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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:43:50 UTC

Update Date

2019-07-23 06:35:08 UTC

HMDB ID

HMDB0041849

Secondary Accession Numbers

HMDB41849

Metabolite Identification

Common Name

Carboxytolbutamide

Description

Carboxytolbutamide 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. Based on a literature review very few articles have been published on Carboxytolbutamide.

Structure

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

HMDB0041849
     RDKit          3D
Carboxytolbutamide
 36 36  0  0  0  0  0  0  0  0999 V2000
    5.0630   -1.4333    1.6347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6728   -0.6324    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -1.3219   -0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3448   -1.5503    0.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7698   -0.3246    0.8672 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1556    0.5023    0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0593    0.1688   -1.2491 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906    1.7071    0.5566 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6699    2.4681   -0.3091 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.0746    3.7519    0.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2210    2.7286   -1.7286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1018    1.4554   -0.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0557    1.5518    0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1969    0.7937    0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4130   -0.1052   -0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6116   -0.9222   -0.5525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7529   -1.7129   -1.5118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5777   -0.8353    0.4294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4398   -0.1867   -1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2972    0.5770   -1.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3273   -1.3147    2.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2005   -2.5144    1.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0196   -0.9889    2.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5482   -0.4812   -0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3457    0.3661    0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3442   -0.6977   -1.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0352   -2.2684   -0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5901   -2.2112    1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5984   -2.0955   -0.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4762    0.7664   -1.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9383    2.1316    1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9056    2.2505    1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9424    0.8717    1.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3053   -0.1056    0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5751   -0.8873   -2.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5516    0.4985   -2.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  2  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  8 31  1  0
 13 32  1  0
 14 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END


  Mrv0541 09131211432D          

 20 20  0  0  0  0            999 V2000
   -1.4289    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  9  1  0  0  0  0
 13  8  1  4  0  0  0
 13 12  2  0  0  0  0
 14 12  1  0  0  0  0
 15 11  1  0  0  0  0
 16 11  2  0  0  0  0
 17 12  1  0  0  0  0
 20 10  1  0  0  0  0
 20 14  1  0  0  0  0
 20 18  2  0  0  0  0
 20 19  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041849

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCN=C(O)NS(=O)(=O)C1=CC=C(C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N2O5S/c1-2-3-8-13-12(17)14-20(18,19)10-6-4-9(5-7-10)11(15)16/h4-7H,2-3,8H2,1H3,(H,15,16)(H2,13,14,17)

> <INCHI_KEY>
GCMVATDSSHTCOS-UHFFFAOYSA-N

> <FORMULA>
C12H16N2O5S

> <MOLECULAR_WEIGHT>
300.331

> <EXACT_MASS>
300.077992322

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.293279827543177

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[(butyl-C-hydroxycarbonimidoyl)amino]sulfonyl}benzoic acid

> <ALOGPS_LOGP>
1.07

> <JCHEM_LOGP>
2.259101473

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.574038535307996

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.513299439701193

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6251370318432868

> <JCHEM_POLAR_SURFACE_AREA>
116.06

> <JCHEM_REFRACTIVITY>
73.0067

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.32e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(butyl-C-hydroxycarbonimidoyl)aminosulfonyl]benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041849
     RDKit          3D
Carboxytolbutamide
 36 36  0  0  0  0  0  0  0  0999 V2000
    5.0630   -1.4333    1.6347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6728   -0.6324    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -1.3219   -0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3448   -1.5503    0.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7698   -0.3246    0.8672 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1556    0.5023    0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0593    0.1688   -1.2491 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906    1.7071    0.5566 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6699    2.4681   -0.3091 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.0746    3.7519    0.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2210    2.7286   -1.7286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1018    1.4554   -0.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0557    1.5518    0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1969    0.7937    0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4130   -0.1052   -0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6116   -0.9222   -0.5525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7529   -1.7129   -1.5118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5777   -0.8353    0.4294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4398   -0.1867   -1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2972    0.5770   -1.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3273   -1.3147    2.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2005   -2.5144    1.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0196   -0.9889    2.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5482   -0.4812   -0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3457    0.3661    0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3442   -0.6977   -1.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0352   -2.2684   -0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5901   -2.2112    1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5984   -2.0955   -0.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4762    0.7664   -1.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9383    2.1316    1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9056    2.2505    1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9424    0.8717    1.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3053   -0.1056    0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5751   -0.8873   -2.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5516    0.4985   -2.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  2  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  8 31  1  0
 13 32  1  0
 14 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0      -2.667  12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.000   7.700   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       1.334   5.390   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.206   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.874   3.850   0.000  0.00  0.00           O+0
HETATM   20  S   UNK     0       1.334   3.850   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    8                                                       
CONECT    4    6    9                                                       
CONECT    5    7    9                                                       
CONECT    6    4   10                                                       
CONECT    7    5   10                                                       
CONECT    8    3   13                                                       
CONECT    9    4    5   11                                                  
CONECT   10    6    7   20                                                  
CONECT   11    9   15   16                                                  
CONECT   12   13   14   17                                                  
CONECT   13    8   12                                                       
CONECT   14   12   20                                                       
CONECT   15   11                                                            
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   20                                                            
CONECT   19   20                                                            
CONECT   20   10   14   18   19                                             
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0041849
HETATM    1  C1  UNL     1       5.063  -1.433   1.635  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.673  -0.632   0.414  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.613  -1.322  -0.399  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.345  -1.550   0.398  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.770  -0.325   0.867  1.00  0.00           N  
HETATM    6  C5  UNL     1       1.156   0.502   0.094  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.059   0.169  -1.249  1.00  0.00           O  
HETATM    8  N2  UNL     1       0.591   1.707   0.557  1.00  0.00           N  
HETATM    9  S1  UNL     1      -0.670   2.468  -0.309  1.00  0.00           S  
HETATM   10  O2  UNL     1      -1.075   3.752   0.349  1.00  0.00           O  
HETATM   11  O3  UNL     1      -0.221   2.729  -1.729  1.00  0.00           O  
HETATM   12  C6  UNL     1      -2.102   1.455  -0.421  1.00  0.00           C  
HETATM   13  C7  UNL     1      -3.056   1.552   0.563  1.00  0.00           C  
HETATM   14  C8  UNL     1      -4.197   0.794   0.540  1.00  0.00           C  
HETATM   15  C9  UNL     1      -4.413  -0.105  -0.501  1.00  0.00           C  
HETATM   16  C10 UNL     1      -5.612  -0.922  -0.552  1.00  0.00           C  
HETATM   17  O4  UNL     1      -5.753  -1.713  -1.512  1.00  0.00           O  
HETATM   18  O5  UNL     1      -6.578  -0.835   0.429  1.00  0.00           O  
HETATM   19  C11 UNL     1      -3.440  -0.187  -1.481  1.00  0.00           C  
HETATM   20  C12 UNL     1      -2.297   0.577  -1.453  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.327  -1.315   2.443  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.200  -2.514   1.414  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.020  -0.989   2.032  1.00  0.00           H  
HETATM   24  H4  UNL     1       5.548  -0.481  -0.255  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.346   0.366   0.779  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.344  -0.698  -1.273  1.00  0.00           H  
HETATM   27  H7  UNL     1       4.035  -2.268  -0.784  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.590  -2.211   1.250  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.598  -2.096  -0.213  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.476   0.766  -1.924  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.938   2.132   1.420  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.906   2.251   1.388  1.00  0.00           H  
HETATM   33  H13 UNL     1      -4.942   0.872   1.313  1.00  0.00           H  
HETATM   34  H14 UNL     1      -7.305  -0.106   0.436  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.575  -0.887  -2.322  1.00  0.00           H  
HETATM   36  H16 UNL     1      -1.552   0.498  -2.226  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6    6
CONECT    6    7    8
CONECT    7   30
CONECT    8    9   31
CONECT    9   10   10   11   11
CONECT    9   12
CONECT   12   13   13   20
CONECT   13   14   32
CONECT   14   15   15   33
CONECT   15   16   19
CONECT   16   17   17   18
CONECT   18   34
CONECT   19   20   20   35
CONECT   20   36
END

HMDB0041849
     RDKit          3D
Carboxytolbutamide
 36 36  0  0  0  0  0  0  0  0999 V2000
    5.0630   -1.4333    1.6347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6728   -0.6324    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6125   -1.3219   -0.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3448   -1.5503    0.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7698   -0.3246    0.8672 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1556    0.5023    0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0593    0.1688   -1.2491 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906    1.7071    0.5566 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6699    2.4681   -0.3091 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.0746    3.7519    0.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2210    2.7286   -1.7286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1018    1.4554   -0.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0557    1.5518    0.5625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1969    0.7937    0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4130   -0.1052   -0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6116   -0.9222   -0.5525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7529   -1.7129   -1.5118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5777   -0.8353    0.4294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4398   -0.1867   -1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2972    0.5770   -1.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3273   -1.3147    2.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2005   -2.5144    1.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0196   -0.9889    2.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5482   -0.4812   -0.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3457    0.3661    0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3442   -0.6977   -1.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0352   -2.2684   -0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5901   -2.2112    1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5984   -2.0955   -0.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4762    0.7664   -1.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9383    2.1316    1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9056    2.2505    1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9424    0.8717    1.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3053   -0.1056    0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5751   -0.8873   -2.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5516    0.4985   -2.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  2  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  7 30  1  0
  8 31  1  0
 13 32  1  0
 14 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Tolbutamide carboxylic acid	HMDB
1-Butyl-3-(4-carboxyphenyl)sulfonylurea	HMDB
4-(((Butylamino)carbonyl)amino)sulfonylbenzoic acid	HMDB
4-{[(butyl-C-hydroxycarbonimidoyl)amino]sulfonyl}benzoate	HMDB
4-{[(butyl-C-hydroxycarbonimidoyl)amino]sulphonyl}benzoate	HMDB
4-{[(butyl-C-hydroxycarbonimidoyl)amino]sulphonyl}benzoic acid	HMDB
Carboxytolbutamide	MeSH

Chemical Formula

C₁₂H₁₆N₂O₅S

Average Molecular Weight

300.331

Monoisotopic Molecular Weight

300.077992322

IUPAC Name

4-{[(butyl-C-hydroxycarbonimidoyl)amino]sulfonyl}benzoic acid

Traditional Name

4-[(butyl-C-hydroxycarbonimidoyl)aminosulfonyl]benzoic acid

CAS Registry Number

2224-10-4

SMILES

CCCCN=C(O)NS(=O)(=O)C1=CC=C(C=C1)C(O)=O

InChI Identifier

InChI=1S/C12H16N2O5S/c1-2-3-8-13-12(17)14-20(18,19)10-6-4-9(5-7-10)11(15)16/h4-7H,2-3,8H2,1H3,(H,15,16)(H2,13,14,17)

InChI Key

GCMVATDSSHTCOS-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
Benzoic acid or derivatives
Benzoic acid
Benzenesulfonyl group
Benzoyl
Sulfonylurea
Aminosulfonyl compound
Sulfonyl
Organosulfonic acid or derivatives
Organic sulfonic acid or derivatives
Carbonic acid derivative
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041849)

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
Water Solubility	0.23 g/L	ALOGPS
logP	1.07	ALOGPS
logP	2.26	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.51	ChemAxon
pKa (Strongest Basic)	-0.63	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	116.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.01 m³·mol⁻¹	ChemAxon
Polarizability	29.29 Å³	ChemAxon
Number of Rings	1	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]+	170.695	31661259
DarkChem	[M-H]-	170.149	31661259
DeepCCS	[M+H]+	167.407	30932474
DeepCCS	[M-H]-	165.049	30932474
DeepCCS	[M-2H]-	197.934	30932474
DeepCCS	[M+Na]+	173.5	30932474
AllCCS	[M+H]+	166.5	32859911
AllCCS	[M+H-H2O]+	163.4	32859911
AllCCS	[M+NH4]+	169.3	32859911
AllCCS	[M+Na]+	170.1	32859911
AllCCS	[M-H]-	165.3	32859911
AllCCS	[M+Na-2H]-	165.7	32859911
AllCCS	[M+HCOO]-	166.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Carboxytolbutamide	CCCCN=C(O)NS(=O)(=O)C1=CC=C(C=C1)C(O)=O	3670.5	Standard polar	33892256
Carboxytolbutamide	CCCCN=C(O)NS(=O)(=O)C1=CC=C(C=C1)C(O)=O	2120.6	Standard non polar	33892256
Carboxytolbutamide	CCCCN=C(O)NS(=O)(=O)C1=CC=C(C=C1)C(O)=O	2662.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Carboxytolbutamide,1TMS,isomer #1	CCCCN=C(NS(=O)(=O)C1=CC=C(C(=O)O)C=C1)O[Si](C)(C)C	2647.4	Semi standard non polar	33892256
Carboxytolbutamide,1TMS,isomer #2	CCCCN=C(O)NS(=O)(=O)C1=CC=C(C(=O)O[Si](C)(C)C)C=C1	2617.5	Semi standard non polar	33892256
Carboxytolbutamide,1TMS,isomer #3	CCCCN=C(O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(C(=O)O)C=C1	2704.4	Semi standard non polar	33892256
Carboxytolbutamide,2TMS,isomer #1	CCCCN=C(NS(=O)(=O)C1=CC=C(C(=O)O[Si](C)(C)C)C=C1)O[Si](C)(C)C	2572.8	Semi standard non polar	33892256
Carboxytolbutamide,2TMS,isomer #2	CCCCN=C(O[Si](C)(C)C)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(C(=O)O)C=C1	2626.4	Semi standard non polar	33892256
Carboxytolbutamide,2TMS,isomer #3	CCCCN=C(O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(C(=O)O[Si](C)(C)C)C=C1	2604.0	Semi standard non polar	33892256
Carboxytolbutamide,3TMS,isomer #1	CCCCN=C(O[Si](C)(C)C)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(C(=O)O[Si](C)(C)C)C=C1	2555.9	Semi standard non polar	33892256
Carboxytolbutamide,3TMS,isomer #1	CCCCN=C(O[Si](C)(C)C)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(C(=O)O[Si](C)(C)C)C=C1	2703.2	Standard non polar	33892256
Carboxytolbutamide,1TBDMS,isomer #1	CCCCN=C(NS(=O)(=O)C1=CC=C(C(=O)O)C=C1)O[Si](C)(C)C(C)(C)C	2907.2	Semi standard non polar	33892256
Carboxytolbutamide,1TBDMS,isomer #2	CCCCN=C(O)NS(=O)(=O)C1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1	2917.4	Semi standard non polar	33892256
Carboxytolbutamide,1TBDMS,isomer #3	CCCCN=C(O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(C(=O)O)C=C1	2953.6	Semi standard non polar	33892256
Carboxytolbutamide,2TBDMS,isomer #1	CCCCN=C(NS(=O)(=O)C1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	3078.2	Semi standard non polar	33892256
Carboxytolbutamide,2TBDMS,isomer #2	CCCCN=C(O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(C(=O)O)C=C1	3145.2	Semi standard non polar	33892256
Carboxytolbutamide,2TBDMS,isomer #3	CCCCN=C(O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1	3154.1	Semi standard non polar	33892256
Carboxytolbutamide,3TBDMS,isomer #1	CCCCN=C(O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1	3306.1	Semi standard non polar	33892256
Carboxytolbutamide,3TBDMS,isomer #1	CCCCN=C(O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1	3405.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Carboxytolbutamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5c-9380000000-59d09aa854b91160aa4b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carboxytolbutamide GC-MS (2 TMS) - 70eV, Positive	splash10-05i0-9325600000-eb497341a5fd25699726	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Carboxytolbutamide 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 - Carboxytolbutamide 10V, Positive-QTOF	splash10-0ue9-6294000000-9bac606abe22a582d894	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxytolbutamide 20V, Positive-QTOF	splash10-05fr-9320000000-9bbb988b0b5fc3ba89be	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxytolbutamide 40V, Positive-QTOF	splash10-0a4l-9100000000-e0796abd2c9b07fa2c35	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxytolbutamide 10V, Negative-QTOF	splash10-0002-0090000000-49a53452527e16129d69	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxytolbutamide 20V, Negative-QTOF	splash10-0zfr-1490000000-25d2054e66420438ed05	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxytolbutamide 40V, Negative-QTOF	splash10-0ufu-9660000000-30bd8776d382a07b5893	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxytolbutamide 10V, Positive-QTOF	splash10-0udi-0394000000-b3ec76878f298e703dee	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxytolbutamide 20V, Positive-QTOF	splash10-001i-1920000000-c03c301eca5a73e4d380	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxytolbutamide 40V, Positive-QTOF	splash10-05fu-7910000000-196103cf6f72ce92929b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxytolbutamide 10V, Negative-QTOF	splash10-0udi-0190000000-e47ec4fb4888d63069c1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxytolbutamide 20V, Negative-QTOF	splash10-0ufr-6690000000-919edaaf3de9594f2445	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carboxytolbutamide 40V, Negative-QTOF	splash10-0kdl-9260000000-cbfc4adb388c579f4edb	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

140373

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

159651

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

Not Available

Showing metabocard for Carboxytolbutamide (HMDB0041849)

MOL for HMDB0041849 (Carboxytolbutamide)

3D MOL for HMDB0041849 (Carboxytolbutamide)

3D SDF for HMDB0041849 (Carboxytolbutamide)

3D-SDF for HMDB0041849 (Carboxytolbutamide)

PDB for HMDB0041849 (Carboxytolbutamide)

3D PDB for HMDB0041849 (Carboxytolbutamide)

SMILES for HMDB0041849 (Carboxytolbutamide)

INCHI for HMDB0041849 (Carboxytolbutamide)

Structure for HMDB0041849 (Carboxytolbutamide)

3D Structure for HMDB0041849 (Carboxytolbutamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra