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Showing metabocard for Telaprevir (HMDB0015616)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:03 UTC
HMDB IDHMDB0015616
Secondary Accession Numbers
  • HMDB15616
Metabolite Identification
Common NameTelaprevir
DescriptionTelaprevir (VX-950) is a highly selective and potent inhibitor of the HCV NS3-4A serine protease. It is a member of a class of antiviral drugs known as protease inhibitors and is the first hepatitis C drug that has demonstrated activity in patients who have failed prior therapy. On April 28, 2011, the FDA Antiviral Drugs Advisory Committee voted 18-0 to recommend approval telaprevir for people with genotype 1 chronic hepatitis C and was approved in the U.S. in May, 2011.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015616 (Telaprevir)

  Mrv0541 02231218132D          

 51 55  0  0  1  0            999 V2000
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M  END
Download

3D MOL for HMDB0015616 (Telaprevir)

HMDB0015616
     RDKit          3D
Telaprevir
102106  0  0  0  0  0  0  0  0999 V2000
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M  END
Download

3D SDF for HMDB0015616 (Telaprevir)

  Mrv0541 02231218132D          

 51 55  0  0  1  0            999 V2000
    7.2607    0.1836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6001   -0.7254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8876   -2.8689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0127   -2.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0015616

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCC[C@]1([H])[C@H](N(C2)C(=O)[C@@H](NC(=O)[C@@H](NC(=O)C1=NC=CN=C1)C1CCCCC1)C(C)(C)C)C(=O)N[C@@H](CCC)C(=O)C(=O)NC1CC1

> <INCHI_IDENTIFIER>
InChI=1S/C36H53N7O6/c1-5-10-25(29(44)34(48)39-23-15-16-23)40-33(47)28-24-14-9-13-22(24)20-43(28)35(49)30(36(2,3)4)42-32(46)27(21-11-7-6-8-12-21)41-31(45)26-19-37-17-18-38-26/h17-19,21-25,27-28,30H,5-16,20H2,1-4H3,(H,39,48)(H,40,47)(H,41,45)(H,42,46)/t22-,24-,25-,27-,28-,30+/m0/s1

> <INCHI_KEY>
BBAWEDCPNXPBQM-GDEBMMAJSA-N

> <FORMULA>
C36H53N7O6

> <MOLECULAR_WEIGHT>
679.8493

> <EXACT_MASS>
679.405732463

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
74.36952961559653

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-{[(1S,3aR,6aS)-2-[(2S)-2-[(2S)-2-cyclohexyl-2-(pyrazin-2-ylformamido)acetamido]-3,3-dimethylbutanoyl]-octahydrocyclopenta[c]pyrrol-1-yl]formamido}-N-cyclopropyl-2-oxohexanamide

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
2.580292300333334

> <ALOGPS_LOGS>
-4.28

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.38745817101361

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.857239072699072

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6902823851666152

> <JCHEM_POLAR_SURFACE_AREA>
179.55999999999995

> <JCHEM_REFRACTIVITY>
180.04029999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
incivek

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0015616 (Telaprevir)

HMDB0015616
     RDKit          3D
Telaprevir
102106  0  0  0  0  0  0  0  0999 V2000
    4.0408    0.6862   -3.6150 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3746    1.8058   -2.8403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7801    1.3109   -1.5743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6953    0.7179   -0.5606 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8226    0.2885    0.5754 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0828   -0.9385    1.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0575   -1.6324    0.8068 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2886   -1.4353    2.3043 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6926   -2.8446    2.7753 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9463   -2.8352    3.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6716    5.3728   -0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4429    4.6737   -2.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9917    4.4602   -0.4756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6197    2.3906   -1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6433    2.3740   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3198   -3.8302    0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2304   -3.4471   -0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6697   -5.0081   -0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5345   -3.5405   -0.9540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7704   -2.6458   -1.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7752   -4.4970   -1.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6991   -5.4627    0.6961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2096   -4.4288    2.0535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4016   -4.1897    1.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3900    3.6609    0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0730    3.1183   -1.5902 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5217    5.9120   -0.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5770    5.5497   -1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9982    4.4227    1.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0367    4.0495   -0.3055 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  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 22 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 18 38  1  0
 38 39  1  0
 38 40  1  0
 38 41  1  0
  4 42  1  0
 42 43  2  0
 42 44  1  0
 44 45  2  0
 44 46  1  0
 46 47  1  0
 47 48  1  0
 48 49  1  0
 15  8  1  0
 31 26  1  0
 37 32  1  0
 49 47  1  0
 13  9  1  0
  1 50  1  0
  1 51  1  0
  1 52  1  0
  2 53  1  0
  2 54  1  0
  3 55  1  0
  3 56  1  0
  4 57  1  6
  5 58  1  0
  8 59  1  1
  9 60  1  6
 10 61  1  0
 10 62  1  0
 11 63  1  0
 11 64  1  0
 12 65  1  0
 12 66  1  0
 13 67  1  1
 14 68  1  0
 14 69  1  0
 18 70  1  1
 19 71  1  0
 22 72  1  6
 23 73  1  0
 27 74  1  0
 29 75  1  0
 30 76  1  0
 32 77  1  0
 33 78  1  0
 33 79  1  0
 34 80  1  0
 34 81  1  0
 35 82  1  0
 35 83  1  0
 36 84  1  0
 36 85  1  0
 37 86  1  0
 37 87  1  0
 39 88  1  0
 39 89  1  0
 39 90  1  0
 40 91  1  0
 40 92  1  0
 40 93  1  0
 41 94  1  0
 41 95  1  0
 41 96  1  0
 46 97  1  0
 47 98  1  0
 48 99  1  0
 48100  1  0
 49101  1  0
 49102  1  0
M  END
Download

PDB for HMDB0015616 (Telaprevir)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      13.553   0.343   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      12.320  -1.354   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      10.780  -6.689   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      18.151   3.456   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      14.662   5.561   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.390  -5.355   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      14.630  -2.688   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      16.090   1.167   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      10.780  -4.022   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       7.700  -4.022   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      17.199   6.385   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       3.850  -2.688   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       5.390  -0.021   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      17.000  -1.918   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.000  -3.458   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.536  -1.442   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.457  -1.449   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.457  -3.927   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.536  -3.934   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.356  -2.688   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.060   0.023   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.090  -2.688   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.320  -4.022   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.090  -5.355   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.614   2.632   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.860  -6.689   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.757  -6.125   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.424  -4.585   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.700  -6.689   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.470  -5.355   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.010  -5.355   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.108   2.952   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.160  -6.689   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.470  -8.023   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.645   3.776   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.390  -8.023   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.700  -9.356   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.160  -9.356   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      16.723   7.850   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      13.632   4.417   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      17.044   9.356   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      15.579   8.881   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      16.169   5.241   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      12.126   4.737   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.160  -4.022   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.390  -2.688   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       6.160  -1.354   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       3.080  -1.354   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       3.850  -0.021   0.000  0.00  0.00           C+0
HETATM   50  H   UNK     0      17.002  -0.686   0.000  0.00  0.00           H+0
HETATM   51  H   UNK     0      17.002  -4.690   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3   31                                                            
CONECT    4   35                                                            
CONECT    5   43                                                            
CONECT    6   45                                                            
CONECT    7   16   19   22                                                  
CONECT    8   21   25                                                       
CONECT    9   23   31                                                       
CONECT   10   30   45                                                       
CONECT   11   39   43                                                       
CONECT   12   46   48                                                       
CONECT   13   47   49                                                       
CONECT   14   15   16   17   50                                             
CONECT   15   14   18   19   51                                             
CONECT   16    7   14   21                                                  
CONECT   17   14   20                                                       
CONECT   18   15   20                                                       
CONECT   19    7   15                                                       
CONECT   20   17   18                                                       
CONECT   21    1    8   16                                                  
CONECT   22    2    7   23                                                  
CONECT   23    9   22   24                                                  
CONECT   24   23   26   27   28                                             
CONECT   25    8   32   35                                                  
CONECT   26   24                                                            
CONECT   27   24                                                            
CONECT   28   24                                                            
CONECT   29   30   33   34                                                  
CONECT   30   10   29   31                                                  
CONECT   31    3    9   30                                                  
CONECT   32   25   40                                                       
CONECT   33   29   36                                                       
CONECT   34   29   37                                                       
CONECT   35    4   25   43                                                  
CONECT   36   33   38                                                       
CONECT   37   34   38                                                       
CONECT   38   36   37                                                       
CONECT   39   11   41   42                                                  
CONECT   40   32   44                                                       
CONECT   41   39   42                                                       
CONECT   42   39   41                                                       
CONECT   43    5   11   35                                                  
CONECT   44   40                                                            
CONECT   45    6   10   46                                                  
CONECT   46   12   45   47                                                  
CONECT   47   13   46                                                       
CONECT   48   12   49                                                       
CONECT   49   13   48                                                       
CONECT   50   14                                                            
CONECT   51   15                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  110    0
END
Download

3D PDB for HMDB0015616 (Telaprevir)

COMPND    HMDB0015616
HETATM    1  C1  UNL     1       4.041   0.686  -3.615  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.375   1.806  -2.840  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.780   1.311  -1.574  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.695   0.718  -0.561  1.00  0.00           C  
HETATM    5  N1  UNL     1       2.823   0.289   0.575  1.00  0.00           N  
HETATM    6  C5  UNL     1       3.083  -0.938   1.211  1.00  0.00           C  
HETATM    7  O1  UNL     1       4.058  -1.632   0.807  1.00  0.00           O  
HETATM    8  C6  UNL     1       2.289  -1.435   2.304  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.693  -2.845   2.775  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.946  -2.835   3.578  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.591  -3.188   4.992  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.136  -2.775   5.080  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.538  -3.113   3.753  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.425  -2.135   3.347  1.00  0.00           C  
HETATM   15  N2  UNL     1       0.903  -1.703   2.065  1.00  0.00           N  
HETATM   16  C13 UNL     1       0.185  -1.616   0.876  1.00  0.00           C  
HETATM   17  O2  UNL     1       0.725  -1.162  -0.209  1.00  0.00           O  
HETATM   18  C14 UNL     1      -1.228  -2.010   0.679  1.00  0.00           C  
HETATM   19  N3  UNL     1      -1.907  -1.119  -0.239  1.00  0.00           N  
HETATM   20  C15 UNL     1      -3.232  -0.684  -0.098  1.00  0.00           C  
HETATM   21  O3  UNL     1      -3.882  -1.125   0.914  1.00  0.00           O  
HETATM   22  C16 UNL     1      -3.975   0.225  -0.991  1.00  0.00           C  
HETATM   23  N4  UNL     1      -5.415   0.119  -0.722  1.00  0.00           N  
HETATM   24  C17 UNL     1      -6.347  -0.182  -1.717  1.00  0.00           C  
HETATM   25  O4  UNL     1      -5.914  -0.369  -2.904  1.00  0.00           O  
HETATM   26  C18 UNL     1      -7.755  -0.279  -1.400  1.00  0.00           C  
HETATM   27  C19 UNL     1      -8.661  -0.570  -2.415  1.00  0.00           C  
HETATM   28  N5  UNL     1      -9.986  -0.670  -2.136  1.00  0.00           N  
HETATM   29  C20 UNL     1     -10.457  -0.494  -0.895  1.00  0.00           C  
HETATM   30  C21 UNL     1      -9.563  -0.202   0.136  1.00  0.00           C  
HETATM   31  N6  UNL     1      -8.264  -0.111  -0.175  1.00  0.00           N  
HETATM   32  C22 UNL     1      -3.608   1.692  -0.787  1.00  0.00           C  
HETATM   33  C23 UNL     1      -2.179   1.986  -1.048  1.00  0.00           C  
HETATM   34  C24 UNL     1      -2.008   3.411  -1.600  1.00  0.00           C  
HETATM   35  C25 UNL     1      -2.891   4.300  -0.754  1.00  0.00           C  
HETATM   36  C26 UNL     1      -4.308   4.053  -1.246  1.00  0.00           C  
HETATM   37  C27 UNL     1      -4.595   2.608  -1.443  1.00  0.00           C  
HETATM   38  C28 UNL     1      -1.322  -3.448   0.183  1.00  0.00           C  
HETATM   39  C29 UNL     1      -2.721  -3.906  -0.035  1.00  0.00           C  
HETATM   40  C30 UNL     1      -0.578  -3.537  -1.149  1.00  0.00           C  
HETATM   41  C31 UNL     1      -0.652  -4.428   1.110  1.00  0.00           C  
HETATM   42  C32 UNL     1       4.626   1.717   0.028  1.00  0.00           C  
HETATM   43  O5  UNL     1       4.377   2.208   1.182  1.00  0.00           O  
HETATM   44  C33 UNL     1       5.831   2.199  -0.603  1.00  0.00           C  
HETATM   45  O6  UNL     1       6.262   1.774  -1.701  1.00  0.00           O  
HETATM   46  N7  UNL     1       6.648   3.229  -0.006  1.00  0.00           N  
HETATM   47  C34 UNL     1       7.848   3.701  -0.646  1.00  0.00           C  
HETATM   48  C35 UNL     1       8.146   5.167  -0.750  1.00  0.00           C  
HETATM   49  C36 UNL     1       9.003   4.220   0.080  1.00  0.00           C  
HETATM   50  H1  UNL     1       4.958   1.057  -4.085  1.00  0.00           H  
HETATM   51  H2  UNL     1       4.318  -0.179  -2.975  1.00  0.00           H  
HETATM   52  H3  UNL     1       3.354   0.251  -4.394  1.00  0.00           H  
HETATM   53  H4  UNL     1       2.499   2.117  -3.500  1.00  0.00           H  
HETATM   54  H5  UNL     1       3.982   2.715  -2.756  1.00  0.00           H  
HETATM   55  H6  UNL     1       1.954   0.587  -1.860  1.00  0.00           H  
HETATM   56  H7  UNL     1       2.198   2.132  -1.056  1.00  0.00           H  
HETATM   57  H8  UNL     1       4.304  -0.088  -0.942  1.00  0.00           H  
HETATM   58  H9  UNL     1       2.067   0.910   0.859  1.00  0.00           H  
HETATM   59  H10 UNL     1       2.360  -0.807   3.236  1.00  0.00           H  
HETATM   60  H11 UNL     1       2.689  -3.568   1.946  1.00  0.00           H  
HETATM   61  H12 UNL     1       4.656  -3.576   3.122  1.00  0.00           H  
HETATM   62  H13 UNL     1       4.418  -1.841   3.482  1.00  0.00           H  
HETATM   63  H14 UNL     1       4.228  -2.552   5.665  1.00  0.00           H  
HETATM   64  H15 UNL     1       3.756  -4.249   5.195  1.00  0.00           H  
HETATM   65  H16 UNL     1       2.129  -1.684   5.257  1.00  0.00           H  
HETATM   66  H17 UNL     1       1.685  -3.338   5.927  1.00  0.00           H  
HETATM   67  H18 UNL     1       1.173  -4.138   3.692  1.00  0.00           H  
HETATM   68  H19 UNL     1       0.486  -1.319   4.114  1.00  0.00           H  
HETATM   69  H20 UNL     1      -0.567  -2.577   3.375  1.00  0.00           H  
HETATM   70  H21 UNL     1      -1.762  -1.999   1.628  1.00  0.00           H  
HETATM   71  H22 UNL     1      -1.359  -0.799  -1.058  1.00  0.00           H  
HETATM   72  H23 UNL     1      -3.850   0.017  -2.070  1.00  0.00           H  
HETATM   73  H24 UNL     1      -5.720   0.280   0.255  1.00  0.00           H  
HETATM   74  H25 UNL     1      -8.271  -0.711  -3.408  1.00  0.00           H  
HETATM   75  H26 UNL     1     -11.509  -0.571  -0.653  1.00  0.00           H  
HETATM   76  H27 UNL     1      -9.899  -0.051   1.164  1.00  0.00           H  
HETATM   77  H28 UNL     1      -3.761   1.847   0.327  1.00  0.00           H  
HETATM   78  H29 UNL     1      -1.537   1.844  -0.156  1.00  0.00           H  
HETATM   79  H30 UNL     1      -1.841   1.338  -1.912  1.00  0.00           H  
HETATM   80  H31 UNL     1      -0.947   3.703  -1.573  1.00  0.00           H  
HETATM   81  H32 UNL     1      -2.424   3.419  -2.619  1.00  0.00           H  
HETATM   82  H33 UNL     1      -2.836   3.989   0.287  1.00  0.00           H  
HETATM   83  H34 UNL     1      -2.672   5.373  -0.915  1.00  0.00           H  
HETATM   84  H35 UNL     1      -4.443   4.674  -2.158  1.00  0.00           H  
HETATM   85  H36 UNL     1      -4.992   4.460  -0.476  1.00  0.00           H  
HETATM   86  H37 UNL     1      -5.620   2.391  -1.034  1.00  0.00           H  
HETATM   87  H38 UNL     1      -4.643   2.374  -2.527  1.00  0.00           H  
HETATM   88  H39 UNL     1      -3.320  -3.830   0.885  1.00  0.00           H  
HETATM   89  H40 UNL     1      -3.230  -3.447  -0.912  1.00  0.00           H  
HETATM   90  H41 UNL     1      -2.670  -5.008  -0.281  1.00  0.00           H  
HETATM   91  H42 UNL     1       0.534  -3.540  -0.954  1.00  0.00           H  
HETATM   92  H43 UNL     1      -0.770  -2.646  -1.772  1.00  0.00           H  
HETATM   93  H44 UNL     1      -0.775  -4.497  -1.669  1.00  0.00           H  
HETATM   94  H45 UNL     1      -0.699  -5.463   0.696  1.00  0.00           H  
HETATM   95  H46 UNL     1      -1.210  -4.429   2.053  1.00  0.00           H  
HETATM   96  H47 UNL     1       0.402  -4.190   1.319  1.00  0.00           H  
HETATM   97  H48 UNL     1       6.390   3.661   0.906  1.00  0.00           H  
HETATM   98  H49 UNL     1       8.073   3.118  -1.590  1.00  0.00           H  
HETATM   99  H50 UNL     1       7.522   5.912  -0.221  1.00  0.00           H  
HETATM  100  H51 UNL     1       8.577   5.550  -1.706  1.00  0.00           H  
HETATM  101  H52 UNL     1       8.998   4.423   1.168  1.00  0.00           H  
HETATM  102  H53 UNL     1      10.037   4.049  -0.305  1.00  0.00           H  
CONECT    1    2   50   51   52
CONECT    2    3   53   54
CONECT    3    4   55   56
CONECT    4    5   42   57
CONECT    5    6   58
CONECT    6    7    7    8
CONECT    8    9   15   59
CONECT    9   10   13   60
CONECT   10   11   61   62
CONECT   11   12   63   64
CONECT   12   13   65   66
CONECT   13   14   67
CONECT   14   15   68   69
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19   38   70
CONECT   19   20   71
CONECT   20   21   21   22
CONECT   22   23   32   72
CONECT   23   24   73
CONECT   24   25   25   26
CONECT   26   27   27   31
CONECT   27   28   74
CONECT   28   29   29
CONECT   29   30   75
CONECT   30   31   31   76
CONECT   32   33   37   77
CONECT   33   34   78   79
CONECT   34   35   80   81
CONECT   35   36   82   83
CONECT   36   37   84   85
CONECT   37   86   87
CONECT   38   39   40   41
CONECT   39   88   89   90
CONECT   40   91   92   93
CONECT   41   94   95   96
CONECT   42   43   43   44
CONECT   44   45   45   46
CONECT   46   47   97
CONECT   47   48   49   98
CONECT   48   49   99  100
CONECT   49  101  102
END
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SMILES for HMDB0015616 (Telaprevir)

[H][C@@]12CCC[C@]1([H])[C@H](N(C2)C(=O)[C@@H](NC(=O)[C@@H](NC(=O)C1=NC=CN=C1)C1CCCCC1)C(C)(C)C)C(=O)N[C@@H](CCC)C(=O)C(=O)NC1CC1
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INCHI for HMDB0015616 (Telaprevir)

InChI=1S/C36H53N7O6/c1-5-10-25(29(44)34(48)39-23-15-16-23)40-33(47)28-24-14-9-13-22(24)20-43(28)35(49)30(36(2,3)4)42-32(46)27(21-11-7-6-8-12-21)41-31(45)26-19-37-17-18-38-26/h17-19,21-25,27-28,30H,5-16,20H2,1-4H3,(H,39,48)(H,40,47)(H,41,45)(H,42,46)/t22-,24-,25-,27-,28-,30+/m0/s1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(1S,3AR,6as)-(2S)-2-cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyl-N-((1S)-1-((cyclopropylamino)oxoacetyl)butyl)octahydrocyclopenta(c)pyrrole-1-carboxamideChEBI
IncivekChEBI
VX 950ChEBI
VX-950ChEBI
IncivoKegg
AIDS-213006HMDB
AIDS213006HMDB
LY-570310HMDB
MP-424HMDB
VRT111950HMDB
VX950 CPDHMDB
Chemical FormulaC36H53N7O6
Average Molecular Weight679.8493
Monoisotopic Molecular Weight679.405732463
IUPAC Name(3S)-3-{[(1S,3aR,6aS)-2-[(2S)-2-[(2S)-2-cyclohexyl-2-(pyrazin-2-ylformamido)acetamido]-3,3-dimethylbutanoyl]-octahydrocyclopenta[c]pyrrol-1-yl]formamido}-N-cyclopropyl-2-oxohexanamide
Traditional Nameincivek
CAS Registry Number402957-28-2
SMILES
[H][C@@]12CCC[C@]1([H])[C@H](N(C2)C(=O)[C@@H](NC(=O)[C@@H](NC(=O)C1=NC=CN=C1)C1CCCCC1)C(C)(C)C)C(=O)N[C@@H](CCC)C(=O)C(=O)NC1CC1
InChI Identifier
InChI=1S/C36H53N7O6/c1-5-10-25(29(44)34(48)39-23-15-16-23)40-33(47)28-24-14-9-13-22(24)20-43(28)35(49)30(36(2,3)4)42-32(46)27(21-11-7-6-8-12-21)41-31(45)26-19-37-17-18-38-26/h17-19,21-25,27-28,30H,5-16,20H2,1-4H3,(H,39,48)(H,40,47)(H,41,45)(H,42,46)/t22-,24-,25-,27-,28-,30+/m0/s1
InChI KeyBBAWEDCPNXPBQM-GDEBMMAJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassHybrid peptides
Direct ParentHybrid peptides
Alternative Parents
Substituents
  • Hybrid peptide
  • Valine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Pyrazine carboxylic acid or derivatives
  • Pyrazinecarboxamide
  • 2-heteroaryl carboxamide
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Pyrazine
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Ketone
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.036 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB05521 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB05521 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB05521
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2279948
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTelaprevir
METLIN IDNot Available
PubChem Compound3010818
PDB IDNot Available
ChEBI ID68595
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceZnabet A, Polak MM, Janssen E, de Kanter FJ, Turner NJ, Orru RV, Ruijter E. A highly efficient synthesis of telaprevir by strategic use of biocatalysis and multicomponent reactions. Chem Commun (Camb). 2010 Nov 14;46(42):7918-20. Epub 2010 Sep 20.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kim JJ, Culley CM, Mohammad RA: Telaprevir: an oral protease inhibitor for hepatitis C virus infection. Am J Health Syst Pharm. 2012 Jan 1;69(1):19-33. doi: 10.2146/ajhp110123. [PubMed:22180548 ]
  2. Liu-Young G, Kozal MJ: Hepatitis C protease and polymerase inhibitors in development. AIDS Patient Care STDS. 2008 Jun;22(6):449-57. doi: 10.1089/apc.2007.0199. [PubMed:18479202 ]
  3. Forestier N, Zeuzem S: Telaprevir for the treatment of hepatitis C. Expert Opin Pharmacother. 2012 Mar;13(4):593-606. doi: 10.1517/14656566.2012.660524. Epub 2012 Feb 15. [PubMed:22332992 ]
  4. Garg V, Kauffman RS, Beaumont M, van Heeswijk RP: Telaprevir: pharmacokinetics and drug interactions. Antivir Ther. 2012;17(7):1211-21. doi: 10.3851/IMP2356. Epub 2012 Sep 7. [PubMed:22954756 ]
  5. Authors unspecified: Telaprevir. Drugs R D. 2010;10(3):179-202. doi: 10.2165/11586020-000000000-00000. [PubMed:20945948 ]

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
  1. Kim JJ, Culley CM, Mohammad RA: Telaprevir: an oral protease inhibitor for hepatitis C virus infection. Am J Health Syst Pharm. 2012 Jan 1;69(1):19-33. doi: 10.2146/ajhp110123. [PubMed:22180548 ]