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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:45:01 UTC

Update Date

2021-09-26 23:16:40 UTC

HMDB ID

HMDB0259248

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Trinexapac-ethyl

Description

trinexapac-ethyl belongs to the class of organic compounds known as vinylogous acids. These are organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety. Based on a literature review a significant number of articles have been published on trinexapac-ethyl. This compound has been identified in human blood as reported by (PMID: 31557052 ). Trinexapac-ethyl is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Trinexapac-ethyl 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

HMDB0259248
     RDKit          3D
Trinexapac-ethyl
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.9846    1.4250   -0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2981    1.1624    0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9300    0.8477    0.5566 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4488   -0.2072   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2209   -0.9957   -0.7310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9939   -0.4330   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4015   -0.6386    1.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0641   -0.7801    1.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8330   -0.7102    2.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6461   -1.0084   -0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8755   -0.6522   -0.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3399   -0.9234   -1.8862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8409    0.0118    0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4838    1.2217    1.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4182    1.3360   -0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7832   -1.6621   -1.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2731   -2.2126   -2.2989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6891   -1.6312   -1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1733    0.5063   -1.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4620    2.2119   -1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9916    1.8524   -0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3358    2.1171    1.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8674    0.4185    1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4767    0.4490   -0.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6951    0.1607    1.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867   -1.6316    1.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8478   -1.7979   -1.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5604   -0.6978    0.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8839    1.3166    2.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5117    1.7385    0.9658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0670    1.8158   -1.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4816    1.5226    0.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1716   -1.5591   -2.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9829   -2.5731   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  2  0
 16 18  1  0
 18  6  1  0
 15 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 18 33  1  0
 18 34  1  0
M  END


  Mrv1572004221603522D          

 18 19  0  0  0  0            999 V2000
    3.1599    7.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599    6.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7309    5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    5.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    5.6645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    4.4270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1599    5.2520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    6.4895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  7  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  2  0  0  0  0
 15 10  2  0  0  0  0
 16 12  1  0  0  0  0
 17 13  2  0  0  0  0
 18  2  1  0  0  0  0
 18 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259248

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)C1CC(=O)C(=C(O)C2CC2)C(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O5/c1-2-18-13(17)8-5-9(14)11(10(15)6-8)12(16)7-3-4-7/h7-8,16H,2-6H2,1H3/b12-11-

> <INCHI_KEY>
RVKCCVTVZORVGD-QXMHVHEDSA-N

> <FORMULA>
C13H16O5

> <MOLECULAR_WEIGHT>
252.266

> <EXACT_MASS>
252.099773615

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
25.90785090771419

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 4-[cyclopropyl(hydroxy)methylidene]-3,5-dioxocyclohexane-1-carboxylate

> <ALOGPS_LOGP>
0.94

> <JCHEM_LOGP>
0.9033613010000006

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.04075007049619

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.373046563101245

> <JCHEM_PKA_STRONGEST_BASIC>
-7.014755967823468

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
64.06630000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trinexapac-ethyl

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259248
     RDKit          3D
Trinexapac-ethyl
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.9846    1.4250   -0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2981    1.1624    0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9300    0.8477    0.5566 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4488   -0.2072   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2209   -0.9957   -0.7310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9939   -0.4330   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4015   -0.6386    1.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0641   -0.7801    1.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8330   -0.7102    2.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6461   -1.0084   -0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8755   -0.6522   -0.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3399   -0.9234   -1.8862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8409    0.0118    0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4838    1.2217    1.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4182    1.3360   -0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7832   -1.6621   -1.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2731   -2.2126   -2.2989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6891   -1.6312   -1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1733    0.5063   -1.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4620    2.2119   -1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9916    1.8524   -0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3358    2.1171    1.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8674    0.4185    1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4767    0.4490   -0.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6951    0.1607    1.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867   -1.6316    1.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8478   -1.7979   -1.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5604   -0.6978    0.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8839    1.3166    2.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5117    1.7385    0.9658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0670    1.8158   -1.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4816    1.5226    0.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1716   -1.5591   -2.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9829   -2.5731   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  2  0
 16 18  1  0
 18  6  1  0
 15 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 18 33  1  0
 18 34  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0       5.898  14.424   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.898  12.884   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.540   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.231   8.264   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.897  10.574   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770   5.954   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.231   9.804   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.897   7.494   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.564   9.804   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.564   8.264   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.770   7.494   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.565  10.574   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.897   5.954   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -0.770  10.574   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.104   8.264   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.898   9.804   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.565  12.114   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   18                                                       
CONECT    3    4    7                                                       
CONECT    4    3    7                                                       
CONECT    5    8    9                                                       
CONECT    6    8   10                                                       
CONECT    7    3    4   12                                                  
CONECT    8    5    6   13                                                  
CONECT    9    5   11   14                                                  
CONECT   10    6   11   15                                                  
CONECT   11    9   10   12                                                  
CONECT   12    7   11   16                                                  
CONECT   13    8   17   18                                                  
CONECT   14    9                                                            
CONECT   15   10                                                            
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18    2   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0259248
HETATM    1  C1  UNL     1       4.985   1.425  -0.604  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.298   1.162   0.712  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.930   0.848   0.557  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.449  -0.207  -0.151  1.00  0.00           C  
HETATM    5  O2  UNL     1       3.221  -0.996  -0.731  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.994  -0.433  -0.241  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.401  -0.639   1.128  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.064  -0.780   1.009  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.833  -0.710   2.016  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.646  -1.008  -0.300  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.875  -0.652  -0.586  1.00  0.00           C  
HETATM   12  O4  UNL     1      -3.340  -0.923  -1.886  1.00  0.00           O  
HETATM   13  C9  UNL     1      -3.841   0.012   0.309  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.484   1.222   1.103  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.418   1.336  -0.067  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.783  -1.662  -1.317  1.00  0.00           C  
HETATM   17  O5  UNL     1      -1.273  -2.213  -2.299  1.00  0.00           O  
HETATM   18  C13 UNL     1       0.689  -1.631  -1.115  1.00  0.00           C  
HETATM   19  H1  UNL     1       5.173   0.506  -1.182  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.462   2.212  -1.192  1.00  0.00           H  
HETATM   21  H3  UNL     1       5.992   1.852  -0.354  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.336   2.117   1.296  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.867   0.419   1.269  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.477   0.449  -0.675  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.695   0.161   1.839  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.787  -1.632   1.504  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.848  -1.798  -1.988  1.00  0.00           H  
HETATM   28  H10 UNL     1      -4.560  -0.698   0.797  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.884   1.317   2.132  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.512   1.738   0.966  1.00  0.00           H  
HETATM   31  H13 UNL     1      -4.067   1.816  -1.005  1.00  0.00           H  
HETATM   32  H14 UNL     1      -5.482   1.523   0.151  1.00  0.00           H  
HETATM   33  H15 UNL     1       1.172  -1.559  -2.091  1.00  0.00           H  
HETATM   34  H16 UNL     1       0.983  -2.573  -0.643  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   18   24
CONECT    7    8   25   26
CONECT    8    9    9   10
CONECT   10   11   11   16
CONECT   11   12   13
CONECT   12   27
CONECT   13   14   15   28
CONECT   14   15   29   30
CONECT   15   31   32
CONECT   16   17   17   18
CONECT   18   33   34
END

HMDB0259248
     RDKit          3D
Trinexapac-ethyl
 34 35  0  0  0  0  0  0  0  0999 V2000
    4.9846    1.4250   -0.6040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2981    1.1624    0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9300    0.8477    0.5566 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4488   -0.2072   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2209   -0.9957   -0.7310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9939   -0.4330   -0.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4015   -0.6386    1.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0641   -0.7801    1.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8330   -0.7102    2.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6461   -1.0084   -0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8755   -0.6522   -0.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3399   -0.9234   -1.8862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8409    0.0118    0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4838    1.2217    1.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4182    1.3360   -0.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7832   -1.6621   -1.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2731   -2.2126   -2.2989 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6891   -1.6312   -1.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1733    0.5063   -1.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4620    2.2119   -1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9916    1.8524   -0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3358    2.1171    1.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8674    0.4185    1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4767    0.4490   -0.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6951    0.1607    1.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867   -1.6316    1.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8478   -1.7979   -1.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5604   -0.6978    0.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8839    1.3166    2.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5117    1.7385    0.9658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0670    1.8158   -1.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4816    1.5226    0.1506 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1716   -1.5591   -2.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9829   -2.5731   -0.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  2  0
 16 18  1  0
 18  6  1  0
 15 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
 18 33  1  0
 18 34  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Ethyl (RS)-4-cyclopropyl(hydroxy)methylene-3,5-dioxocyclohexanecarboxylate	ChEBI
Ethyl 4-(cyclopropylhydroxymethylene)-3,5-dioxocyclohexanecarboxylate	ChEBI
Ethyl (RS)-4-cyclopropyl(hydroxy)methylene-3,5-dioxocyclohexanecarboxylic acid	Generator
Ethyl 4-(cyclopropylhydroxymethylene)-3,5-dioxocyclohexanecarboxylic acid	Generator

Chemical Formula

C₁₃H₁₆O₅

Average Molecular Weight

252.266

Monoisotopic Molecular Weight

252.099773615

IUPAC Name

ethyl 4-[cyclopropyl(hydroxy)methylidene]-3,5-dioxocyclohexane-1-carboxylate

Traditional Name

trinexapac-ethyl

CAS Registry Number

Not Available

SMILES

CCOC(=O)C1CC(=O)C(=C(O)C2CC2)C(=O)C1

InChI Identifier

InChI=1S/C13H16O5/c1-2-18-13(17)8-5-9(14)11(10(15)6-8)12(16)7-3-4-7/h7-8,16H,2-6H2,1H3/b12-11-

InChI Key

RVKCCVTVZORVGD-QXMHVHEDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vinylogous acids. These are organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Vinylogous acids

Sub Class

Not Available

Direct Parent

Vinylogous acids

Alternative Parents

Substituents

Vinylogous acid
Cyclic ketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Enol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

ethyl ester (CHEBI:81817 )
beta-hydroxy ketone (CHEBI:81817 )
enol (CHEBI:81817 )
cyclohexanones (CHEBI:81817 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	0.94	ALOGPS
logP	0.9	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	64.07 m³·mol⁻¹	ChemAxon
Polarizability	25.91 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
DeepCCS	[M+H]+	158.371	30932474
DeepCCS	[M-H]-	156.013	30932474
DeepCCS	[M-2H]-	188.899	30932474
DeepCCS	[M+Na]+	164.465	30932474
AllCCS	[M+H]+	157.7	32859911
AllCCS	[M+H-H2O]+	154.1	32859911
AllCCS	[M+NH4]+	161.1	32859911
AllCCS	[M+Na]+	162.1	32859911
AllCCS	[M-H]-	160.9	32859911
AllCCS	[M+Na-2H]-	160.9	32859911
AllCCS	[M+HCOO]-	161.1	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.	5.66 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0559 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.28 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2027.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	267.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	132.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	100.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	523.7 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	458.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	87.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	859.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	363.1 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	1286.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	239.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	373.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	360.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	154.4 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	174.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trinexapac-ethyl	CCOC(=O)C1CC(=O)C(=C(O)C2CC2)C(=O)C1	2985.3	Standard polar	33892256
Trinexapac-ethyl	CCOC(=O)C1CC(=O)C(=C(O)C2CC2)C(=O)C1	1816.0	Standard non polar	33892256
Trinexapac-ethyl	CCOC(=O)C1CC(=O)C(=C(O)C2CC2)C(=O)C1	1912.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Trinexapac-ethyl,2TMS,isomer #1	CCOC(=O)C1C=C(O[Si](C)(C)C)C(=C(O[Si](C)(C)C)C2CC2)C(=O)C1	2149.9	Semi standard non polar	33892256
Trinexapac-ethyl,2TMS,isomer #1	CCOC(=O)C1C=C(O[Si](C)(C)C)C(=C(O[Si](C)(C)C)C2CC2)C(=O)C1	2045.0	Standard non polar	33892256
Trinexapac-ethyl,2TMS,isomer #1	CCOC(=O)C1C=C(O[Si](C)(C)C)C(=C(O[Si](C)(C)C)C2CC2)C(=O)C1	2502.7	Standard polar	33892256
Trinexapac-ethyl,2TMS,isomer #2	CCOC(=O)C1C=C(O[Si](C)(C)C)C(=C(O)C2CC2)C(O[Si](C)(C)C)=C1	2116.6	Semi standard non polar	33892256
Trinexapac-ethyl,2TMS,isomer #2	CCOC(=O)C1C=C(O[Si](C)(C)C)C(=C(O)C2CC2)C(O[Si](C)(C)C)=C1	1988.7	Standard non polar	33892256
Trinexapac-ethyl,2TMS,isomer #2	CCOC(=O)C1C=C(O[Si](C)(C)C)C(=C(O)C2CC2)C(O[Si](C)(C)C)=C1	2828.3	Standard polar	33892256
Trinexapac-ethyl,3TMS,isomer #1	CCOC(=O)C1C=C(O[Si](C)(C)C)C(=C(O[Si](C)(C)C)C2CC2)C(O[Si](C)(C)C)=C1	2146.4	Semi standard non polar	33892256
Trinexapac-ethyl,3TMS,isomer #1	CCOC(=O)C1C=C(O[Si](C)(C)C)C(=C(O[Si](C)(C)C)C2CC2)C(O[Si](C)(C)C)=C1	2106.1	Standard non polar	33892256
Trinexapac-ethyl,3TMS,isomer #1	CCOC(=O)C1C=C(O[Si](C)(C)C)C(=C(O[Si](C)(C)C)C2CC2)C(O[Si](C)(C)C)=C1	2456.3	Standard polar	33892256
Trinexapac-ethyl,2TBDMS,isomer #1	CCOC(=O)C1C=C(O[Si](C)(C)C(C)(C)C)C(=C(O[Si](C)(C)C(C)(C)C)C2CC2)C(=O)C1	2591.2	Semi standard non polar	33892256
Trinexapac-ethyl,2TBDMS,isomer #1	CCOC(=O)C1C=C(O[Si](C)(C)C(C)(C)C)C(=C(O[Si](C)(C)C(C)(C)C)C2CC2)C(=O)C1	2370.9	Standard non polar	33892256
Trinexapac-ethyl,2TBDMS,isomer #1	CCOC(=O)C1C=C(O[Si](C)(C)C(C)(C)C)C(=C(O[Si](C)(C)C(C)(C)C)C2CC2)C(=O)C1	2701.8	Standard polar	33892256
Trinexapac-ethyl,2TBDMS,isomer #2	CCOC(=O)C1C=C(O[Si](C)(C)C(C)(C)C)C(=C(O)C2CC2)C(O[Si](C)(C)C(C)(C)C)=C1	2570.0	Semi standard non polar	33892256
Trinexapac-ethyl,2TBDMS,isomer #2	CCOC(=O)C1C=C(O[Si](C)(C)C(C)(C)C)C(=C(O)C2CC2)C(O[Si](C)(C)C(C)(C)C)=C1	2318.7	Standard non polar	33892256
Trinexapac-ethyl,2TBDMS,isomer #2	CCOC(=O)C1C=C(O[Si](C)(C)C(C)(C)C)C(=C(O)C2CC2)C(O[Si](C)(C)C(C)(C)C)=C1	2921.4	Standard polar	33892256
Trinexapac-ethyl,3TBDMS,isomer #1	CCOC(=O)C1C=C(O[Si](C)(C)C(C)(C)C)C(=C(O[Si](C)(C)C(C)(C)C)C2CC2)C(O[Si](C)(C)C(C)(C)C)=C1	2826.2	Semi standard non polar	33892256
Trinexapac-ethyl,3TBDMS,isomer #1	CCOC(=O)C1C=C(O[Si](C)(C)C(C)(C)C)C(=C(O[Si](C)(C)C(C)(C)C)C2CC2)C(O[Si](C)(C)C(C)(C)C)=C1	2550.7	Standard non polar	33892256
Trinexapac-ethyl,3TBDMS,isomer #1	CCOC(=O)C1C=C(O[Si](C)(C)C(C)(C)C)C(=C(O[Si](C)(C)C(C)(C)C)C2CC2)C(O[Si](C)(C)C(C)(C)C)=C1	2739.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Trinexapac-ethyl GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-8950000000-a9bb6a9e78eb50b2f991	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trinexapac-ethyl GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trinexapac-ethyl GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trinexapac-ethyl GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trinexapac-ethyl GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trinexapac-ethyl GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	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 - Trinexapac-ethyl 10V, Positive-QTOF	splash10-014i-9140000000-eba5dca16afe66f8772e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trinexapac-ethyl 20V, Positive-QTOF	splash10-014i-9340000000-6bb872c68c4df4f46327	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trinexapac-ethyl 40V, Positive-QTOF	splash10-014i-9100000000-aba0db6f7c77425ca8aa	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trinexapac-ethyl 10V, Negative-QTOF	splash10-0udi-1390000000-b79a1289db62de7d4335	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trinexapac-ethyl 20V, Negative-QTOF	splash10-014i-9530000000-c6d779f431e2d695bd44	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trinexapac-ethyl 40V, Negative-QTOF	splash10-014r-9700000000-24cd868e86cb48699cb3	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	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

83439

KEGG Compound ID

C18541

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

81817

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1080341

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 Trinexapac-ethyl (HMDB0259248)

MOL for HMDB0259248 (Trinexapac-ethyl)

3D MOL for HMDB0259248 (Trinexapac-ethyl)

3D SDF for HMDB0259248 (Trinexapac-ethyl)

3D-SDF for HMDB0259248 (Trinexapac-ethyl)

PDB for HMDB0259248 (Trinexapac-ethyl)

3D PDB for HMDB0259248 (Trinexapac-ethyl)

SMILES for HMDB0259248 (Trinexapac-ethyl)

INCHI for HMDB0259248 (Trinexapac-ethyl)

Structure for HMDB0259248 (Trinexapac-ethyl)

3D Structure for HMDB0259248 (Trinexapac-ethyl)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra