard polar	33892256
Torasemide,1TBDMS,isomer #2	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)N(C(=O)NC(C)C)[Si](C)(C)C(C)(C)C)=C1	3196.8	Semi standard non polar	33892256
Torasemide,1TBDMS,isomer #2	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)N(C(=O)NC(C)C)[Si](C)(C)C(C)(C)C)=C1	3030.3	Standard non polar	33892256
Torasemide,1TBDMS,isomer #2	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)N(C(=O)NC(C)C)[Si](C)(C)C(C)(C)C)=C1	4325.1	Standard polar	33892256
Torasemide,1TBDMS,isomer #3	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)NC(=O)NC(C)C)[Si](C)(C)C(C)(C)C)=C1	3060.1	Semi standard non polar	33892256
Torasemide,1TBDMS,isomer #3	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)NC(=O)NC(C)C)[Si](C)(C)C(C)(C)C)=C1	3030.9	Standard non polar	33892256
Torasemide,1TBDMS,isomer #3	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)NC(=O)NC(C)C)[Si](C)(C)C(C)(C)C)=C1	4102.5	Standard polar	33892256
Torasemide,2TBDMS,isomer #1	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)NC(=O)N(C(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3219.4	Semi standard non polar	33892256
Torasemide,2TBDMS,isomer #1	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)NC(=O)N(C(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3450.4	Standard non polar	33892256
Torasemide,2TBDMS,isomer #1	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)NC(=O)N(C(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3834.2	Standard polar	33892256
Torasemide,2TBDMS,isomer #2	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)N(C(=O)N(C(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3396.3	Semi standard non polar	33892256
Torasemide,2TBDMS,isomer #2	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)N(C(=O)N(C(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3520.9	Standard non polar	33892256
Torasemide,2TBDMS,isomer #2	CC1=CC=CC(NC2=CC=NC=C2S(=O)(=O)N(C(=O)N(C(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	4032.1	Standard polar	33892256
Torasemide,2TBDMS,isomer #3	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)N(C(=O)NC(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3208.5	Semi standard non polar	33892256
Torasemide,2TBDMS,isomer #3	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)N(C(=O)NC(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3389.6	Standard non polar	33892256
Torasemide,2TBDMS,isomer #3	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)N(C(=O)NC(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3955.5	Standard polar	33892256
Torasemide,3TBDMS,isomer #1	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)N(C(=O)N(C(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3434.8	Semi standard non polar	33892256
Torasemide,3TBDMS,isomer #1	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)N(C(=O)N(C(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3916.0	Standard non polar	33892256
Torasemide,3TBDMS,isomer #1	CC1=CC=CC(N(C2=CC=NC=C2S(=O)(=O)N(C(=O)N(C(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3729.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Torasemide GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-7922000000-38709aad9fb92fea20e1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Torasemide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Torasemide 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 - Torasemide LC-ESI-QFT , negative-QTOF	splash10-03di-0090000000-bcaf4981571fb662df86	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide LC-ESI-QFT , negative-QTOF	splash10-03di-0090000000-00cc7369c05298ea1c97	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide LC-ESI-QFT , negative-QTOF	splash10-03di-0490000000-60171fe07a2f255596e3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide LC-ESI-QFT , negative-QTOF	splash10-01ot-2950000000-359d6835f9bf703a0701	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide LC-ESI-QFT , negative-QTOF	splash10-000t-3910000000-a5ec65a6dbedfe7a30d3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide LC-ESI-QFT , negative-QTOF	splash10-0564-6900000000-051171526b146f5d076c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide LC-ESI-QFT , negative-QTOF	splash10-03di-0190000000-1b2efe76058c7bf06b4a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide LC-ESI-QFT , positive-QTOF	splash10-03di-0091000000-548edfa45514c501788d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide LC-ESI-QFT , positive-QTOF	splash10-03di-0090000000-d7326b2b38380cd06e26	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide LC-ESI-QFT , positive-QTOF	splash10-03di-0490000000-b9f43c4768937947d77f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide LC-ESI-QFT , positive-QTOF	splash10-001i-0940000000-7b7084526f7c13bf6443	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide LC-ESI-QFT , positive-QTOF	splash10-00lr-0910000000-81aa8c9ff5d9a3cd3c10	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide LC-ESI-QFT , positive-QTOF	splash10-0159-0900000000-87860a9931a8414432cf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide , positive-QTOF	splash10-03di-1590000000-1b7d966c20cec1451f6c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide , positive-QTOF	splash10-03di-0490000000-bd8b6af3fe8d0f10e117	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide , positive-QTOF	splash10-02ai-2940000000-5beb0e7e25d393903803	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide LC-ESI-QFT , positive-QTOF	splash10-03di-0390000000-314819093d7d5a1f48f4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide 30V, Negative-QTOF	splash10-03di-0090000000-6b7078f4aeb0a9155866	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Torasemide 15V, Negative-QTOF	splash10-03di-0090000000-11bcaf88b642f06fcc7e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Torasemide 10V, Positive-QTOF	splash10-01ot-2069000000-943a38503d89c086bae7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Torasemide 20V, Positive-QTOF	splash10-0bt9-8191000000-b93ec223bde95bf1c738	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Torasemide 40V, Positive-QTOF	splash10-0a4l-9210000000-19f11559fea4b58be1cf	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Torasemide 10V, Negative-QTOF	splash10-0002-3269000000-93ec6053a659f34ee77f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Torasemide 20V, Negative-QTOF	splash10-06si-1490000000-5dfeefbdd22794dac739	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Torasemide 40V, Negative-QTOF	splash10-0a4l-9430000000-1d7767a4763c0a30541a	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Torsemide Action Pathway		Not Available

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 DB00214	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00214	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00214

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

38123

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Torasemide

METLIN ID

Not Available

PubChem Compound

41781

PDB ID

Not Available

ChEBI ID

9637

Food Biomarker Ontology

Not Available

VMH ID

TMD

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Dunn CJ, Fitton A, Brogden RN: Torasemide. An update of its pharmacological properties and therapeutic efficacy. Drugs. 1995 Jan;49(1):121-42. [PubMed:7705212 ]
Authors unspecified: FDA approved new drug bulletin: torsemide (Demadex), trimetrexate glucuronate (neuTrexin). RN. 1994 May;57(5):53-6. [PubMed:8197389 ]

Enzymes

Enzyme Details

1. 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

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

2. Cytochrome P450 2C9

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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

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

4. Cytochrome P450 2C8

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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

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 ]

Transporters

Enzyme Details

1. Solute carrier family 12 member 1

General function:: Involved in transport
Specific function:: Electrically silent transporter system. Mediates sodium and chloride reabsorption. Plays a vital role in the regulation of ionic balance and cell volume
Gene Name:: SLC12A1
Uniprot ID:: Q13621
Molecular weight:: 121449.1

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Vormfelde SV, Sehrt D, Toliat MR, Schirmer M, Meineke I, Tzvetkov M, Nurnberg P, Brockmoller J: Genetic variation in the renal sodium transporters NKCC2, NCC, and ENaC in relation to the effects of loop diuretic drugs. Clin Pharmacol Ther. 2007 Sep;82(3):300-9. Epub 2007 Apr 25. [PubMed:17460608 ]
Fortuno A, Muniz P, Ravassa S, Rodriguez JA, Fortuno MA, Zalba G, Diez J: Torasemide inhibits angiotensin II-induced vasoconstriction and intracellular calcium increase in the aorta of spontaneously hypertensive rats. Hypertension. 1999 Jul;34(1):138-43. [PubMed:10406837 ]

Showing metabocard for Torasemide (HMDB0014359)

MOL for HMDB0014359 (Torasemide)

3D MOL for HMDB0014359 (Torasemide)

3D SDF for HMDB0014359 (Torasemide)

3D-SDF for HMDB0014359 (Torasemide)

PDB for HMDB0014359 (Torasemide)

3D PDB for HMDB0014359 (Torasemide)

SMILES for HMDB0014359 (Torasemide)

INCHI for HMDB0014359 (Torasemide)

Structure for HMDB0014359 (Torasemide)

3D Structure for HMDB0014359 (Torasemide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

Transporters

References