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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (2) Show 3 proteins XML

enzymes (1)transporters (2) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014635

Secondary Accession Numbers

HMDB14635

Metabolite Identification

Common Name

Fosinopril

Description

Fosinopril is a phosphinic acid-containing ester prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is rapidly hydrolyzed to fosinoprilat, its principle active metabolite. Fosinoprilat inhibits ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Fosinopril may be used to treat mild to moderate hypertension, as an adjunct in the treatment of congestive heart failure, and to slow the rate of progression of renal disease in hypertensive individuals with diabetes mellitus and microalbuminuria or overt nephropathy.

Structure

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

492
  Mrv0541 02231214432D          

 39 41  0  0  1  0            999 V2000
    5.8714    1.5817    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9507    0.9143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2305    1.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1067    1.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3564    2.2491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2040    2.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6618    2.8304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8179    1.9904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0811    0.3331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6686   -0.9366    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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 35 39  1  0  0  0  0
 36 38  2  0  0  0  0
 37 38  1  0  0  0  0
M  END

HMDB0014635
     RDKit          3D
Fosinopril
 85 87  0  0  0  0  0  0  0  0999 V2000
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M  END

492
  Mrv0541 02231214432D          

 39 41  0  0  1  0            999 V2000
    5.8714    1.5817    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9507    0.9143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1769    2.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1201   -0.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5125    1.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0339   -1.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0275    0.7418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3329    1.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7013   -1.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4823    2.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4551   -1.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6151   -2.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9672    3.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1225   -1.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2825   -2.8195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0363   -2.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7877    3.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  6  2  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  2 21  1  0  0  0  0
  3 20  2  0  0  0  0
  4 21  2  0  0  0  0
  5 25  1  0  0  0  0
  7 25  1  0  0  0  0
  7 32  1  0  0  0  0
  8 32  2  0  0  0  0
  9 13  1  0  0  0  0
  9 16  1  0  0  0  0
  9 20  1  0  0  0  0
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 20 22  1  0  0  0  0
 23 24  1  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 33  2  0  0  0  0
 31 34  1  0  0  0  0
 32 35  1  0  0  0  0
 33 36  1  0  0  0  0
 34 37  2  0  0  0  0
 35 39  1  0  0  0  0
 36 38  2  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014635

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)OC(OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@@H](C[C@H]1C(O)=O)C1CCCCC1)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H46NO7P/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35)/t25-,26+,30?,39?/m1/s1

> <INCHI_KEY>
BIDNLKIUORFRQP-FKDWWROVSA-N

> <FORMULA>
C30H46NO7P

> <MOLECULAR_WEIGHT>
563.6625

> <EXACT_MASS>
563.301189343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
61.17035325610999

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4S)-4-cyclohexyl-1-(2-{[2-methyl-1-(propanoyloxy)propoxy](4-phenylbutyl)phosphoryl}acetyl)pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
4.71

> <JCHEM_LOGP>
5.485800000000001

> <ALOGPS_LOGS>
-5.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.381608178475936

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.870142961809244

> <JCHEM_PKA_STRONGEST_BASIC>
-4.42899974084534

> <JCHEM_POLAR_SURFACE_AREA>
110.21

> <JCHEM_REFRACTIVITY>
149.11959999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fosinopril

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014635
     RDKit          3D
Fosinopril
 85 87  0  0  0  0  0  0  0  0999 V2000
   -2.4769    5.1538   -3.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6678    3.8820   -2.9428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0717    3.1601   -1.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1665    2.5051   -1.6540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3109    3.1606   -0.5504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6480    2.4964    0.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6529    1.6062    0.9354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726    0.0047    0.9453 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.9887   -0.4861    2.3963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7825   -0.2937    0.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0033   -1.7902    0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4094   -2.1701    0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5183   -3.6799    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8501   -4.1761   -0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3149    1.7667    1.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1642    2.8403    3.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0142    6.0189   -2.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.2960   -5.4943   -1.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4946   -5.2908   -2.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2760   -4.4461   -2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5742   -1.5965   -0.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -1.9115    0.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6251    0.0942   -1.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758    1.6154   -0.9336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6479    1.1208    0.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1925    1.1683   -0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9789    0.8802    1.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6587   -0.9280    1.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7225   -1.2867    0.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0549    0.4435    0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536    1.0928   -1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4165   -0.3152   -1.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8429   -1.7772   -2.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2231   -0.2527   -3.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2921   -1.0237   -2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2103   -1.8819   -0.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2562   -1.8547    0.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7418   -1.1055    1.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2248   -1.5622    1.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625    2.5728    2.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0008    4.1157    1.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898    4.6299    2.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6848    5.3295    0.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6982    3.8671    0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7624    1.9001    2.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2607    2.6731    3.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8392    3.4915    3.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
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  8  9  2  0
  8 10  1  0
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 19 14  1  0
 33 23  1  0
 31 26  1  0
  1 40  1  0
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 24 61  1  0
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 38 81  1  0
 38 82  1  0
 39 83  1  0
 39 84  1  0
 39 85  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 492                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  P   UNK     0      10.960   2.953   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0       3.641   1.707   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.897   3.274   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.799   3.274   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.865   4.198   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       9.714   3.858   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      14.302   5.283   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      16.460   3.715   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       7.618   0.622   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       6.848  -1.748   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.848  -3.288   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.602  -0.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.094  -0.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.514  -4.058   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.182  -4.058   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.078   0.622   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.514  -5.598   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.182  -5.598   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.848  -6.368   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.523   1.868   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.173   1.868   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.055   1.707   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.206   2.047   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.045   0.516   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.397   4.037   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.291  -0.389   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.023   2.631   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.130  -1.921   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.118   1.385   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.555   2.470   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.376  -2.826   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.834   5.123   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.783  -2.200   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.215  -4.358   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.739   6.368   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      17.029  -3.105   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      15.461  -5.263   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      16.868  -4.637   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      18.270   6.207   0.000  0.00  0.00           C+0
CONECT    1    5    6   22   23                                             
CONECT    2   21                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5    1   25                                                       
CONECT    6    1                                                            
CONECT    7   25   32                                                       
CONECT    8   32                                                            
CONECT    9   13   16   20                                                  
CONECT   10   11   12   13                                                  
CONECT   11   10   14   15                                                  
CONECT   12   10   16                                                       
CONECT   13    9   10                                                       
CONECT   14   11   17                                                       
CONECT   15   11   18                                                       
CONECT   16    9   12   21                                                  
CONECT   17   14   19                                                       
CONECT   18   15   19                                                       
CONECT   19   17   18                                                       
CONECT   20    3    9   22                                                  
CONECT   21    2    4   16                                                  
CONECT   22    1   20                                                       
CONECT   23    1   24                                                       
CONECT   24   23   26                                                       
CONECT   25    5    7   27                                                  
CONECT   26   24   28                                                       
CONECT   27   25   29   30                                                  
CONECT   28   26   31                                                       
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   28   33   34                                                  
CONECT   32    7    8   35                                                  
CONECT   33   31   36                                                       
CONECT   34   31   37                                                       
CONECT   35   32   39                                                       
CONECT   36   33   38                                                       
CONECT   37   34   38                                                       
CONECT   38   36   37                                                       
CONECT   39   35                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

COMPND    HMDB0014635
HETATM    1  C1  UNL     1      -2.477   5.154  -3.061  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.668   3.882  -2.943  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.072   3.160  -1.693  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.166   2.505  -1.654  1.00  0.00           O  
HETATM    5  O2  UNL     1      -1.311   3.161  -0.550  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.648   2.496   0.654  1.00  0.00           C  
HETATM    7  O3  UNL     1      -0.653   1.606   0.935  1.00  0.00           O  
HETATM    8  P1  UNL     1      -1.073   0.005   0.945  1.00  0.00           P  
HETATM    9  O4  UNL     1      -0.989  -0.486   2.396  1.00  0.00           O  
HETATM   10  C5  UNL     1      -2.783  -0.294   0.418  1.00  0.00           C  
HETATM   11  C6  UNL     1      -3.003  -1.790   0.526  1.00  0.00           C  
HETATM   12  C7  UNL     1      -4.409  -2.170   0.107  1.00  0.00           C  
HETATM   13  C8  UNL     1      -4.518  -3.680   0.252  1.00  0.00           C  
HETATM   14  C9  UNL     1      -5.850  -4.176  -0.129  1.00  0.00           C  
HETATM   15  C10 UNL     1      -6.857  -4.286   0.785  1.00  0.00           C  
HETATM   16  C11 UNL     1      -8.112  -4.762   0.386  1.00  0.00           C  
HETATM   17  C12 UNL     1      -8.335  -5.120  -0.927  1.00  0.00           C  
HETATM   18  C13 UNL     1      -7.322  -5.011  -1.854  1.00  0.00           C  
HETATM   19  C14 UNL     1      -6.080  -4.535  -1.435  1.00  0.00           C  
HETATM   20  C15 UNL     1       0.005  -1.054  -0.037  1.00  0.00           C  
HETATM   21  C16 UNL     1       1.071  -0.330  -0.754  1.00  0.00           C  
HETATM   22  O5  UNL     1       0.852   0.145  -1.902  1.00  0.00           O  
HETATM   23  N1  UNL     1       2.350  -0.154  -0.182  1.00  0.00           N  
HETATM   24  C17 UNL     1       3.498   0.533  -0.780  1.00  0.00           C  
HETATM   25  C18 UNL     1       4.615   0.310   0.167  1.00  0.00           C  
HETATM   26  C19 UNL     1       5.971   0.213  -0.472  1.00  0.00           C  
HETATM   27  C20 UNL     1       6.980  -0.005   0.637  1.00  0.00           C  
HETATM   28  C21 UNL     1       8.338  -0.270   0.073  1.00  0.00           C  
HETATM   29  C22 UNL     1       8.402  -0.000  -1.409  1.00  0.00           C  
HETATM   30  C23 UNL     1       7.394  -0.793  -2.186  1.00  0.00           C  
HETATM   31  C24 UNL     1       6.089  -0.960  -1.413  1.00  0.00           C  
HETATM   32  C25 UNL     1       4.220  -0.964   0.880  1.00  0.00           C  
HETATM   33  C26 UNL     1       2.728  -0.652   1.127  1.00  0.00           C  
HETATM   34  C27 UNL     1       2.655   0.464   2.092  1.00  0.00           C  
HETATM   35  O6  UNL     1       2.928   0.186   3.305  1.00  0.00           O  
HETATM   36  O7  UNL     1       2.315   1.767   1.760  1.00  0.00           O  
HETATM   37  C28 UNL     1      -1.913   3.482   1.767  1.00  0.00           C  
HETATM   38  C29 UNL     1      -3.056   4.413   1.427  1.00  0.00           C  
HETATM   39  C30 UNL     1      -2.164   2.840   3.084  1.00  0.00           C  
HETATM   40  H1  UNL     1      -2.014   6.019  -2.581  1.00  0.00           H  
HETATM   41  H2  UNL     1      -3.492   5.009  -2.603  1.00  0.00           H  
HETATM   42  H3  UNL     1      -2.662   5.394  -4.128  1.00  0.00           H  
HETATM   43  H4  UNL     1      -1.958   3.227  -3.794  1.00  0.00           H  
HETATM   44  H5  UNL     1      -0.593   4.074  -2.967  1.00  0.00           H  
HETATM   45  H6  UNL     1      -2.632   1.996   0.457  1.00  0.00           H  
HETATM   46  H7  UNL     1      -3.521   0.182   1.077  1.00  0.00           H  
HETATM   47  H8  UNL     1      -2.906  -0.042  -0.657  1.00  0.00           H  
HETATM   48  H9  UNL     1      -2.231  -2.387   0.042  1.00  0.00           H  
HETATM   49  H10 UNL     1      -2.950  -2.026   1.629  1.00  0.00           H  
HETATM   50  H11 UNL     1      -4.647  -1.844  -0.918  1.00  0.00           H  
HETATM   51  H12 UNL     1      -5.130  -1.739   0.837  1.00  0.00           H  
HETATM   52  H13 UNL     1      -3.690  -4.165  -0.321  1.00  0.00           H  
HETATM   53  H14 UNL     1      -4.345  -3.939   1.317  1.00  0.00           H  
HETATM   54  H15 UNL     1      -6.698  -4.009   1.813  1.00  0.00           H  
HETATM   55  H16 UNL     1      -8.910  -4.847   1.116  1.00  0.00           H  
HETATM   56  H17 UNL     1      -9.296  -5.494  -1.277  1.00  0.00           H  
HETATM   57  H18 UNL     1      -7.495  -5.291  -2.879  1.00  0.00           H  
HETATM   58  H19 UNL     1      -5.276  -4.446  -2.157  1.00  0.00           H  
HETATM   59  H20 UNL     1      -0.574  -1.596  -0.844  1.00  0.00           H  
HETATM   60  H21 UNL     1       0.421  -1.911   0.570  1.00  0.00           H  
HETATM   61  H22 UNL     1       3.625   0.094  -1.781  1.00  0.00           H  
HETATM   62  H23 UNL     1       3.276   1.615  -0.934  1.00  0.00           H  
HETATM   63  H24 UNL     1       4.648   1.121   0.907  1.00  0.00           H  
HETATM   64  H25 UNL     1       6.192   1.168  -0.967  1.00  0.00           H  
HETATM   65  H26 UNL     1       6.979   0.880   1.332  1.00  0.00           H  
HETATM   66  H27 UNL     1       6.659  -0.928   1.183  1.00  0.00           H  
HETATM   67  H28 UNL     1       8.722  -1.287   0.292  1.00  0.00           H  
HETATM   68  H29 UNL     1       9.055   0.443   0.561  1.00  0.00           H  
HETATM   69  H30 UNL     1       8.354   1.093  -1.630  1.00  0.00           H  
HETATM   70  H31 UNL     1       9.416  -0.315  -1.756  1.00  0.00           H  
HETATM   71  H32 UNL     1       7.843  -1.777  -2.430  1.00  0.00           H  
HETATM   72  H33 UNL     1       7.223  -0.253  -3.155  1.00  0.00           H  
HETATM   73  H34 UNL     1       5.292  -1.024  -2.151  1.00  0.00           H  
HETATM   74  H35 UNL     1       6.210  -1.882  -0.790  1.00  0.00           H  
HETATM   75  H36 UNL     1       4.256  -1.855   0.224  1.00  0.00           H  
HETATM   76  H37 UNL     1       4.742  -1.105   1.846  1.00  0.00           H  
HETATM   77  H38 UNL     1       2.225  -1.562   1.440  1.00  0.00           H  
HETATM   78  H39 UNL     1       2.863   2.573   2.008  1.00  0.00           H  
HETATM   79  H40 UNL     1      -1.001   4.116   1.848  1.00  0.00           H  
HETATM   80  H41 UNL     1      -3.690   4.630   2.316  1.00  0.00           H  
HETATM   81  H42 UNL     1      -2.685   5.329   0.963  1.00  0.00           H  
HETATM   82  H43 UNL     1      -3.698   3.867   0.698  1.00  0.00           H  
HETATM   83  H44 UNL     1      -2.762   1.900   2.929  1.00  0.00           H  
HETATM   84  H45 UNL     1      -1.261   2.673   3.691  1.00  0.00           H  
HETATM   85  H46 UNL     1      -2.839   3.492   3.699  1.00  0.00           H  
CONECT    1    2   40   41   42
CONECT    2    3   43   44
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   37   45
CONECT    7    8
CONECT    8    9    9   10   20
CONECT   10   11   46   47
CONECT   11   12   48   49
CONECT   12   13   50   51
CONECT   13   14   52   53
CONECT   14   15   15   19
CONECT   15   16   54
CONECT   16   17   17   55
CONECT   17   18   56
CONECT   18   19   19   57
CONECT   19   58
CONECT   20   21   59   60
CONECT   21   22   22   23
CONECT   23   24   33
CONECT   24   25   61   62
CONECT   25   26   32   63
CONECT   26   27   31   64
CONECT   27   28   65   66
CONECT   28   29   67   68
CONECT   29   30   69   70
CONECT   30   31   71   72
CONECT   31   73   74
CONECT   32   33   75   76
CONECT   33   34   77
CONECT   34   35   35   36
CONECT   36   78
CONECT   37   38   39   79
CONECT   38   80   81   82
CONECT   39   83   84   85
END

HMDB0014635
     RDKit          3D
Fosinopril
 85 87  0  0  0  0  0  0  0  0999 V2000
   -2.4769    5.1538   -3.0613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6678    3.8820   -2.9428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0717    3.1601   -1.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1665    2.5051   -1.6540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3109    3.1606   -0.5504 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6480    2.4964    0.6539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6529    1.6062    0.9354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726    0.0047    0.9453 P   0  0  0  0  0  5  0  0  0  0  0  0
   -0.9887   -0.4861    2.3963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7825   -0.2937    0.4182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0033   -1.7902    0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4094   -2.1701    0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5183   -3.6799    0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8501   -4.1761   -0.1287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8567   -4.2856    0.7847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1124   -4.7616    0.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3351   -5.1199   -0.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3222   -5.0114   -1.8539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0797   -4.5352   -1.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0048   -1.0536   -0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711   -0.3304   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8521    0.1450   -1.9015 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3504   -0.1539   -0.1820 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4982    0.5329   -0.7800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6152    0.3102    0.1670 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9706    0.2127   -0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9799   -0.0051    0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3379   -0.2697    0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4023   -0.0001   -1.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3943   -0.7931   -2.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0890   -0.9599   -1.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2204   -0.9635    0.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279   -0.6515    1.1275 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6551    0.4642    2.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282    0.1860    3.3052 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3149    1.7667    1.7595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9126    3.4819    1.7668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0558    4.4130    1.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1642    2.8403    3.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0142    6.0189   -2.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4919    5.0092   -2.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6616    5.3935   -4.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9584    3.2266   -3.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5932    4.0739   -2.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6323    1.9956    0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5209    0.1819    1.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9063   -0.0419   -0.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2308   -2.3870    0.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9498   -2.0259    1.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6472   -1.8436   -0.9182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1300   -1.7393    0.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6900   -4.1655   -0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3445   -3.9391    1.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6977   -4.0094    1.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9099   -4.8469    1.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2960   -5.4943   -1.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4946   -5.2908   -2.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2760   -4.4461   -2.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5742   -1.5965   -0.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -1.9115    0.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6251    0.0942   -1.7815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758    1.6154   -0.9336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6479    1.1208    0.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1925    1.1683   -0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9789    0.8802    1.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6587   -0.9280    1.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7225   -1.2867    0.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0549    0.4435    0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536    1.0928   -1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4165   -0.3152   -1.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8429   -1.7772   -2.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2231   -0.2527   -3.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2921   -1.0237   -2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2103   -1.8819   -0.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2562   -1.8547    0.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7418   -1.1055    1.8462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2248   -1.5622    1.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625    2.5728    2.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0008    4.1157    1.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6898    4.6299    2.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6848    5.3295    0.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6982    3.8671    0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7624    1.9001    2.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2607    2.6731    3.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8392    3.4915    3.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  8 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 25 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  2  0
 34 36  1  0
  6 37  1  0
 37 38  1  0
 37 39  1  0
 19 14  1  0
 33 23  1  0
 31 26  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  0
  2 44  1  0
  6 45  1  0
 10 46  1  0
 10 47  1  0
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 15 54  1  0
 16 55  1  0
 17 56  1  0
 18 57  1  0
 19 58  1  0
 20 59  1  0
 20 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  1
 26 64  1  0
 27 65  1  0
 27 66  1  0
 28 67  1  0
 28 68  1  0
 29 69  1  0
 29 70  1  0
 30 71  1  0
 30 72  1  0
 31 73  1  0
 31 74  1  0
 32 75  1  0
 32 76  1  0
 33 77  1  1
 36 78  1  0
 37 79  1  0
 38 80  1  0
 38 81  1  0
 38 82  1  0
 39 83  1  0
 39 84  1  0
 39 85  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S,4S)-4-Cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid	ChEBI
(2S,4S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid	ChEBI
(S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid	ChEBI
(2S,4S)-4-Cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylate	Generator
(2S,4S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylate	Generator
(S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylate	Generator
Fosinopril sodium	HMDB
Monopril	HMDB
Newace	HMDB
Squibb brand OF fosinopril sodium	HMDB
Staril	HMDB
Bristol-myers squibb brand OF fosinopril sodium	HMDB
Dynacil	HMDB
Fosenopril	HMDB
Fosinopril, (1(s(r)),2 alpha,4 beta)-isomer	HMDB
Fosinopril, (1(s(s)),2 alpha,4 beta)-isomer	HMDB
Fositens	HMDB
Sanol brand OF fosinopril sodium	HMDB
Sodium, fosinopril	HMDB
Tensocardil	HMDB
Bristol myers squibb brand OF fosinopril sodium	HMDB
Ferrer brand OF fosinopril sodium	HMDB
Fosinil	HMDB
Fosinorm	HMDB
Schwarz brand OF fosinopril sodium	HMDB
Esteve brand OF fosinopril sodium	HMDB
Fosinopril, (1(s(r)),2 alpha,4 alpha)-(D-pro)-isomer	HMDB
Fozitec	HMDB
Hiperlex	HMDB
Merck lipha santé brand OF fosinopril	HMDB
Tenso stop	HMDB

Chemical Formula

C₃₀H₄₆NO₇P

Average Molecular Weight

563.6625

Monoisotopic Molecular Weight

563.301189343

IUPAC Name

(2S,4S)-4-cyclohexyl-1-(2-{[2-methyl-1-(propanoyloxy)propoxy](4-phenylbutyl)phosphoryl}acetyl)pyrrolidine-2-carboxylic acid

Traditional Name

fosinopril

CAS Registry Number

98048-97-6

SMILES

CCC(=O)OC(OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@@H](C[C@H]1C(O)=O)C1CCCCC1)C(C)C

InChI Identifier

InChI=1S/C30H46NO7P/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35)/t25-,26+,30?,39?/m1/s1

InChI Key

BIDNLKIUORFRQP-FKDWWROVSA-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
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Pyrrolidine
Carboxylic acid ester
Carboxamide group
Phosphinic acid ester
Organoheterocyclic compound
Carboxylic acid
Azacycle
Organophosphorus compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Hydrocarbon derivative
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

L-proline derivative (CHEBI:5163 )
phosphinic ester (CHEBI:5163 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014635)
Membrane (HMDB: HMDB0014635)

Source

Exogenous

Exogenous (HMDB: HMDB0014635)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Fosinopril Action Pathway (PathBank: SMP0000149)

Metabolic pathway

Fosinopril Metabolism Pathway (PathBank: SMP0000594)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	149 - 153 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.001 g/L	Not Available
LogP	6.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.001 g/L	ALOGPS
logP	4.71	ALOGPS
logP	5.49	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	110.21 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	149.12 m³·mol⁻¹	ChemAxon
Polarizability	61.17 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	230.355	31661259
DarkChem	[M-H]-	219.409	31661259
DeepCCS	[M+H]+	230.501	30932474
DeepCCS	[M-H]-	228.404	30932474
DeepCCS	[M-2H]-	261.647	30932474
DeepCCS	[M+Na]+	236.705	30932474
AllCCS	[M+H]+	229.9	32859911
AllCCS	[M+H-H2O]+	228.8	32859911
AllCCS	[M+NH4]+	231.0	32859911
AllCCS	[M+Na]+	231.2	32859911
AllCCS	[M-H]-	210.4	32859911
AllCCS	[M+Na-2H]-	213.2	32859911
AllCCS	[M+HCOO]-	216.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	10.62 minutes	32390414
Predicted by Siyang on May 30, 2022	20.5054 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.32 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	53.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3522.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	305.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	269.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	186.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	390.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	939.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	893.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1758.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	782.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2122.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	502.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	520.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	131.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	205.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fosinopril	CCC(=O)OC(OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@@H](C[C@H]1C(O)=O)C1CCCCC1)C(C)C	4533.5	Standard polar	33892256
Fosinopril	CCC(=O)OC(OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@@H](C[C@H]1C(O)=O)C1CCCCC1)C(C)C	3492.3	Standard non polar	33892256
Fosinopril	CCC(=O)OC(OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@@H](C[C@H]1C(O)=O)C1CCCCC1)C(C)C	3978.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fosinopril,1TMS,isomer #1	CCC(=O)OC(OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@H](C2CCCCC2)C[C@H]1C(=O)O[Si](C)(C)C)C(C)C	3894.7	Semi standard non polar	33892256
Fosinopril,1TBDMS,isomer #1	CCC(=O)OC(OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@H](C2CCCCC2)C[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)C(C)C	4095.2	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Fosinopril Action Pathway		Not Available
Fosinopril Metabolism 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 DB00492	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00492	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00492

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

50469

KEGG Compound ID

C07016

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fosinopril

METLIN ID

Not Available

PubChem Compound

55891

PDB ID

Not Available

ChEBI ID

5163

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

Sharma S, Deitchman D, Eni JS, Gelperin K, Ilgenfritz JP, Blumenthal M: The hemodynamic effects of long-term ACE inhibition with fosinopril in patients with heart failure. Fosinopril Hemodynamics Study Group. Am J Ther. 1999 Jul;6(4):181-9. [PubMed:11329095 ]
David D, Jallad N, Germino FW, Willett MS, de Silva J, Weidner SM, Mills DJ: A Comparison of the Cough Profile of Fosinopril and Enalapril in Hypertensive Patients with a History of ACE Inhibitor-Associated Cough. Am J Ther. 1995 Oct;2(10):806-813. [PubMed:11854791 ]

Enzymes

Enzyme Details

1. 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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Ondetti MA: Structural relationships of angiotensin converting-enzyme inhibitors to pharmacologic activity. Circulation. 1988 Jun;77(6 Pt 2):I74-8. [PubMed:2836111 ]
Piepho RW: Overview of the angiotensin-converting-enzyme inhibitors. Am J Health Syst Pharm. 2000 Oct 1;57 Suppl 1:S3-7. [PubMed:11030016 ]
Sharma S, Deitchman D, Eni JS, Gelperin K, Ilgenfritz JP, Blumenthal M: The hemodynamic effects of long-term ACE inhibition with fosinopril in patients with heart failure. Fosinopril Hemodynamics Study Group. Am J Ther. 1999 Jul;6(4):181-9. [PubMed:11329095 ]

Transporters

Enzyme Details

1. 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

Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [PubMed:18713951 ]

Enzyme Details

2. Solute carrier family 15 member 2

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:: SLC15A2
Uniprot ID:: Q16348
Molecular weight:: 81782.8

References

Knutter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M: Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. [PubMed:18713951 ]

Showing metabocard for Fosinopril (HMDB0014635)

MOL for HMDB0014635 (Fosinopril)

3D MOL for HMDB0014635 (Fosinopril)

3D SDF for HMDB0014635 (Fosinopril)

3D-SDF for HMDB0014635 (Fosinopril)

PDB for HMDB0014635 (Fosinopril)

3D PDB for HMDB0014635 (Fosinopril)

SMILES for HMDB0014635 (Fosinopril)

INCHI for HMDB0014635 (Fosinopril)

Structure for HMDB0014635 (Fosinopril)

3D Structure for HMDB0014635 (Fosinopril)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

Transporters

References

References