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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:49:22 UTC

Update Date

2021-09-26 23:17:42 UTC

HMDB ID

HMDB0259873

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Vorapaxar

Description

N-(9-{2-[5-(3-fluorophenyl)pyridin-2-yl]ethenyl}-1-methyl-3-oxo-dodecahydronaphtho[2,3-c]furan-6-yl)ethoxycarboximidic acid belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Based on a literature review very few articles have been published on N-(9-{2-[5-(3-fluorophenyl)pyridin-2-yl]ethenyl}-1-methyl-3-oxo-dodecahydronaphtho[2,3-c]furan-6-yl)ethoxycarboximidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Vorapaxar is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Vorapaxar 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


  Mrv1533004241523252D          

 36 40  0  0  0  0            999 V2000
    6.9246   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 14 34  1  0  0  0  0
 34 35  2  0  0  0  0
 32 36  1  0  0  0  0
M  END

HMDB0259873
     RDKit          3D
Vorapaxar
 69 73  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1533004241523252D          

 36 40  0  0  0  0            999 V2000
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 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 27 31  1  0  0  0  0
 15 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 14 34  1  0  0  0  0
 34 35  2  0  0  0  0
 32 36  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259873

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)NC1CCC2C(CC3C(C(C)OC3=O)C2C=CC2=NC=C(C=C2)C2=CC(F)=CC=C2)C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H33FN2O4/c1-3-35-29(34)32-23-10-11-24-20(14-23)15-26-27(17(2)36-28(26)33)25(24)12-9-22-8-7-19(16-31-22)18-5-4-6-21(30)13-18/h4-9,12-13,16-17,20,23-27H,3,10-11,14-15H2,1-2H3,(H,32,34)

> <INCHI_KEY>
ZBGXUVOIWDMMJE-UHFFFAOYSA-N

> <FORMULA>
C29H33FN2O4

> <MOLECULAR_WEIGHT>
492.591

> <EXACT_MASS>
492.242435714

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
54.725694190100626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl N-(9-{2-[5-(3-fluorophenyl)pyridin-2-yl]ethenyl}-1-methyl-3-oxo-dodecahydronaphtho[2,3-c]furan-6-yl)carbamate

> <ALOGPS_LOGP>
5.01

> <JCHEM_LOGP>
5.036946574

> <ALOGPS_LOGS>
-5.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.77897320606042

> <JCHEM_PKA_STRONGEST_BASIC>
4.3164105017860805

> <JCHEM_POLAR_SURFACE_AREA>
77.52000000000001

> <JCHEM_REFRACTIVITY>
134.5236

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.54e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vorapaxar

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259873
     RDKit          3D
Vorapaxar
 69 73  0  0  0  0  0  0  0  0999 V2000
    8.4427    3.2717    0.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7171    3.8508   -0.8851 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7719    2.9430   -1.4049 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7199    2.4586   -0.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5912    2.8324    0.5374 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7632    1.5388   -1.1802 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6609    1.0402   -0.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3822    1.3718   -1.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030    0.5768   -0.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232   -0.3733    0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6833   -0.8283    0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7152   -0.4937   -0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819   -2.3039    1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6296   -2.6506    2.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7125   -4.0909    2.3542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0711   -4.6572    3.4159 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047   -4.7583    1.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4052   -3.9481    0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9404   -4.6110    0.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3794   -2.5900    1.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087   -1.5510    0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9741   -0.9505    0.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050   -1.0337   -1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0233   -0.4445   -1.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7933   -0.5220   -2.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0557    0.0329   -2.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5521    0.6777   -1.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8694    1.2806   -1.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0918    2.3982   -0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2929    3.0316   -0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3521    2.5299   -0.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1354    1.4155   -1.7163 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1508    0.9123   -2.4457 F   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9089    0.7892   -1.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7190    0.7169    0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896    0.1728    0.0506 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3707    3.9910    1.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5276    3.1661    0.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9847    2.2961    0.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4027    4.1360   -1.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1807    4.8008   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8892    1.2416   -2.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069    1.4688    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167    2.4803   -0.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.3018   -2.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574    1.2913   -0.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8324    0.0416   -1.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8785    0.0994    1.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0710   -0.2898    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6887   -0.8655    0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3731   -0.8398   -1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6692   -2.9053    0.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7369   -2.4839    1.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5763   -1.9985    2.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7695   -3.8637   -0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7420   -3.8622    0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0495   -5.2665   -0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0665   -5.2589    1.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494   -2.5698    1.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6263   -1.9800   -0.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3796   -0.4438    0.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2933   -1.5481   -1.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4446   -1.0238   -3.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6935   -0.0066   -3.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2636    2.8091    0.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4175    3.9035    0.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3246    3.0159   -0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8058   -0.0806   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0564    1.2089    0.9294 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  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  3
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 27 35  1  0
 35 36  2  0
 12  7  1  0
 20 14  1  0
 36 24  1  0
 21 10  1  0
 34 28  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  2 41  1  0
  6 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 21 60  1  0
 22 61  1  0
 23 62  1  0
 25 63  1  0
 26 64  1  0
 29 65  1  0
 30 66  1  0
 31 67  1  0
 34 68  1  0
 35 69  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      12.926  -3.317   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.592  -2.547   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.592  -1.007   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      10.259  -0.237   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.925  -1.007   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      10.259   1.303   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.590   6.693   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.590   8.233   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.257   9.003   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       2.257  10.543   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.590  11.313   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.924  10.543   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.924   9.003   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.590  12.853   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.257  13.623   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.257  15.163   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.590  15.933   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.924  15.163   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.924  13.623   0.000  0.00  0.00           C+0
HETATM   31  F   UNK     0       0.923  15.933   0.000  0.00  0.00           F+0
HETATM   32  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.220   2.843   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.650   0.132   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15   34                                                  
CONECT   15   14   16   32                                                  
CONECT   16   15   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25   22   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   27                                                            
CONECT   32   15   33   36                                                  
CONECT   33   32   34                                                       
CONECT   34   33   14   35                                                  
CONECT   35   34                                                            
CONECT   36   32                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

COMPND    HMDB0259873
HETATM    1  C1  UNL     1       8.443   3.272   0.302  1.00  0.00           C  
HETATM    2  C2  UNL     1       7.717   3.851  -0.885  1.00  0.00           C  
HETATM    3  O1  UNL     1       6.772   2.943  -1.405  1.00  0.00           O  
HETATM    4  C3  UNL     1       5.720   2.459  -0.651  1.00  0.00           C  
HETATM    5  O2  UNL     1       5.591   2.832   0.537  1.00  0.00           O  
HETATM    6  N1  UNL     1       4.763   1.539  -1.180  1.00  0.00           N  
HETATM    7  C4  UNL     1       3.661   1.040  -0.368  1.00  0.00           C  
HETATM    8  C5  UNL     1       2.382   1.372  -1.076  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.203   0.577  -0.711  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.323  -0.373   0.427  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.683  -0.828   0.772  1.00  0.00           C  
HETATM   12  C9  UNL     1       3.715  -0.494  -0.310  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.782  -2.304   1.122  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.630  -2.651   2.045  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.712  -4.091   2.354  1.00  0.00           C  
HETATM   16  O3  UNL     1       2.071  -4.657   3.416  1.00  0.00           O  
HETATM   17  O4  UNL     1       1.305  -4.758   1.211  1.00  0.00           O  
HETATM   18  C13 UNL     1       0.405  -3.948   0.518  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.940  -4.611   0.491  1.00  0.00           C  
HETATM   20  C15 UNL     1       0.379  -2.590   1.197  1.00  0.00           C  
HETATM   21  C16 UNL     1       0.409  -1.551   0.131  1.00  0.00           C  
HETATM   22  C17 UNL     1      -0.974  -0.950   0.073  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.705  -1.034  -1.022  1.00  0.00           C  
HETATM   24  C19 UNL     1      -3.023  -0.445  -1.032  1.00  0.00           C  
HETATM   25  C20 UNL     1      -3.793  -0.522  -2.161  1.00  0.00           C  
HETATM   26  C21 UNL     1      -5.056   0.033  -2.199  1.00  0.00           C  
HETATM   27  C22 UNL     1      -5.552   0.678  -1.079  1.00  0.00           C  
HETATM   28  C23 UNL     1      -6.869   1.281  -1.057  1.00  0.00           C  
HETATM   29  C24 UNL     1      -7.092   2.398  -0.272  1.00  0.00           C  
HETATM   30  C25 UNL     1      -8.293   3.032  -0.189  1.00  0.00           C  
HETATM   31  C26 UNL     1      -9.352   2.530  -0.932  1.00  0.00           C  
HETATM   32  C27 UNL     1      -9.135   1.416  -1.716  1.00  0.00           C  
HETATM   33  F1  UNL     1     -10.151   0.912  -2.446  1.00  0.00           F  
HETATM   34  C28 UNL     1      -7.909   0.789  -1.786  1.00  0.00           C  
HETATM   35  C29 UNL     1      -4.719   0.717   0.024  1.00  0.00           C  
HETATM   36  N2  UNL     1      -3.490   0.173   0.051  1.00  0.00           N  
HETATM   37  H1  UNL     1       8.371   3.991   1.150  1.00  0.00           H  
HETATM   38  H2  UNL     1       9.528   3.166   0.029  1.00  0.00           H  
HETATM   39  H3  UNL     1       7.985   2.296   0.539  1.00  0.00           H  
HETATM   40  H4  UNL     1       8.403   4.136  -1.711  1.00  0.00           H  
HETATM   41  H5  UNL     1       7.181   4.801  -0.619  1.00  0.00           H  
HETATM   42  H6  UNL     1       4.889   1.242  -2.170  1.00  0.00           H  
HETATM   43  H7  UNL     1       3.707   1.469   0.657  1.00  0.00           H  
HETATM   44  H8  UNL     1       2.217   2.480  -0.921  1.00  0.00           H  
HETATM   45  H9  UNL     1       2.615   1.302  -2.181  1.00  0.00           H  
HETATM   46  H10 UNL     1       0.357   1.291  -0.481  1.00  0.00           H  
HETATM   47  H11 UNL     1       0.832   0.042  -1.638  1.00  0.00           H  
HETATM   48  H12 UNL     1       0.879   0.099   1.355  1.00  0.00           H  
HETATM   49  H13 UNL     1       3.071  -0.290   1.689  1.00  0.00           H  
HETATM   50  H14 UNL     1       4.689  -0.866   0.001  1.00  0.00           H  
HETATM   51  H15 UNL     1       3.373  -0.840  -1.304  1.00  0.00           H  
HETATM   52  H16 UNL     1       2.669  -2.905   0.214  1.00  0.00           H  
HETATM   53  H17 UNL     1       3.737  -2.484   1.655  1.00  0.00           H  
HETATM   54  H18 UNL     1       1.576  -1.998   2.918  1.00  0.00           H  
HETATM   55  H19 UNL     1       0.769  -3.864  -0.543  1.00  0.00           H  
HETATM   56  H20 UNL     1      -1.742  -3.862   0.433  1.00  0.00           H  
HETATM   57  H21 UNL     1      -1.050  -5.267  -0.420  1.00  0.00           H  
HETATM   58  H22 UNL     1      -1.067  -5.259   1.407  1.00  0.00           H  
HETATM   59  H23 UNL     1      -0.549  -2.570   1.812  1.00  0.00           H  
HETATM   60  H24 UNL     1       0.626  -1.980  -0.880  1.00  0.00           H  
HETATM   61  H25 UNL     1      -1.380  -0.444   0.934  1.00  0.00           H  
HETATM   62  H26 UNL     1      -1.293  -1.548  -1.896  1.00  0.00           H  
HETATM   63  H27 UNL     1      -3.445  -1.024  -3.078  1.00  0.00           H  
HETATM   64  H28 UNL     1      -5.694  -0.007  -3.068  1.00  0.00           H  
HETATM   65  H29 UNL     1      -6.264   2.809   0.323  1.00  0.00           H  
HETATM   66  H30 UNL     1      -8.418   3.904   0.441  1.00  0.00           H  
HETATM   67  H31 UNL     1     -10.325   3.016  -0.885  1.00  0.00           H  
HETATM   68  H32 UNL     1      -7.806  -0.081  -2.421  1.00  0.00           H  
HETATM   69  H33 UNL     1      -5.056   1.209   0.929  1.00  0.00           H  
CONECT    1    2   37   38   39
CONECT    2    3   40   41
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   42
CONECT    7    8   12   43
CONECT    8    9   44   45
CONECT    9   10   46   47
CONECT   10   11   21   48
CONECT   11   12   13   49
CONECT   12   50   51
CONECT   13   14   52   53
CONECT   14   15   20   54
CONECT   15   16   16   17
CONECT   17   18
CONECT   18   19   20   55
CONECT   19   56   57   58
CONECT   20   21   59
CONECT   21   22   60
CONECT   22   23   23   61
CONECT   23   24   62
CONECT   24   25   25   36
CONECT   25   26   63
CONECT   26   27   27   64
CONECT   27   28   35
CONECT   28   29   29   34
CONECT   29   30   65
CONECT   30   31   31   66
CONECT   31   32   67
CONECT   32   33   34   34
CONECT   34   68
CONECT   35   36   36   69
END

HMDB0259873
     RDKit          3D
Vorapaxar
 69 73  0  0  0  0  0  0  0  0999 V2000
    8.4427    3.2717    0.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7171    3.8508   -0.8851 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7719    2.9430   -1.4049 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7199    2.4586   -0.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5912    2.8324    0.5374 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7632    1.5388   -1.1802 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6609    1.0402   -0.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3822    1.3718   -1.0764 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030    0.5768   -0.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3232   -0.3733    0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6833   -0.8283    0.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7152   -0.4937   -0.3098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819   -2.3039    1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6296   -2.6506    2.0454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7125   -4.0909    2.3542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0711   -4.6572    3.4159 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047   -4.7583    1.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4052   -3.9481    0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9404   -4.6110    0.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3794   -2.5900    1.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087   -1.5510    0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9741   -0.9505    0.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7050   -1.0337   -1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0233   -0.4445   -1.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7933   -0.5220   -2.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0557    0.0329   -2.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5521    0.6777   -1.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8694    1.2806   -1.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0918    2.3982   -0.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2929    3.0316   -0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3521    2.5299   -0.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1354    1.4155   -1.7163 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1508    0.9123   -2.4457 F   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9089    0.7892   -1.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7190    0.7169    0.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4896    0.1728    0.0506 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3707    3.9910    1.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5276    3.1661    0.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9847    2.2961    0.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4027    4.1360   -1.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1807    4.8008   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8892    1.2416   -2.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069    1.4688    0.6568 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167    2.4803   -0.9214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.3018   -2.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574    1.2913   -0.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8324    0.0416   -1.6375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8785    0.0994    1.3546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0710   -0.2898    1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6887   -0.8655    0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3731   -0.8398   -1.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6692   -2.9053    0.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7369   -2.4839    1.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5763   -1.9985    2.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7695   -3.8637   -0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7420   -3.8622    0.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0495   -5.2665   -0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0665   -5.2589    1.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494   -2.5698    1.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6263   -1.9800   -0.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3796   -0.4438    0.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2933   -1.5481   -1.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4446   -1.0238   -3.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6935   -0.0066   -3.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2636    2.8091    0.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4175    3.9035    0.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3246    3.0159   -0.8850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8058   -0.0806   -2.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0564    1.2089    0.9294 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  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  3
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 27 35  1  0
 35 36  2  0
 12  7  1  0
 20 14  1  0
 36 24  1  0
 21 10  1  0
 34 28  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  2 41  1  0
  6 42  1  0
  7 43  1  0
  8 44  1  0
  8 45  1  0
  9 46  1  0
  9 47  1  0
 10 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  0
 13 53  1  0
 14 54  1  0
 18 55  1  0
 19 56  1  0
 19 57  1  0
 19 58  1  0
 20 59  1  0
 21 60  1  0
 22 61  1  0
 23 62  1  0
 25 63  1  0
 26 64  1  0
 29 65  1  0
 30 66  1  0
 31 67  1  0
 34 68  1  0
 35 69  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(9-{2-[5-(3-fluorophenyl)pyridin-2-yl]ethenyl}-1-methyl-3-oxo-dodecahydronaphtho[2,3-c]furan-6-yl)ethoxycarboximidate	Generator

Chemical Formula

C₂₉H₃₃FN₂O₄

Average Molecular Weight

492.591

Monoisotopic Molecular Weight

492.242435714

IUPAC Name

ethyl N-(9-{2-[5-(3-fluorophenyl)pyridin-2-yl]ethenyl}-1-methyl-3-oxo-dodecahydronaphtho[2,3-c]furan-6-yl)carbamate

Traditional Name

vorapaxar

CAS Registry Number

Not Available

SMILES

CCOC(=O)NC1CCC2C(CC3C(C(C)OC3=O)C2C=CC2=NC=C(C=C2)C2=CC(F)=CC=C2)C1

InChI Identifier

InChI=1S/C29H33FN2O4/c1-3-35-29(34)32-23-10-11-24-20(14-23)15-26-27(17(2)36-28(26)33)25(24)12-9-22-8-7-19(16-31-22)18-5-4-6-21(30)13-18/h4-9,12-13,16-17,20,23-27H,3,10-11,14-15H2,1-2H3,(H,32,34)

InChI Key

ZBGXUVOIWDMMJE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
3-phenylpyridine
Fluorobenzene
Halobenzene
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Gamma butyrolactone
Pyridine
Benzenoid
Heteroaromatic compound
Oxolane
Carbamic acid ester
Carboxylic acid ester
Lactone
Oxacycle
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Organohalogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
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: 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	5.01	ALOGPS
logP	5.04	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	14.78	ChemAxon
pKa (Strongest Basic)	4.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	134.52 m³·mol⁻¹	ChemAxon
Polarizability	54.73 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	222.613	32859911
AllCCS	[M+H-H2O]+	220.667	32859911
AllCCS	[M+Na]+	224.899	32859911
AllCCS	[M+NH4]+	224.392	32859911
AllCCS	[M-H]-	216.74	32859911
AllCCS	[M+Na-2H]-	218.466	32859911
AllCCS	[M+HCOO]-	220.52	32859911
DeepCCS	[M+H]+	212.846	30932474
DeepCCS	[M-H]-	210.451	30932474
DeepCCS	[M-2H]-	243.476	30932474
DeepCCS	[M+Na]+	218.958	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vorapaxar	CCOC(=O)NC1CCC2C(CC3C(C(C)OC3=O)C2C=CC2=NC=C(C=C2)C2=CC(F)=CC=C2)C1	5250.3	Standard polar	33892256
Vorapaxar	CCOC(=O)NC1CCC2C(CC3C(C(C)OC3=O)C2C=CC2=NC=C(C=C2)C2=CC(F)=CC=C2)C1	3960.1	Standard non polar	33892256
Vorapaxar	CCOC(=O)NC1CCC2C(CC3C(C(C)OC3=O)C2C=CC2=NC=C(C=C2)C2=CC(F)=CC=C2)C1	4168.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vorapaxar,1TMS,isomer #1	CCOC(=O)N(C1CCC2C(CC3C(=O)OC(C)C3C2C=CC2=CC=C(C3=CC=CC(F)=C3)C=N2)C1)[Si](C)(C)C	4132.3	Semi standard non polar	33892256
Vorapaxar,1TMS,isomer #1	CCOC(=O)N(C1CCC2C(CC3C(=O)OC(C)C3C2C=CC2=CC=C(C3=CC=CC(F)=C3)C=N2)C1)[Si](C)(C)C	3940.9	Standard non polar	33892256
Vorapaxar,1TMS,isomer #1	CCOC(=O)N(C1CCC2C(CC3C(=O)OC(C)C3C2C=CC2=CC=C(C3=CC=CC(F)=C3)C=N2)C1)[Si](C)(C)C	5224.5	Standard polar	33892256
Vorapaxar,1TBDMS,isomer #1	CCOC(=O)N(C1CCC2C(CC3C(=O)OC(C)C3C2C=CC2=CC=C(C3=CC=CC(F)=C3)C=N2)C1)[Si](C)(C)C(C)(C)C	4362.6	Semi standard non polar	33892256
Vorapaxar,1TBDMS,isomer #1	CCOC(=O)N(C1CCC2C(CC3C(=O)OC(C)C3C2C=CC2=CC=C(C3=CC=CC(F)=C3)C=N2)C1)[Si](C)(C)C(C)(C)C	4179.9	Standard non polar	33892256
Vorapaxar,1TBDMS,isomer #1	CCOC(=O)N(C1CCC2C(CC3C(=O)OC(C)C3C2C=CC2=CC=C(C3=CC=CC(F)=C3)C=N2)C1)[Si](C)(C)C(C)(C)C	5227.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Vorapaxar GC-MS (Non-derivatized) - 70eV, Positive	splash10-00mk-2405900000-c1c0160d651eeaf405ff	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vorapaxar GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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

28657700

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72455102

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 Vorapaxar (HMDB0259873)

MOL for HMDB0259873 (Vorapaxar)

3D MOL for HMDB0259873 (Vorapaxar)

3D SDF for HMDB0259873 (Vorapaxar)

3D-SDF for HMDB0259873 (Vorapaxar)

PDB for HMDB0259873 (Vorapaxar)

3D PDB for HMDB0259873 (Vorapaxar)

SMILES for HMDB0259873 (Vorapaxar)

INCHI for HMDB0259873 (Vorapaxar)

Structure for HMDB0259873 (Vorapaxar)

3D Structure for HMDB0259873 (Vorapaxar)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra