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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:58 UTC

HMDB ID

HMDB0015416

Secondary Accession Numbers

HMDB15416

Metabolite Identification

Common Name

Fosamprenavir

Description

Fosamprenavir is only found in individuals that have used or taken this drug. It is a prodrug of amprenavir, an inhibitor of human immunodeficiency virus (HIV) protease.Fosamprenavir is rapidly hydrolyzed to amprenavir by cellular phosphatases in the gut epithelium as it is absorbed. Amprenavir is an inhibitor of HIV-1 protease. During HIV replication, HIV protease cleaves viral polypeptide products of the Gag and Gag-Pol genes to form structural proteins of the virion core and essential viral enzymes. Amprenavir interferes with this process by binding to the active site of HIV-1 protease, thereby preventing the processing of viral Gag and Gag-Pol polyprotein precursors, resulting in the formation of immature non-infectious viral particles.

Structure

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

1319
  Mrv0541 02231215222D          

 39 41  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
    3.3810    1.9964    0.0000 P   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
    5.9370    3.3445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5447    4.7490    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
    2.9685   -1.1931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9685    2.7108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    1.5839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.1069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955    2.4089    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
    4.5080    0.8694    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2224    1.2819    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5080    0.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3645   -0.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6515    3.7570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7935   -2.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4051    3.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.5194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7377    4.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9572    4.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9370   -1.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  1  7  2  0  0  0  0
  1 12  1  0  0  0  0
  1 23  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  2  9  1  0  0  0  0
  2 11  2  0  0  0  0
 15  3  1  1  0  0  0
 22  4  1  6  0  0  0
  4 27  1  0  0  0  0
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 10 27  2  0  0  0  0
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 16 13  1  1  0  0  0
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 23 32  2  0  0  0  0
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 30 34  1  0  0  0  0
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 34 38  2  0  0  0  0
 35 38  1  0  0  0  0
 36 39  2  0  0  0  0
 37 39  1  0  0  0  0
M  END

HMDB0015416
     RDKit          3D
Fosamprenavir
 75 77  0  0  0  0  0  0  0  0999 V2000
    0.4056    2.2163   -2.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5616    1.3010   -2.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8889    1.9462   -2.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4810   -0.0463   -1.8558 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1417   -0.1853    0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6254   -1.4778    0.0015 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0294   -2.5080    0.5312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4397   -3.3239    1.8617 P   0  0  0  0  0  5  0  0  0  0  0  0
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   -0.4794   -5.0022    1.5422 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7996   -3.1828    3.0845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0929   -1.2852    0.2860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9508   -2.1914   -0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8017   -3.6249   -0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9243    1.1032    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7441    3.4469    0.4062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8195    4.6225    0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7897    5.7786    0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0556    5.2500    0.0124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9917    3.9348   -0.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6851   -0.6606    0.4710 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.1356   -2.0797    0.2211 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2298   -0.6622    1.9324 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1351    0.3206    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1961   -0.0262   -0.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3377    0.7241   -0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5089    1.8659    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6799    2.6515    0.3815 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124    2.1821    1.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2587    1.4458    1.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5146    3.1185   -2.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645    2.6181   -1.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5589    1.7457   -2.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350    1.1878   -3.6237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7286    1.2570   -2.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    2.3358   -1.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0810    2.7902   -2.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5364   -0.5156   -2.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2782   -0.7193   -2.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5144    0.6474   -0.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6550   -1.6899   -1.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695   -5.4490    2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1050   -6.2579    1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2203   -3.7855    1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1227    0.0815   -1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9598    3.3053    1.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4370    4.4665   -0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0205    4.7331    0.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5384    6.5504   -0.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7177    6.2607    1.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7847    3.7509   -1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9042    3.4303    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0881   -0.9287   -0.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4474    1.7417    1.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
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 37 73  1  0
 38 74  1  0
 39 75  1  0
M  END

1319
  Mrv0541 02231215222D          

 39 41  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
    3.3810    1.9964    0.0000 P   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
    5.9370    3.3445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5447    4.7490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0955    2.4089    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
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    4.5080   -3.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -3.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  1  7  2  0  0  0  0
  1 12  1  0  0  0  0
  1 23  1  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  2  9  1  0  0  0  0
  2 11  2  0  0  0  0
 15  3  1  1  0  0  0
 22  4  1  6  0  0  0
  4 27  1  0  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
 10 27  2  0  0  0  0
 12 17  1  0  0  0  0
 12 18  1  0  0  0  0
 16 13  1  1  0  0  0
 13 27  1  0  0  0  0
 14 39  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 24  1  0  0  0  0
 20 25  1  0  0  0  0
 21 30  2  0  0  0  0
 21 31  1  0  0  0  0
 22 26  1  0  0  0  0
 22 28  1  0  0  0  0
 23 32  2  0  0  0  0
 23 33  1  0  0  0  0
 26 29  1  0  0  0  0
 30 34  1  0  0  0  0
 31 35  2  0  0  0  0
 32 36  1  0  0  0  0
 33 37  2  0  0  0  0
 34 38  2  0  0  0  0
 35 38  1  0  0  0  0
 36 39  2  0  0  0  0
 37 39  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015416

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CN(C[C@@H](OP(O)(O)=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/C25H36N3O9PS/c1-18(2)15-28(39(33,34)22-10-8-20(26)9-11-22)16-24(37-38(30,31)32)23(14-19-6-4-3-5-7-19)27-25(29)36-21-12-13-35-17-21/h3-11,18,21,23-24H,12-17,26H2,1-2H3,(H,27,29)(H2,30,31,32)/t21-,23-,24+/m0/s1

> <INCHI_KEY>
MLBVMOWEQCZNCC-OEMFJLHTSA-N

> <FORMULA>
C25H36N3O9PS

> <MOLECULAR_WEIGHT>
585.607

> <EXACT_MASS>
585.190986967

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
57.773308813859536

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S)-1-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-3-({[(3S)-oxolan-3-yloxy]carbonyl}amino)-4-phenylbutan-2-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
1.918751501181241

> <ALOGPS_LOGS>
-2.93

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.280487011775452

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2226719408768485

> <JCHEM_PKA_STRONGEST_BASIC>
2.447282443018397

> <JCHEM_POLAR_SURFACE_AREA>
177.72000000000003

> <JCHEM_REFRACTIVITY>
144.95439999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.85e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fosamprenavir

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015416
     RDKit          3D
Fosamprenavir
 75 77  0  0  0  0  0  0  0  0999 V2000
    0.4056    2.2163   -2.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5616    1.3010   -2.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8889    1.9462   -2.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4810   -0.0463   -1.8558 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212   -0.1612   -0.4812 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -0.1853    0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6254   -1.4778    0.0015 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0294   -2.5080    0.5312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4397   -3.3239    1.8617 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.6859   -2.8875    2.5603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4794   -5.0022    1.5422 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7996   -3.1828    3.0845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0929   -1.2852    0.2860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9508   -2.1914   -0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8017   -3.6249   -0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9598   -4.3430   -1.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833   -5.7245   -1.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6585   -6.4523   -0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4939   -5.7408    0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5709   -4.3496    0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3749    0.0527   -0.3715 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9243    1.1032    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1977    0.9704    1.5689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1954    2.3192   -0.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7441    3.4469    0.4062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8195    4.6225    0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7897    5.7786    0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0556    5.2500    0.0124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9917    3.9348   -0.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6851   -0.6606    0.4710 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.1356   -2.0797    0.2211 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2298   -0.6622    1.9324 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1351    0.3206    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1961   -0.0262   -0.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3377    0.7241   -0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5089    1.8659    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6799    2.6515    0.3815 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124    2.1821    1.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2587    1.4458    1.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5146    3.1185   -2.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645    2.6181   -1.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5589    1.7457   -2.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350    1.1878   -3.6237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7286    1.2570   -2.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    2.3358   -1.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0810    2.7902   -2.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5364   -0.5156   -2.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2782   -0.7193   -2.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2847    0.0760    1.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5144    0.6474   -0.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6550   -1.6899   -1.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695   -5.4490    2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5678   -3.7172    2.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4103   -1.2405    1.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7629   -1.9294   -1.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0404   -1.8979   -0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3495   -3.7867   -2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2236   -6.2618   -1.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5956   -7.5271   -0.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1050   -6.2579    1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2203   -3.7855    1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1227    0.0815   -1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9598    3.3053    1.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4370    4.4665   -0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0205    4.7331    0.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5384    6.5504   -0.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7177    6.2607    1.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7847    3.7509   -1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9042    3.4303    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0881   -0.9287   -0.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1756    0.4323   -1.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9267    3.2252    1.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2863    2.6504   -0.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5341    3.0849    1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4474    1.7417    1.8822 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
  8  9  1  0
  9 10  2  0
  9 11  1  0
  9 12  1  0
  7 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 13 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
  5 30  1  0
 30 31  2  0
 30 32  2  0
 30 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 36 38  1  0
 38 39  2  0
 20 15  1  0
 29 25  1  0
 39 33  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  0
  3 44  1  0
  3 45  1  0
  3 46  1  0
  4 47  1  0
  4 48  1  0
  6 49  1  0
  6 50  1  0
  7 51  1  6
 11 52  1  0
 12 53  1  0
 13 54  1  1
 14 55  1  0
 14 56  1  0
 16 57  1  0
 17 58  1  0
 18 59  1  0
 19 60  1  0
 20 61  1  0
 21 62  1  0
 25 63  1  1
 26 64  1  0
 26 65  1  0
 27 66  1  0
 27 67  1  0
 29 68  1  0
 29 69  1  0
 34 70  1  0
 35 71  1  0
 37 72  1  0
 37 73  1  0
 38 74  1  0
 39 75  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1319                                              
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  P   UNK     0       6.311   3.727   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0       7.081   2.393   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.082   6.243   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      14.083   8.865   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       5.541  -2.227   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.541   5.060   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.977   2.957   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      12.416   3.933   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       7.645   4.497   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       7.081  -0.687   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       9.748   3.933   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       7.081  -8.387   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       8.415   1.623   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748   2.393   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415   0.083   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748   0.083   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.082   1.623   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -0.687   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.082   0.083   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.416   7.013   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.081  -3.767   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.080   0.083   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.414  -2.227   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.823   6.387   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.082   4.703   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.577   8.544   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.853   7.531   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.748  -0.687   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.416  -0.687   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.748  -4.537   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.415  -4.537   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.748  -2.227   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.416  -2.227   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.748  -6.077   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.415  -6.077   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.082  -2.997   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.081  -6.847   0.000  0.00  0.00           C+0
CONECT    1    6    7   12   23                                             
CONECT    2    3    8    9   11                                             
CONECT    3    2   15                                                       
CONECT    4   22   27                                                       
CONECT    5   28   29                                                       
CONECT    6    1                                                            
CONECT    7    1                                                            
CONECT    8    2                                                            
CONECT    9    2                                                            
CONECT   10   27                                                            
CONECT   11    2                                                            
CONECT   12    1   17   18                                                  
CONECT   13   16   27                                                       
CONECT   14   39                                                            
CONECT   15    3   16   17                                                  
CONECT   16   13   15   19                                                  
CONECT   17   12   15                                                       
CONECT   18   12   20                                                       
CONECT   19   16   21                                                       
CONECT   20   18   24   25                                                  
CONECT   21   19   30   31                                                  
CONECT   22    4   26   28                                                  
CONECT   23    1   32   33                                                  
CONECT   24   20                                                            
CONECT   25   20                                                            
CONECT   26   22   29                                                       
CONECT   27    4   10   13                                                  
CONECT   28    5   22                                                       
CONECT   29    5   26                                                       
CONECT   30   21   34                                                       
CONECT   31   21   35                                                       
CONECT   32   23   36                                                       
CONECT   33   23   37                                                       
CONECT   34   30   38                                                       
CONECT   35   31   38                                                       
CONECT   36   32   39                                                       
CONECT   37   33   39                                                       
CONECT   38   34   35                                                       
CONECT   39   14   36   37                                                  
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

COMPND    HMDB0015416
HETATM    1  C1  UNL     1       0.406   2.216  -2.186  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.562   1.301  -2.489  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.889   1.946  -2.208  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.481  -0.046  -1.856  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.421  -0.161  -0.481  1.00  0.00           N  
HETATM    6  C5  UNL     1       0.142  -0.185   0.135  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.625  -1.478   0.001  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.029  -2.508   0.531  1.00  0.00           O  
HETATM    9  P1  UNL     1      -0.440  -3.324   1.862  1.00  0.00           P  
HETATM   10  O2  UNL     1      -1.686  -2.887   2.560  1.00  0.00           O  
HETATM   11  O3  UNL     1      -0.479  -5.002   1.542  1.00  0.00           O  
HETATM   12  O4  UNL     1       0.800  -3.183   3.085  1.00  0.00           O  
HETATM   13  C7  UNL     1      -2.093  -1.285   0.286  1.00  0.00           C  
HETATM   14  C8  UNL     1      -2.951  -2.191  -0.554  1.00  0.00           C  
HETATM   15  C9  UNL     1      -2.802  -3.625  -0.466  1.00  0.00           C  
HETATM   16  C10 UNL     1      -1.960  -4.343  -1.298  1.00  0.00           C  
HETATM   17  C11 UNL     1      -1.883  -5.725  -1.232  1.00  0.00           C  
HETATM   18  C12 UNL     1      -2.659  -6.452  -0.317  1.00  0.00           C  
HETATM   19  C13 UNL     1      -3.494  -5.741   0.511  1.00  0.00           C  
HETATM   20  C14 UNL     1      -3.571  -4.350   0.446  1.00  0.00           C  
HETATM   21  N2  UNL     1      -2.375   0.053  -0.371  1.00  0.00           N  
HETATM   22  C15 UNL     1      -2.924   1.103   0.344  1.00  0.00           C  
HETATM   23  O5  UNL     1      -3.198   0.970   1.569  1.00  0.00           O  
HETATM   24  O6  UNL     1      -3.195   2.319  -0.226  1.00  0.00           O  
HETATM   25  C16 UNL     1      -3.744   3.447   0.406  1.00  0.00           C  
HETATM   26  C17 UNL     1      -2.820   4.622   0.139  1.00  0.00           C  
HETATM   27  C18 UNL     1      -3.790   5.779   0.129  1.00  0.00           C  
HETATM   28  O7  UNL     1      -5.056   5.250   0.012  1.00  0.00           O  
HETATM   29  C19 UNL     1      -4.992   3.935  -0.352  1.00  0.00           C  
HETATM   30  S1  UNL     1       2.685  -0.661   0.471  1.00  0.00           S  
HETATM   31  O8  UNL     1       3.136  -2.080   0.221  1.00  0.00           O  
HETATM   32  O9  UNL     1       2.230  -0.662   1.932  1.00  0.00           O  
HETATM   33  C20 UNL     1       4.135   0.321   0.459  1.00  0.00           C  
HETATM   34  C21 UNL     1       5.196  -0.026  -0.347  1.00  0.00           C  
HETATM   35  C22 UNL     1       6.338   0.724  -0.370  1.00  0.00           C  
HETATM   36  C23 UNL     1       6.509   1.866   0.399  1.00  0.00           C  
HETATM   37  N3  UNL     1       7.680   2.652   0.381  1.00  0.00           N  
HETATM   38  C24 UNL     1       5.412   2.182   1.201  1.00  0.00           C  
HETATM   39  C25 UNL     1       4.259   1.446   1.241  1.00  0.00           C  
HETATM   40  H1  UNL     1       0.515   3.118  -2.845  1.00  0.00           H  
HETATM   41  H2  UNL     1       0.465   2.618  -1.164  1.00  0.00           H  
HETATM   42  H3  UNL     1      -0.559   1.746  -2.352  1.00  0.00           H  
HETATM   43  H4  UNL     1       1.535   1.188  -3.624  1.00  0.00           H  
HETATM   44  H5  UNL     1       3.729   1.257  -2.391  1.00  0.00           H  
HETATM   45  H6  UNL     1       2.968   2.336  -1.183  1.00  0.00           H  
HETATM   46  H7  UNL     1       3.081   2.790  -2.955  1.00  0.00           H  
HETATM   47  H8  UNL     1       0.536  -0.516  -2.290  1.00  0.00           H  
HETATM   48  H9  UNL     1       2.278  -0.719  -2.336  1.00  0.00           H  
HETATM   49  H10 UNL     1       0.285   0.076   1.227  1.00  0.00           H  
HETATM   50  H11 UNL     1      -0.514   0.647  -0.238  1.00  0.00           H  
HETATM   51  H12 UNL     1      -0.655  -1.690  -1.142  1.00  0.00           H  
HETATM   52  H13 UNL     1      -1.069  -5.449   2.213  1.00  0.00           H  
HETATM   53  H14 UNL     1       1.568  -3.717   2.748  1.00  0.00           H  
HETATM   54  H15 UNL     1      -2.410  -1.241   1.306  1.00  0.00           H  
HETATM   55  H16 UNL     1      -2.763  -1.929  -1.657  1.00  0.00           H  
HETATM   56  H17 UNL     1      -4.040  -1.898  -0.451  1.00  0.00           H  
HETATM   57  H18 UNL     1      -1.350  -3.787  -2.021  1.00  0.00           H  
HETATM   58  H19 UNL     1      -1.224  -6.262  -1.890  1.00  0.00           H  
HETATM   59  H20 UNL     1      -2.596  -7.527  -0.274  1.00  0.00           H  
HETATM   60  H21 UNL     1      -4.105  -6.258   1.230  1.00  0.00           H  
HETATM   61  H22 UNL     1      -4.220  -3.786   1.088  1.00  0.00           H  
HETATM   62  H23 UNL     1      -2.123   0.082  -1.365  1.00  0.00           H  
HETATM   63  H24 UNL     1      -3.960   3.305   1.469  1.00  0.00           H  
HETATM   64  H25 UNL     1      -2.437   4.467  -0.903  1.00  0.00           H  
HETATM   65  H26 UNL     1      -2.021   4.733   0.872  1.00  0.00           H  
HETATM   66  H27 UNL     1      -3.538   6.550  -0.606  1.00  0.00           H  
HETATM   67  H28 UNL     1      -3.718   6.261   1.145  1.00  0.00           H  
HETATM   68  H29 UNL     1      -4.785   3.751  -1.425  1.00  0.00           H  
HETATM   69  H30 UNL     1      -5.904   3.430   0.012  1.00  0.00           H  
HETATM   70  H31 UNL     1       5.088  -0.929  -0.970  1.00  0.00           H  
HETATM   71  H32 UNL     1       7.176   0.432  -1.021  1.00  0.00           H  
HETATM   72  H33 UNL     1       7.927   3.225   1.202  1.00  0.00           H  
HETATM   73  H34 UNL     1       8.286   2.650  -0.451  1.00  0.00           H  
HETATM   74  H35 UNL     1       5.534   3.085   1.819  1.00  0.00           H  
HETATM   75  H36 UNL     1       3.447   1.742   1.882  1.00  0.00           H  
CONECT    1    2   40   41   42
CONECT    2    3    4   43
CONECT    3   44   45   46
CONECT    4    5   47   48
CONECT    5    6   30
CONECT    6    7   49   50
CONECT    7    8   13   51
CONECT    8    9
CONECT    9   10   10   11   12
CONECT   11   52
CONECT   12   53
CONECT   13   14   21   54
CONECT   14   15   55   56
CONECT   15   16   16   20
CONECT   16   17   57
CONECT   17   18   18   58
CONECT   18   19   59
CONECT   19   20   20   60
CONECT   20   61
CONECT   21   22   62
CONECT   22   23   23   24
CONECT   24   25
CONECT   25   26   29   63
CONECT   26   27   64   65
CONECT   27   28   66   67
CONECT   28   29
CONECT   29   68   69
CONECT   30   31   31   32   32
CONECT   30   33
CONECT   33   34   34   39
CONECT   34   35   70
CONECT   35   36   36   71
CONECT   36   37   38
CONECT   37   72   73
CONECT   38   39   39   74
CONECT   39   75
END

HMDB0015416
     RDKit          3D
Fosamprenavir
 75 77  0  0  0  0  0  0  0  0999 V2000
    0.4056    2.2163   -2.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5616    1.3010   -2.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8889    1.9462   -2.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4810   -0.0463   -1.8558 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212   -0.1612   -0.4812 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -0.1853    0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6254   -1.4778    0.0015 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0294   -2.5080    0.5312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4397   -3.3239    1.8617 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.6859   -2.8875    2.5603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4794   -5.0022    1.5422 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7996   -3.1828    3.0845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0929   -1.2852    0.2860 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9508   -2.1914   -0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8017   -3.6249   -0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9598   -4.3430   -1.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833   -5.7245   -1.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6585   -6.4523   -0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4939   -5.7408    0.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5709   -4.3496    0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3749    0.0527   -0.3715 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9243    1.1032    0.3441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1977    0.9704    1.5689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1954    2.3192   -0.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7441    3.4469    0.4062 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8195    4.6225    0.1386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7897    5.7786    0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0556    5.2500    0.0124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9917    3.9348   -0.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6851   -0.6606    0.4710 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.1356   -2.0797    0.2211 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2298   -0.6622    1.9324 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1351    0.3206    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1961   -0.0262   -0.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3377    0.7241   -0.3699 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5089    1.8659    0.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6799    2.6515    0.3815 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4124    2.1821    1.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2587    1.4458    1.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5146    3.1185   -2.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645    2.6181   -1.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5589    1.7457   -2.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350    1.1878   -3.6237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7286    1.2570   -2.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    2.3358   -1.1835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0810    2.7902   -2.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5364   -0.5156   -2.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2782   -0.7193   -2.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2847    0.0760    1.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5144    0.6474   -0.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6550   -1.6899   -1.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695   -5.4490    2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5678   -3.7172    2.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4103   -1.2405    1.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7629   -1.9294   -1.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0404   -1.8979   -0.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3495   -3.7867   -2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2236   -6.2618   -1.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5956   -7.5271   -0.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1050   -6.2579    1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2203   -3.7855    1.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1227    0.0815   -1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9598    3.3053    1.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4370    4.4665   -0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0205    4.7331    0.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5384    6.5504   -0.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7177    6.2607    1.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7847    3.7509   -1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9042    3.4303    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0881   -0.9287   -0.9697 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1756    0.4323   -1.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9267    3.2252    1.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2863    2.6504   -0.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5341    3.0849    1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4474    1.7417    1.8822 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
  8  9  1  0
  9 10  2  0
  9 11  1  0
  9 12  1  0
  7 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 13 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
  5 30  1  0
 30 31  2  0
 30 32  2  0
 30 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 36 38  1  0
 38 39  2  0
 20 15  1  0
 29 25  1  0
 39 33  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  0
  3 44  1  0
  3 45  1  0
  3 46  1  0
  4 47  1  0
  4 48  1  0
  6 49  1  0
  6 50  1  0
  7 51  1  6
 11 52  1  0
 12 53  1  0
 13 54  1  1
 14 55  1  0
 14 56  1  0
 16 57  1  0
 17 58  1  0
 18 59  1  0
 19 60  1  0
 20 61  1  0
 21 62  1  0
 25 63  1  1
 26 64  1  0
 26 65  1  0
 27 66  1  0
 27 67  1  0
 29 68  1  0
 29 69  1  0
 34 70  1  0
 35 71  1  0
 37 72  1  0
 37 73  1  0
 38 74  1  0
 39 75  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
FOS-apv	ChEBI
(3-(((4-Aminophenyl)sulfonyl)(2-methylpropyl)amino)-1-(phenylmethyl)-2-(phosphonooxy)propyl)carbamic acid C-(tetrahydro-3-furanyl) ester	HMDB
Fosamprenavir calcium	HMDB
VX175 CPD	HMDB
Lexiva	HMDB
GW908 CPD	HMDB
Fos-amprenavir	HMDB

Chemical Formula

C₂₅H₃₆N₃O₉PS

Average Molecular Weight

585.607

Monoisotopic Molecular Weight

585.190986967

IUPAC Name

{[(2R,3S)-1-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-3-({[(3S)-oxolan-3-yloxy]carbonyl}amino)-4-phenylbutan-2-yl]oxy}phosphonic acid

Traditional Name

fosamprenavir

CAS Registry Number

226700-79-4

SMILES

CC(C)CN(C[C@@H](OP(O)(O)=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/C25H36N3O9PS/c1-18(2)15-28(39(33,34)22-10-8-20(26)9-11-22)16-24(37-38(30,31)32)23(14-19-6-4-3-5-7-19)27-25(29)36-21-12-13-35-17-21/h3-11,18,21,23-24H,12-17,26H2,1-2H3,(H,27,29)(H2,30,31,32)/t21-,23-,24+/m0/s1

InChI Key

MLBVMOWEQCZNCC-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
Phosphoethanolamine
Aniline or substituted anilines
Monoalkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Organosulfonic acid amide
Alkyl phosphate
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Aminosulfonyl compound
Tetrahydrofuran
Sulfonyl
Carboximidic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Amine
Organic nitrogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfonamide (CHEBI:82941 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015416)
Membrane (HMDB: HMDB0015416)

Source

Exogenous

Exogenous (HMDB: HMDB0015416)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.68 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.68 g/L	ALOGPS
logP	0.84	ALOGPS
logP	1.92	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	2.45	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	177.72 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	144.95 m³·mol⁻¹	ChemAxon
Polarizability	57.77 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]+	232.205	31661259
DarkChem	[M-H]-	222.971	31661259
DeepCCS	[M+H]+	221.662	30932474
DeepCCS	[M-H]-	219.837	30932474
DeepCCS	[M-2H]-	253.079	30932474
DeepCCS	[M+Na]+	227.268	30932474
AllCCS	[M+H]+	231.5	32859911
AllCCS	[M+H-H2O]+	230.2	32859911
AllCCS	[M+NH4]+	232.7	32859911
AllCCS	[M+Na]+	233.1	32859911
AllCCS	[M-H]-	220.0	32859911
AllCCS	[M+Na-2H]-	222.2	32859911
AllCCS	[M+HCOO]-	224.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fosamprenavir	CC(C)CN(C[C@@H](OP(O)(O)=O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C1	6529.6	Standard polar	33892256
Fosamprenavir	CC(C)CN(C[C@@H](OP(O)(O)=O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C1	4161.2	Standard non polar	33892256
Fosamprenavir	CC(C)CN(C[C@@H](OP(O)(O)=O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CCOC1)S(=O)(=O)C1=CC=C(N)C=C1	4603.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fosamprenavir,1TMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O)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	4546.6	Semi standard non polar	33892256
Fosamprenavir,1TMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O)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	3971.1	Standard non polar	33892256
Fosamprenavir,1TMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O)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	6705.9	Standard polar	33892256
Fosamprenavir,1TMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O)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	4668.1	Semi standard non polar	33892256
Fosamprenavir,1TMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O)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	3990.2	Standard non polar	33892256
Fosamprenavir,1TMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O)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	6612.1	Standard polar	33892256
Fosamprenavir,1TMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	4448.3	Semi standard non polar	33892256
Fosamprenavir,1TMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	4007.5	Standard non polar	33892256
Fosamprenavir,1TMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	7151.2	Standard polar	33892256
Fosamprenavir,2TMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C)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	4456.4	Semi standard non polar	33892256
Fosamprenavir,2TMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C)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	4011.4	Standard non polar	33892256
Fosamprenavir,2TMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C)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	6144.9	Standard polar	33892256
Fosamprenavir,2TMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O)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	4578.9	Semi standard non polar	33892256
Fosamprenavir,2TMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O)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	4045.0	Standard non polar	33892256
Fosamprenavir,2TMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O)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	5873.7	Standard polar	33892256
Fosamprenavir,2TMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	4374.5	Semi standard non polar	33892256
Fosamprenavir,2TMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	4058.8	Standard non polar	33892256
Fosamprenavir,2TMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	6387.6	Standard polar	33892256
Fosamprenavir,2TMS,isomer #4	CC(C)CN(C[C@@H](OP(=O)(O)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	4504.3	Semi standard non polar	33892256
Fosamprenavir,2TMS,isomer #4	CC(C)CN(C[C@@H](OP(=O)(O)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	4098.0	Standard non polar	33892256
Fosamprenavir,2TMS,isomer #4	CC(C)CN(C[C@@H](OP(=O)(O)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	6215.3	Standard polar	33892256
Fosamprenavir,2TMS,isomer #5	CC(C)CN(C[C@@H](OP(=O)(O)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	4427.0	Semi standard non polar	33892256
Fosamprenavir,2TMS,isomer #5	CC(C)CN(C[C@@H](OP(=O)(O)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	4092.0	Standard non polar	33892256
Fosamprenavir,2TMS,isomer #5	CC(C)CN(C[C@@H](OP(=O)(O)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	6203.5	Standard polar	33892256
Fosamprenavir,3TMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C)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	4520.9	Semi standard non polar	33892256
Fosamprenavir,3TMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C)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	4087.3	Standard non polar	33892256
Fosamprenavir,3TMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C)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	5327.6	Standard polar	33892256
Fosamprenavir,3TMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C)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	4330.8	Semi standard non polar	33892256
Fosamprenavir,3TMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C)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	4096.6	Standard non polar	33892256
Fosamprenavir,3TMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C)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	5898.9	Standard polar	33892256
Fosamprenavir,3TMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	4466.2	Semi standard non polar	33892256
Fosamprenavir,3TMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	4136.4	Standard non polar	33892256
Fosamprenavir,3TMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	5585.0	Standard polar	33892256
Fosamprenavir,3TMS,isomer #4	CC(C)CN(C[C@@H](OP(=O)(O)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	4437.5	Semi standard non polar	33892256
Fosamprenavir,3TMS,isomer #4	CC(C)CN(C[C@@H](OP(=O)(O)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	4138.6	Standard non polar	33892256
Fosamprenavir,3TMS,isomer #4	CC(C)CN(C[C@@H](OP(=O)(O)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	5549.3	Standard polar	33892256
Fosamprenavir,3TMS,isomer #5	CC(C)CN(C[C@@H](OP(=O)(O)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	4350.9	Semi standard non polar	33892256
Fosamprenavir,3TMS,isomer #5	CC(C)CN(C[C@@H](OP(=O)(O)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	4196.6	Standard non polar	33892256
Fosamprenavir,3TMS,isomer #5	CC(C)CN(C[C@@H](OP(=O)(O)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	5834.0	Standard polar	33892256
Fosamprenavir,4TMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C)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	4450.8	Semi standard non polar	33892256
Fosamprenavir,4TMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C)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	4175.6	Standard non polar	33892256
Fosamprenavir,4TMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C)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	5090.4	Standard polar	33892256
Fosamprenavir,4TMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C)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	4468.3	Semi standard non polar	33892256
Fosamprenavir,4TMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C)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	4179.6	Standard non polar	33892256
Fosamprenavir,4TMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C)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	5061.9	Standard polar	33892256
Fosamprenavir,4TMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	4417.4	Semi standard non polar	33892256
Fosamprenavir,4TMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	4230.1	Standard non polar	33892256
Fosamprenavir,4TMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	5276.6	Standard polar	33892256
Fosamprenavir,1TBDMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O)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	4749.6	Semi standard non polar	33892256
Fosamprenavir,1TBDMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O)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	4159.7	Standard non polar	33892256
Fosamprenavir,1TBDMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O)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	6700.9	Standard polar	33892256
Fosamprenavir,1TBDMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O)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	4896.2	Semi standard non polar	33892256
Fosamprenavir,1TBDMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O)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	4204.4	Standard non polar	33892256
Fosamprenavir,1TBDMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O)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	6542.2	Standard polar	33892256
Fosamprenavir,1TBDMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	4704.6	Semi standard non polar	33892256
Fosamprenavir,1TBDMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	4232.0	Standard non polar	33892256
Fosamprenavir,1TBDMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	7028.3	Standard polar	33892256
Fosamprenavir,2TBDMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C(C)(C)C)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	4862.3	Semi standard non polar	33892256
Fosamprenavir,2TBDMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C(C)(C)C)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	4376.5	Standard non polar	33892256
Fosamprenavir,2TBDMS,isomer #1	CC(C)CN(C[C@@H](OP(=O)(O[Si](C)(C)C(C)(C)C)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	6158.3	Standard polar	33892256
Fosamprenavir,2TBDMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O)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	5021.5	Semi standard non polar	33892256
Fosamprenavir,2TBDMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O)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	4436.4	Standard non polar	33892256
Fosamprenavir,2TBDMS,isomer #2	CC(C)CN(C[C@@H](OP(=O)(O)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	5875.1	Standard polar	33892256
Fosamprenavir,2TBDMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	4814.3	Semi standard non polar	33892256
Fosamprenavir,2TBDMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	4464.5	Standard non polar	33892256
Fosamprenavir,2TBDMS,isomer #3	CC(C)CN(C[C@@H](OP(=O)(O)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	6316.4	Standard polar	33892256
Fosamprenavir,2TBDMS,isomer #4	CC(C)CN(C[C@@H](OP(=O)(O)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	4961.9	Semi standard non polar	33892256
Fosamprenavir,2TBDMS,isomer #4	CC(C)CN(C[C@@H](OP(=O)(O)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	4525.9	Standard non polar	33892256
Fosamprenavir,2TBDMS,isomer #4	CC(C)CN(C[C@@H](OP(=O)(O)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	6118.4	Standard polar	33892256
Fosamprenavir,2TBDMS,isomer #5	CC(C)CN(C[C@@H](OP(=O)(O)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	4889.6	Semi standard non polar	33892256
Fosamprenavir,2TBDMS,isomer #5	CC(C)CN(C[C@@H](OP(=O)(O)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	4504.8	Standard non polar	33892256
Fosamprenavir,2TBDMS,isomer #5	CC(C)CN(C[C@@H](OP(=O)(O)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	6077.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Fosamprenavir GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9105310000-2bf3c66449e76886fd4c	2017-09-01	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosamprenavir 10V, Positive-QTOF	splash10-0a4r-9000410000-a4ed06be5677009d5152	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosamprenavir 20V, Positive-QTOF	splash10-0a4i-9000000000-61429bd749fc1970bd15	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosamprenavir 40V, Positive-QTOF	splash10-0a4i-9010000000-df39dc7519473ac39907	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosamprenavir 10V, Negative-QTOF	splash10-002b-9200740000-56d180057627a10f872b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosamprenavir 20V, Negative-QTOF	splash10-004i-9110210000-4b73b6264e2b0dc68d44	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosamprenavir 40V, Negative-QTOF	splash10-004i-9100000000-3a6decb74ff0fdced13c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosamprenavir 10V, Positive-QTOF	splash10-014r-0002290000-038010146a2a01b7eebb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosamprenavir 20V, Positive-QTOF	splash10-0a4i-1905120000-7521d85769a28d8d932f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosamprenavir 40V, Positive-QTOF	splash10-0006-9402000000-876d1f5a14cf58401c37	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosamprenavir 10V, Negative-QTOF	splash10-001i-1100290000-28479e86b726902fdcd4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosamprenavir 20V, Negative-QTOF	splash10-0a4j-5500960000-455bc30cc4df2fda337b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fosamprenavir 40V, Negative-QTOF	splash10-056s-9710200000-83e2b28117cea7dea8d7	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
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 DB01319	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01319	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01319

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

116245

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fosamprenavir

METLIN ID

Not Available

PubChem Compound

131536

PDB ID

Not Available

ChEBI ID

82941

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

Wire MB, Shelton MJ, Studenberg S: Fosamprenavir : clinical pharmacokinetics and drug interactions of the amprenavir prodrug. Clin Pharmacokinet. 2006;45(2):137-68. [PubMed:16485915 ]
Falcoz C, Jenkins JM, Bye C, Hardman TC, Kenney KB, Studenberg S, Fuder H, Prince WT: Pharmacokinetics of GW433908, a prodrug of amprenavir, in healthy male volunteers. J Clin Pharmacol. 2002 Aug;42(8):887-98. [PubMed:12162471 ]
Wood R, Arasteh K, Stellbrink HJ, Teofilo E, Raffi F, Pollard RB, Eron J, Yeo J, Millard J, Wire MB, Naderer OJ: Six-week randomized controlled trial to compare the tolerabilities, pharmacokinetics, and antiviral activities of GW433908 and amprenavir in human immunodeficiency virus type 1-infected patients. Antimicrob Agents Chemother. 2004 Jan;48(1):116-23. [PubMed:14693528 ]
Furfine ES, Baker CT, Hale MR, Reynolds DJ, Salisbury JA, Searle AD, Studenberg SD, Todd D, Tung RD, Spaltenstein A: Preclinical pharmacology and pharmacokinetics of GW433908, a water-soluble prodrug of the human immunodeficiency virus protease inhibitor amprenavir. Antimicrob Agents Chemother. 2004 Mar;48(3):791-8. [PubMed:14982766 ]
Sension M: Initial therapy for human immunodeficiency virus: broadening the options. HIV Clin Trials. 2004 Mar-Apr;5(2):99-111. [PubMed:15116286 ]
Chapman TM, Plosker GL, Perry CM: Fosamprenavir: a review of its use in the management of antiretroviral therapy-naive patients with HIV infection. Drugs. 2004;64(18):2101-24. [PubMed:15341507 ]
Hoffman RM, Umeh OC, Garris C, Givens N, Currier JS: Evaluation of sex differences of fosamprenavir (with and without ritonavir) in HIV-infected men and women. HIV Clin Trials. 2007 Nov-Dec;8(6):371-80. [PubMed:18042502 ]
Smith KY, Weinberg WG, Dejesus E, Fischl MA, Liao Q, Ross LL, Pakes GE, Pappa KA, Lancaster CT: Fosamprenavir or atazanavir once daily boosted with ritonavir 100 mg, plus tenofovir/emtricitabine, for the initial treatment of HIV infection: 48-week results of ALERT. AIDS Res Ther. 2008 Mar 28;5:5. doi: 10.1186/1742-6405-5-5. [PubMed:18373851 ]

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

Wire MB, Shelton MJ, Studenberg S: Fosamprenavir : clinical pharmacokinetics and drug interactions of the amprenavir prodrug. Clin Pharmacokinet. 2006;45(2):137-68. [PubMed:16485915 ]
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 ]

Showing metabocard for Fosamprenavir (HMDB0015416)

MOL for HMDB0015416 (Fosamprenavir)

3D MOL for HMDB0015416 (Fosamprenavir)

3D SDF for HMDB0015416 (Fosamprenavir)

3D-SDF for HMDB0015416 (Fosamprenavir)

PDB for HMDB0015416 (Fosamprenavir)

3D PDB for HMDB0015416 (Fosamprenavir)

SMILES for HMDB0015416 (Fosamprenavir)

INCHI for HMDB0015416 (Fosamprenavir)

Structure for HMDB0015416 (Fosamprenavir)

3D Structure for HMDB0015416 (Fosamprenavir)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References