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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (3) Show 7 proteins XML

enzymes (4)transporters (3) Show 7 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:56 UTC

HMDB ID

HMDB0015328

Secondary Accession Numbers

HMDB15328

Metabolite Identification

Common Name

Captopril

Description

Captopril, also known as capoten or acepress, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Captopril is a drug which is used for the treatment of essential or renovascular hypertension (usually administered with other drugs, particularly thiazide diuretics). may be used to treat congestive heart failure in combination with other drugs (e.g. cardiac glycosides, diuretics, β-adrenergic blockers). may improve survival in patients with left ventricular dysfunction following myocardial infarction. may be used to treat nephropathy, including diabetic nephropathy. . Captopril is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, captopril is involved in captopril action pathway. A L-proline derivative in which L-proline is substituted on nitrogen with a (2S)-2-methyl-3-sulfanylpropanoyl group.

Structure

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

HMDB0015328
     RDKit          3D
Captopril
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.0375    0.8066   -0.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7996    0.6013   -0.1265 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1749   -0.4486    0.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5823    0.1539    1.9175 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7419    0.0195   -0.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1116   -0.3572   -2.1585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047   -0.1512   -0.6209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6582   -0.7088   -1.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8629    0.1516   -1.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5810    0.7762    0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2300    0.2066    0.6252 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4886   -1.0042    1.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1597   -2.1339    1.0418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -0.8614    2.6909 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5582   -0.1418   -1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6354    1.6293   -0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6614    1.1382   -2.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209    1.5390    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3093   -0.5766    1.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4192   -1.3816    0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4527    0.9361    1.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8054   -1.7568   -1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3700   -0.6707   -2.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7589   -0.4833   -1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9584    0.9215   -1.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3727    0.5545    0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4807    1.8629    0.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6591    0.9276    1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9343   -1.5486    3.4289 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
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11  7  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  1
  3 19  1  0
  3 20  1  0
  4 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  1
 14 29  1  0
M  END

1197
  Mrv0541 02231215192D          

 14 14  0  0  1  0            999 V2000
    1.6500   -1.6166    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.3790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1443    1.6406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7026    0.2815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.8585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    1.3435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4916    2.1281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666    2.1281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4115    1.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.3790    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5311    1.0885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  2 10  2  0  0  0  0
  3 12  1  0  0  0  0
  4 12  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0015328

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H](CS)C(=O)N1CCC[C@H]1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H15NO3S/c1-6(5-14)8(11)10-4-2-3-7(10)9(12)13/h6-7,14H,2-5H2,1H3,(H,12,13)/t6-,7+/m1/s1

> <INCHI_KEY>
FAKRSMQSSFJEIM-RQJHMYQMSA-N

> <FORMULA>
C9H15NO3S

> <MOLECULAR_WEIGHT>
217.285

> <EXACT_MASS>
217.077264041

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.720078468093135

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
0.7269212306666664

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.09607365334312

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.018634760841246

> <JCHEM_PKA_STRONGEST_BASIC>
-1.187420826167036

> <JCHEM_POLAR_SURFACE_AREA>
57.61

> <JCHEM_REFRACTIVITY>
54.63490000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.52e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
captopril

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015328
     RDKit          3D
Captopril
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.0375    0.8066   -0.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7996    0.6013   -0.1265 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1749   -0.4486    0.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5823    0.1539    1.9175 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7419    0.0195   -0.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1116   -0.3572   -2.1585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047   -0.1512   -0.6209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6582   -0.7088   -1.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8629    0.1516   -1.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5810    0.7762    0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2300    0.2066    0.6252 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4886   -1.0042    1.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1597   -2.1339    1.0418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -0.8614    2.6909 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5582   -0.1418   -1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6354    1.6293   -0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6614    1.1382   -2.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209    1.5390    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3093   -0.5766    1.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4192   -1.3816    0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4527    0.9361    1.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8054   -1.7568   -1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3700   -0.6707   -2.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7589   -0.4833   -1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9584    0.9215   -1.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3727    0.5545    0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4807    1.8629    0.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6591    0.9276    1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9343   -1.5486    3.4289 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
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11  7  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  1
  3 19  1  0
  3 20  1  0
  4 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  1
 14 29  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1197                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       3.080  -3.018   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       7.081  -0.707   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.603   3.062   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.778   0.525   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       5.748   1.603   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.993   2.508   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.518   3.972   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.978   3.972   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.501   2.508   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748   0.063   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -0.707   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.458   2.032   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -2.247   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   0.063   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2   10                                                            
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5    6    9   10                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    5    8                                                       
CONECT   10    2    5   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12    3    4    6                                                  
CONECT   13    1   11                                                       
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0015328
HETATM    1  C1  UNL     1       3.038   0.807  -0.997  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.800   0.601  -0.127  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.175  -0.449   0.926  1.00  0.00           C  
HETATM    4  S1  UNL     1       3.582   0.154   1.918  1.00  0.00           S  
HETATM    5  C4  UNL     1       0.742   0.020  -0.982  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.112  -0.357  -2.159  1.00  0.00           O  
HETATM    7  N1  UNL     1      -0.605  -0.151  -0.621  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.658  -0.709  -1.436  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.863   0.152  -1.160  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.581   0.776   0.187  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.230   0.207   0.625  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.489  -1.004   1.467  1.00  0.00           C  
HETATM   13  O2  UNL     1      -1.160  -2.134   1.042  1.00  0.00           O  
HETATM   14  O3  UNL     1      -2.080  -0.861   2.691  1.00  0.00           O  
HETATM   15  H1  UNL     1       3.558  -0.142  -1.131  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.635   1.629  -0.598  1.00  0.00           H  
HETATM   17  H3  UNL     1       2.661   1.138  -2.006  1.00  0.00           H  
HETATM   18  H4  UNL     1       1.521   1.539   0.356  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.309  -0.577   1.585  1.00  0.00           H  
HETATM   20  H6  UNL     1       2.419  -1.382   0.405  1.00  0.00           H  
HETATM   21  H7  UNL     1       4.453   0.936   1.139  1.00  0.00           H  
HETATM   22  H8  UNL     1      -1.805  -1.757  -1.172  1.00  0.00           H  
HETATM   23  H9  UNL     1      -1.370  -0.671  -2.522  1.00  0.00           H  
HETATM   24  H10 UNL     1      -3.759  -0.483  -1.115  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.958   0.922  -1.948  1.00  0.00           H  
HETATM   26  H12 UNL     1      -3.373   0.554   0.923  1.00  0.00           H  
HETATM   27  H13 UNL     1      -2.481   1.863   0.079  1.00  0.00           H  
HETATM   28  H14 UNL     1      -0.659   0.928   1.200  1.00  0.00           H  
HETATM   29  H15 UNL     1      -1.934  -1.549   3.429  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    5   18
CONECT    3    4   19   20
CONECT    4   21
CONECT    5    6    6    7
CONECT    7    8   11
CONECT    8    9   22   23
CONECT    9   10   24   25
CONECT   10   11   26   27
CONECT   11   12   28
CONECT   12   13   13   14
CONECT   14   29
END

HMDB0015328
     RDKit          3D
Captopril
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.0375    0.8066   -0.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7996    0.6013   -0.1265 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1749   -0.4486    0.9257 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5823    0.1539    1.9175 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7419    0.0195   -0.9817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1116   -0.3572   -2.1585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047   -0.1512   -0.6209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6582   -0.7088   -1.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8629    0.1516   -1.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5810    0.7762    0.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2300    0.2066    0.6252 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4886   -1.0042    1.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1597   -2.1339    1.0418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -0.8614    2.6909 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5582   -0.1418   -1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6354    1.6293   -0.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6614    1.1382   -2.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209    1.5390    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3093   -0.5766    1.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4192   -1.3816    0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4527    0.9361    1.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8054   -1.7568   -1.1719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3700   -0.6707   -2.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7589   -0.4833   -1.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9584    0.9215   -1.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3727    0.5545    0.9229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4807    1.8629    0.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6591    0.9276    1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9343   -1.5486    3.4289 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
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11  7  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  1
  3 19  1  0
  3 20  1  0
  4 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  1
 14 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S)-1-[(2S)-2-Methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid	ChEBI
Acepress	ChEBI
Apopril	ChEBI
Capoten	ChEBI
Captolane	ChEBI
Captoprilum	ChEBI
Captopryl	ChEBI
Captoril	ChEBI
Cesplon	ChEBI
CP	ChEBI
D-2-Methyl-3-mercaptopropanoyl-L-proline	ChEBI
D-3-Mercapto-2-methylpropanoyl-L-proline	ChEBI
Dilabar	ChEBI
Garranil	ChEBI
Hypertil	ChEBI
L-Captopril	ChEBI
Lopirin	ChEBI
Tenosbon	ChEBI
Tensobon	ChEBI
Tensoprel	ChEBI
(2S)-1-[(2S)-2-Methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylate	Generator
(2S)-1-[(2S)-2-Methyl-3-sulphanylpropanoyl]pyrrolidine-2-carboxylate	Generator
(2S)-1-[(2S)-2-Methyl-3-sulphanylpropanoyl]pyrrolidine-2-carboxylic acid	Generator
(S)-1-(3-Mercapto-2-methyl-1-oxopropyl)-L-proline	HMDB

Chemical Formula

C₉H₁₅NO₃S

Average Molecular Weight

217.285

Monoisotopic Molecular Weight

217.077264041

IUPAC Name

(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

captopril

CAS Registry Number

62571-86-2

SMILES

C[C@H](CS)C(=O)N1CCC[C@H]1C(O)=O

InChI Identifier

InChI=1S/C9H15NO3S/c1-6(5-14)8(11)10-4-2-3-7(10)9(12)13/h6-7,14H,2-5H2,1H3,(H,12,13)/t6-,7+/m1/s1

InChI Key

FAKRSMQSSFJEIM-RQJHMYQMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline and derivatives

Alternative Parents

Substituents

N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Proline or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid
Monocarboxylic acid or derivatives
Alkylthiol
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organosulfur compound
Carbonyl group
Organic oxide
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

L-proline derivative (CHEBI:3380 )
alkanethiol (CHEBI:3380 )
pyrrolidinemonocarboxylic acid (CHEBI:3380 )
N-acylpyrrolidine (CHEBI:3380 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Captopril Action Pathway (PathBank: SMP0000146)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	106 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4.52 g/L	Not Available
LogP	0.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	142.5	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.52 g/L	ALOGPS
logP	1.02	ALOGPS
logP	0.73	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	4.02	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	54.63 m³·mol⁻¹	ChemAxon
Polarizability	21.72 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]+	149.376	31661259
DarkChem	[M-H]-	146.11	31661259
DeepCCS	[M+H]+	147.02	30932474
DeepCCS	[M-H]-	144.662	30932474
DeepCCS	[M-2H]-	178.709	30932474
DeepCCS	[M+Na]+	153.41	30932474
AllCCS	[M+H]+	147.0	32859911
AllCCS	[M+H-H2O]+	143.3	32859911
AllCCS	[M+NH4]+	150.5	32859911
AllCCS	[M+Na]+	151.5	32859911
AllCCS	[M-H]-	147.9	32859911
AllCCS	[M+Na-2H]-	148.9	32859911
AllCCS	[M+HCOO]-	150.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Captopril	C[C@H](CS)C(=O)N1CCC[C@H]1C(O)=O	2884.2	Standard polar	33892256
Captopril	C[C@H](CS)C(=O)N1CCC[C@H]1C(O)=O	1910.0	Standard non polar	33892256
Captopril	C[C@H](CS)C(=O)N1CCC[C@H]1C(O)=O	1952.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Captopril,1TMS,isomer #1	C[C@H](CS)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	1879.3	Semi standard non polar	33892256
Captopril,1TMS,isomer #2	C[C@H](CS[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	1974.6	Semi standard non polar	33892256
Captopril,2TMS,isomer #1	C[C@H](CS[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2006.2	Semi standard non polar	33892256
Captopril,2TMS,isomer #1	C[C@H](CS[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2051.6	Standard non polar	33892256
Captopril,2TMS,isomer #1	C[C@H](CS[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2429.3	Standard polar	33892256
Captopril,1TBDMS,isomer #1	C[C@H](CS)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2128.0	Semi standard non polar	33892256
Captopril,1TBDMS,isomer #2	C[C@H](CS[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	2210.4	Semi standard non polar	33892256
Captopril,2TBDMS,isomer #1	C[C@H](CS[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2469.1	Semi standard non polar	33892256
Captopril,2TBDMS,isomer #1	C[C@H](CS[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2503.0	Standard non polar	33892256
Captopril,2TBDMS,isomer #1	C[C@H](CS[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2596.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Captopril GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9400000000-51d6dae57d8b305064ac	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Captopril GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9410000000-65f35f9df00d94abb290	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Captopril GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Captopril 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 - Captopril LC-ESI-qTof , Positive-QTOF	splash10-014i-0940000000-26ddf220b67fb8dcdff0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril LC-ESI-QFT , negative-QTOF	splash10-001i-0910000000-8797427ebbfead8313f9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril , positive-QTOF	splash10-014i-0940000000-26ddf220b67fb8dcdff0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril , positive-QTOF	splash10-01b9-8910000000-d831e8d48402a4c5fe73	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril LC-ESI-QFT , positive-QTOF	splash10-01b9-9720000000-8218e12ef8f7e988c312	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril 10V, Positive-QTOF	splash10-014i-0490000000-368990ca74ad93e14251	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril 10V, Positive-QTOF	splash10-014i-0290000000-1fecd0b4a33bc6afc4f2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril 20V, Positive-QTOF	splash10-01b9-0940000000-089a033b51be30f3a297	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril 10V, Positive-QTOF	splash10-014i-3950000000-02525f49c5ae7c64e751	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril 50V, Positive-QTOF	splash10-00di-9100000000-2d3dff49389d32966270	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril 50V, Positive-QTOF	splash10-00di-9000000000-5fec50f211615a61cd58	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril 30V, Positive-QTOF	splash10-00di-9200000000-955e87fa6bbc3b688dc5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril 30V, Positive-QTOF	splash10-00di-9300000000-12f0a42fb63fd9a341e4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril 30V, Positive-QTOF	splash10-00di-9100000000-8a3f39d9e1f9e0ddfa3a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril 35V, Positive-QTOF	splash10-01b9-9720000000-cc5d5a56e386ed3da5df	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril 35V, Negative-QTOF	splash10-001i-0910000000-8797427ebbfead8313f9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril 50V, Positive-QTOF	splash10-014i-4920000000-abe7ab7a43bb4ab37f27	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril 10V, Positive-QTOF	splash10-014i-0390000000-443943c884569fe9bdde	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Captopril 10V, Positive-QTOF	splash10-014i-2950000000-6310d54f5354a953ff47	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captopril 10V, Positive-QTOF	splash10-014i-0890000000-6471cadb8251b2cde228	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captopril 20V, Positive-QTOF	splash10-0uk9-3920000000-93e7eef38f7bf8d57f56	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captopril 40V, Positive-QTOF	splash10-0udi-9400000000-f8b12a12ec76d0508922	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captopril 10V, Negative-QTOF	splash10-00lr-1930000000-21d83329a778cc965f80	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captopril 20V, Negative-QTOF	splash10-00yr-2910000000-30e872740f7cb996700d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Captopril 40V, Negative-QTOF	splash10-015c-9500000000-9c8558c81f9491de8c08	2016-08-04	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Captopril Action Pathway		Not Available

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 DB01197	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01197	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01197

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

40130

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Captopril

METLIN ID

Not Available

PubChem Compound

44093

PDB ID

X8Z

ChEBI ID

3380

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

Atkinson AB, Robertson JI: Captopril in the treatment of clinical hypertension and cardiac failure. Lancet. 1979 Oct 20;2(8147):836-9. [PubMed:90928 ]
Patchett AA, Harris E, Tristram EW, Wyvratt MJ, Wu MT, Taub D, Peterson ER, Ikeler TJ, ten Broeke J, Payne LG, Ondeyka DL, Thorsett ED, Greenlee WJ, Lohr NS, Hoffsommer RD, Joshua H, Ruyle WV, Rothrock JW, Aster SD, Maycock AL, Robinson FM, Hirschmann R, Sweet CS, Ulm EH, Gross DM, Vassil TC, Stone CA: A new class of angiotensin-converting enzyme inhibitors. Nature. 1980 Nov 20;288(5788):280-3. [PubMed:6253826 ]
Smith CG, Vane JR: The discovery of captopril. FASEB J. 2003 May;17(8):788-9. [PubMed:12724335 ]

Enzymes

Enzyme Details

1. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

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. Angiotensin-converting enzyme

General function:: Involved in metallopeptidase activity
Specific function:: Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent vasodilator. Has also a glycosidase activity which releases GPI-anchored proteins from the membrane by cleaving the mannose linkage in the GPI moiety
Gene Name:: ACE
Uniprot ID:: P12821
Molecular weight:: 149713.7

References

Andujar-Sanchez M, Jara-Perez V, Camara-Artigas A: Thermodynamic determination of the binding constants of angiotensin-converting enzyme inhibitors by a displacement method. FEBS Lett. 2007 Jul 24;581(18):3449-54. Epub 2007 Jun 27. [PubMed:17618628 ]
Dalkas GA, Marchand D, Galleyrand JC, Martinez J, Spyroulias GA, Cordopatis P, Cavelier F: Study of a lipophilic captopril analogue binding to angiotensin I converting enzyme. J Pept Sci. 2010 Feb;16(2):91-7. doi: 10.1002/psc.1201. [PubMed:20014331 ]
Natesh R, Schwager SL, Evans HR, Sturrock ED, Acharya KR: Structural details on the binding of antihypertensive drugs captopril and enalaprilat to human testicular angiotensin I-converting enzyme. Biochemistry. 2004 Jul 13;43(27):8718-24. [PubMed:15236580 ]
Piepho RW: Overview of the angiotensin-converting-enzyme inhibitors. Am J Health Syst Pharm. 2000 Oct 1;57 Suppl 1:S3-7. [PubMed:11030016 ]
Song JC, White CM: Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet. 2002;41(3):207-24. [PubMed:11929321 ]
Tzakos AG, Naqvi N, Comporozos K, Pierattelli R, Theodorou V, Husain A, Gerothanassis IP: The molecular basis for the selection of captopril cis and trans conformations by angiotensin I converting enzyme. Bioorg Med Chem Lett. 2006 Oct 1;16(19):5084-7. Epub 2006 Aug 2. [PubMed:16889963 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. Matrix metalloproteinase-9

General function:: Involved in metalloendopeptidase activity
Specific function:: May play an essential role in local proteolysis of the extracellular matrix and in leukocyte migration. Could play a role in bone osteoclastic resorption. Cleaves KiSS1 at a Gly-|-Leu bond. Cleaves type IV and type V collagen into large C-terminal three quarter fragments and shorter N-terminal one quarter fragments. Degrades fibronectin but not laminin or Pz-peptide
Gene Name:: MMP9
Uniprot ID:: P14780
Molecular weight:: 78457.5

References

Okada M, Kikuzuki R, Harada T, Hori Y, Yamawaki H, Hara Y: Captopril attenuates matrix metalloproteinase-2 and -9 in monocrotaline-induced right ventricular hypertrophy in rats. J Pharmacol Sci. 2008 Dec;108(4):487-94. Epub 2008 Dec 5. [PubMed:19057128 ]
Reinhardt D, Sigusch HH, Hensse J, Tyagi SC, Korfer R, Figulla HR: Cardiac remodelling in end stage heart failure: upregulation of matrix metalloproteinase (MMP) irrespective of the underlying disease, and evidence for a direct inhibitory effect of ACE inhibitors on MMP. Heart. 2002 Nov;88(5):525-30. [PubMed:12381651 ]
Williams RN, Parsons SL, Morris TM, Rowlands BJ, Watson SA: Inhibition of matrix metalloproteinase activity and growth of gastric adenocarcinoma cells by an angiotensin converting enzyme inhibitor in in vitro and murine models. Eur J Surg Oncol. 2005 Nov;31(9):1042-50. Epub 2005 Jul 1. [PubMed:15993560 ]
Yamamoto D, Takai S, Miyazaki M: Inhibitory profiles of captopril on matrix metalloproteinase-9 activity. Eur J Pharmacol. 2008 Jul 7;588(2-3):277-9. doi: 10.1016/j.ejphar.2008.04.031. Epub 2008 May 22. [PubMed:18501888 ]

Enzyme Details

4. 72 kDa type IV collagenase

General function:: Involved in metalloendopeptidase activity
Specific function:: PEX, the C-terminal non-catalytic fragment of MMP2, posseses anti-angiogenic and anti-tumor properties and inhibits cell migration and cell adhesion to FGF2 and vitronectin. Ligand for integrinv/beta3 on the surface of blood vessels
Gene Name:: MMP2
Uniprot ID:: P08253
Molecular weight:: 73881.7

References

Brower GL, Levick SP, Janicki JS: Inhibition of matrix metalloproteinase activity by ACE inhibitors prevents left ventricular remodeling in a rat model of heart failure. Am J Physiol Heart Circ Physiol. 2007 Jun;292(6):H3057-64. Epub 2007 Feb 16. [PubMed:17308006 ]
Okada M, Kikuzuki R, Harada T, Hori Y, Yamawaki H, Hara Y: Captopril attenuates matrix metalloproteinase-2 and -9 in monocrotaline-induced right ventricular hypertrophy in rats. J Pharmacol Sci. 2008 Dec;108(4):487-94. Epub 2008 Dec 5. [PubMed:19057128 ]
Prontera C, Mariani B, Rossi C, Poggi A, Rotilio D: Inhibition of gelatinase A (MMP-2) by batimastat and captopril reduces tumor growth and lung metastases in mice bearing Lewis lung carcinoma. Int J Cancer. 1999 May 31;81(5):761-6. [PubMed:10328230 ]
Reinhardt D, Sigusch HH, Hensse J, Tyagi SC, Korfer R, Figulla HR: Cardiac remodelling in end stage heart failure: upregulation of matrix metalloproteinase (MMP) irrespective of the underlying disease, and evidence for a direct inhibitory effect of ACE inhibitors on MMP. Heart. 2002 Nov;88(5):525-30. [PubMed:12381651 ]
Williams RN, Parsons SL, Morris TM, Rowlands BJ, Watson SA: Inhibition of matrix metalloproteinase activity and growth of gastric adenocarcinoma cells by an angiotensin converting enzyme inhibitor in in vitro and murine models. Eur J Surg Oncol. 2005 Nov;31(9):1042-50. Epub 2005 Jul 1. [PubMed:15993560 ]
Yamamoto D, Takai S, Hirahara I, Kusano E: Captopril directly inhibits matrix metalloproteinase-2 activity in continuous ambulatory peritoneal dialysis therapy. Clin Chim Acta. 2010 May 2;411(9-10):762-4. doi: 10.1016/j.cca.2010.02.059. Epub 2010 Feb 22. [PubMed:20184869 ]

Transporters

Enzyme Details

1. 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

Takara K, Kakumoto M, Tanigawara Y, Funakoshi J, Sakaeda T, Okumura K: Interaction of digoxin with antihypertensive drugs via MDR1. Life Sci. 2002 Feb 15;70(13):1491-500. [PubMed:11895100 ]

Enzyme Details

2. Solute carrier family 15 member 1

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:: SLC15A1
Uniprot ID:: P46059
Molecular weight:: 78805.3

References

Watanabe K, Sawano T, Terada K, Endo T, Sakata M, Sato J: Studies on intestinal absorption of sulpiride (1): carrier-mediated uptake of sulpiride in the human intestinal cell line Caco-2. Biol Pharm Bull. 2002 Jul;25(7):885-90. [PubMed:12132663 ]
Temple CS, Boyd CA: Proton-coupled oligopeptide transport by rat renal cortical brush border membrane vesicles: a functional analysis using ACE inhibitors to determine the isoform of the transporter. Biochim Biophys Acta. 1998 Aug 14;1373(1):277-81. [PubMed:9733984 ]

Enzyme Details

3. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Kuze K, Graves P, Leahy A, Wilson P, Stuhlmann H, You G: Heterologous expression and functional characterization of a mouse renal organic anion transporter in mammalian cells. J Biol Chem. 1999 Jan 15;274(3):1519-24. [PubMed:9880528 ]

Showing metabocard for Captopril (HMDB0015328)

MOL for HMDB0015328 (Captopril)

3D MOL for HMDB0015328 (Captopril)

3D SDF for HMDB0015328 (Captopril)

3D-SDF for HMDB0015328 (Captopril)

PDB for HMDB0015328 (Captopril)

3D PDB for HMDB0015328 (Captopril)

SMILES for HMDB0015328 (Captopril)

INCHI for HMDB0015328 (Captopril)

Structure for HMDB0015328 (Captopril)

3D Structure for HMDB0015328 (Captopril)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

Transporters

References

References

References