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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:52 UTC

Update Date

2020-02-26 21:39:21 UTC

HMDB ID

HMDB0014025

Secondary Accession Numbers

HMDB14025

Metabolite Identification

Common Name

3-Hydroxychlorpropamide

Description

3-Hydroxychlorpropamide is only found in individuals that have used or taken Chlorpropamide. 3-Hydroxychlorpropamide is a metabolite of Chlorpropamide. 3-hydroxychlorpropamide belongs to the family of Benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Structure

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

HMDB0014025
     RDKit          3D
3-Hydroxychlorpropamide
 31 31  0  0  0  0  0  0  0  0999 V2000
   -5.1368   -0.0890    0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3874   -1.3770    0.5364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2698   -1.0996   -0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3125   -0.1574    0.0799 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1893    0.2394   -0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0555   -0.2621   -1.8411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2215    1.1623   -0.2051 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167    1.6055   -1.1801 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.2762    3.1160   -1.2051 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8416    1.1976   -2.6061 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068    0.9243   -0.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3992    1.6125    0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5705    1.0746    0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9902   -0.1652    0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4767   -0.8911    0.9777 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2040   -0.8781   -0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6265   -2.1449   -0.9040 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0236   -0.3294   -0.9807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0793   -0.0783    0.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5491    0.7969    0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4281   -0.0296    1.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9006   -1.7281    1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0911   -2.1361    0.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7179   -0.7031   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8031   -2.0827   -0.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627    0.2213    1.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3272    1.5709    0.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1033    2.6186    0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2016    1.6279    1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0385   -2.6704   -1.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4565   -0.9458   -1.6815 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  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
 12 28  1  0
 13 29  1  0
 17 30  1  0
 18 31  1  0
M  END

  Mrv0541 06191310432D          

 18 18  0  0  0  0            999 V2000
    9.2187   -7.8376    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.2187   -4.5376    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.3936   -4.5376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0437   -4.5376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6477   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2187   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9331   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6477   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2187   -5.3626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6477   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9331   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9331   -5.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5042   -5.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3621   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9331   -6.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5042   -6.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2187   -7.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6476   -7.0126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 17  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  2  0  0  0  0
  2  6  1  0  0  0  0
  2  9  1  0  0  0  0
  5 11  2  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8 10  1  0  0  0  0
  9 12  2  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 15 17  2  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014025

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCNC(=O)NS(=O)(=O)C1=CC(O)=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H13ClN2O4S/c1-2-5-12-10(15)13-18(16,17)7-3-4-8(11)9(14)6-7/h3-4,6,14H,2,5H2,1H3,(H2,12,13,15)

> <INCHI_KEY>
RXFPYNAVFFDUJE-UHFFFAOYSA-N

> <FORMULA>
C10H13ClN2O4S

> <MOLECULAR_WEIGHT>
292.739

> <EXACT_MASS>
292.028455311

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.941807130907257

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-chloro-3-hydroxybenzenesulfonyl)-3-propylurea

> <ALOGPS_LOGP>
1.75

> <JCHEM_LOGP>
1.6378251276666662

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.061811516818263

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.320019416791854

> <JCHEM_PKA_STRONGEST_BASIC>
-6.801469798012115

> <JCHEM_POLAR_SURFACE_AREA>
95.5

> <JCHEM_REFRACTIVITY>
67.4135

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(4-chloro-3-hydroxybenzenesulfonyl)-3-propylurea

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014025
     RDKit          3D
3-Hydroxychlorpropamide
 31 31  0  0  0  0  0  0  0  0999 V2000
   -5.1368   -0.0890    0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3874   -1.3770    0.5364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2698   -1.0996   -0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3125   -0.1574    0.0799 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1893    0.2394   -0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0555   -0.2621   -1.8411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2215    1.1623   -0.2051 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167    1.6055   -1.1801 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.2762    3.1160   -1.2051 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8416    1.1976   -2.6061 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068    0.9243   -0.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3992    1.6125    0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5705    1.0746    0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9902   -0.1652    0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4767   -0.8911    0.9777 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2040   -0.8781   -0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6265   -2.1449   -0.9040 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0236   -0.3294   -0.9807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0793   -0.0783    0.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5491    0.7969    0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4281   -0.0296    1.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9006   -1.7281    1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0911   -2.1361    0.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7179   -0.7031   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8031   -2.0827   -0.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627    0.2213    1.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3272    1.5709    0.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1033    2.6186    0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2016    1.6279    1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0385   -2.6704   -1.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4565   -0.9458   -1.6815 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  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
 12 28  1  0
 13 29  1  0
 17 30  1  0
 18 31  1  0
M  END

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1 Cl   UNK     0      17.208 -14.630   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0      17.208  -8.470   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      15.668  -8.470   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      18.748  -8.470   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      19.876  -6.930   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      17.208  -6.930   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      18.542  -4.620   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      19.876  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.208 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.876  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.542  -6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.542 -10.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.875 -10.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.209  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.542 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.875 -12.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.208 -13.090   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      19.876 -13.090   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2    3    4    6    9                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5   11                                                            
CONECT    6    2   11                                                       
CONECT    7    8   11                                                       
CONECT    8    7   10                                                       
CONECT    9    2   12   13                                                  
CONECT   10    8   14                                                       
CONECT   11    5    6    7                                                  
CONECT   12    9   15                                                       
CONECT   13    9   16                                                       
CONECT   14   10                                                            
CONECT   15   12   17   18                                                  
CONECT   16   13   17                                                       
CONECT   17    1   15   16                                                  
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0014025
HETATM    1  C1  UNL     1      -5.137  -0.089   0.868  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.387  -1.377   0.536  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.270  -1.100  -0.452  1.00  0.00           C  
HETATM    4  N1  UNL     1      -2.313  -0.157   0.080  1.00  0.00           N  
HETATM    5  C4  UNL     1      -1.189   0.239  -0.681  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.056  -0.262  -1.841  1.00  0.00           O  
HETATM    7  N2  UNL     1      -0.221   1.162  -0.205  1.00  0.00           N  
HETATM    8  S1  UNL     1       1.117   1.606  -1.180  1.00  0.00           S  
HETATM    9  O2  UNL     1       1.276   3.116  -1.205  1.00  0.00           O  
HETATM   10  O3  UNL     1       0.842   1.198  -2.606  1.00  0.00           O  
HETATM   11  C5  UNL     1       2.607   0.924  -0.582  1.00  0.00           C  
HETATM   12  C6  UNL     1       3.399   1.613   0.304  1.00  0.00           C  
HETATM   13  C7  UNL     1       4.571   1.075   0.782  1.00  0.00           C  
HETATM   14  C8  UNL     1       4.990  -0.165   0.393  1.00  0.00           C  
HETATM   15 CL1  UNL     1       6.477  -0.891   0.978  1.00  0.00          CL  
HETATM   16  C9  UNL     1       4.204  -0.878  -0.503  1.00  0.00           C  
HETATM   17  O4  UNL     1       4.626  -2.145  -0.904  1.00  0.00           O  
HETATM   18  C10 UNL     1       3.024  -0.329  -0.981  1.00  0.00           C  
HETATM   19  H1  UNL     1      -6.079  -0.078   0.255  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.549   0.797   0.574  1.00  0.00           H  
HETATM   21  H3  UNL     1      -5.428  -0.030   1.929  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.901  -1.728   1.468  1.00  0.00           H  
HETATM   23  H5  UNL     1      -5.091  -2.136   0.164  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.718  -0.703  -1.391  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.803  -2.083  -0.689  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.463   0.221   1.028  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.327   1.571   0.741  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.103   2.619   0.648  1.00  0.00           H  
HETATM   29  H11 UNL     1       5.202   1.628   1.492  1.00  0.00           H  
HETATM   30  H12 UNL     1       4.039  -2.670  -1.568  1.00  0.00           H  
HETATM   31  H13 UNL     1       2.456  -0.946  -1.682  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5   26
CONECT    5    6    6    7
CONECT    7    8   27
CONECT    8    9    9   10   10
CONECT    8   11
CONECT   11   12   12   18
CONECT   12   13   28
CONECT   13   14   14   29
CONECT   14   15   16
CONECT   16   17   18   18
CONECT   17   30
CONECT   18   31
END

HMDB0014025
     RDKit          3D
3-Hydroxychlorpropamide
 31 31  0  0  0  0  0  0  0  0999 V2000
   -5.1368   -0.0890    0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3874   -1.3770    0.5364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2698   -1.0996   -0.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3125   -0.1574    0.0799 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1893    0.2394   -0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0555   -0.2621   -1.8411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2215    1.1623   -0.2051 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167    1.6055   -1.1801 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.2762    3.1160   -1.2051 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8416    1.1976   -2.6061 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6068    0.9243   -0.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3992    1.6125    0.3037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5705    1.0746    0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9902   -0.1652    0.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4767   -0.8911    0.9777 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2040   -0.8781   -0.5025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6265   -2.1449   -0.9040 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0236   -0.3294   -0.9807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0793   -0.0783    0.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5491    0.7969    0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4281   -0.0296    1.9288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9006   -1.7281    1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0911   -2.1361    0.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7179   -0.7031   -1.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8031   -2.0827   -0.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627    0.2213    1.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3272    1.5709    0.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1033    2.6186    0.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2016    1.6279    1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0385   -2.6704   -1.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4565   -0.9458   -1.6815 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  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
 12 28  1  0
 13 29  1  0
 17 30  1  0
 18 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(4-Chloro-3-hydroxybenzenesulfonyl)propane-1-carbamimidate	HMDB
N-(4-Chloro-3-hydroxybenzenesulphonyl)propane-1-carbamimidate	HMDB
N-(4-Chloro-3-hydroxybenzenesulphonyl)propane-1-carbamimidic acid	HMDB

Chemical Formula

C₁₀H₁₃ClN₂O₄S

Average Molecular Weight

292.739

Monoisotopic Molecular Weight

292.028455311

IUPAC Name

1-(4-chloro-3-hydroxybenzenesulfonyl)-3-propylurea

Traditional Name

1-(4-chloro-3-hydroxybenzenesulfonyl)-3-propylurea

CAS Registry Number

Not Available

SMILES

CCCNC(=O)NS(=O)(=O)C1=CC(O)=C(Cl)C=C1

InChI Identifier

InChI=1S/C10H13ClN2O4S/c1-2-5-12-10(15)13-18(16,17)7-3-4-8(11)9(14)6-7/h3-4,6,14H,2,5H2,1H3,(H2,12,13,15)

InChI Key

RXFPYNAVFFDUJE-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
2-chlorophenol
2-halophenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Chlorobenzene
Halobenzene
Sulfonylurea
Phenol
Aryl chloride
Aryl halide
Aminosulfonyl compound
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Carbonic acid derivative
Organic nitrogen compound
Organochloride
Organohalogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
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

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0014025)
Kidney (HMDB: HMDB0014025)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014025)

Source

Endogenous

Endogenous (HMDB: HMDB0014025)

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	0.48 g/L	ALOGPS
logP	1.75	ALOGPS
logP	1.64	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.32	ChemAxon
pKa (Strongest Basic)	-6.8	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	3	ChemAxon
Refractivity	67.41 m³·mol⁻¹	ChemAxon
Polarizability	27.94 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
DeepCCS	[M+H]+	164.911	30932474
DeepCCS	[M-H]-	162.553	30932474
DeepCCS	[M-2H]-	195.439	30932474
DeepCCS	[M+Na]+	171.005	30932474
AllCCS	[M+H]+	161.7	32859911
AllCCS	[M+H-H2O]+	158.5	32859911
AllCCS	[M+NH4]+	164.7	32859911
AllCCS	[M+Na]+	165.5	32859911
AllCCS	[M-H]-	159.4	32859911
AllCCS	[M+Na-2H]-	159.9	32859911
AllCCS	[M+HCOO]-	160.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxychlorpropamide	CCCNC(=O)NS(=O)(=O)C1=CC(O)=C(Cl)C=C1	4054.3	Standard polar	33892256
3-Hydroxychlorpropamide	CCCNC(=O)NS(=O)(=O)C1=CC(O)=C(Cl)C=C1	1928.5	Standard non polar	33892256
3-Hydroxychlorpropamide	CCCNC(=O)NS(=O)(=O)C1=CC(O)=C(Cl)C=C1	2414.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxychlorpropamide,1TMS,isomer #1	CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C)=C1	2496.1	Semi standard non polar	33892256
3-Hydroxychlorpropamide,1TMS,isomer #2	CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C(O)=C1)[Si](C)(C)C	2406.4	Semi standard non polar	33892256
3-Hydroxychlorpropamide,1TMS,isomer #3	CCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O)=C1	2396.7	Semi standard non polar	33892256
3-Hydroxychlorpropamide,2TMS,isomer #1	CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	2452.5	Semi standard non polar	33892256
3-Hydroxychlorpropamide,2TMS,isomer #1	CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	2607.2	Standard non polar	33892256
3-Hydroxychlorpropamide,2TMS,isomer #1	CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	3118.9	Standard polar	33892256
3-Hydroxychlorpropamide,2TMS,isomer #2	CCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C)=C1	2430.4	Semi standard non polar	33892256
3-Hydroxychlorpropamide,2TMS,isomer #2	CCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C)=C1	2481.3	Standard non polar	33892256
3-Hydroxychlorpropamide,2TMS,isomer #2	CCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C)=C1	3250.0	Standard polar	33892256
3-Hydroxychlorpropamide,2TMS,isomer #3	CCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O)=C1)[Si](C)(C)C	2329.6	Semi standard non polar	33892256
3-Hydroxychlorpropamide,2TMS,isomer #3	CCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O)=C1)[Si](C)(C)C	2621.9	Standard non polar	33892256
3-Hydroxychlorpropamide,2TMS,isomer #3	CCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O)=C1)[Si](C)(C)C	3146.7	Standard polar	33892256
3-Hydroxychlorpropamide,3TMS,isomer #1	CCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	2411.6	Semi standard non polar	33892256
3-Hydroxychlorpropamide,3TMS,isomer #1	CCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	2761.1	Standard non polar	33892256
3-Hydroxychlorpropamide,3TMS,isomer #1	CCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	2921.1	Standard polar	33892256
3-Hydroxychlorpropamide,1TBDMS,isomer #1	CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C(C)(C)C)=C1	2774.4	Semi standard non polar	33892256
3-Hydroxychlorpropamide,1TBDMS,isomer #2	CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C(O)=C1)[Si](C)(C)C(C)(C)C	2621.1	Semi standard non polar	33892256
3-Hydroxychlorpropamide,1TBDMS,isomer #3	CCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O)=C1	2647.3	Semi standard non polar	33892256
3-Hydroxychlorpropamide,2TBDMS,isomer #1	CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2916.0	Semi standard non polar	33892256
3-Hydroxychlorpropamide,2TBDMS,isomer #1	CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	3091.2	Standard non polar	33892256
3-Hydroxychlorpropamide,2TBDMS,isomer #1	CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	3216.2	Standard polar	33892256
3-Hydroxychlorpropamide,2TBDMS,isomer #2	CCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C(C)(C)C)=C1	2952.0	Semi standard non polar	33892256
3-Hydroxychlorpropamide,2TBDMS,isomer #2	CCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C(C)(C)C)=C1	2978.6	Standard non polar	33892256
3-Hydroxychlorpropamide,2TBDMS,isomer #2	CCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C(C)(C)C)=C1	3336.8	Standard polar	33892256
3-Hydroxychlorpropamide,2TBDMS,isomer #3	CCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O)=C1)[Si](C)(C)C(C)(C)C	2833.4	Semi standard non polar	33892256
3-Hydroxychlorpropamide,2TBDMS,isomer #3	CCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O)=C1)[Si](C)(C)C(C)(C)C	3115.5	Standard non polar	33892256
3-Hydroxychlorpropamide,2TBDMS,isomer #3	CCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O)=C1)[Si](C)(C)C(C)(C)C	3204.4	Standard polar	33892256
3-Hydroxychlorpropamide,3TBDMS,isomer #1	CCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	3172.9	Semi standard non polar	33892256
3-Hydroxychlorpropamide,3TBDMS,isomer #1	CCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	3501.4	Standard non polar	33892256
3-Hydroxychlorpropamide,3TBDMS,isomer #1	CCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	3136.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxychlorpropamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-9540000000-32a696ffbd1c5d5bbb9f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxychlorpropamide GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9521000000-b6821daf7262d34986d7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxychlorpropamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxychlorpropamide 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 - 3-Hydroxychlorpropamide 10V, Positive-QTOF	splash10-0a4l-5190000000-20f50c3b74ff7ae8871d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxychlorpropamide 20V, Positive-QTOF	splash10-0a4l-9130000000-d1f48905062354513183	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxychlorpropamide 40V, Positive-QTOF	splash10-0006-9200000000-5724fbfec34c86c6818d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxychlorpropamide 10V, Negative-QTOF	splash10-052f-1090000000-cea1129a5bbbf48d146d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxychlorpropamide 20V, Negative-QTOF	splash10-0a4i-1190000000-f87fcb79dfb309960a13	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxychlorpropamide 40V, Negative-QTOF	splash10-056r-9650000000-c6092a0d50fbc4a970e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxychlorpropamide 10V, Negative-QTOF	splash10-0006-0090000000-75b008683a366c287095	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxychlorpropamide 20V, Negative-QTOF	splash10-0a4l-0390000000-e67eeff8dcd2506c5592	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxychlorpropamide 40V, Negative-QTOF	splash10-001i-9420000000-3bbf221122058c4fbc26	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxychlorpropamide 10V, Positive-QTOF	splash10-0006-1390000000-533fc383547375697911	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxychlorpropamide 20V, Positive-QTOF	splash10-004l-1910000000-6c2254e1941e1abead49	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxychlorpropamide 40V, Positive-QTOF	splash10-004l-4900000000-0632cd5babaead18b7fa	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

30776729

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131750724

PDB ID

Not Available

ChEBI ID

143302

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 3-Hydroxychlorpropamide (HMDB0014025)

MOL for HMDB0014025 (3-Hydroxychlorpropamide)

3D MOL for HMDB0014025 (3-Hydroxychlorpropamide)

3D SDF for HMDB0014025 (3-Hydroxychlorpropamide)

3D-SDF for HMDB0014025 (3-Hydroxychlorpropamide)

PDB for HMDB0014025 (3-Hydroxychlorpropamide)

3D PDB for HMDB0014025 (3-Hydroxychlorpropamide)

SMILES for HMDB0014025 (3-Hydroxychlorpropamide)

INCHI for HMDB0014025 (3-Hydroxychlorpropamide)

Structure for HMDB0014025 (3-Hydroxychlorpropamide)

3D Structure for HMDB0014025 (3-Hydroxychlorpropamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra