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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:29 UTC

Update Date

2021-09-14 15:46:17 UTC

HMDB ID

HMDB0013929

Secondary Accession Numbers

HMDB13929

Metabolite Identification

Common Name

2-Oxoclopidogrel

Description

2-Oxoclopidogrel is a thiolactone intermediate of clopidogrel, an antithrombotic prodrug (PMID: 23249383 ).. Hepatic cytochrome P450 (P450) enzymes catalyze the conversion of clopidogrel to 2-oxo-clopidogrel via CYP3A oxidation. After oxidation, 2-oxoclopidogrel is then subsequently hydrolyzed to the clopidogrel active metabolite known as CAM (PMID: 25970225 ). 2-oxoclopidogrel can form four isomers (H1, H2, H3 and H4) of CAM, in which H4 only found in humans. The H4 isomer exhibits twice the activity of the H2 isomer (PMID: 28602635 ). The H4 isomer blocks adenosine diphosphate (ADP) binding to the P2Y12 receptor which thereby inhibits ADP induced platelet aggregation. 2-oxoclopidogrel is only found in individuals that have used or taken Clopidogrel.

Structure

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

HMDB0013929
     RDKit          3D
2-Oxoclopidogrel
 38 40  0  0  0  0  0  0  0  0999 V2000
   -1.1440    3.7162   -0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6152    2.3896   -0.5138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3741    1.3142   -0.9408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5507    1.4913   -1.4114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8591   -0.0774   -0.8712 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8734   -0.8662   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5712   -0.4329    0.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5291   -1.1885    1.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8111   -2.4451    1.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1372   -2.9223    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1941   -2.1489   -0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753   -2.8081   -1.9843 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4525   -0.0950   -0.3960 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    0.3382    0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9201   -0.4433    1.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7435   -1.0494    0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5143   -1.1748    0.8999 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9798    0.3404    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0269    0.9594    0.2845 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8877    0.6172   -0.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963   -0.0491   -0.6455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4814   -0.0017   -1.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474    3.7474    0.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3497    3.8637   -1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3452    4.4067   -0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8244   -0.4361   -1.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3365    0.5833    1.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0377   -0.7824    2.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5684   -3.0848    1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4071   -3.9295   -0.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119    1.4153    0.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554    0.2454    1.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5675   -1.2578    2.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5575    0.2331    2.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3573   -2.0004    0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0037    1.3866   -1.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584   -0.8080   -2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548    0.9536   -1.9361 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 11  6  1  0
 22 13  1  0
 21 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  6
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 20 36  1  0
 22 37  1  0
 22 38  1  0
M  END

  Mrv0541 06191310322D          

 22 24  0  0  1  0            999 V2000
    6.2454   -3.2039    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.5987   -5.5180    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.9601   -2.7914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3890   -2.7914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3890   -4.4416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3890   -5.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1034   -4.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6745   -4.0291    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1034   -5.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8180   -4.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8180   -5.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9601   -4.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5987   -4.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6745   -3.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0802   -4.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2454   -4.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9601   -5.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5309   -4.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2454   -5.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5309   -5.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9601   -1.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9052   -4.8541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  2 11  1  0  0  0  0
  2 15  1  0  0  0  0
  3 14  1  0  0  0  0
  3 21  1  0  0  0  0
  4 14  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 12  1  0  0  0  0
  8 14  1  1  0  0  0
  9 11  1  0  0  0  0
 10 13  2  0  0  0  0
 12 16  1  0  0  0  0
 12 17  2  0  0  0  0
 16 18  2  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  2  0  0  0  0
 15 22  2  0  0  0  0
 10 11  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013929

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)[C@@H](N1CCC2SC(=O)C=C2C1)C1=CC=CC=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C16H16ClNO3S/c1-21-16(20)15(11-4-2-3-5-12(11)17)18-7-6-13-10(9-18)8-14(19)22-13/h2-5,8,13,15H,6-7,9H2,1H3/t13?,15-/m0/s1

> <INCHI_KEY>
JBSAZVIMJUOBNB-WUJWULDRSA-N

> <FORMULA>
C16H16ClNO3S

> <MOLECULAR_WEIGHT>
337.821

> <EXACT_MASS>
337.05394178

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.851766525081786

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2S)-2-(2-chlorophenyl)-2-{2-oxo-2H,4H,5H,6H,7H,7aH-thieno[3,2-c]pyridin-5-yl}acetate

> <ALOGPS_LOGP>
2.75

> <JCHEM_LOGP>
2.8675791276666667

> <ALOGPS_LOGS>
-3.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.28373757495149

> <JCHEM_PKA_STRONGEST_BASIC>
4.506039584483413

> <JCHEM_POLAR_SURFACE_AREA>
46.61

> <JCHEM_REFRACTIVITY>
88.00800000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S)-2-(2-chlorophenyl)-2-{2-oxo-4H,6H,7H,7aH-thieno[3,2-c]pyridin-5-yl}acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013929
     RDKit          3D
2-Oxoclopidogrel
 38 40  0  0  0  0  0  0  0  0999 V2000
   -1.1440    3.7162   -0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6152    2.3896   -0.5138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3741    1.3142   -0.9408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5507    1.4913   -1.4114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8591   -0.0774   -0.8712 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8734   -0.8662   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5712   -0.4329    0.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5291   -1.1885    1.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8111   -2.4451    1.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1372   -2.9223    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1941   -2.1489   -0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753   -2.8081   -1.9843 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4525   -0.0950   -0.3960 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    0.3382    0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9201   -0.4433    1.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7435   -1.0494    0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5143   -1.1748    0.8999 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9798    0.3404    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0269    0.9594    0.2845 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8877    0.6172   -0.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963   -0.0491   -0.6455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4814   -0.0017   -1.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474    3.7474    0.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3497    3.8637   -1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3452    4.4067   -0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8244   -0.4361   -1.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3365    0.5833    1.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0377   -0.7824    2.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5684   -3.0848    1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4071   -3.9295   -0.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119    1.4153    0.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554    0.2454    1.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5675   -1.2578    2.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5575    0.2331    2.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3573   -2.0004    0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0037    1.3866   -1.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584   -0.8080   -2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548    0.9536   -1.9361 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 11  6  1  0
 22 13  1  0
 21 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  6
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 20 36  1  0
 22 37  1  0
 22 38  1  0
M  END

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1 Cl   UNK     0      11.658  -5.981   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0      19.784 -10.300   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      12.992  -5.211   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      15.659  -5.211   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      15.659  -8.291   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      15.659  -9.831   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.993  -7.521   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.326  -7.521   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.993 -10.601   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.327  -8.291   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.327  -9.831   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.992  -8.291   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.784  -7.822   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.326  -5.981   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.683  -9.061   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.658  -7.521   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.992  -9.831   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.324  -8.291   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.658 -10.601   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.324  -9.831   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.992  -3.671   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      22.223  -9.061   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   11   15                                                       
CONECT    3   14   21                                                       
CONECT    4   14                                                            
CONECT    5    6    7    8                                                  
CONECT    6    5    9                                                       
CONECT    7    5   10                                                       
CONECT    8    5   12   14                                                  
CONECT    9    6   11                                                       
CONECT   10    7   13   11                                                  
CONECT   11    2    9   10                                                  
CONECT   12    8   16   17                                                  
CONECT   13   10   15                                                       
CONECT   14    3    4    8                                                  
CONECT   15    2   22   13                                                  
CONECT   16    1   12   18                                                  
CONECT   17   12   19                                                       
CONECT   18   16   20                                                       
CONECT   19   17   20                                                       
CONECT   20   18   19                                                       
CONECT   21    3                                                            
CONECT   22   15                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0013929
HETATM    1  C1  UNL     1      -1.144   3.716  -0.596  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.615   2.390  -0.514  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.374   1.314  -0.941  1.00  0.00           C  
HETATM    4  O2  UNL     1      -2.551   1.491  -1.411  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.859  -0.077  -0.871  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.873  -0.866  -0.141  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.571  -0.433   0.964  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.529  -1.189   1.614  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.811  -2.445   1.141  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.137  -2.922   0.036  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.194  -2.149  -0.585  1.00  0.00           C  
HETATM   12 CL1  UNL     1      -1.375  -2.808  -1.984  1.00  0.00          CL  
HETATM   13  N1  UNL     1       0.453  -0.095  -0.396  1.00  0.00           N  
HETATM   14  C10 UNL     1       0.792   0.338   0.882  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.920  -0.443   1.543  1.00  0.00           C  
HETATM   16  C12 UNL     1       2.743  -1.049   0.436  1.00  0.00           C  
HETATM   17  S1  UNL     1       4.514  -1.175   0.900  1.00  0.00           S  
HETATM   18  C13 UNL     1       4.980   0.340   0.082  1.00  0.00           C  
HETATM   19  O3  UNL     1       6.027   0.959   0.285  1.00  0.00           O  
HETATM   20  C14 UNL     1       3.888   0.617  -0.804  1.00  0.00           C  
HETATM   21  C15 UNL     1       2.796  -0.049  -0.645  1.00  0.00           C  
HETATM   22  C16 UNL     1       1.481  -0.002  -1.397  1.00  0.00           C  
HETATM   23  H1  UNL     1      -2.047   3.747   0.014  1.00  0.00           H  
HETATM   24  H2  UNL     1      -1.350   3.864  -1.688  1.00  0.00           H  
HETATM   25  H3  UNL     1      -0.345   4.407  -0.252  1.00  0.00           H  
HETATM   26  H4  UNL     1      -0.824  -0.436  -1.964  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.337   0.583   1.315  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.038  -0.782   2.479  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.568  -3.085   1.629  1.00  0.00           H  
HETATM   30  H8  UNL     1      -3.407  -3.929  -0.292  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.112   1.415   0.885  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.055   0.245   1.577  1.00  0.00           H  
HETATM   33  H11 UNL     1       1.567  -1.258   2.179  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.558   0.233   2.139  1.00  0.00           H  
HETATM   35  H13 UNL     1       2.357  -2.000   0.070  1.00  0.00           H  
HETATM   36  H14 UNL     1       4.004   1.387  -1.596  1.00  0.00           H  
HETATM   37  H15 UNL     1       1.458  -0.808  -2.154  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.355   0.954  -1.936  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   13   26
CONECT    6    7    7   11
CONECT    7    8   27
CONECT    8    9    9   28
CONECT    9   10   29
CONECT   10   11   11   30
CONECT   11   12
CONECT   13   14   22
CONECT   14   15   31   32
CONECT   15   16   33   34
CONECT   16   17   21   35
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   21   21   36
CONECT   21   22
CONECT   22   37   38
END

HMDB0013929
     RDKit          3D
2-Oxoclopidogrel
 38 40  0  0  0  0  0  0  0  0999 V2000
   -1.1440    3.7162   -0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6152    2.3896   -0.5138 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3741    1.3142   -0.9408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5507    1.4913   -1.4114 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8591   -0.0774   -0.8712 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8734   -0.8662   -0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5712   -0.4329    0.9641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5291   -1.1885    1.6143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8111   -2.4451    1.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1372   -2.9223    0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1941   -2.1489   -0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3753   -2.8081   -1.9843 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4525   -0.0950   -0.3960 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    0.3382    0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9201   -0.4433    1.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7435   -1.0494    0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5143   -1.1748    0.8999 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9798    0.3404    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0269    0.9594    0.2845 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8877    0.6172   -0.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963   -0.0491   -0.6455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4814   -0.0017   -1.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474    3.7474    0.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3497    3.8637   -1.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3452    4.4067   -0.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8244   -0.4361   -1.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3365    0.5833    1.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0377   -0.7824    2.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5684   -3.0848    1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4071   -3.9295   -0.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1119    1.4153    0.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0554    0.2454    1.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5675   -1.2578    2.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5575    0.2331    2.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3573   -2.0004    0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0037    1.3866   -1.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4584   -0.8080   -2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548    0.9536   -1.9361 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 11  6  1  0
 22 13  1  0
 21 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  6
  7 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 20 36  1  0
 22 37  1  0
 22 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-oxo-Clopidogrel	HMDB
(2S)Methyl 2-(2-chlorophenyl)-2-(2-oxo-7,7a-dihydrothieno(3,2-c)pyridin-5(2H,4H,6H)-yl)acetate	HMDB

Chemical Formula

C₁₆H₁₆ClNO₃S

Average Molecular Weight

337.821

Monoisotopic Molecular Weight

337.05394178

IUPAC Name

methyl (2S)-2-(2-chlorophenyl)-2-{2-oxo-2H,4H,5H,6H,7H,7aH-thieno[3,2-c]pyridin-5-yl}acetate

Traditional Name

methyl (2S)-2-(2-chlorophenyl)-2-{2-oxo-4H,6H,7H,7aH-thieno[3,2-c]pyridin-5-yl}acetate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H](N1CCC2SC(=O)C=C2C1)C1=CC=CC=C1Cl

InChI Identifier

InChI=1S/C16H16ClNO3S/c1-21-16(20)15(11-4-2-3-5-12(11)17)18-7-6-13-10(9-18)8-14(19)22-13/h2-5,8,13,15H,6-7,9H2,1H3/t13?,15-/m0/s1

InChI Key

JBSAZVIMJUOBNB-WUJWULDRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid esters

Alternative Parents

Substituents

Alpha-amino acid ester
Thienopyridine
Chlorobenzene
Halobenzene
Aralkylamine
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Piperidine
Benzenoid
Methyl ester
Carbothioic s-lactone
2,5-dihydrothiophene
Tertiary aliphatic amine
Thiocarboxylic acid ester
Tertiary amine
Carboxylic acid ester
Thiocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Organohalogen compound
Organopnictogen compound
Organochloride
Organic oxygen compound
Organonitrogen compound
Carbonyl group
Amine
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0013929)
Kidney (HMDB: HMDB0013929)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013929)

Source

Endogenous

Endogenous (HMDB: HMDB0013929)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Clopidogrel Action Pathway (PathBank: SMP0000260)

Metabolic pathway

Clopidogrel Metabolism Pathway (PathBank: SMP0000610)

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
Water Solubility	0.053 g/L	ALOGPS
logP	2.75	ALOGPS
logP	2.87	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.28	ChemAxon
pKa (Strongest Basic)	4.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.61 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.01 m³·mol⁻¹	ChemAxon
Polarizability	33.85 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	174.305	30932474
DeepCCS	[M-H]-	171.947	30932474
DeepCCS	[M-2H]-	206.226	30932474
DeepCCS	[M+Na]+	181.338	30932474
AllCCS	[M+H]+	174.2	32859911
AllCCS	[M+H-H2O]+	171.2	32859911
AllCCS	[M+NH4]+	177.0	32859911
AllCCS	[M+Na]+	177.8	32859911
AllCCS	[M-H]-	175.0	32859911
AllCCS	[M+Na-2H]-	174.8	32859911
AllCCS	[M+HCOO]-	174.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Oxoclopidogrel	COC(=O)[C@@H](N1CCC2SC(=O)C=C2C1)C1=CC=CC=C1Cl	3807.3	Standard polar	33892256
2-Oxoclopidogrel	COC(=O)[C@@H](N1CCC2SC(=O)C=C2C1)C1=CC=CC=C1Cl	2646.2	Standard non polar	33892256
2-Oxoclopidogrel	COC(=O)[C@@H](N1CCC2SC(=O)C=C2C1)C1=CC=CC=C1Cl	2675.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Oxoclopidogrel GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0190000000-489b988baa99d3ba5ff1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Oxoclopidogrel 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 10V, Positive-QTOF	splash10-000i-0119000000-8a5e7008cac66b267421	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 20V, Positive-QTOF	splash10-059i-0196000000-26909a713c5535a89bf5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 40V, Positive-QTOF	splash10-004j-4590000000-bc0e44783d88160ecf93	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 10V, Negative-QTOF	splash10-000i-0009000000-9bddc2d228e1e448d914	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 20V, Negative-QTOF	splash10-0f7c-0159000000-6c8164efb2cd0531f5ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 40V, Negative-QTOF	splash10-03dl-6791000000-0473925e521b6029585b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 10V, Negative-QTOF	splash10-000i-0049000000-adb4e0342f064419581d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 20V, Negative-QTOF	splash10-0059-5192000000-e19d0ffa95f84bc89156	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 40V, Negative-QTOF	splash10-001i-9682000000-aef34ebc8a3f6b9a9ce6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 10V, Positive-QTOF	splash10-000i-0009000000-584cee3804a36ce3f821	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 20V, Positive-QTOF	splash10-000i-0229000000-10f9eb47c9a85cda3886	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxoclopidogrel 40V, Positive-QTOF	splash10-03fr-0944000000-9d423bbf8f92a15c9fd8	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

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

28518812

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56848893

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

Zhu Y, Zhou J: In vitro biotransformation studies of 2-oxo-clopidogrel: multiple thiolactone ring-opening pathways further attenuate prodrug activation. Chem Res Toxicol. 2013 Jan 18;26(1):179-90. doi: 10.1021/tx300460k. Epub 2012 Dec 28. [PubMed:23249383 ]
Dansette PM, Levent D, Hessani A, Mansuy D: Bioactivation of clopidogrel and prasugrel: factors determining the stereochemistry of the thiol metabolite double bond. Chem Res Toxicol. 2015 Jun 15;28(6):1338-45. doi: 10.1021/acs.chemrestox.5b00133. Epub 2015 May 21. [PubMed:25970225 ]
Lyngby JG, Court MH, Lee PM: Validation of a method for quantitation of the clopidogrel active metabolite, clopidogrel, clopidogrel carboxylic acid, and 2-oxo-clopidogrel in feline plasma. J Vet Cardiol. 2017 Aug;19(4):384-395. doi: 10.1016/j.jvc.2017.03.004. Epub 2017 Jun 9. [PubMed:28602635 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Saw J, Steinhubl SR, Berger PB, Kereiakes DJ, Serebruany VL, Brennan D, Topol EJ: Lack of adverse clopidogrel-atorvastatin clinical interaction from secondary analysis of a randomized, placebo-controlled clopidogrel trial. Circulation. 2003 Aug 26;108(8):921-4. Epub 2003 Aug 18. [PubMed:12925453 ]
Neubauer H, Gunesdogan B, Hanefeld C, Spiecker M, Mugge A: Lipophilic statins interfere with the inhibitory effects of clopidogrel on platelet function--a flow cytometry study. Eur Heart J. 2003 Oct;24(19):1744-9. [PubMed:14522569 ]
Lau WC, Gurbel PA, Watkins PB, Neer CJ, Hopp AS, Carville DG, Guyer KE, Tait AR, Bates ER: Contribution of hepatic cytochrome P450 3A4 metabolic activity to the phenomenon of clopidogrel resistance. Circulation. 2004 Jan 20;109(2):166-71. Epub 2004 Jan 5. [PubMed:14707025 ]
Mukherjee D, Kline-Rogers E, Fang J, Munir K, Eagle KA: Lack of clopidogrel-CYP3A4 statin interaction in patients with acute coronary syndrome. Heart. 2005 Jan;91(1):23-6. [PubMed:15604326 ]
Poulsen TS, Vinholt P, Mickley H, Korsholm L, Kristensen SR, Damkier P: Existence of a clinically relevant interaction between clopidogrel and HMG-CoA reductase inhibitors? Re-evaluating the evidence. Basic Clin Pharmacol Toxicol. 2005 Feb;96(2):103-10. [PubMed:15679472 ]
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 ]
Clarke TA, Waskell LA: The metabolism of clopidogrel is catalyzed by human cytochrome P450 3A and is inhibited by atorvastatin. Drug Metab Dispos. 2003 Jan;31(1):53-9. [PubMed:12485953 ]

Enzyme Details

2. Cytochrome P450 2C9

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

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2C19

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

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [PubMed:17101742 ]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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

5. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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

6. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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

7. Cytochrome P450 2C8

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

References

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

Enzyme Details

8. P2Y purinoceptor 12

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for ADP and ATP coupled to G-proteins that inhibit the adenylyl cyclase second messenger system. Not activated by UDP and UTP. Involved in platelets aggregation
Gene Name:: P2RY12
Uniprot ID:: Q9H244
Molecular weight:: 39438.4

References

Dorsam RT, Murugappan S, Ding Z, Kunapuli SP: Clopidogrel: interactions with the P2Y12 receptor and clinical relevance. Hematology. 2003 Dec;8(6):359-65. [PubMed:14668029 ]
Herbert JM, Savi P: P2Y12, a new platelet ADP receptor, target of clopidogrel. Semin Vasc Med. 2003 May;3(2):113-22. [PubMed:15199474 ]
Taubert D, Kastrati A, Harlfinger S, Gorchakova O, Lazar A, von Beckerath N, Schomig A, Schomig E: Pharmacokinetics of clopidogrel after administration of a high loading dose. Thromb Haemost. 2004 Aug;92(2):311-6. [PubMed:15269827 ]
Wang L, Jacobsen SE, Bengtsson A, Erlinge D: P2 receptor mRNA expression profiles in human lymphocytes, monocytes and CD34+ stem and progenitor cells. BMC Immunol. 2004 Aug 3;5:16. [PubMed:15291969 ]
Wihlborg AK, Wang L, Braun OO, Eyjolfsson A, Gustafsson R, Gudbjartsson T, Erlinge D: ADP receptor P2Y12 is expressed in vascular smooth muscle cells and stimulates contraction in human blood vessels. Arterioscler Thromb Vasc Biol. 2004 Oct;24(10):1810-5. Epub 2004 Aug 12. [PubMed:15308557 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Gladding P, Webster M, Zeng I, Farrell H, Stewart J, Ruygrok P, Ormiston J, El-Jack S, Armstrong G, Kay P, Scott D, Gunes A, Dahl ML: The pharmacogenetics and pharmacodynamics of clopidogrel response: an analysis from the PRINC (Plavix Response in Coronary Intervention) trial. JACC Cardiovasc Interv. 2008 Dec;1(6):620-7. doi: 10.1016/j.jcin.2008.09.008. [PubMed:19463375 ]
Savi P, Zachayus JL, Delesque-Touchard N, Labouret C, Herve C, Uzabiaga MF, Pereillo JM, Culouscou JM, Bono F, Ferrara P, Herbert JM: The active metabolite of Clopidogrel disrupts P2Y12 receptor oligomers and partitions them out of lipid rafts. Proc Natl Acad Sci U S A. 2006 Jul 18;103(29):11069-74. Epub 2006 Jul 11. [PubMed:16835302 ]
van Gestel MA, Heemskerk JW, Slaaf DW, Heijnen VV, Reneman RS, oude Egbrink MG: In vivo blockade of platelet ADP receptor P2Y12 reduces embolus and thrombus formation but not thrombus stability. Arterioscler Thromb Vasc Biol. 2003 Mar 1;23(3):518-23. Epub 2003 Jan 23. [PubMed:12615691 ]

Showing metabocard for 2-Oxoclopidogrel (HMDB0013929)

MOL for HMDB0013929 (2-Oxoclopidogrel)

3D MOL for HMDB0013929 (2-Oxoclopidogrel)

3D SDF for HMDB0013929 (2-Oxoclopidogrel)

3D-SDF for HMDB0013929 (2-Oxoclopidogrel)

PDB for HMDB0013929 (2-Oxoclopidogrel)

3D PDB for HMDB0013929 (2-Oxoclopidogrel)

SMILES for HMDB0013929 (2-Oxoclopidogrel)

INCHI for HMDB0013929 (2-Oxoclopidogrel)

Structure for HMDB0013929 (2-Oxoclopidogrel)

3D Structure for HMDB0013929 (2-Oxoclopidogrel)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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