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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:15:11 UTC

Update Date

2021-09-26 23:07:53 UTC

HMDB ID

HMDB0254105

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Linotroban

Description

2-{[5-(2-benzenesulfonamidoethyl)thiophen-2-yl]oxy}acetic acid belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring. 2-{[5-(2-benzenesulfonamidoethyl)thiophen-2-yl]oxy}acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Linotroban is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Linotroban is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0254105
     RDKit          3D
Linotroban
 37 38  0  0  0  0  0  0  0  0999 V2000
    7.7917   -1.5973   -0.7410 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5451   -0.7015    0.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5861   -0.3062    0.9524 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1851   -0.0645    0.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3718   -0.7198   -0.7093 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0151   -0.7490   -0.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0355   -1.3532   -1.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8565   -1.2599   -0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.4791    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2191    0.0242    0.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6341    0.7585   -0.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3847    1.7256    0.2598 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7092    1.0279    1.0464 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.0442   -0.0627    2.0065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1785    2.0643    2.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0810    0.4116    0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6414    1.2741   -0.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9269    1.0409   -1.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6403   -0.0473   -0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0326   -0.8501    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8267   -0.5957    0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0612    0.0684    0.6607 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5362   -0.5639    1.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7655   -0.1855    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3056    1.0311    0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3344   -1.7380   -2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323   -2.0651   -1.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -0.9799    0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1954    0.4589    1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2806    1.5016   -0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8766    0.2363   -1.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0193    2.1512   -0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0884    2.1343   -0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3524    1.6386   -1.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6434   -0.1935   -0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5589   -1.8391    0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5065   -1.1962    1.6430 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9 22  1  0
 22  6  1  0
 21 16  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END


  Mrv1572004221605062D          

 22 23  0  0  0  0            999 V2000
    5.9045   -4.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3894   -4.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0840   -4.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0539   -3.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7485   -3.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0216    0.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2765    1.1035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7116   -0.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0472   -1.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    2.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1966    0.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2334   -3.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    3.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    1.5884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5623   -1.7697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    4.0634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    4.0634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6515   -2.1878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1442   -2.8589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    2.4134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9416    1.1035    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8978   -2.5234    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 11  6  2  0  0  0  0
 11  8  1  0  0  0  0
 12  4  2  0  0  0  0
 12  5  1  0  0  0  0
 13 10  1  0  0  0  0
 14  7  2  0  0  0  0
 15  9  1  0  0  0  0
 16 13  2  0  0  0  0
 17 13  1  0  0  0  0
 20 10  1  0  0  0  0
 20 14  1  0  0  0  0
 21 11  1  0  0  0  0
 21 14  1  0  0  0  0
 22 12  1  0  0  0  0
 22 15  1  0  0  0  0
 22 18  2  0  0  0  0
 22 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254105

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)COC1=CC=C(CCNS(=O)(=O)C2=CC=CC=C2)S1

> <INCHI_IDENTIFIER>
InChI=1S/C14H15NO5S2/c16-13(17)10-20-14-7-6-11(21-14)8-9-15-22(18,19)12-4-2-1-3-5-12/h1-7,15H,8-10H2,(H,16,17)

> <INCHI_KEY>
ISSKMEQROMFEHL-UHFFFAOYSA-N

> <FORMULA>
C14H15NO5S2

> <MOLECULAR_WEIGHT>
341.4

> <EXACT_MASS>
341.039164935

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
33.209723079704546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{[5-(2-benzenesulfonamidoethyl)thiophen-2-yl]oxy}acetic acid

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
2.2152763609999995

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.184172343642183

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6330727089274353

> <JCHEM_PKA_STRONGEST_BASIC>
-5.053037901317278

> <JCHEM_POLAR_SURFACE_AREA>
92.7

> <JCHEM_REFRACTIVITY>
81.18819999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[5-(2-benzenesulfonamidoethyl)thiophen-2-yl]oxy}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0254105
     RDKit          3D
Linotroban
 37 38  0  0  0  0  0  0  0  0999 V2000
    7.7917   -1.5973   -0.7410 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5451   -0.7015    0.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5861   -0.3062    0.9524 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1851   -0.0645    0.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3718   -0.7198   -0.7093 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0151   -0.7490   -0.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0355   -1.3532   -1.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8565   -1.2599   -0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.4791    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2191    0.0242    0.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6341    0.7585   -0.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3847    1.7256    0.2598 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7092    1.0279    1.0464 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.0442   -0.0627    2.0065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1785    2.0643    2.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0810    0.4116    0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6414    1.2741   -0.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9269    1.0409   -1.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6403   -0.0473   -0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0326   -0.8501    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8267   -0.5957    0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0612    0.0684    0.6607 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5362   -0.5639    1.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7655   -0.1855    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3056    1.0311    0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3344   -1.7380   -2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323   -2.0651   -1.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -0.9799    0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1954    0.4589    1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2806    1.5016   -0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8766    0.2363   -1.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0193    2.1512   -0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0884    2.1343   -0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3524    1.6386   -1.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6434   -0.1935   -0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5589   -1.8391    0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5065   -1.1962    1.6430 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9 22  1  0
 22  6  1  0
 21 16  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      11.022  -8.931   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.927  -7.685   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.490  -8.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.301  -6.278   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.864  -7.363   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.240   0.595   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.716   2.060   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.795  -0.651   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.421  -2.058   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.137   5.275   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.700   0.595   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.769  -6.117   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.137   6.815   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.470   2.965   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       8.516  -3.303   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       7.803   7.585   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.470   7.585   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      10.549  -4.084   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.736  -5.337   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.470   4.505   0.000  0.00  0.00           O+0
HETATM   21  S   UNK     0       9.224   2.060   0.000  0.00  0.00           S+0
HETATM   22  S   UNK     0       9.143  -4.710   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2   12                                                       
CONECT    5    3   12                                                       
CONECT    6    7   11                                                       
CONECT    7    6   14                                                       
CONECT    8    9   11                                                       
CONECT    9    8   15                                                       
CONECT   10   13   20                                                       
CONECT   11    6    8   21                                                  
CONECT   12    4    5   22                                                  
CONECT   13   10   16   17                                                  
CONECT   14    7   20   21                                                  
CONECT   15    9   22                                                       
CONECT   16   13                                                            
CONECT   17   13                                                            
CONECT   18   22                                                            
CONECT   19   22                                                            
CONECT   20   10   14                                                       
CONECT   21   11   14                                                       
CONECT   22   12   15   18   19                                             
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0254105
HETATM    1  O1  UNL     1       7.792  -1.597  -0.741  1.00  0.00           O  
HETATM    2  C1  UNL     1       7.545  -0.702   0.114  1.00  0.00           C  
HETATM    3  O2  UNL     1       8.586  -0.306   0.952  1.00  0.00           O  
HETATM    4  C2  UNL     1       6.185  -0.065   0.221  1.00  0.00           C  
HETATM    5  O3  UNL     1       5.372  -0.720  -0.709  1.00  0.00           O  
HETATM    6  C3  UNL     1       4.015  -0.749  -0.587  1.00  0.00           C  
HETATM    7  C4  UNL     1       3.035  -1.353  -1.238  1.00  0.00           C  
HETATM    8  C5  UNL     1       1.856  -1.260  -0.889  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.465  -0.479   0.078  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.219   0.024   0.586  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.634   0.758  -0.500  1.00  0.00           C  
HETATM   12  N1  UNL     1      -1.385   1.726   0.260  1.00  0.00           N  
HETATM   13  S1  UNL     1      -2.709   1.028   1.046  1.00  0.00           S  
HETATM   14  O4  UNL     1      -2.044  -0.063   2.007  1.00  0.00           O  
HETATM   15  O5  UNL     1      -3.179   2.064   2.070  1.00  0.00           O  
HETATM   16  C9  UNL     1      -4.081   0.412   0.331  1.00  0.00           C  
HETATM   17  C10 UNL     1      -4.641   1.274  -0.613  1.00  0.00           C  
HETATM   18  C11 UNL     1      -5.927   1.041  -1.109  1.00  0.00           C  
HETATM   19  C12 UNL     1      -6.640  -0.047  -0.628  1.00  0.00           C  
HETATM   20  C13 UNL     1      -6.033  -0.850   0.278  1.00  0.00           C  
HETATM   21  C14 UNL     1      -4.827  -0.596   0.735  1.00  0.00           C  
HETATM   22  S2  UNL     1       3.061   0.068   0.661  1.00  0.00           S  
HETATM   23  H1  UNL     1       8.536  -0.564   1.933  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.766  -0.185   1.231  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.306   1.031   0.058  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.334  -1.738  -2.319  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.032  -2.065  -1.218  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.437  -0.980   0.580  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.195   0.459   1.539  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.281   1.502  -0.868  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.877   0.236  -1.293  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.019   2.151  -0.681  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.088   2.134  -0.968  1.00  0.00           H  
HETATM   34  H12 UNL     1      -6.352   1.639  -1.892  1.00  0.00           H  
HETATM   35  H13 UNL     1      -7.643  -0.194  -0.968  1.00  0.00           H  
HETATM   36  H14 UNL     1      -6.559  -1.839   0.453  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.506  -1.196   1.643  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   23
CONECT    4    5   24   25
CONECT    5    6
CONECT    6    7    7   22
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   10   22
CONECT   10   11   28   29
CONECT   11   12   30   31
CONECT   12   13   32
CONECT   13   14   14   15   15
CONECT   13   16
CONECT   16   17   17   21
CONECT   17   18   33
CONECT   18   19   19   34
CONECT   19   20   35
CONECT   20   21   21   36
CONECT   21   37
END

HMDB0254105
     RDKit          3D
Linotroban
 37 38  0  0  0  0  0  0  0  0999 V2000
    7.7917   -1.5973   -0.7410 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5451   -0.7015    0.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5861   -0.3062    0.9524 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1851   -0.0645    0.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3718   -0.7198   -0.7093 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0151   -0.7490   -0.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0355   -1.3532   -1.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8565   -1.2599   -0.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.4791    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2191    0.0242    0.5858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6341    0.7585   -0.4996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3847    1.7256    0.2598 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7092    1.0279    1.0464 S   0  0  0  0  0  6  0  0  0  0  0  0
   -2.0442   -0.0627    2.0065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1785    2.0643    2.0705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0810    0.4116    0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6414    1.2741   -0.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9269    1.0409   -1.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6403   -0.0473   -0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0326   -0.8501    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8267   -0.5957    0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0612    0.0684    0.6607 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5362   -0.5639    1.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7655   -0.1855    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3056    1.0311    0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3344   -1.7380   -2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0323   -2.0651   -1.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -0.9799    0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1954    0.4589    1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2806    1.5016   -0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8766    0.2363   -1.2935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0193    2.1512   -0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0884    2.1343   -0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3524    1.6386   -1.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6434   -0.1935   -0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5589   -1.8391    0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5065   -1.1962    1.6430 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  2  0
 13 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9 22  1  0
 22  6  1  0
 21 16  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-{[5-(2-benzenesulfonamidoethyl)thiophen-2-yl]oxy}acetate	Generator
2-{[5-(2-benzenesulphonamidoethyl)thiophen-2-yl]oxy}acetate	Generator
2-{[5-(2-benzenesulphonamidoethyl)thiophen-2-yl]oxy}acetic acid	Generator
Linotroban	MeSH

Chemical Formula

C₁₄H₁₅NO₅S₂

Average Molecular Weight

341.4

Monoisotopic Molecular Weight

341.039164935

IUPAC Name

2-{[5-(2-benzenesulfonamidoethyl)thiophen-2-yl]oxy}acetic acid

Traditional Name

{[5-(2-benzenesulfonamidoethyl)thiophen-2-yl]oxy}acetic acid

CAS Registry Number

Not Available

SMILES

OC(=O)COC1=CC=C(CCNS(=O)(=O)C2=CC=CC=C2)S1

InChI Identifier

InChI=1S/C14H15NO5S2/c16-13(17)10-20-14-7-6-11(21-14)8-9-15-22(18,19)12-4-2-1-3-5-12/h1-7,15H,8-10H2,(H,16,17)

InChI Key

ISSKMEQROMFEHL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Benzenesulfonamides

Alternative Parents

Substituents

Benzenesulfonamide
Benzenesulfonyl group
Alkyl aryl ether
2,5-disubstituted thiophene
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Thiophene
Aminosulfonyl compound
Heteroaromatic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Carboxylic acid
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.99	ALOGPS
logP	2.22	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	92.7 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	81.19 m³·mol⁻¹	ChemAxon
Polarizability	33.21 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]+	166.613	30932474
DeepCCS	[M-H]-	164.255	30932474
DeepCCS	[M-2H]-	197.705	30932474
DeepCCS	[M+Na]+	172.932	30932474
AllCCS	[M+H]+	173.9	32859911
AllCCS	[M+H-H2O]+	170.9	32859911
AllCCS	[M+NH4]+	176.7	32859911
AllCCS	[M+Na]+	177.5	32859911
AllCCS	[M-H]-	172.5	32859911
AllCCS	[M+Na-2H]-	172.5	32859911
AllCCS	[M+HCOO]-	172.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Linotroban	OC(=O)COC1=CC=C(CCNS(=O)(=O)C2=CC=CC=C2)S1	4911.3	Standard polar	33892256
Linotroban	OC(=O)COC1=CC=C(CCNS(=O)(=O)C2=CC=CC=C2)S1	2956.2	Standard non polar	33892256
Linotroban	OC(=O)COC1=CC=C(CCNS(=O)(=O)C2=CC=CC=C2)S1	3030.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Linotroban,2TMS,isomer #1	C[Si](C)(C)OC(=O)COC1=CC=C(CCN([Si](C)(C)C)S(=O)(=O)C2=CC=CC=C2)S1	2883.2	Semi standard non polar	33892256
Linotroban,2TMS,isomer #1	C[Si](C)(C)OC(=O)COC1=CC=C(CCN([Si](C)(C)C)S(=O)(=O)C2=CC=CC=C2)S1	2830.4	Standard non polar	33892256
Linotroban,2TMS,isomer #1	C[Si](C)(C)OC(=O)COC1=CC=C(CCN([Si](C)(C)C)S(=O)(=O)C2=CC=CC=C2)S1	3763.0	Standard polar	33892256
Linotroban,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)COC1=CC=C(CCN([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=CC=C2)S1	3405.8	Semi standard non polar	33892256
Linotroban,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)COC1=CC=C(CCN([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=CC=C2)S1	3287.4	Standard non polar	33892256
Linotroban,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)COC1=CC=C(CCN([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=CC=C2)S1	3758.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Linotroban GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-5940000000-862817a40e4bb51e7471	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Linotroban GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Linotroban GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Linotroban GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Linotroban GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Linotroban GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	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 - Linotroban 10V, Positive-QTOF	splash10-0006-1739000000-301b183b13e94877dc86	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linotroban 20V, Positive-QTOF	splash10-000l-2910000000-aab891569417573cec14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linotroban 40V, Positive-QTOF	splash10-016r-9500000000-7056cc7a0240b072b17f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linotroban 10V, Negative-QTOF	splash10-0006-2229000000-532171ce3bc9efb53be8	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linotroban 20V, Negative-QTOF	splash10-0006-2953000000-2b9c15dae7a606e835a4	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linotroban 40V, Negative-QTOF	splash10-002f-6930000000-ecad516532ee9c2da9ff	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linotroban 10V, Positive-QTOF	splash10-0006-0109000000-979c62f329ff4f369ca9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linotroban 20V, Positive-QTOF	splash10-06rl-3901000000-46684284a1fea3c43957	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linotroban 40V, Positive-QTOF	splash10-002f-3900000000-84b840abf648b1555846	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linotroban 10V, Negative-QTOF	splash10-0006-0009000000-25342ffb884ba86ec491	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linotroban 20V, Negative-QTOF	splash10-01ox-0925000000-7a7fb29ed186f8ee3a5a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linotroban 40V, Negative-QTOF	splash10-053r-4920000000-9d76f2fd81e9d02c949e	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65940

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Linotroban (HMDB0254105)

MOL for HMDB0254105 (Linotroban)

3D MOL for HMDB0254105 (Linotroban)

3D SDF for HMDB0254105 (Linotroban)

3D-SDF for HMDB0254105 (Linotroban)

PDB for HMDB0254105 (Linotroban)

3D PDB for HMDB0254105 (Linotroban)

SMILES for HMDB0254105 (Linotroban)

INCHI for HMDB0254105 (Linotroban)

Structure for HMDB0254105 (Linotroban)

3D Structure for HMDB0254105 (Linotroban)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra