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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014810

Secondary Accession Numbers

HMDB14810

Metabolite Identification

Common Name

Chlorpropamide

Description

Chlorpropamide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating I cells of the pancreas to release insulin. Sulfonylureas increase both basal insulin secretion and meal-stimulated insulin release. Medications in this class differ in their dose, rate of absorption, duration of action, route of elimination and binding site on their target pancreatic I cell receptor. Sulfonylureas also increase peripheral glucose utilization, decrease hepatic gluconeogenesis and may increase the number and sensitivity of insulin receptors. Sulfonylureas are associated with weight gain, though less so than insulin. Due to their mechanism of action, sulfonylureas may cause hypoglycemia and require consistent food intake to decrease this risk. The risk of hypoglycemia is increased in elderly, debilitated and malnourished individuals. Chlorpropamide is not recommended for the treatment of NIDDM as it increases blood pressure and the risk of retinopathy (UKPDS-33). Up to 80% of the single oral dose of chlorpropramide is metabolized, likely in the liver; 80-90% of the dose is excreted in urine as unchanged drug and metabolites. Renal and hepatic dysfunction may increase the risk of hypoglycemia.

Structure

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

HMDB0014810
     RDKit          3D
Chlorpropamide
 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.6525    1.4923   -0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2455    1.3734    0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4044    0.1877    1.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1842    0.2408    0.2423 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813   -0.7597    0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3348   -1.7306    1.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188   -0.6330   -0.4641 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2241   -1.8289   -0.3865 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.9282   -2.7624    0.7606 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2800   -2.5858   -1.6932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7176   -0.9873   -0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1065   -0.7973    1.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2949   -0.1289    1.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0963    0.3514    0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6060    1.1984    0.8536 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.7089    0.1623   -0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5321   -0.5004   -1.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7904    1.4161   -1.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4069    0.7218   -0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1707    2.4911   -0.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6792    2.2975    0.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1590    1.3883    1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0901    0.1856    2.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118   -0.7825    0.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0567    1.0574   -0.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0932    0.1704   -1.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5147   -1.1536    2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5954    0.0158    2.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3552    0.5478   -1.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2332   -0.6478   -2.0786 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  2  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  7 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
 17 30  1  0
M  END

672
  Mrv0541 02231214552D          

 17 17  0  0  0  0            999 V2000
    2.4751   -3.5063    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185    3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -2.6813    0.0000 C   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
M  END
> <DATABASE_ID>
HMDB0014810

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H13ClN2O3S/c1-2-7-12-10(14)13-17(15,16)9-5-3-8(11)4-6-9/h3-6H,2,7H2,1H3,(H2,12,13,14)

> <INCHI_KEY>
RKWGIWYCVPQPMF-UHFFFAOYSA-N

> <FORMULA>
C10H13ClN2O3S

> <MOLECULAR_WEIGHT>
276.74

> <EXACT_MASS>
276.033540689

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.057008511382723

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-chlorobenzenesulfonyl)-3-propylurea

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
1.941390449333333

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.070932277227744

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.32916679400861

> <JCHEM_POLAR_SURFACE_AREA>
75.27

> <JCHEM_REFRACTIVITY>
65.43260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chlorpropamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014810
     RDKit          3D
Chlorpropamide
 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.6525    1.4923   -0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2455    1.3734    0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4044    0.1877    1.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1842    0.2408    0.2423 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813   -0.7597    0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3348   -1.7306    1.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188   -0.6330   -0.4641 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2241   -1.8289   -0.3865 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.9282   -2.7624    0.7606 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2800   -2.5858   -1.6932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7176   -0.9873   -0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1065   -0.7973    1.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2949   -0.1289    1.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0963    0.3514    0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6060    1.1984    0.8536 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.7089    0.1623   -0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5321   -0.5004   -1.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7904    1.4161   -1.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4069    0.7218   -0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1707    2.4911   -0.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6792    2.2975    0.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1590    1.3883    1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0901    0.1856    2.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118   -0.7825    0.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0567    1.0574   -0.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0932    0.1704   -1.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5147   -1.1536    2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5954    0.0158    2.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3552    0.5478   -1.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2332   -0.6478   -2.0786 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  2  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  7 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 672                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       4.620  -6.545   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0       4.620  -0.385   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       3.080  -0.385   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.160  -0.385   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.288   1.155   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       4.620   1.155   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       5.954   3.465   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.288   4.235   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.620  -1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.288   5.775   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.954   1.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.954  -2.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.286  -2.695   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.621   6.545   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.954  -4.235   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.286  -4.235   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.620  -5.005   0.000  0.00  0.00           C+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                                                       
CONECT   16   13   17                                                       
CONECT   17    1   15   16                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0014810
HETATM    1  C1  UNL     1      -4.652   1.492  -0.728  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.245   1.373   0.706  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.404   0.188   1.020  1.00  0.00           C  
HETATM    4  N1  UNL     1      -2.184   0.241   0.242  1.00  0.00           N  
HETATM    5  C4  UNL     1      -1.181  -0.760   0.330  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.335  -1.731   1.098  1.00  0.00           O  
HETATM    7  N2  UNL     1      -0.019  -0.633  -0.464  1.00  0.00           N  
HETATM    8  S1  UNL     1       1.224  -1.829  -0.386  1.00  0.00           S  
HETATM    9  O2  UNL     1       0.928  -2.762   0.761  1.00  0.00           O  
HETATM   10  O3  UNL     1       1.280  -2.586  -1.693  1.00  0.00           O  
HETATM   11  C5  UNL     1       2.718  -0.987  -0.065  1.00  0.00           C  
HETATM   12  C6  UNL     1       3.106  -0.797   1.243  1.00  0.00           C  
HETATM   13  C7  UNL     1       4.295  -0.129   1.543  1.00  0.00           C  
HETATM   14  C8  UNL     1       5.096   0.351   0.505  1.00  0.00           C  
HETATM   15 CL1  UNL     1       6.606   1.198   0.854  1.00  0.00          CL  
HETATM   16  C9  UNL     1       4.709   0.162  -0.802  1.00  0.00           C  
HETATM   17  C10 UNL     1       3.532  -0.500  -1.052  1.00  0.00           C  
HETATM   18  H1  UNL     1      -3.790   1.416  -1.411  1.00  0.00           H  
HETATM   19  H2  UNL     1      -5.407   0.722  -0.959  1.00  0.00           H  
HETATM   20  H3  UNL     1      -5.171   2.491  -0.829  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.679   2.298   0.995  1.00  0.00           H  
HETATM   22  H5  UNL     1      -5.159   1.388   1.349  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.090   0.186   2.093  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.912  -0.782   0.860  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.057   1.057  -0.402  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.093   0.170  -1.090  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.515  -1.154   2.079  1.00  0.00           H  
HETATM   28  H11 UNL     1       4.595   0.016   2.563  1.00  0.00           H  
HETATM   29  H12 UNL     1       5.355   0.548  -1.570  1.00  0.00           H  
HETATM   30  H13 UNL     1       3.233  -0.648  -2.079  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4   23   24
CONECT    4    5   25
CONECT    5    6    6    7
CONECT    7    8   26
CONECT    8    9    9   10   10
CONECT    8   11
CONECT   11   12   12   17
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   15   16
CONECT   16   17   17   29
CONECT   17   30
END

HMDB0014810
     RDKit          3D
Chlorpropamide
 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.6525    1.4923   -0.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2455    1.3734    0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4044    0.1877    1.0197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1842    0.2408    0.2423 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813   -0.7597    0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3348   -1.7306    1.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188   -0.6330   -0.4641 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2241   -1.8289   -0.3865 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.9282   -2.7624    0.7606 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2800   -2.5858   -1.6932 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7176   -0.9873   -0.0653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1065   -0.7973    1.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2949   -0.1289    1.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0963    0.3514    0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6060    1.1984    0.8536 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.7089    0.1623   -0.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5321   -0.5004   -1.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7904    1.4161   -1.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4069    0.7218   -0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1707    2.4911   -0.8294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6792    2.2975    0.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1590    1.3883    1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0901    0.1856    2.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9118   -0.7825    0.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0567    1.0574   -0.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0932    0.1704   -1.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5147   -1.1536    2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5954    0.0158    2.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3552    0.5478   -1.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2332   -0.6478   -2.0786 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  2  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  7 26  1  0
 12 27  1  0
 13 28  1  0
 16 29  1  0
 17 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(p-Chlorobenzenesulfonyl)-3-propylurea	ChEBI
1-(p-Chlorophenylsulfonyl)-3-propylurea	ChEBI
1-Propyl-3-(p-chlorobenzenesulfonyl)urea	ChEBI
4-Chloro-N-((propylamino)carbonyl)benzenesulfonamide	ChEBI
4-Chloro-N-[(propylamino)carbonyl]benzenesulfonamide	ChEBI
Chlorpropamidum	ChEBI
Clorpropamida	ChEBI
N-(4-Chlorophenylsulfonyl)-n'-propylurea	ChEBI
N-(p-Chlorobenzenesulfonyl)-n'-propylurea	ChEBI
N-Propyl-n'-(p-chlorobenzenesulfonyl)urea	ChEBI
N-Propyl-n'-p-chlorophenylsulfonylcarbamide	ChEBI
Diabinese	Kegg
1-(p-Chlorobenzenesulphonyl)-3-propylurea	Generator
1-(p-Chlorophenylsulphonyl)-3-propylurea	Generator
1-Propyl-3-(p-chlorobenzenesulphonyl)urea	Generator
4-Chloro-N-((propylamino)carbonyl)benzenesulphonamide	Generator
4-Chloro-N-[(propylamino)carbonyl]benzenesulphonamide	Generator
N-(4-Chlorophenylsulphonyl)-n'-propylurea	Generator
N-(p-Chlorobenzenesulphonyl)-n'-propylurea	Generator
N-Propyl-n'-(p-chlorobenzenesulphonyl)urea	Generator
N-Propyl-n'-p-chlorophenylsulphonylcarbamide	Generator
Chlorporpamide	HMDB
Apotex brand OF chlorpropamide	HMDB
Farmasierra brand OF chlorpropamide	HMDB
Insogen	HMDB
Clorpropamid	HMDB
Pfizer brand OF chlorpropamide	HMDB
Apo-chlorpropamide	HMDB
Byk gulden brand OF chlorpropamide	HMDB
Glucamide	HMDB
Meldian	HMDB

Chemical Formula

C₁₀H₁₃ClN₂O₃S

Average Molecular Weight

276.74

Monoisotopic Molecular Weight

276.033540689

IUPAC Name

1-(4-chlorobenzenesulfonyl)-3-propylurea

Traditional Name

chlorpropamide

CAS Registry Number

94-20-2

SMILES

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

InChI Identifier

InChI=1S/C10H13ClN2O3S/c1-2-7-12-10(14)13-17(15,16)9-5-3-8(11)4-6-9/h3-6H,2,7H2,1H3,(H2,12,13,14)

InChI Key

RKWGIWYCVPQPMF-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
Chlorobenzene
Halobenzene
Sulfonylurea
Aryl chloride
Aryl halide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Carboximidic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monochlorobenzenes (CHEBI:3650 )
N-sulfonylurea (CHEBI:3650 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014810)
Membrane (HMDB: HMDB0014810)

Source

Exogenous

Exogenous (HMDB: HMDB0014810)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	127 - 129 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.16 g/L	Not Available
LogP	1.8	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	158.493	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000785

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.16 g/L	ALOGPS
logP	2.15	ALOGPS
logP	1.94	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.33	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.27 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	65.43 m³·mol⁻¹	ChemAxon
Polarizability	27.06 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]+	159.591	30932474
DeepCCS	[M-H]-	157.232	30932474
DeepCCS	[M-2H]-	190.118	30932474
DeepCCS	[M+Na]+	165.684	30932474
AllCCS	[M+H]+	158.8	32859911
AllCCS	[M+H-H2O]+	155.5	32859911
AllCCS	[M+NH4]+	161.9	32859911
AllCCS	[M+Na]+	162.8	32859911
AllCCS	[M-H]-	157.1	32859911
AllCCS	[M+Na-2H]-	157.6	32859911
AllCCS	[M+HCOO]-	158.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chlorpropamide	CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1	3623.0	Standard polar	33892256
Chlorpropamide	CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1	1659.8	Standard non polar	33892256
Chlorpropamide	CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1	2229.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chlorpropamide,1TMS,isomer #1	CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C	2240.7	Semi standard non polar	33892256
Chlorpropamide,1TMS,isomer #1	CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C	2331.4	Standard non polar	33892256
Chlorpropamide,1TMS,isomer #1	CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C	3146.6	Standard polar	33892256
Chlorpropamide,1TMS,isomer #2	CCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1	2224.8	Semi standard non polar	33892256
Chlorpropamide,1TMS,isomer #2	CCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1	2211.1	Standard non polar	33892256
Chlorpropamide,1TMS,isomer #2	CCCNC(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1	3175.9	Standard polar	33892256
Chlorpropamide,2TMS,isomer #1	CCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C	2184.8	Semi standard non polar	33892256
Chlorpropamide,2TMS,isomer #1	CCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C	2462.0	Standard non polar	33892256
Chlorpropamide,2TMS,isomer #1	CCCN(C(=O)N([Si](C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C	2867.2	Standard polar	33892256
Chlorpropamide,1TBDMS,isomer #1	CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	2475.3	Semi standard non polar	33892256
Chlorpropamide,1TBDMS,isomer #1	CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	2565.5	Standard non polar	33892256
Chlorpropamide,1TBDMS,isomer #1	CCCN(C(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	3156.9	Standard polar	33892256
Chlorpropamide,1TBDMS,isomer #2	CCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1	2465.9	Semi standard non polar	33892256
Chlorpropamide,1TBDMS,isomer #2	CCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1	2454.0	Standard non polar	33892256
Chlorpropamide,1TBDMS,isomer #2	CCCNC(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1	3199.8	Standard polar	33892256
Chlorpropamide,2TBDMS,isomer #1	CCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	2703.0	Semi standard non polar	33892256
Chlorpropamide,2TBDMS,isomer #1	CCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	2933.2	Standard non polar	33892256
Chlorpropamide,2TBDMS,isomer #1	CCCN(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	2971.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorpropamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0113-9540000000-ff74b5bd46b836406ce0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorpropamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chlorpropamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide LC-ESI-qTof , Positive-QTOF	splash10-0002-0093000000-fa4d8bff1a5b0d68d8ea	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide LC-ESI-qTof , Positive-QTOF	splash10-006x-0910000000-a09d8795a568a12a0da3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide LC-ESI-qTof , Positive-QTOF	splash10-03dr-2910000000-7ee6a1f4754e3058ddb6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide , positive-QTOF	splash10-0002-0093000000-fa4d8bff1a5b0d68d8ea	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide , positive-QTOF	splash10-006x-0910000000-a09d8795a568a12a0da3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide , positive-QTOF	splash10-03dr-2910000000-7ee6a1f4754e3058ddb6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide 40V, Positive-QTOF	splash10-03di-1900000000-31862fa36dca6aa815d5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide 15V, Negative-QTOF	splash10-000i-0930000000-a4253aba18424677d03f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide 10V, Positive-QTOF	splash10-03kc-4920000000-e03da1b44dcb4895f948	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide 20V, Positive-QTOF	splash10-03k9-2900000000-a8d91ed685eb991c0ac7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide 30V, Negative-QTOF	splash10-000i-0900000000-85959c7674668f778a7c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide 45V, Negative-QTOF	splash10-000i-0900000000-f4650a1be90ea4cf8904	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide 75V, Negative-QTOF	splash10-004i-9800000000-20116e7d84b9426dc372	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide 60V, Negative-QTOF	splash10-004r-1900000000-8e5466a5890f95e1d7f1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide 90V, Positive-QTOF	splash10-004i-9100000000-c0d2de9234d984d4f5f5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide 40V, Negative-QTOF	splash10-004i-9700000000-2dbf7aa3bcc58d7e7a0d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide 20V, Negative-QTOF	splash10-000i-0900000000-5c15ec0e7d272f3993ed	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide 90V, Negative-QTOF	splash10-004i-9100000000-f15d3a6d15e1e36c1800	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chlorpropamide 10V, Negative-QTOF	splash10-000i-0930000000-87e8123fe243c4d02b51	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpropamide 10V, Positive-QTOF	splash10-056u-8590000000-b6a0b930daf60d890749	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpropamide 20V, Positive-QTOF	splash10-052f-9300000000-86daf757c19ffd3a6335	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpropamide 40V, Positive-QTOF	splash10-0006-9100000000-56249e018d50bc39c02c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpropamide 10V, Negative-QTOF	splash10-00or-1290000000-3bb07392bdb6a7a3e697	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpropamide 20V, Negative-QTOF	splash10-000i-1930000000-99f0f1615af7f850d180	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chlorpropamide 40V, Negative-QTOF	splash10-009i-6920000000-44e9f4535c61cee0a9c3	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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 DB00672	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00672	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00672

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2626

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chlorpropamide

METLIN ID

Not Available

PubChem Compound

2727

PDB ID

Not Available

ChEBI ID

3650

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 Chlorpropamide (HMDB0014810)

MOL for HMDB0014810 (Chlorpropamide)

3D MOL for HMDB0014810 (Chlorpropamide)

3D SDF for HMDB0014810 (Chlorpropamide)

3D-SDF for HMDB0014810 (Chlorpropamide)

PDB for HMDB0014810 (Chlorpropamide)

3D PDB for HMDB0014810 (Chlorpropamide)

SMILES for HMDB0014810 (Chlorpropamide)

INCHI for HMDB0014810 (Chlorpropamide)

Structure for HMDB0014810 (Chlorpropamide)

3D Structure for HMDB0014810 (Chlorpropamide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra