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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (19) Show 23 proteins XML

enzymes (4)transporters (19) Show 23 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015166

Secondary Accession Numbers

HMDB15166

Metabolite Identification

Common Name

Probenecid

Description

Probenecid, also known as probenecid acid or benemid, 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. Probenecid is a drug which is used for the reduction of serum uric acid concentrations in chronic gouty arthritis and tophaceous gout in patients with frequent disabling gout attacks. has also been effectively used to promote uric acid excretion in hyperuricemia secondary to the administration of thiazide and related diuretics. . A sulfonamide in which the nitrogen of 4-sulfamoylbenzoic acid is substituted with two propyl groups. Probenecid is a weakly acidic compound (based on its pKa).

Structure

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

HMDB0015166
     RDKit          3D
Probenecid
 38 38  0  0  0  0  0  0  0  0999 V2000
   -1.5574   -0.7749    3.7696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9601   -0.1210    2.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2209   -0.8086    1.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5547   -0.2413    0.0471 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9053   -1.1166   -0.9994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2278   -0.9607   -1.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5224    0.3430   -2.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5251    1.0389   -0.3592 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.7042    2.0980    0.7326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707    1.7251   -1.6236 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383    0.5865   -0.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6786    0.1386   -1.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0159   -0.2147   -1.7852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8685   -0.1330   -0.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2741   -0.5067   -0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7704   -0.9135   -1.8648 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0790   -0.4079    0.3198 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3187    0.3169    0.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9786    0.6675    0.5709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5941   -0.3371    4.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3113   -0.5509    4.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4266   -1.8684    3.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0297   -0.3252    2.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6966    0.9320    2.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1441   -0.6389    1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4638   -1.8942    1.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7757   -2.1624   -0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1089   -1.0223   -1.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0883   -1.1937   -0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3011   -1.7448   -2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5645    0.2304   -2.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8812    0.5819   -3.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6306    1.1993   -1.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0480    0.0567   -2.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4604   -0.5674   -2.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9978   -0.8237    0.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542    0.3933    1.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5826    1.0148    1.5037 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  1  0
  4  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
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  2  0
 19 11  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
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
 12 34  1  0
 13 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
M  END

1032
  Mrv0541 02231215112D          

 19 19  0  0  0  0            999 V2000
    3.0791    0.8745    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540    0.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9041    0.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.8381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.8381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.6995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  2  0  0  0  0
  1  6  1  0  0  0  0
  1 11  1  0  0  0  0
  4 19  1  0  0  0  0
  5 19  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  2  0  0  0  0
 11 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015166

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H19NO4S/c1-3-9-14(10-4-2)19(17,18)12-7-5-11(6-8-12)13(15)16/h5-8H,3-4,9-10H2,1-2H3,(H,15,16)

> <INCHI_KEY>
DBABZHXKTCFAPX-UHFFFAOYSA-N

> <FORMULA>
C13H19NO4S

> <MOLECULAR_WEIGHT>
285.359

> <EXACT_MASS>
285.103478791

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.963000414702236

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(dipropylsulfamoyl)benzoic acid

> <ALOGPS_LOGP>
1.52

> <JCHEM_LOGP>
2.442872324333333

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.534349644303132

> <JCHEM_POLAR_SURFACE_AREA>
74.67999999999999

> <JCHEM_REFRACTIVITY>
73.8107

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
probenecid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015166
     RDKit          3D
Probenecid
 38 38  0  0  0  0  0  0  0  0999 V2000
   -1.5574   -0.7749    3.7696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9601   -0.1210    2.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2209   -0.8086    1.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5547   -0.2413    0.0471 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9053   -1.1166   -0.9994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2278   -0.9607   -1.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5224    0.3430   -2.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5251    1.0389   -0.3592 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.7042    2.0980    0.7326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707    1.7251   -1.6236 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383    0.5865   -0.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6786    0.1386   -1.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0159   -0.2147   -1.7852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8685   -0.1330   -0.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2741   -0.5067   -0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7704   -0.9135   -1.8648 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0790   -0.4079    0.3198 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3187    0.3169    0.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9786    0.6675    0.5709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5941   -0.3371    4.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3113   -0.5509    4.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4266   -1.8684    3.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0297   -0.3252    2.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6966    0.9320    2.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1441   -0.6389    1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4638   -1.8942    1.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7757   -2.1624   -0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1089   -1.0223   -1.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0883   -1.1937   -0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3011   -1.7448   -2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5645    0.2304   -2.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8812    0.5819   -3.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6306    1.1993   -1.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0480    0.0567   -2.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4604   -0.5674   -2.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9978   -0.8237    0.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542    0.3933    1.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5826    1.0148    1.5037 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  1  0
  4  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
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  2  0
 19 11  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
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
 12 34  1  0
 13 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1032                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       5.748   1.632   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       4.207   1.632   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.288   1.632   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.414  -5.298   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.081  -5.298   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       5.748   3.172   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.081   3.942   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414   3.942   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   5.483   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   5.483   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748   0.092   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415   6.253   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080   6.253   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -0.678   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -0.678   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414  -2.218   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081  -2.218   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748  -2.988   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.748  -4.528   0.000  0.00  0.00           C+0
CONECT    1    2    3    6   11                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   19                                                            
CONECT    5   19                                                            
CONECT    6    1    7    8                                                  
CONECT    7    6    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   12                                                       
CONECT   10    8   13                                                       
CONECT   11    1   14   15                                                  
CONECT   12    9                                                            
CONECT   13   10                                                            
CONECT   14   11   16                                                       
CONECT   15   11   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   18                                                       
CONECT   18   16   17   19                                                  
CONECT   19    4    5   18                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0015166
HETATM    1  C1  UNL     1      -1.557  -0.775   3.770  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.960  -0.121   2.463  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.221  -0.809   1.306  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.555  -0.241   0.047  1.00  0.00           N  
HETATM    5  C4  UNL     1      -1.905  -1.117  -0.999  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.228  -0.961  -1.642  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.522   0.343  -2.298  1.00  0.00           C  
HETATM    8  S1  UNL     1      -0.525   1.039  -0.359  1.00  0.00           S  
HETATM    9  O1  UNL     1      -0.704   2.098   0.733  1.00  0.00           O  
HETATM   10  O2  UNL     1      -0.971   1.725  -1.624  1.00  0.00           O  
HETATM   11  C7  UNL     1       1.138   0.587  -0.510  1.00  0.00           C  
HETATM   12  C8  UNL     1       1.679   0.139  -1.694  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.016  -0.215  -1.785  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.869  -0.133  -0.690  1.00  0.00           C  
HETATM   15  C11 UNL     1       5.274  -0.507  -0.795  1.00  0.00           C  
HETATM   16  O3  UNL     1       5.770  -0.913  -1.865  1.00  0.00           O  
HETATM   17  O4  UNL     1       6.079  -0.408   0.320  1.00  0.00           O  
HETATM   18  C12 UNL     1       3.319   0.317   0.492  1.00  0.00           C  
HETATM   19  C13 UNL     1       1.979   0.667   0.571  1.00  0.00           C  
HETATM   20  H1  UNL     1      -0.594  -0.337   4.115  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.311  -0.551   4.557  1.00  0.00           H  
HETATM   22  H3  UNL     1      -1.427  -1.868   3.666  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.030  -0.325   2.316  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.697   0.932   2.529  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.144  -0.639   1.508  1.00  0.00           H  
HETATM   26  H7  UNL     1      -1.464  -1.894   1.289  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.776  -2.162  -0.635  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.109  -1.022  -1.803  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.088  -1.194  -0.981  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.301  -1.745  -2.456  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.564   0.230  -2.744  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.881   0.582  -3.171  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.631   1.199  -1.616  1.00  0.00           H  
HETATM   34  H15 UNL     1       1.048   0.057  -2.584  1.00  0.00           H  
HETATM   35  H16 UNL     1       3.460  -0.567  -2.700  1.00  0.00           H  
HETATM   36  H17 UNL     1       6.998  -0.824   0.397  1.00  0.00           H  
HETATM   37  H18 UNL     1       3.954   0.393   1.367  1.00  0.00           H  
HETATM   38  H19 UNL     1       1.583   1.015   1.504  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5    8
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7   31   32   33
CONECT    8    9    9   10   10
CONECT    8   11
CONECT   11   12   12   19
CONECT   12   13   34
CONECT   13   14   14   35
CONECT   14   15   18
CONECT   15   16   16   17
CONECT   17   36
CONECT   18   19   19   37
CONECT   19   38
END

HMDB0015166
     RDKit          3D
Probenecid
 38 38  0  0  0  0  0  0  0  0999 V2000
   -1.5574   -0.7749    3.7696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9601   -0.1210    2.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2209   -0.8086    1.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5547   -0.2413    0.0471 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9053   -1.1166   -0.9994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2278   -0.9607   -1.6418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5224    0.3430   -2.2984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5251    1.0389   -0.3592 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.7042    2.0980    0.7326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9707    1.7251   -1.6236 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383    0.5865   -0.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6786    0.1386   -1.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0159   -0.2147   -1.7852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8685   -0.1330   -0.6901 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2741   -0.5067   -0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7704   -0.9135   -1.8648 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0790   -0.4079    0.3198 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3187    0.3169    0.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9786    0.6675    0.5709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5941   -0.3371    4.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3113   -0.5509    4.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4266   -1.8684    3.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0297   -0.3252    2.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6966    0.9320    2.5290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1441   -0.6389    1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4638   -1.8942    1.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7757   -2.1624   -0.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1089   -1.0223   -1.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0883   -1.1937   -0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3011   -1.7448   -2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5645    0.2304   -2.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8812    0.5819   -3.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6306    1.1993   -1.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0480    0.0567   -2.5844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4604   -0.5674   -2.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9978   -0.8237    0.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9542    0.3933    1.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5826    1.0148    1.5037 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  1  0
  4  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
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  2  0
 19 11  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
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
 12 34  1  0
 13 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-((Dipropylamino)sulfonyl)benzoic acid	ChEBI
4-(Di-N-propylsulfamoyl)benzoesaeure	ChEBI
4-(N,N-Dipropylsulfamoyl)benzoesaeure	ChEBI
p-(Dipropylsulfamoyl)benzoic acid	ChEBI
Probenecid acid	ChEBI
Probenecida	ChEBI
Probenecide	ChEBI
Probenecidum	ChEBI
Benemid	Kegg
4-((Dipropylamino)sulfonyl)benzoate	Generator
4-((Dipropylamino)sulphonyl)benzoate	Generator
4-((Dipropylamino)sulphonyl)benzoic acid	Generator
4-(Di-N-propylsulphamoyl)benzoesaeure	Generator
4-(N,N-Dipropylsulphamoyl)benzoesaeure	Generator
p-(Dipropylsulfamoyl)benzoate	Generator
p-(Dipropylsulphamoyl)benzoate	Generator
p-(Dipropylsulphamoyl)benzoic acid	Generator
Probenicid	HMDB
Biokanol brand OF probenecid	HMDB
Ophthalmic brand OF probenecid	HMDB
Probenecid martec brand	HMDB
Merck brand OF probenecid	HMDB
Probenecid major brand	HMDB
Probenecid parmed brand	HMDB
Probenecid weimer	HMDB
Zenith brand OF probenecid	HMDB
Benecid	HMDB
Benuryl	HMDB
ICN brand OF probenecid	HMDB
IDIS brand OF probenecid	HMDB
Martec brand OF probenecid	HMDB
Pro-cid	HMDB
Probecid	HMDB
Probenecid zenith brand	HMDB
Major brand OF probenecid	HMDB
Parmed brand OF probenecid	HMDB
Valdecasas brand OF probenecid	HMDB

Chemical Formula

C₁₃H₁₉NO₄S

Average Molecular Weight

285.359

Monoisotopic Molecular Weight

285.103478791

IUPAC Name

4-(dipropylsulfamoyl)benzoic acid

Traditional Name

probenecid

CAS Registry Number

57-66-9

SMILES

CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(O)=O

InChI Identifier

InChI=1S/C13H19NO4S/c1-3-9-14(10-4-2)19(17,18)12-7-5-11(6-8-12)13(15)16/h5-8H,3-4,9-10H2,1-2H3,(H,15,16)

InChI Key

DBABZHXKTCFAPX-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Benzenesulfonamides

Alternative Parents

Substituents

Benzenesulfonamide
Benzoic acid or derivatives
Benzoic acid
Benzenesulfonyl group
Benzoyl
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Aminosulfonyl compound
Sulfonyl
Organosulfonic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organooxygen compound
Organosulfur compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

sulfonamide (CHEBI:8426 )
benzoic acids (CHEBI:8426 )

Ontology

Not Available

Urine (PMID: 21059682)
Feces (PMID: 27275383)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015166)
Membrane (HMDB: HMDB0015166)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	195 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.42 g/L	Not Available
LogP	2.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	161.436	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000794

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.42 g/L	ALOGPS
logP	1.52	ALOGPS
logP	2.44	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.68 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	73.81 m³·mol⁻¹	ChemAxon
Polarizability	29.96 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]+	168.022	31661259
DarkChem	[M-H]-	166.505	31661259
DeepCCS	[M+H]+	167.005	30932474
DeepCCS	[M-H]-	164.647	30932474
DeepCCS	[M-2H]-	197.533	30932474
DeepCCS	[M+Na]+	173.099	30932474
AllCCS	[M+H]+	165.8	32859911
AllCCS	[M+H-H2O]+	162.6	32859911
AllCCS	[M+NH4]+	168.8	32859911
AllCCS	[M+Na]+	169.7	32859911
AllCCS	[M-H]-	163.7	32859911
AllCCS	[M+Na-2H]-	164.2	32859911
AllCCS	[M+HCOO]-	164.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Probenecid	CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(O)=O	3686.0	Standard polar	33892256
Probenecid	CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(O)=O	2386.4	Standard non polar	33892256
Probenecid	CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(O)=O	2298.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Probenecid,1TMS,isomer #1	CCCN(CCC)S(=O)(=O)C1=CC=C(C(=O)O[Si](C)(C)C)C=C1	2229.3	Semi standard non polar	33892256
Probenecid,1TBDMS,isomer #1	CCCN(CCC)S(=O)(=O)C1=CC=C(C(=O)O[Si](C)(C)C(C)(C)C)C=C1	2510.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Probenecid GC-MS (Non-derivatized) - 70eV, Positive	splash10-005c-9430000000-66fa2eec09e65b520fd4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Probenecid GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9322000000-86b32ee67219d76aee32	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Probenecid 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 - Probenecid LC-ESI-qTof , Positive-QTOF	splash10-0f76-0190000000-ce053a8c64308bc3ebbb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Probenecid LC-ESI-qTof , Positive-QTOF	splash10-0f76-0190000000-f6f2df3671a359ea4574	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Probenecid , positive-QTOF	splash10-0f76-0190000000-f6f2df3671a359ea4574	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Probenecid , positive-QTOF	splash10-0f76-0190000000-ce053a8c64308bc3ebbb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Probenecid , positive-QTOF	splash10-0fen-3950100000-c43ebdb497f6a0e8c974	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Probenecid 75V, Positive-QTOF	splash10-03di-9000000000-5663daf3af027bcf4bd5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Probenecid 75V, Negative-QTOF	splash10-03di-9000000000-3280579def3da504b6e3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Probenecid 90V, Negative-QTOF	splash10-03di-9000000000-f7e60026073ba954d843	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Probenecid 30V, Negative-QTOF	splash10-03dm-3920000000-d373c6be2068a852f878	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Probenecid 15V, Negative-QTOF	splash10-000y-1980000000-e8ccc1214006fa858e38	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Probenecid 45V, Negative-QTOF	splash10-03di-9500000000-62dfa7da11ed364a0fe9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Probenecid 60V, Negative-QTOF	splash10-03di-9100000000-40231ffb30b72d29e268	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Probenecid 10V, Positive-QTOF	splash10-00ko-2090000000-e9339c027711ad986a00	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Probenecid 20V, Positive-QTOF	splash10-0006-9270000000-89113f1adccbbe5ce2c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Probenecid 40V, Positive-QTOF	splash10-0006-9000000000-c76de17d7d7e7fff001c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Probenecid 10V, Negative-QTOF	splash10-001i-0090000000-fcc637b2f7443930eaa9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Probenecid 20V, Negative-QTOF	splash10-000x-0390000000-d84958808d58246de403	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Probenecid 40V, Negative-QTOF	splash10-03kc-4900000000-81cfffb64fe9ae84692a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Probenecid 10V, Negative-QTOF	splash10-000x-0090000000-7babe007c72f09d68c2e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Probenecid 20V, Negative-QTOF	splash10-0006-1190000000-7f80163c40b7f72b3e08	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Probenecid 40V, Negative-QTOF	splash10-03di-9000000000-b04d355dbd4b8be3a462	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Probenecid 10V, Positive-QTOF	splash10-000i-0090000000-b62a8dd0c7fbd3f45a69	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Probenecid 20V, Positive-QTOF	splash10-0kh3-9450000000-b314f1bcfa44850dacf4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Probenecid 40V, Positive-QTOF	splash10-0a4l-9520000000-e8ccc0bfff93660781c8	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
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 DB01032	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01032	21059682	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB01032

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4742

KEGG Compound ID

C07372

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Probenecid

METLIN ID

Not Available

PubChem Compound

4911

PDB ID

Not Available

ChEBI ID

8426

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

Butler D: Wartime tactic doubles power of scarce bird-flu drug. Nature. 2005 Nov 3;438(7064):6. [PubMed:16267514 ]

Only showing the first 10 proteins. There are 23 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 1C1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent high affinity transport of organic anions such as the thyroid hormones thyroxine (T4) and rT3. Other potential substrates, such as triiodothyronine (T3), 17-beta-glucuronosyl estradiol, estrone-3-sulfate and sulfobromophthalein (BSP) are transported with much lower efficiency
Gene Name:: SLCO1C1
Uniprot ID:: Q9NYB5
Molecular weight:: 78695.6

References

Tohyama K, Kusuhara H, Sugiyama Y: Involvement of multispecific organic anion transporter, Oatp14 (Slc21a14), in the transport of thyroxine across the blood-brain barrier. Endocrinology. 2004 Sep;145(9):4384-91. Epub 2004 May 27. [PubMed:15166123 ]

Enzyme Details

2. Monocarboxylate transporter 1

General function:: Involved in transmembrane transport
Specific function:: Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate
Gene Name:: SLC16A1
Uniprot ID:: P53985
Molecular weight:: 53957.7

References

Broer S, Broer A, Schneider HP, Stegen C, Halestrap AP, Deitmer JW: Characterization of the high-affinity monocarboxylate transporter MCT2 in Xenopus laevis oocytes. Biochem J. 1999 Aug 1;341 ( Pt 3):529-35. [PubMed:10417314 ]

Enzyme Details

3. Monocarboxylate transporter 2

General function:: Involved in transmembrane transport
Specific function:: Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate. MCT2 is a high affinity pyruvate transporter
Gene Name:: SLC16A7
Uniprot ID:: O60669
Molecular weight:: 52185.7

References

Broer S, Broer A, Schneider HP, Stegen C, Halestrap AP, Deitmer JW: Characterization of the high-affinity monocarboxylate transporter MCT2 in Xenopus laevis oocytes. Biochem J. 1999 Aug 1;341 ( Pt 3):529-35. [PubMed:10417314 ]

Enzyme Details

4. Solute carrier family 22 member 5

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:: SLC22A5
Uniprot ID:: O76082
Molecular weight:: 62751.1

References

Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [PubMed:10525100 ]

Enzyme Details

5. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Hong J, Lambert JD, Lee SH, Sinko PJ, Yang CS: Involvement of multidrug resistance-associated proteins in regulating cellular levels of (-)-epigallocatechin-3-gallate and its methyl metabolites. Biochem Biophys Res Commun. 2003 Oct 10;310(1):222-7. [PubMed:14511674 ]
Ilias A, Urban Z, Seidl TL, Le Saux O, Sinko E, Boyd CD, Sarkadi B, Varadi A: Loss of ATP-dependent transport activity in pseudoxanthoma elasticum-associated mutants of human ABCC6 (MRP6). J Biol Chem. 2002 May 10;277(19):16860-7. Epub 2002 Mar 5. [PubMed:11880368 ]
Bakos E, Evers R, Sinko E, Varadi A, Borst P, Sarkadi B: Interactions of the human multidrug resistance proteins MRP1 and MRP2 with organic anions. Mol Pharmacol. 2000 Apr;57(4):760-8. [PubMed:10727523 ]
Horikawa M, Kato Y, Tyson CA, Sugiyama Y: The potential for an interaction between MRP2 (ABCC2) and various therapeutic agents: probenecid as a candidate inhibitor of the biliary excretion of irinotecan metabolites. Drug Metab Pharmacokinet. 2002;17(1):23-33. [PubMed:15618649 ]
Zamek-Gliszczynski MJ, Xiong H, Patel NJ, Turncliff RZ, Pollack GM, Brouwer KL: Pharmacokinetics of 5 (and 6)-carboxy-2',7'-dichlorofluorescein and its diacetate promoiety in the liver. J Pharmacol Exp Ther. 2003 Feb;304(2):801-9. [PubMed:12538836 ]
Dahan A, Sabit H, Amidon GL: The H2 receptor antagonist nizatidine is a P-glycoprotein substrate: characterization of its intestinal epithelial cell efflux transport. AAPS J. 2009 Jun;11(2):205-13. doi: 10.1208/s12248-009-9092-5. Epub 2009 Mar 25. [PubMed:19319690 ]
Chen C, Scott D, Hanson E, Franco J, Berryman E, Volberg M, Liu X: Impact of Mrp2 on the biliary excretion and intestinal absorption of furosemide, probenecid, and methotrexate using Eisai hyperbilirubinemic rats. Pharm Res. 2003 Jan;20(1):31-7. [PubMed:12608533 ]

Enzyme Details

6. Multidrug resistance-associated protein 1

General function:: Involved in ATP binding
Specific function:: Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:: ABCC1
Uniprot ID:: P33527
Molecular weight:: 171589.5

References

Hong J, Lambert JD, Lee SH, Sinko PJ, Yang CS: Involvement of multidrug resistance-associated proteins in regulating cellular levels of (-)-epigallocatechin-3-gallate and its methyl metabolites. Biochem Biophys Res Commun. 2003 Oct 10;310(1):222-7. [PubMed:14511674 ]
Ilias A, Urban Z, Seidl TL, Le Saux O, Sinko E, Boyd CD, Sarkadi B, Varadi A: Loss of ATP-dependent transport activity in pseudoxanthoma elasticum-associated mutants of human ABCC6 (MRP6). J Biol Chem. 2002 May 10;277(19):16860-7. Epub 2002 Mar 5. [PubMed:11880368 ]
Payen L, Delugin L, Courtois A, Trinquart Y, Guillouzo A, Fardel O: Reversal of MRP-mediated multidrug resistance in human lung cancer cells by the antiprogestatin drug RU486. Biochem Biophys Res Commun. 1999 May 19;258(3):513-8. [PubMed:10329417 ]
Bakos E, Evers R, Sinko E, Varadi A, Borst P, Sarkadi B: Interactions of the human multidrug resistance proteins MRP1 and MRP2 with organic anions. Mol Pharmacol. 2000 Apr;57(4):760-8. [PubMed:10727523 ]
Hooijberg JH, Broxterman HJ, Kool M, Assaraf YG, Peters GJ, Noordhuis P, Scheper RJ, Borst P, Pinedo HM, Jansen G: Antifolate resistance mediated by the multidrug resistance proteins MRP1 and MRP2. Cancer Res. 1999 Jun 1;59(11):2532-5. [PubMed:10363967 ]
Legrand O, Simonin G, Beauchamp-Nicoud A, Zittoun R, Marie JP: Simultaneous activity of MRP1 and Pgp is correlated with in vitro resistance to daunorubicin and with in vivo resistance in adult acute myeloid leukemia. Blood. 1999 Aug 1;94(3):1046-56. [PubMed:10419897 ]
Legrand O, Simonin G, Perrot JY, Zittoun R, Marie JP: Both Pgp and MRP1 activities using calcein-AM contribute to drug resistance in AML. Adv Exp Med Biol. 1999;457:161-75. [PubMed:10500791 ]
Evers R, de Haas M, Sparidans R, Beijnen J, Wielinga PR, Lankelma J, Borst P: Vinblastine and sulfinpyrazone export by the multidrug resistance protein MRP2 is associated with glutathione export. Br J Cancer. 2000 Aug;83(3):375-83. [PubMed:10917554 ]
Issandou M, Grand-Perret T: Multidrug resistance P-glycoprotein is not involved in cholesterol esterification. Biochem Biophys Res Commun. 2000 Dec 20;279(2):369-77. [PubMed:11118294 ]

Enzyme Details

7. Multidrug resistance-associated protein 6

General function:: Involved in ATP binding
Specific function:: May participate directly in the active transport of drugs into subcellular organelles or influence drug distribution indirectly. Transports glutathione conjugates as leukotriene-c4 (LTC4) and N-ethylmaleimide S-glutathione (NEM-GS)
Gene Name:: ABCC6
Uniprot ID:: O95255
Molecular weight:: 164904.8

References

Ilias A, Urban Z, Seidl TL, Le Saux O, Sinko E, Boyd CD, Sarkadi B, Varadi A: Loss of ATP-dependent transport activity in pseudoxanthoma elasticum-associated mutants of human ABCC6 (MRP6). J Biol Chem. 2002 May 10;277(19):16860-7. Epub 2002 Mar 5. [PubMed:11880368 ]

Enzyme Details

8. Canalicular multispecific organic anion transporter 2

General function:: Involved in ATP binding
Specific function:: May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:: ABCC3
Uniprot ID:: O15438
Molecular weight:: 169341.1

References

Zelcer N, Saeki T, Reid G, Beijnen JH, Borst P: Characterization of drug transport by the human multidrug resistance protein 3 (ABCC3). J Biol Chem. 2001 Dec 7;276(49):46400-7. [PubMed:11581266 ]
Zeng H, Chen ZS, Belinsky MG, Rea PA, Kruh GD: Transport of methotrexate (MTX) and folates by multidrug resistance protein (MRP) 3 and MRP1: effect of polyglutamylation on MTX transport. Cancer Res. 2001 Oct 1;61(19):7225-32. [PubMed:11585759 ]
Zamek-Gliszczynski MJ, Xiong H, Patel NJ, Turncliff RZ, Pollack GM, Brouwer KL: Pharmacokinetics of 5 (and 6)-carboxy-2',7'-dichlorofluorescein and its diacetate promoiety in the liver. J Pharmacol Exp Ther. 2003 Feb;304(2):801-9. [PubMed:12538836 ]

Enzyme Details

9. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Gao J, Murase O, Schowen RL, Aube J, Borchardt RT: A functional assay for quantitation of the apparent affinities of ligands of P-glycoprotein in Caco-2 cells. Pharm Res. 2001 Feb;18(2):171-6. [PubMed:11405287 ]
Honda Y, Ushigome F, Koyabu N, Morimoto S, Shoyama Y, Uchiumi T, Kuwano M, Ohtani H, Sawada Y: Effects of grapefruit juice and orange juice components on P-glycoprotein- and MRP2-mediated drug efflux. Br J Pharmacol. 2004 Dec;143(7):856-64. Epub 2004 Oct 25. [PubMed:15504753 ]
Minderman H, Brooks TA, O'Loughlin KL, Ojima I, Bernacki RJ, Baer MR: Broad-spectrum modulation of ATP-binding cassette transport proteins by the taxane derivatives ortataxel (IDN-5109, BAY 59-8862) and tRA96023. Cancer Chemother Pharmacol. 2004 May;53(5):363-9. Epub 2004 Jan 27. [PubMed:15060738 ]

Enzyme Details

10. Solute carrier family 22 member 11

General function:: Involved in transporter activity
Specific function:: Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds
Gene Name:: SLC22A11
Uniprot ID:: Q9NSA0
Molecular weight:: 59970.9

References

Enomoto A, Takeda M, Shimoda M, Narikawa S, Kobayashi Y, Kobayashi Y, Yamamoto T, Sekine T, Cha SH, Niwa T, Endou H: Interaction of human organic anion transporters 2 and 4 with organic anion transport inhibitors. J Pharmacol Exp Ther. 2002 Jun;301(3):797-802. [PubMed:12023506 ]
Babu E, Takeda M, Narikawa S, Kobayashi Y, Enomoto A, Tojo A, Cha SH, Sekine T, Sakthisekaran D, Endou H: Role of human organic anion transporter 4 in the transport of ochratoxin A. Biochim Biophys Acta. 2002 Jun 12;1590(1-3):64-75. [PubMed:12063169 ]
Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]
Hashimoto T, Narikawa S, Huang XL, Minematsu T, Usui T, Kamimura H, Endou H: Characterization of the renal tubular transport of zonampanel, a novel alpha-amino-3-hydroxy-5-methylisoxazole-4-propionic acid receptor antagonist, by human organic anion transporters. Drug Metab Dispos. 2004 Oct;32(10):1096-102. [PubMed:15377641 ]
Khamdang S, Takeda M, Shimoda M, Noshiro R, Narikawa S, Huang XL, Enomoto A, Piyachaturawat P, Endou H: Interactions of human- and rat-organic anion transporters with pravastatin and cimetidine. J Pharmacol Sci. 2004 Feb;94(2):197-202. [PubMed:14978359 ]

Only showing the first 10 proteins. There are 23 proteins in total.

Show all enzymes and transporters

Showing metabocard for Probenecid (HMDB0015166)

MOL for HMDB0015166 (Probenecid)

3D MOL for HMDB0015166 (Probenecid)

3D SDF for HMDB0015166 (Probenecid)

3D-SDF for HMDB0015166 (Probenecid)

PDB for HMDB0015166 (Probenecid)

3D PDB for HMDB0015166 (Probenecid)

SMILES for HMDB0015166 (Probenecid)

INCHI for HMDB0015166 (Probenecid)

Structure for HMDB0015166 (Probenecid)

3D Structure for HMDB0015166 (Probenecid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

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Transporters

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