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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-23 05:49:20 UTC

Update Date

2020-02-26 21:26:23 UTC

HMDB ID

HMDB0006408

Secondary Accession Numbers

HMDB0060976
HMDB06408
HMDB60976

Metabolite Identification

Common Name

4-Hydroxy tolbutamide

Description

4-Hydroxy tolbutamide 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. 4-Hydroxy tolbutamide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on 4-Hydroxy tolbutamide.

Structure

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

HMDB0006408
     RDKit          3D
4-Hydroxy tolbutamide
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.6304    1.0985   -0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358    0.7970    1.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4708   -0.6731    1.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8376   -1.1291   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6561   -0.3887   -0.4642 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5731   -0.2541    0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5816   -0.7146    1.5577 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4726    0.4781   -0.1071 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7668    1.3007   -0.7134 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.6072    1.4762   -2.2401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7318    2.7488   -0.2252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3890    0.6687   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6121   -0.7123   -0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9127   -1.2166   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9905   -0.3734    0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3894   -0.8942    0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2602   -1.9354    1.1805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7778    0.9961   -0.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5021    1.4562   -0.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0425    1.3018   -1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2710    1.9825    0.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3045    0.2428   -0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7678    1.3119    0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2362    1.0756    2.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4586   -1.2294    1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8029   -0.9573    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6413   -2.2404   -0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5612   -1.0352   -1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5827    0.1135   -1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0951    0.3935    1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7621   -1.3689   -0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0729   -2.2828    0.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7861   -1.3616   -0.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0947   -0.1389    0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9240   -2.6958    0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6272    1.6239    0.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3251    2.5358   -0.3794 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  1  0
  6  7  2  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  1  0
 15 18  1  0
 18 19  2  0
 19 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
M  END


  Mrv0541 02231220392D          

 19 19  0  0  0  0            999 V2000
    7.6706   -6.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2581   -6.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6706   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4956   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9081   -6.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4956   -6.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7331   -6.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1456   -6.8332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4331   -6.1187    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.4331   -5.2937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4331   -6.9437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6081   -6.1187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1956   -5.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6081   -4.6898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3706   -5.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9581   -4.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1331   -4.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7206   -3.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8956   -3.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  6  1  1  0  0  0  0
  7  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  2  1  0  0  0  0
 10  9  2  0  0  0  0
 11  9  2  0  0  0  0
 12  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
 15 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006408

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCNC(=O)NS(=O)(=O)C1=CC=C(CO)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H18N2O4S/c1-2-3-8-13-12(16)14-19(17,18)11-6-4-10(9-15)5-7-11/h4-7,15H,2-3,8-9H2,1H3,(H2,13,14,16)

> <INCHI_KEY>
SJRHYONYKZIRPM-UHFFFAOYSA-N

> <FORMULA>
C12H18N2O4S

> <MOLECULAR_WEIGHT>
286.347

> <EXACT_MASS>
286.098727764

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.642206906788765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-butyl-1-[4-(hydroxymethyl)benzenesulfonyl]urea

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
1.0145646706666667

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.841880631884592

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.328637595745938

> <JCHEM_PKA_STRONGEST_BASIC>
-2.891407388207461

> <JCHEM_POLAR_SURFACE_AREA>
95.5

> <JCHEM_REFRACTIVITY>
72.0447

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxytolbutamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006408
     RDKit          3D
4-Hydroxy tolbutamide
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.6304    1.0985   -0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358    0.7970    1.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4708   -0.6731    1.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8376   -1.1291   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6561   -0.3887   -0.4642 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5731   -0.2541    0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5816   -0.7146    1.5577 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4726    0.4781   -0.1071 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7668    1.3007   -0.7134 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.6072    1.4762   -2.2401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7318    2.7488   -0.2252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3890    0.6687   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6121   -0.7123   -0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9127   -1.2166   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9905   -0.3734    0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3894   -0.8942    0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2602   -1.9354    1.1805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7778    0.9961   -0.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5021    1.4562   -0.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0425    1.3018   -1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2710    1.9825    0.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3045    0.2428   -0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7678    1.3119    0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2362    1.0756    2.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4586   -1.2294    1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8029   -0.9573    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6413   -2.2404   -0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5612   -1.0352   -1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5827    0.1135   -1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0951    0.3935    1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7621   -1.3689   -0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0729   -2.2828    0.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7861   -1.3616   -0.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0947   -0.1389    0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9240   -2.6958    0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6272    1.6239    0.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3251    2.5358   -0.3794 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  1  0
  6  7  2  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  1  0
 15 18  1  0
 18 19  2  0
 19 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      14.318 -12.755   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.548 -11.422   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.318 -10.088   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.858 -10.088   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.628 -11.422   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.858 -12.755   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.168 -11.422   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      18.938 -12.755   0.000  0.00  0.00           O+0
HETATM    9  S   UNK     0      12.008 -11.422   0.000  0.00  0.00           S+0
HETATM   10  O   UNK     0      12.008  -9.882   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      12.008 -12.962   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      10.468 -11.422   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       9.698 -10.088   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.468  -8.754   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       8.158 -10.088   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       7.388  -8.754   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.848  -8.754   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.078  -7.421   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.538  -7.421   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7                                                            
CONECT    9    2   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0006408
HETATM    1  C1  UNL     1       5.630   1.099  -0.087  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.736   0.797   1.084  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.471  -0.673   1.110  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.838  -1.129  -0.153  1.00  0.00           C  
HETATM    5  N1  UNL     1       2.656  -0.389  -0.464  1.00  0.00           N  
HETATM    6  C5  UNL     1       1.573  -0.254   0.436  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.582  -0.715   1.558  1.00  0.00           O  
HETATM    8  N2  UNL     1       0.473   0.478  -0.107  1.00  0.00           N  
HETATM    9  S1  UNL     1      -0.767   1.301  -0.713  1.00  0.00           S  
HETATM   10  O2  UNL     1      -0.607   1.476  -2.240  1.00  0.00           O  
HETATM   11  O3  UNL     1      -0.732   2.749  -0.225  1.00  0.00           O  
HETATM   12  C6  UNL     1      -2.389   0.669  -0.415  1.00  0.00           C  
HETATM   13  C7  UNL     1      -2.612  -0.712  -0.303  1.00  0.00           C  
HETATM   14  C8  UNL     1      -3.913  -1.217  -0.083  1.00  0.00           C  
HETATM   15  C9  UNL     1      -4.990  -0.373   0.028  1.00  0.00           C  
HETATM   16  C10 UNL     1      -6.389  -0.894   0.256  1.00  0.00           C  
HETATM   17  O4  UNL     1      -6.260  -1.935   1.181  1.00  0.00           O  
HETATM   18  C11 UNL     1      -4.778   0.996  -0.085  1.00  0.00           C  
HETATM   19  C12 UNL     1      -3.502   1.456  -0.301  1.00  0.00           C  
HETATM   20  H1  UNL     1       5.042   1.302  -1.000  1.00  0.00           H  
HETATM   21  H2  UNL     1       6.271   1.983   0.173  1.00  0.00           H  
HETATM   22  H3  UNL     1       6.304   0.243  -0.334  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.768   1.312   0.966  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.236   1.076   2.051  1.00  0.00           H  
HETATM   25  H6  UNL     1       5.459  -1.229   1.280  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.803  -0.957   1.941  1.00  0.00           H  
HETATM   27  H8  UNL     1       3.641  -2.240  -0.107  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.561  -1.035  -1.037  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.583   0.113  -1.394  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.095   0.394   1.118  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.762  -1.369  -0.400  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.073  -2.283   0.016  1.00  0.00           H  
HETATM   33  H14 UNL     1      -6.786  -1.362  -0.685  1.00  0.00           H  
HETATM   34  H15 UNL     1      -7.095  -0.139   0.545  1.00  0.00           H  
HETATM   35  H16 UNL     1      -5.924  -2.696   0.653  1.00  0.00           H  
HETATM   36  H17 UNL     1      -5.627   1.624   0.005  1.00  0.00           H  
HETATM   37  H18 UNL     1      -3.325   2.536  -0.379  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   29
CONECT    6    7    7    8
CONECT    8    9   30
CONECT    9   10   10   11   11
CONECT    9   12
CONECT   12   13   13   19
CONECT   13   14   31
CONECT   14   15   15   32
CONECT   15   16   18
CONECT   16   17   33   34
CONECT   17   35
CONECT   18   19   19   36
CONECT   19   37
END

HMDB0006408
     RDKit          3D
4-Hydroxy tolbutamide
 37 37  0  0  0  0  0  0  0  0999 V2000
    5.6304    1.0985   -0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7358    0.7970    1.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4708   -0.6731    1.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8376   -1.1291   -0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6561   -0.3887   -0.4642 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5731   -0.2541    0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5816   -0.7146    1.5577 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4726    0.4781   -0.1071 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7668    1.3007   -0.7134 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.6072    1.4762   -2.2401 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7318    2.7488   -0.2252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3890    0.6687   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6121   -0.7123   -0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9127   -1.2166   -0.0831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9905   -0.3734    0.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3894   -0.8942    0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2602   -1.9354    1.1805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7778    0.9961   -0.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5021    1.4562   -0.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0425    1.3018   -1.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2710    1.9825    0.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3045    0.2428   -0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7678    1.3119    0.9657 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2362    1.0756    2.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4586   -1.2294    1.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8029   -0.9573    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6413   -2.2404   -0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5612   -1.0352   -1.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5827    0.1135   -1.3936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0951    0.3935    1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7621   -1.3689   -0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0729   -2.2828    0.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7861   -1.3616   -0.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0947   -0.1389    0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9240   -2.6958    0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6272    1.6239    0.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3251    2.5358   -0.3794 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  1  0
  6  7  2  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  1  0
 15 18  1  0
 18 19  2  0
 19 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Butyl-3-(4-hydroxymethylphenyl)sulfonylurea	ChEBI
Hydroxymethyltolbutamide	ChEBI
Hydroxytolbutamide	ChEBI
Methylhydroxytolbutamide	ChEBI
1-Butyl-3-(4-hydroxymethylphenyl)sulphonylurea	Generator
4 Hydroxy tolbutamide	HMDB
4-Hydroxytolbutamide	HMDB
N-((butylamino)Carbonyl)-4-(hydroxymethyl)benzenesulfonamide	MeSH, HMDB

Chemical Formula

C₁₂H₁₈N₂O₄S

Average Molecular Weight

286.347

Monoisotopic Molecular Weight

286.098727764

IUPAC Name

3-butyl-1-[4-(hydroxymethyl)benzenesulfonyl]urea

Traditional Name

hydroxytolbutamide

CAS Registry Number

1185112-19-9

SMILES

CCCCNC(=O)NS(=O)(=O)C1=CC=C(CO)C=C1

InChI Identifier

InChI=1S/C12H18N2O4S/c1-2-3-8-13-12(16)14-19(17,18)11-6-4-10(9-15)5-7-11/h4-7,15H,2-3,8-9H2,1H3,(H2,13,14,16)

InChI Key

SJRHYONYKZIRPM-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
Benzyl alcohol
Sulfonylurea
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Carbonic acid derivative
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary alcohol
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Alcohol
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aromatic alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

ureas (CHEBI:63799 )
sulfonamide (CHEBI:63799 )
benzyl alcohols (CHEBI:63799 )

Ontology

Not Available

Kidney (HMDB: HMDB0060976)
Liver (HMDB: HMDB0060976)

Biofluid or Excreta

Non-excretory biofluid

Blood (HMDB: HMDB0060976)

Excreta

Urine (HMDB: HMDB0060976)

Cellular substructure

Cytoplasm (HMDB: HMDB0060976)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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	0.68 g/L	ALOGPS
logP	1.13	ALOGPS
logP	1.01	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	4.33	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.5 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	72.04 m³·mol⁻¹	ChemAxon
Polarizability	29.64 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]+	167.46	31661259
DarkChem	[M-H]-	166.703	31661259
DeepCCS	[M+H]+	169.387	30932474
DeepCCS	[M-H]-	167.029	30932474
DeepCCS	[M-2H]-	199.915	30932474
DeepCCS	[M+Na]+	175.48	30932474
AllCCS	[M+H]+	164.1	32859911
AllCCS	[M+H-H2O]+	160.9	32859911
AllCCS	[M+NH4]+	167.0	32859911
AllCCS	[M+Na]+	167.9	32859911
AllCCS	[M-H]-	164.0	32859911
AllCCS	[M+Na-2H]-	164.5	32859911
AllCCS	[M+HCOO]-	165.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy tolbutamide	CCCCNC(=O)NS(=O)(=O)C1=CC=C(CO)C=C1	4211.6	Standard polar	33892256
4-Hydroxy tolbutamide	CCCCNC(=O)NS(=O)(=O)C1=CC=C(CO)C=C1	1782.9	Standard non polar	33892256
4-Hydroxy tolbutamide	CCCCNC(=O)NS(=O)(=O)C1=CC=C(CO)C=C1	2564.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy tolbutamide,1TMS,isomer #1	CCCCNC(=O)NS(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C1	2638.5	Semi standard non polar	33892256
4-Hydroxy tolbutamide,1TMS,isomer #2	CCCCN(C(=O)NS(=O)(=O)C1=CC=C(CO)C=C1)[Si](C)(C)C	2518.8	Semi standard non polar	33892256
4-Hydroxy tolbutamide,1TMS,isomer #3	CCCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO)C=C1	2501.4	Semi standard non polar	33892256
4-Hydroxy tolbutamide,2TMS,isomer #1	CCCCN(C(=O)NS(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C1)[Si](C)(C)C	2544.1	Semi standard non polar	33892256
4-Hydroxy tolbutamide,2TMS,isomer #1	CCCCN(C(=O)NS(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C1)[Si](C)(C)C	2584.5	Standard non polar	33892256
4-Hydroxy tolbutamide,2TMS,isomer #1	CCCCN(C(=O)NS(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C1)[Si](C)(C)C	3190.5	Standard polar	33892256
4-Hydroxy tolbutamide,2TMS,isomer #2	CCCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C1	2548.1	Semi standard non polar	33892256
4-Hydroxy tolbutamide,2TMS,isomer #2	CCCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C1	2474.1	Standard non polar	33892256
4-Hydroxy tolbutamide,2TMS,isomer #2	CCCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C1	3303.3	Standard polar	33892256
4-Hydroxy tolbutamide,2TMS,isomer #3	CCCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO)C=C1)[Si](C)(C)C	2437.0	Semi standard non polar	33892256
4-Hydroxy tolbutamide,2TMS,isomer #3	CCCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO)C=C1)[Si](C)(C)C	2648.0	Standard non polar	33892256
4-Hydroxy tolbutamide,2TMS,isomer #3	CCCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO)C=C1)[Si](C)(C)C	3245.3	Standard polar	33892256
4-Hydroxy tolbutamide,3TMS,isomer #1	CCCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C1)[Si](C)(C)C	2480.4	Semi standard non polar	33892256
4-Hydroxy tolbutamide,3TMS,isomer #1	CCCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C1)[Si](C)(C)C	2711.4	Standard non polar	33892256
4-Hydroxy tolbutamide,3TMS,isomer #1	CCCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C)C=C1)[Si](C)(C)C	2985.8	Standard polar	33892256
4-Hydroxy tolbutamide,1TBDMS,isomer #1	CCCCNC(=O)NS(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1	2879.5	Semi standard non polar	33892256
4-Hydroxy tolbutamide,1TBDMS,isomer #2	CCCCN(C(=O)NS(=O)(=O)C1=CC=C(CO)C=C1)[Si](C)(C)C(C)(C)C	2761.1	Semi standard non polar	33892256
4-Hydroxy tolbutamide,1TBDMS,isomer #3	CCCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO)C=C1	2782.0	Semi standard non polar	33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #1	CCCCN(C(=O)NS(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3000.4	Semi standard non polar	33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #1	CCCCN(C(=O)NS(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2994.0	Standard non polar	33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #1	CCCCN(C(=O)NS(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3278.8	Standard polar	33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #2	CCCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1	3054.8	Semi standard non polar	33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #2	CCCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1	2896.7	Standard non polar	33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #2	CCCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1	3374.9	Standard polar	33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #3	CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO)C=C1)[Si](C)(C)C(C)(C)C	2976.9	Semi standard non polar	33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #3	CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO)C=C1)[Si](C)(C)C(C)(C)C	3098.2	Standard non polar	33892256
4-Hydroxy tolbutamide,2TBDMS,isomer #3	CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO)C=C1)[Si](C)(C)C(C)(C)C	3314.3	Standard polar	33892256
4-Hydroxy tolbutamide,3TBDMS,isomer #1	CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3229.9	Semi standard non polar	33892256
4-Hydroxy tolbutamide,3TBDMS,isomer #1	CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3342.4	Standard non polar	33892256
4-Hydroxy tolbutamide,3TBDMS,isomer #1	CCCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	3170.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy tolbutamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0c00-7980000000-79f53f4297ab2ff88696	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy tolbutamide GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9823000000-8735d28a2bdfb4492da6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy tolbutamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy tolbutamide 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 - 4-Hydroxy tolbutamide 10V, Positive-QTOF	splash10-00ri-6790000000-15179d796c15f8bff29d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 20V, Positive-QTOF	splash10-05g0-9500000000-211280021c7662da1508	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 40V, Positive-QTOF	splash10-0a4i-9100000000-9025f9817a60f20e38ef	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 10V, Negative-QTOF	splash10-000i-1290000000-4449465e9857aca8ee5f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 20V, Negative-QTOF	splash10-052r-1930000000-d20c0dffd148ceeeb600	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 40V, Negative-QTOF	splash10-0573-8900000000-d3376933c13afb8faea0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 10V, Negative-QTOF	splash10-000i-0930000000-af56d043bc014bed1adc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 20V, Negative-QTOF	splash10-000i-1900000000-f59e8d27a50f370ff6a9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 40V, Negative-QTOF	splash10-004i-9300000000-b6b22115bf1475d3d935	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 10V, Positive-QTOF	splash10-000i-3940000000-12a4c46026f2e5b3ba5f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 20V, Positive-QTOF	splash10-0ab9-3900000000-e692b3121c16132704a9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy tolbutamide 40V, Positive-QTOF	splash10-0abc-9700000000-c7adc54472f91da241bd	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

FDB023913

KNApSAcK ID

Not Available

Chemspider ID

3529

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2299999

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3656

PDB ID

Not Available

ChEBI ID

63799

Food Biomarker Ontology

Not Available

VMH ID

4MTOLBUTAMIDE

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 4-Hydroxy tolbutamide (HMDB0006408)

MOL for HMDB0006408 (4-Hydroxy tolbutamide)

3D MOL for HMDB0006408 (4-Hydroxy tolbutamide)

3D SDF for HMDB0006408 (4-Hydroxy tolbutamide)

3D-SDF for HMDB0006408 (4-Hydroxy tolbutamide)

PDB for HMDB0006408 (4-Hydroxy tolbutamide)

3D PDB for HMDB0006408 (4-Hydroxy tolbutamide)

SMILES for HMDB0006408 (4-Hydroxy tolbutamide)

INCHI for HMDB0006408 (4-Hydroxy tolbutamide)

Structure for HMDB0006408 (4-Hydroxy tolbutamide)

3D Structure for HMDB0006408 (4-Hydroxy tolbutamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra