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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7)transporters (2) Show 9 proteins XML

enzymes (7)transporters (2) Show 9 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014839

Secondary Accession Numbers

HMDB14839

Metabolite Identification

Common Name

Amprenavir

Description

Amprenavir, also known as agenerase or vertex VX478, belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring. Amprenavir is a drug which is used for the treatment of hiv-1 infection in combination with other antiretroviral agents. It was patented in 1992 and approved for medical use in 1999. Incorporation of an amino alcohol moiety proved crucial to inhibitory activity for many of these agents. Research aimed at development of renin inhibitors as potential antihypertensive agents had led to the discovery of compounds that blocked the action of this peptide cleaving enzyme. Amprenavir is a moderately basic compound (based on its pKa). Amprenavir is a potentially toxic compound. Structure–activity studies on renin inhibitors proved to be of great value for developing HIV protease inhibitors. Amprenavir (original brand name Agenerase, GlaxoSmithKline) is a protease inhibitor used to treat HIV infection. The convenient dosing came at a price, as the dose required is 1,200 mg, delivered in 8 (eight) very large 150 mg gel capsules or 24 (twenty-four) 50 mg gel capsules twice daily. This unit is closely related to the one found in the statine, an unusual amino acid that forms part of the pepstatin, a fermentation product that inhibits protease enzymes. The amino acid sequence cleaved by renin was found to be fortuitously the same as that required to produce the HIV peptide coat. Production of amprenavir was discontinued by the manufacturer on December 31, 2004; a prodrug version (fosamprenavir), is available. It was approved by the Food and Drug Administration on April 15, 1999, for twice-a-day dosing instead of needing to be taken every eight hours.

Structure

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

701
  Mrv0541 02231214562D          

 35 37  0  0  1  0            999 V2000
    3.7935   -1.1931    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.2819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    3.3445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4878    4.0345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685   -1.1931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6185   -1.1931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.1069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.3681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.1069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -4.4932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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 32 34  2  0  0  0  0
 33 34  1  0  0  0  0
M  END

HMDB0014839
     RDKit          3D
Amprenavir
 70 72  0  0  0  0  0  0  0  0999 V2000
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 35 70  1  0
M  END

701
  Mrv0541 02231214562D          

 35 37  0  0  1  0            999 V2000
    3.7935   -1.1931    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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 18 27  1  0  0  0  0
 21 25  1  0  0  0  0
 22 28  2  0  0  0  0
 22 29  1  0  0  0  0
 26 30  1  0  0  0  0
 27 31  2  0  0  0  0
 28 32  1  0  0  0  0
 29 33  2  0  0  0  0
 30 35  2  0  0  0  0
 31 35  1  0  0  0  0
 32 34  2  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014839

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)/t21-,23-,24+/m0/s1

> <INCHI_KEY>
YMARZQAQMVYCKC-OEMFJLHTSA-N

> <FORMULA>
C25H35N3O6S

> <MOLECULAR_WEIGHT>
505.627

> <EXACT_MASS>
505.224656557

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
53.60424163797374

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate

> <ALOGPS_LOGP>
1.85

> <JCHEM_LOGP>
2.426952677

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.241567005895977

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.614255356778301

> <JCHEM_PKA_STRONGEST_BASIC>
2.3863099248148067

> <JCHEM_POLAR_SURFACE_AREA>
131.19

> <JCHEM_REFRACTIVITY>
134.0815

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
amprenavir

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014839
     RDKit          3D
Amprenavir
 70 72  0  0  0  0  0  0  0  0999 V2000
   -4.5170    1.9237    0.9526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1648    2.3574    0.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2427    2.6134   -0.9957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0176    1.5428    0.9391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9170    0.2027    0.6233 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5724   -0.1907   -0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628   -0.6651   -0.8836 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0473   -1.0398   -2.2129 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8981    0.3209   -0.5173 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9170    1.5212   -1.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9876    2.4598   -1.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2669    2.3277   -1.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2938    3.1734   -1.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0785    4.1806   -0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8270    4.3358    0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7923    3.4824   -0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1737   -0.3847   -0.6786 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0745   -0.5604    0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649   -0.0967    1.5241 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2830   -1.2200    0.2765 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2024   -1.4152    1.3206 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5583   -2.8694    1.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0150   -2.7688    1.9091 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5217   -1.6945    1.2227 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5293   -0.7914    0.9782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4695   -0.9924    1.6514 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.3968   -2.0283    1.9671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8462   -0.3929    2.9779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7955   -1.8840    0.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1047   -1.5483    1.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1440   -2.2535    0.6274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9354   -3.3048   -0.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0190   -4.0087   -0.7751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6119   -3.6429   -0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5570   -2.9554    0.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2760    2.7571    0.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8738    1.1475    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5325    1.5162    1.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0125    3.3906    0.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8983    3.5306   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2749    2.9294   -1.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753    1.8338   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0197    1.6268    2.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0895    2.1442    0.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2386   -1.0251   -0.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396    0.6038   -1.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0195   -1.5785   -0.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5522   -0.4810   -2.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7882    0.6452    0.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0612    1.1888   -2.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0354    2.0696   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4803    1.5468   -2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2760    3.0309   -1.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9032    4.8334   -0.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6651    5.1322    0.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8153    3.6047    0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4480   -0.7776   -1.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8883   -0.9965    2.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4937   -3.3996    0.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0025   -3.3642    2.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1418   -2.6650    3.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5710   -3.7040    1.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5851   -0.4798   -0.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7327    0.1287    1.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3432   -0.7065    1.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1823   -1.9605    0.8552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9661   -3.8923   -0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8578   -4.6382   -1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4244   -4.4907   -1.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5373   -3.2348   -0.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  5 26  1  0
 26 27  2  0
 26 28  2  0
 26 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 32 34  1  0
 34 35  2  0
 16 11  1  0
 25 21  1  0
 35 29  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  1
  8 48  1  0
  9 49  1  1
 10 50  1  0
 10 51  1  0
 12 52  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  0
 16 56  1  0
 17 57  1  0
 21 58  1  1
 22 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 25 63  1  0
 25 64  1  0
 30 65  1  0
 31 66  1  0
 33 67  1  0
 33 68  1  0
 34 69  1  0
 35 70  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 701                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       7.081  -2.227   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       7.081   2.393   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.415   6.243   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.644   7.531   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.541  -2.227   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       8.621  -2.227   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.081   3.933   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       7.081  -0.687   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       9.748   3.933   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       7.081  -8.387   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       8.415   1.623   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.748   2.393   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415   0.083   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748   0.083   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.082   1.623   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414  -0.687   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081   7.013   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.416   2.393   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -2.227   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080   0.083   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.920   8.544   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.081  -3.767   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.674   6.387   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.415   4.703   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.414   8.865   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.416   3.933   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.750   1.623   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.748  -4.537   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.415  -4.537   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.750   4.703   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.083   2.393   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.748  -6.077   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.415  -6.077   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.081  -6.847   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.083   3.933   0.000  0.00  0.00           C+0
CONECT    1    5    6    8   22                                             
CONECT    2   11                                                            
CONECT    3   17   24                                                       
CONECT    4   23   25                                                       
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7   24                                                            
CONECT    8    1   13   14                                                  
CONECT    9   12   24                                                       
CONECT   10   34                                                            
CONECT   11    2   12   13                                                  
CONECT   12    9   11   15                                                  
CONECT   13    8   11                                                       
CONECT   14    8   16                                                       
CONECT   15   12   18                                                       
CONECT   16   14   19   20                                                  
CONECT   17    3   21   23                                                  
CONECT   18   15   26   27                                                  
CONECT   19   16                                                            
CONECT   20   16                                                            
CONECT   21   17   25                                                       
CONECT   22    1   28   29                                                  
CONECT   23    4   17                                                       
CONECT   24    3    7    9                                                  
CONECT   25    4   21                                                       
CONECT   26   18   30                                                       
CONECT   27   18   31                                                       
CONECT   28   22   32                                                       
CONECT   29   22   33                                                       
CONECT   30   26   35                                                       
CONECT   31   27   35                                                       
CONECT   32   28   34                                                       
CONECT   33   29   34                                                       
CONECT   34   10   32   33                                                  
CONECT   35   30   31                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

COMPND    HMDB0014839
HETATM    1  C1  UNL     1      -4.517   1.924   0.953  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.165   2.357   0.488  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.243   2.613  -0.996  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.018   1.543   0.939  1.00  0.00           C  
HETATM    5  N1  UNL     1      -1.917   0.203   0.623  1.00  0.00           N  
HETATM    6  C5  UNL     1      -1.572  -0.191  -0.694  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.163  -0.665  -0.884  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.047  -1.040  -2.213  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.898   0.321  -0.517  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.917   1.521  -1.447  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.988   2.460  -1.027  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.267   2.328  -1.553  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.294   3.173  -1.192  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.079   4.181  -0.293  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.827   4.336   0.244  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.792   3.482  -0.121  1.00  0.00           C  
HETATM   17  N2  UNL     1       2.174  -0.385  -0.679  1.00  0.00           N  
HETATM   18  C15 UNL     1       3.074  -0.560   0.400  1.00  0.00           C  
HETATM   19  O2  UNL     1       2.765  -0.097   1.524  1.00  0.00           O  
HETATM   20  O3  UNL     1       4.283  -1.220   0.276  1.00  0.00           O  
HETATM   21  C16 UNL     1       5.202  -1.415   1.321  1.00  0.00           C  
HETATM   22  C17 UNL     1       5.558  -2.869   1.510  1.00  0.00           C  
HETATM   23  C18 UNL     1       7.015  -2.769   1.909  1.00  0.00           C  
HETATM   24  O4  UNL     1       7.522  -1.695   1.223  1.00  0.00           O  
HETATM   25  C19 UNL     1       6.529  -0.791   0.978  1.00  0.00           C  
HETATM   26  S1  UNL     1      -2.469  -0.992   1.651  1.00  0.00           S  
HETATM   27  O5  UNL     1      -1.397  -2.028   1.967  1.00  0.00           O  
HETATM   28  O6  UNL     1      -2.846  -0.393   2.978  1.00  0.00           O  
HETATM   29  C20 UNL     1      -3.796  -1.884   0.934  1.00  0.00           C  
HETATM   30  C21 UNL     1      -5.105  -1.548   1.195  1.00  0.00           C  
HETATM   31  C22 UNL     1      -6.144  -2.254   0.627  1.00  0.00           C  
HETATM   32  C23 UNL     1      -5.935  -3.305  -0.209  1.00  0.00           C  
HETATM   33  N3  UNL     1      -7.019  -4.009  -0.775  1.00  0.00           N  
HETATM   34  C24 UNL     1      -4.612  -3.643  -0.471  1.00  0.00           C  
HETATM   35  C25 UNL     1      -3.557  -2.955   0.083  1.00  0.00           C  
HETATM   36  H1  UNL     1      -5.276   2.757   0.838  1.00  0.00           H  
HETATM   37  H2  UNL     1      -4.874   1.148   0.249  1.00  0.00           H  
HETATM   38  H3  UNL     1      -4.533   1.516   1.961  1.00  0.00           H  
HETATM   39  H4  UNL     1      -3.013   3.391   0.942  1.00  0.00           H  
HETATM   40  H5  UNL     1      -3.898   3.531  -1.113  1.00  0.00           H  
HETATM   41  H6  UNL     1      -2.275   2.929  -1.424  1.00  0.00           H  
HETATM   42  H7  UNL     1      -3.775   1.834  -1.560  1.00  0.00           H  
HETATM   43  H8  UNL     1      -2.020   1.627   2.078  1.00  0.00           H  
HETATM   44  H9  UNL     1      -1.090   2.144   0.685  1.00  0.00           H  
HETATM   45  H10 UNL     1      -2.239  -1.025  -1.000  1.00  0.00           H  
HETATM   46  H11 UNL     1      -1.740   0.604  -1.450  1.00  0.00           H  
HETATM   47  H12 UNL     1       0.019  -1.578  -0.250  1.00  0.00           H  
HETATM   48  H13 UNL     1      -0.552  -0.481  -2.764  1.00  0.00           H  
HETATM   49  H14 UNL     1       0.788   0.645   0.512  1.00  0.00           H  
HETATM   50  H15 UNL     1       1.061   1.189  -2.509  1.00  0.00           H  
HETATM   51  H16 UNL     1      -0.035   2.070  -1.437  1.00  0.00           H  
HETATM   52  H17 UNL     1       3.480   1.547  -2.266  1.00  0.00           H  
HETATM   53  H18 UNL     1       5.276   3.031  -1.631  1.00  0.00           H  
HETATM   54  H19 UNL     1       4.903   4.833  -0.024  1.00  0.00           H  
HETATM   55  H20 UNL     1       2.665   5.132   0.952  1.00  0.00           H  
HETATM   56  H21 UNL     1       0.815   3.605   0.298  1.00  0.00           H  
HETATM   57  H22 UNL     1       2.448  -0.778  -1.604  1.00  0.00           H  
HETATM   58  H23 UNL     1       4.888  -0.996   2.285  1.00  0.00           H  
HETATM   59  H24 UNL     1       5.494  -3.400   0.526  1.00  0.00           H  
HETATM   60  H25 UNL     1       5.002  -3.364   2.309  1.00  0.00           H  
HETATM   61  H26 UNL     1       7.142  -2.665   3.007  1.00  0.00           H  
HETATM   62  H27 UNL     1       7.571  -3.704   1.622  1.00  0.00           H  
HETATM   63  H28 UNL     1       6.585  -0.480  -0.092  1.00  0.00           H  
HETATM   64  H29 UNL     1       6.733   0.129   1.575  1.00  0.00           H  
HETATM   65  H30 UNL     1      -5.343  -0.706   1.868  1.00  0.00           H  
HETATM   66  H31 UNL     1      -7.182  -1.960   0.855  1.00  0.00           H  
HETATM   67  H32 UNL     1      -7.966  -3.892  -0.388  1.00  0.00           H  
HETATM   68  H33 UNL     1      -6.858  -4.638  -1.575  1.00  0.00           H  
HETATM   69  H34 UNL     1      -4.424  -4.491  -1.145  1.00  0.00           H  
HETATM   70  H35 UNL     1      -2.537  -3.235  -0.133  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3    4   39
CONECT    3   40   41   42
CONECT    4    5   43   44
CONECT    5    6   26
CONECT    6    7   45   46
CONECT    7    8    9   47
CONECT    8   48
CONECT    9   10   17   49
CONECT   10   11   50   51
CONECT   11   12   12   16
CONECT   12   13   52
CONECT   13   14   14   53
CONECT   14   15   54
CONECT   15   16   16   55
CONECT   16   56
CONECT   17   18   57
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   25   58
CONECT   22   23   59   60
CONECT   23   24   61   62
CONECT   24   25
CONECT   25   63   64
CONECT   26   27   27   28   28
CONECT   26   29
CONECT   29   30   30   35
CONECT   30   31   65
CONECT   31   32   32   66
CONECT   32   33   34
CONECT   33   67   68
CONECT   34   35   35   69
CONECT   35   70
END

HMDB0014839
     RDKit          3D
Amprenavir
 70 72  0  0  0  0  0  0  0  0999 V2000
   -4.5170    1.9237    0.9526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1648    2.3574    0.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2427    2.6134   -0.9957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0176    1.5428    0.9391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9170    0.2027    0.6233 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5724   -0.1907   -0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1628   -0.6651   -0.8836 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0473   -1.0398   -2.2129 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8981    0.3209   -0.5173 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9170    1.5212   -1.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9876    2.4598   -1.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2669    2.3277   -1.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2938    3.1734   -1.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0785    4.1806   -0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8270    4.3358    0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7923    3.4824   -0.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1737   -0.3847   -0.6786 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0745   -0.5604    0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649   -0.0967    1.5241 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2830   -1.2200    0.2765 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2024   -1.4152    1.3206 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5583   -2.8694    1.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0150   -2.7688    1.9091 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5217   -1.6945    1.2227 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5293   -0.7914    0.9782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4695   -0.9924    1.6514 S   0  0  0  0  0  6  0  0  0  0  0  0
   -1.3968   -2.0283    1.9671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8462   -0.3929    2.9779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7955   -1.8840    0.9345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1047   -1.5483    1.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1440   -2.2535    0.6274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9354   -3.3048   -0.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0190   -4.0087   -0.7751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6119   -3.6429   -0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5570   -2.9554    0.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2760    2.7571    0.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8738    1.1475    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5325    1.5162    1.9613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0125    3.3906    0.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8983    3.5306   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2749    2.9294   -1.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753    1.8338   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0197    1.6268    2.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0895    2.1442    0.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2386   -1.0251   -0.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7396    0.6038   -1.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0195   -1.5785   -0.2505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5522   -0.4810   -2.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7882    0.6452    0.5122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0612    1.1888   -2.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0354    2.0696   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4803    1.5468   -2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2760    3.0309   -1.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9032    4.8334   -0.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6651    5.1322    0.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8153    3.6047    0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4480   -0.7776   -1.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8883   -0.9965    2.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4937   -3.3996    0.5263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0025   -3.3642    2.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1418   -2.6650    3.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5710   -3.7040    1.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5851   -0.4798   -0.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7327    0.1287    1.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3432   -0.7065    1.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1823   -1.9605    0.8552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9661   -3.8923   -0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8578   -4.6382   -1.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4244   -4.4907   -1.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5373   -3.2348   -0.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  9 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  5 26  1  0
 26 27  2  0
 26 28  2  0
 26 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 32 34  1  0
 34 35  2  0
 16 11  1  0
 25 21  1  0
 35 29  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  6 45  1  0
  6 46  1  0
  7 47  1  1
  8 48  1  0
  9 49  1  1
 10 50  1  0
 10 51  1  0
 12 52  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  0
 16 56  1  0
 17 57  1  0
 21 58  1  1
 22 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 25 63  1  0
 25 64  1  0
 30 65  1  0
 31 66  1  0
 33 67  1  0
 33 68  1  0
 34 69  1  0
 35 70  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamate	ChEBI
Agenerase	ChEBI
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamic acid	Generator
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulphonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamate	Generator
(3S)-Tetrahydro-3-furanyl ((1S,2R)-3-(((4-aminophenyl)sulphonyl)(2-methylpropyl)amino)-2-hydroxy-1-(phenylmethyl)propyl)carbamic acid	Generator
AMP	HMDB
AMV	HMDB
VX-478	HMDB
GlaxoSmithKline brand OF amprenavir	HMDB
Vertex VX478	HMDB
Glaxo wellcome brand OF amprenavir	HMDB
Tetrahydro-3-furyl N-(3-(4-amino-N-isobutylbenzenesulfonamido)-1-benzyl-2-hydroxypropyl)carbamate	HMDB

Chemical Formula

C₂₅H₃₅N₃O₆S

Average Molecular Weight

505.627

Monoisotopic Molecular Weight

505.224656557

IUPAC Name

(3S)-oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate

Traditional Name

amprenavir

CAS Registry Number

161814-49-9

SMILES

CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C1

InChI Identifier

InChI=1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)/t21-,23-,24+/m0/s1

InChI Key

YMARZQAQMVYCKC-OEMFJLHTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Aminobenzenesulfonamides

Alternative Parents

Substituents

Aminobenzenesulfonamide
Phenylbutylamine
Amphetamine or derivatives
Benzenesulfonyl group
Aniline or substituted anilines
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Aminosulfonyl compound
Carbamic acid ester
Tetrahydrofuran
Sulfonyl
Carbonic acid derivative
Secondary alcohol
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Amine
Alcohol
Carbonyl group
Primary amine
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

carbamate ester (CHEBI:40050 )
sulfonamide (CHEBI:40050 )
tetrahydrofuryl ester (CHEBI:40050 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)
Feces (PMID: 28923537)

Cellular substructure

Cytoplasm (HMDB: HMDB0014839)
Membrane (HMDB: HMDB0014839)

Source

Exogenous

Exogenous (HMDB: HMDB0014839)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antiviral drug (HMDB: HMDB0014839)

Biological role

Modulator

Inhibitor

HIV protease inhibitor (HMDB: HMDB0014839)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.049 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.049 g/L	ALOGPS
logP	1.85	ALOGPS
logP	2.43	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	2.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	131.19 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	134.08 m³·mol⁻¹	ChemAxon
Polarizability	53.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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
DarkChem	[M+H]+	215.827	31661259
DarkChem	[M-H]-	208.984	31661259
DeepCCS	[M+H]+	220.904	30932474
DeepCCS	[M-H]-	218.901	30932474
DeepCCS	[M-2H]-	252.143	30932474
DeepCCS	[M+Na]+	226.817	30932474
AllCCS	[M+H]+	219.6	32859911
AllCCS	[M+H-H2O]+	217.8	32859911
AllCCS	[M+NH4]+	221.3	32859911
AllCCS	[M+Na]+	221.8	32859911
AllCCS	[M-H]-	209.4	32859911
AllCCS	[M+Na-2H]-	211.1	32859911
AllCCS	[M+HCOO]-	213.0	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.	6.65 minutes	32390414
Predicted by Siyang on May 30, 2022	14.0016 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.26 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	40.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2429.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	185.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	192.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	120.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	507.2 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	505.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	78.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1154.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	566.6 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	1470.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	344.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	404.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	187.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	128.4 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	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Amprenavir	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C1	6596.2	Standard polar	33892256
Amprenavir	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C1	4061.3	Standard non polar	33892256
Amprenavir	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C1	4087.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Amprenavir,1TMS,isomer #1	CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C1	4047.3	Semi standard non polar	33892256
Amprenavir,1TMS,isomer #2	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	4181.4	Semi standard non polar	33892256
Amprenavir,1TMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	3908.6	Semi standard non polar	33892256
Amprenavir,2TMS,isomer #1	CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	4111.0	Semi standard non polar	33892256
Amprenavir,2TMS,isomer #1	CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	3651.9	Standard non polar	33892256
Amprenavir,2TMS,isomer #1	CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	5089.5	Standard polar	33892256
Amprenavir,2TMS,isomer #2	CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	3894.0	Semi standard non polar	33892256
Amprenavir,2TMS,isomer #2	CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	3656.5	Standard non polar	33892256
Amprenavir,2TMS,isomer #2	CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	5503.0	Standard polar	33892256
Amprenavir,2TMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	4017.1	Semi standard non polar	33892256
Amprenavir,2TMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	3757.4	Standard non polar	33892256
Amprenavir,2TMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	5178.3	Standard polar	33892256
Amprenavir,2TMS,isomer #4	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	4060.9	Semi standard non polar	33892256
Amprenavir,2TMS,isomer #4	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	3751.0	Standard non polar	33892256
Amprenavir,2TMS,isomer #4	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	5195.6	Standard polar	33892256
Amprenavir,3TMS,isomer #1	CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	4017.5	Semi standard non polar	33892256
Amprenavir,3TMS,isomer #1	CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	3749.3	Standard non polar	33892256
Amprenavir,3TMS,isomer #1	CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	4820.2	Standard polar	33892256
Amprenavir,3TMS,isomer #2	CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	4036.8	Semi standard non polar	33892256
Amprenavir,3TMS,isomer #2	CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	3750.6	Standard non polar	33892256
Amprenavir,3TMS,isomer #2	CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	4811.0	Standard polar	33892256
Amprenavir,3TMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	3979.9	Semi standard non polar	33892256
Amprenavir,3TMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	3847.8	Standard non polar	33892256
Amprenavir,3TMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	4898.6	Standard polar	33892256
Amprenavir,4TMS,isomer #1	CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	4005.7	Semi standard non polar	33892256
Amprenavir,4TMS,isomer #1	CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	3857.5	Standard non polar	33892256
Amprenavir,4TMS,isomer #1	CC(C)CN(C[C@@H](O[Si](C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	4556.8	Standard polar	33892256
Amprenavir,1TBDMS,isomer #1	CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C1	4272.9	Semi standard non polar	33892256
Amprenavir,1TBDMS,isomer #2	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	4402.6	Semi standard non polar	33892256
Amprenavir,1TBDMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	4172.2	Semi standard non polar	33892256
Amprenavir,2TBDMS,isomer #1	CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	4555.0	Semi standard non polar	33892256
Amprenavir,2TBDMS,isomer #1	CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	4109.5	Standard non polar	33892256
Amprenavir,2TBDMS,isomer #1	CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	5130.2	Standard polar	33892256
Amprenavir,2TBDMS,isomer #2	CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	4369.0	Semi standard non polar	33892256
Amprenavir,2TBDMS,isomer #2	CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	4123.9	Standard non polar	33892256
Amprenavir,2TBDMS,isomer #2	CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	5462.0	Standard polar	33892256
Amprenavir,2TBDMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	4479.4	Semi standard non polar	33892256
Amprenavir,2TBDMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	4211.1	Standard non polar	33892256
Amprenavir,2TBDMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	5191.4	Standard polar	33892256
Amprenavir,2TBDMS,isomer #4	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4494.1	Semi standard non polar	33892256
Amprenavir,2TBDMS,isomer #4	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4199.2	Standard non polar	33892256
Amprenavir,2TBDMS,isomer #4	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	5175.1	Standard polar	33892256
Amprenavir,3TBDMS,isomer #1	CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	4684.9	Semi standard non polar	33892256
Amprenavir,3TBDMS,isomer #1	CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	4411.7	Standard non polar	33892256
Amprenavir,3TBDMS,isomer #1	CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	4897.5	Standard polar	33892256
Amprenavir,3TBDMS,isomer #2	CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4660.1	Semi standard non polar	33892256
Amprenavir,3TBDMS,isomer #2	CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4393.6	Standard non polar	33892256
Amprenavir,3TBDMS,isomer #2	CC(C)CN(C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4851.2	Standard polar	33892256
Amprenavir,3TBDMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4614.3	Semi standard non polar	33892256
Amprenavir,3TBDMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4497.6	Standard non polar	33892256
Amprenavir,3TBDMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CCOC1)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4925.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Amprenavir GC-MS (Non-derivatized) - 70eV, Positive	splash10-022d-8491400000-418cbb7f08471fa84619	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amprenavir GC-MS (1 TMS) - 70eV, Positive	splash10-03kc-7192320000-fa264cdbd41779709c30	2017-10-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amprenavir LC-ESI-qTof , Positive-QTOF	splash10-05mk-2692510000-696582f37a165753c2f5	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amprenavir 10V, Positive-QTOF	splash10-0a4r-9000500000-e60fa95c31e43c49b031	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amprenavir 20V, Positive-QTOF	splash10-0a4i-9001100000-2c5d3283dd48ceae82dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amprenavir 40V, Positive-QTOF	splash10-0a4i-9010000000-cd15933ef1ecd45d9b1c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amprenavir 10V, Negative-QTOF	splash10-0gbi-4304930000-6cf1884fae8acb8332ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amprenavir 20V, Negative-QTOF	splash10-0173-9432500000-a4d70ca4c7ac6bd2930d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amprenavir 40V, Negative-QTOF	splash10-052f-9825100000-b5b4efee0204074368f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amprenavir 10V, Positive-QTOF	splash10-000i-0046920000-a443e441b8dc951bec99	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amprenavir 20V, Positive-QTOF	splash10-0a4i-2922000000-15960e61915142ff5b1e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amprenavir 40V, Positive-QTOF	splash10-0006-9200000000-78c87a49bf59b5f6c014	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amprenavir 10V, Negative-QTOF	splash10-0uxr-2302980000-1c2dbf56f0de2b3df597	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amprenavir 20V, Negative-QTOF	splash10-0a4i-3911710000-48ad17f577dc556faafc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amprenavir 40V, Negative-QTOF	splash10-0a4i-7900200000-41ad730c9ba505f33793	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00701	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00701	21059682	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Metastatic melanoma	28923537	details

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

Metastatic melanoma
Frankel AE, Coughlin LA, Kim J, Froehlich TW, Xie Y, Frenkel EP, Koh AY: Metagenomic Shotgun Sequencing and Unbiased Metabolomic Profiling Identify Specific Human Gut Microbiota and Metabolites Associated with Immune Checkpoint Therapy Efficacy in Melanoma Patients. Neoplasia. 2017 Oct;19(10):848-855. doi: 10.1016/j.neo.2017.08.004. Epub 2017 Sep 15. [PubMed:28923537 ]

Associated OMIM IDs

None

External Links

DrugBank ID

DB00701

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58532

KEGG Compound ID

C08086

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Amprenavir

METLIN ID

Not Available

PubChem Compound

65016

PDB ID

478

ChEBI ID

40050

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

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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

References

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

Enzyme Details

2. Cytochrome P450 2C9

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

References

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

Enzyme Details

3. Cytochrome P450 2C19

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

References

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

Enzyme Details

4. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

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

Enzyme Details

5. Cytochrome P450 2B6

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

References

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

Enzyme Details

6. Cytochrome P450 3A5

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

References

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

Enzyme Details

7. Cytochrome P450 2C8

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

References

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

Transporters

Enzyme Details

1. Multidrug resistance-associated protein 1

General function:: Involved in ATP binding
Specific function:: Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o- glucuronide, methotrexate, antiviral drugs and other xenobiotics. Confers resistance to anticancer drugs. Hydrolyzes ATP with low efficiency
Gene Name:: ABCC1
Uniprot ID:: P33527
Molecular weight:: 171589.5

References

Olson DP, Scadden DT, D'Aquila RT, De Pasquale MP: The protease inhibitor ritonavir inhibits the functional activity of the multidrug resistance related-protein 1 (MRP-1). AIDS. 2002 Sep 6;16(13):1743-7. [PubMed:12218384 ]

Enzyme Details

2. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Perloff MD, von Moltke LL, Fahey JM, Daily JP, Greenblatt DJ: Induction of P-glycoprotein expression by HIV protease inhibitors in cell culture. AIDS. 2000 Jun 16;14(9):1287-9. [PubMed:10894301 ]
Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]

Showing metabocard for Amprenavir (HMDB0014839)

MOL for HMDB0014839 (Amprenavir)

3D MOL for HMDB0014839 (Amprenavir)

3D SDF for HMDB0014839 (Amprenavir)

3D-SDF for HMDB0014839 (Amprenavir)

PDB for HMDB0014839 (Amprenavir)

3D PDB for HMDB0014839 (Amprenavir)

SMILES for HMDB0014839 (Amprenavir)

INCHI for HMDB0014839 (Amprenavir)

Structure for HMDB0014839 (Amprenavir)

3D Structure for HMDB0014839 (Amprenavir)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

Transporters

References

References