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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 23:06:14 UTC

Update Date

2021-09-26 23:17:57 UTC

HMDB ID

HMDB0260038

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Zofenoprilat

Description

1-(2-methyl-3-sulfanylpropanoyl)-4-(phenylsulfanyl)pyrrolidine-2-carboxylic acid belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Based on a literature review very few articles have been published on 1-(2-methyl-3-sulfanylpropanoyl)-4-(phenylsulfanyl)pyrrolidine-2-carboxylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Zofenoprilat is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Zofenoprilat is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0260038
     RDKit          3D
Zofenoprilat
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.3832   -1.0424    0.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896   -0.8023   -0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3841   -1.8729   -1.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2695   -1.5847   -2.9721 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7706    0.5576   -0.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5134    1.3666   -1.5613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4896    1.0096   -0.4906 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4554    0.3395    0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4002    1.3869    0.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025    1.3655    0.3436 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9638   -0.1259    0.8010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642   -1.1265    1.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0229   -2.2873    1.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3343   -2.4863    1.5199 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9532   -1.4942    0.7934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2771   -0.3301    0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2070    2.7156    0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9349    2.3473   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0471    2.3145   -1.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505    1.2561   -2.4574 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584    3.4829   -2.2218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3870   -1.4553    1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6672   -1.8354    1.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1511   -0.1293    1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3308   -0.9070   -1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4281   -1.9307   -0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.8890   -1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4987   -1.9487   -3.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277   -0.2195   -0.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8073   -0.3431    1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000    1.3141    2.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3353   -1.0134    1.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5341   -3.0707    2.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8437   -3.3998    1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9989   -1.6483    0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7992    0.4296   -0.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5539    3.4801    0.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9267    3.1025    1.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7578    3.0658   -0.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3429    4.4088   -1.9829 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  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18  7  1  0
 16 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 21 40  1  0
M  END


  Mrv1652309122101062D          

 21 22  0  0  0  0            999 V2000
    3.4656   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.1759    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4131   -0.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0284   -2.0811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341   -3.2361    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5986   -3.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835   -4.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -5.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275   -5.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4425   -4.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -4.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0260038

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CS)C(=O)N1CC(CC1C(O)=O)SC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H19NO3S2/c1-10(9-20)14(17)16-8-12(7-13(16)15(18)19)21-11-5-3-2-4-6-11/h2-6,10,12-13,20H,7-9H2,1H3,(H,18,19)

> <INCHI_KEY>
UQWLOWFDKAFKAP-UHFFFAOYSA-N

> <FORMULA>
C15H19NO3S2

> <MOLECULAR_WEIGHT>
325.44

> <EXACT_MASS>
325.080635824

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
34.037113901883586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2-methyl-3-sulfanylpropanoyl)-4-(phenylsulfanyl)pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
2.59

> <JCHEM_LOGP>
2.4137539820000002

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.096073526391148

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9114754743443285

> <JCHEM_PKA_STRONGEST_BASIC>
-1.275879235384934

> <JCHEM_POLAR_SURFACE_AREA>
57.61

> <JCHEM_REFRACTIVITY>
86.68380000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(2-methyl-3-sulfanylpropanoyl)-4-(phenylsulfanyl)pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0260038
     RDKit          3D
Zofenoprilat
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.3832   -1.0424    0.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896   -0.8023   -0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3841   -1.8729   -1.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2695   -1.5847   -2.9721 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7706    0.5576   -0.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5134    1.3666   -1.5613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4896    1.0096   -0.4906 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4554    0.3395    0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4002    1.3869    0.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025    1.3655    0.3436 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9638   -0.1259    0.8010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642   -1.1265    1.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0229   -2.2873    1.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3343   -2.4863    1.5199 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9532   -1.4942    0.7934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2771   -0.3301    0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2070    2.7156    0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9349    2.3473   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0471    2.3145   -1.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505    1.2561   -2.4574 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584    3.4829   -2.2218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3870   -1.4553    1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6672   -1.8354    1.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1511   -0.1293    1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3308   -0.9070   -1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4281   -1.9307   -0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.8890   -1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4987   -1.9487   -3.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277   -0.2195   -0.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8073   -0.3431    1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000    1.3141    2.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3353   -1.0134    1.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5341   -3.0707    2.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8437   -3.3998    1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9989   -1.6483    0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7992    0.4296   -0.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5539    3.4801    0.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9267    3.1025    1.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7578    3.0658   -0.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3429    4.4088   -1.9829 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  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18  7  1  0
 16 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 21 40  1  0
M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  C   UNK     0       6.469  -0.885   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0       3.802   2.195   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.468  -0.115   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       3.802  -2.425   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.048  -3.330   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.572  -4.795   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.032  -4.795   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.091  -2.854   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.771  -1.348   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.053  -3.885   0.000  0.00  0.00           O+0
HETATM   15  S   UNK     0       5.477  -6.041   0.000  0.00  0.00           S+0
HETATM   16  C   UNK     0       4.851  -7.448   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.756  -8.693   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.129 -10.100   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.598 -10.261   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.693  -9.015   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.319  -7.609   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10    7   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0260038
HETATM    1  C1  UNL     1      -3.383  -1.042   0.877  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.290  -0.802  -0.608  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.384  -1.873  -1.199  1.00  0.00           C  
HETATM    4  S1  UNL     1      -2.270  -1.585  -2.972  1.00  0.00           S  
HETATM    5  C4  UNL     1      -2.771   0.558  -0.903  1.00  0.00           C  
HETATM    6  O1  UNL     1      -3.513   1.367  -1.561  1.00  0.00           O  
HETATM    7  N1  UNL     1      -1.490   1.010  -0.491  1.00  0.00           N  
HETATM    8  C5  UNL     1      -0.455   0.340   0.244  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.400   1.387   0.920  1.00  0.00           C  
HETATM   10  S2  UNL     1       2.102   1.365   0.344  1.00  0.00           S  
HETATM   11  C7  UNL     1       2.964  -0.126   0.801  1.00  0.00           C  
HETATM   12  C8  UNL     1       2.364  -1.126   1.525  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.023  -2.287   1.884  1.00  0.00           C  
HETATM   14  C10 UNL     1       4.334  -2.486   1.520  1.00  0.00           C  
HETATM   15  C11 UNL     1       4.953  -1.494   0.793  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.277  -0.330   0.439  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.207   2.716   0.525  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.935   2.347  -0.754  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.047   2.314  -1.848  1.00  0.00           C  
HETATM   20  O2  UNL     1       0.350   1.256  -2.457  1.00  0.00           O  
HETATM   21  O3  UNL     1       0.658   3.483  -2.222  1.00  0.00           O  
HETATM   22  H1  UNL     1      -4.387  -1.455   1.136  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.667  -1.835   1.162  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.151  -0.129   1.465  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.331  -0.907  -1.017  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.428  -1.931  -0.673  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.858  -2.889  -1.077  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.499  -1.949  -3.559  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.228  -0.220  -0.445  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.807  -0.343   1.016  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.400   1.314   2.017  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.335  -1.013   1.834  1.00  0.00           H  
HETATM   33  H12 UNL     1       2.534  -3.071   2.458  1.00  0.00           H  
HETATM   34  H13 UNL     1       4.844  -3.400   1.806  1.00  0.00           H  
HETATM   35  H14 UNL     1       5.999  -1.648   0.500  1.00  0.00           H  
HETATM   36  H15 UNL     1       4.799   0.430  -0.135  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.554   3.480   0.279  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.927   3.102   1.256  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.758   3.066  -0.896  1.00  0.00           H  
HETATM   40  H19 UNL     1       0.343   4.409  -1.983  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    5   25
CONECT    3    4   26   27
CONECT    4   28
CONECT    5    6    6    7
CONECT    7    8   18
CONECT    8    9   29   30
CONECT    9   10   17   31
CONECT   10   11
CONECT   11   12   12   16
CONECT   12   13   32
CONECT   13   14   14   33
CONECT   14   15   34
CONECT   15   16   16   35
CONECT   16   36
CONECT   17   18   37   38
CONECT   18   19   39
CONECT   19   20   20   21
CONECT   21   40
END

HMDB0260038
     RDKit          3D
Zofenoprilat
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.3832   -1.0424    0.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896   -0.8023   -0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3841   -1.8729   -1.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2695   -1.5847   -2.9721 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7706    0.5576   -0.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5134    1.3666   -1.5613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4896    1.0096   -0.4906 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4554    0.3395    0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4002    1.3869    0.9199 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025    1.3655    0.3436 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9638   -0.1259    0.8010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3642   -1.1265    1.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0229   -2.2873    1.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3343   -2.4863    1.5199 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9532   -1.4942    0.7934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2771   -0.3301    0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2070    2.7156    0.5248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9349    2.3473   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0471    2.3145   -1.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3505    1.2561   -2.4574 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584    3.4829   -2.2218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3870   -1.4553    1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6672   -1.8354    1.1625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1511   -0.1293    1.4649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3308   -0.9070   -1.0174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4281   -1.9307   -0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.8890   -1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4987   -1.9487   -3.5586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277   -0.2195   -0.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8073   -0.3431    1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000    1.3141    2.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3353   -1.0134    1.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5341   -3.0707    2.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8437   -3.3998    1.8056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9989   -1.6483    0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7992    0.4296   -0.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5539    3.4801    0.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9267    3.1025    1.2557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7578    3.0658   -0.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3429    4.4088   -1.9829 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  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18  7  1  0
 16 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 21 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(2-Methyl-3-sulfanylpropanoyl)-4-(phenylsulfanyl)pyrrolidine-2-carboxylate	Generator
1-(2-Methyl-3-sulphanylpropanoyl)-4-(phenylsulphanyl)pyrrolidine-2-carboxylate	Generator
1-(2-Methyl-3-sulphanylpropanoyl)-4-(phenylsulphanyl)pyrrolidine-2-carboxylic acid	Generator

Chemical Formula

C₁₅H₁₉NO₃S₂

Average Molecular Weight

325.44

Monoisotopic Molecular Weight

325.080635824

IUPAC Name

1-(2-methyl-3-sulfanylpropanoyl)-4-(phenylsulfanyl)pyrrolidine-2-carboxylic acid

Traditional Name

1-(2-methyl-3-sulfanylpropanoyl)-4-(phenylsulfanyl)pyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(CS)C(=O)N1CC(CC1C(O)=O)SC1=CC=CC=C1

InChI Identifier

InChI=1S/C15H19NO3S2/c1-10(9-20)14(17)16-8-12(7-13(16)15(18)19)21-11-5-3-2-4-6-11/h2-6,10,12-13,20H,7-9H2,1H3,(H,18,19)

InChI Key

UQWLOWFDKAFKAP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Proline or derivatives
Aryl thioether
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Thiophenol ether
Alkylarylthioether
Monocyclic benzene moiety
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Thioether
Sulfenyl compound
Alkylthiol
Azacycle
Organoheterocyclic compound
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Carbonyl group
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.59	ALOGPS
logP	2.41	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	3.91	ChemAxon
pKa (Strongest Basic)	-1.3	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	5	ChemAxon
Refractivity	86.68 m³·mol⁻¹	ChemAxon
Polarizability	34.04 Å³	ChemAxon
Number of Rings	2	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
AllCCS	[M+H]+	172.361	32859911
AllCCS	[M+H-H2O]+	169.472	32859911
AllCCS	[M+Na]+	175.793	32859911
AllCCS	[M+NH4]+	175.028	32859911
AllCCS	[M-H]-	172.592	32859911
AllCCS	[M+Na-2H]-	172.801	32859911
AllCCS	[M+HCOO]-	173.152	32859911
DeepCCS	[M+H]+	183.252	30932474
DeepCCS	[M-H]-	180.894	30932474
DeepCCS	[M-2H]-	213.779	30932474
DeepCCS	[M+Na]+	189.441	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zofenoprilat	CC(CS)C(=O)N1CC(CC1C(O)=O)SC1=CC=CC=C1	4072.5	Standard polar	33892256
Zofenoprilat	CC(CS)C(=O)N1CC(CC1C(O)=O)SC1=CC=CC=C1	2549.9	Standard non polar	33892256
Zofenoprilat	CC(CS)C(=O)N1CC(CC1C(O)=O)SC1=CC=CC=C1	2681.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Zofenoprilat,2TMS,isomer #1	CC(CS[Si](C)(C)C)C(=O)N1CC(SC2=CC=CC=C2)CC1C(=O)O[Si](C)(C)C	2771.6	Semi standard non polar	33892256
Zofenoprilat,2TMS,isomer #1	CC(CS[Si](C)(C)C)C(=O)N1CC(SC2=CC=CC=C2)CC1C(=O)O[Si](C)(C)C	2690.5	Standard non polar	33892256
Zofenoprilat,2TMS,isomer #1	CC(CS[Si](C)(C)C)C(=O)N1CC(SC2=CC=CC=C2)CC1C(=O)O[Si](C)(C)C	3313.0	Standard polar	33892256
Zofenoprilat,2TBDMS,isomer #1	CC(CS[Si](C)(C)C(C)(C)C)C(=O)N1CC(SC2=CC=CC=C2)CC1C(=O)O[Si](C)(C)C(C)(C)C	3262.0	Semi standard non polar	33892256
Zofenoprilat,2TBDMS,isomer #1	CC(CS[Si](C)(C)C(C)(C)C)C(=O)N1CC(SC2=CC=CC=C2)CC1C(=O)O[Si](C)(C)C(C)(C)C	3131.9	Standard non polar	33892256
Zofenoprilat,2TBDMS,isomer #1	CC(CS[Si](C)(C)C(C)(C)C)C(=O)N1CC(SC2=CC=CC=C2)CC1C(=O)O[Si](C)(C)C(C)(C)C	3467.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Zofenoprilat GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w4j-5890000000-0975b8fdd106757ef3a8	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zofenoprilat GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zofenoprilat GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zofenoprilat GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zofenoprilat GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zofenoprilat GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2342839

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3086142

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Zofenoprilat (HMDB0260038)

MOL for HMDB0260038 (Zofenoprilat)

3D MOL for HMDB0260038 (Zofenoprilat)

3D SDF for HMDB0260038 (Zofenoprilat)

3D-SDF for HMDB0260038 (Zofenoprilat)

PDB for HMDB0260038 (Zofenoprilat)

3D PDB for HMDB0260038 (Zofenoprilat)

SMILES for HMDB0260038 (Zofenoprilat)

INCHI for HMDB0260038 (Zofenoprilat)

Structure for HMDB0260038 (Zofenoprilat)

3D Structure for HMDB0260038 (Zofenoprilat)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra