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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

HMDB0015393

Secondary Accession Numbers

HMDB15393

Metabolite Identification

Common Name

Darunavir

Description

Darunavir is only found in individuals that have used or taken this drug. It is a protease inhibitor used to treat HIV. It acts on the HIV aspartyl protease which the virus needs to cleave the HIV polyprotein into its functional fragments.Darunavir is a HIV protease inhibitor which prevents HIV replication by binding to the enzyme's active site, thereby preventing the dimerization and the catalytic activity of the HIV-1 protease. Darunavir selectively inhibits the cleavage of HIV encoded Gag-Pol polyproteins in virus-infected cells, which prevents the formation of mature infectious virus particles. Structual analyses suggests that the close contact that darunavir has with the main chains of the protease active site amino acids (Asp-29 and Asp-30) is an important contributing factor to its potency and wide spectrum of activity against multi-protease inhibitor resistant HIV-1 variants. Darunavir can also adapt to the changing shape of a protease enzyme because of its molecular flexibility. Darunavir is known to bind to two distinct sites on the enzyme: the active site cavity and the surface of one of the flexible flaps in the protease dimer.

Structure

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

1264
  Mrv0541 02231215222D          

 40 43  0  0  1  0            999 V2000
    5.2174    1.5520    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.7471   -4.4910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3125   -4.4874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4922   -2.3713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5612   -0.2874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1331   -2.8129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8305    0.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6043    2.1040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4302   -1.4151    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6654    0.9388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4256    4.0044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5318   -3.4110    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5318   -4.2360    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7471   -3.1560    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  7  2  0  0  0  0
  1  8  2  0  0  0  0
  1 10  1  0  0  0  0
  1 26  1  0  0  0  0
  2 13  1  0  0  0  0
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 14  4  1  6  0  0  0
  4 20  1  0  0  0  0
 19  5  1  6  0  0  0
  6 20  2  0  0  0  0
 18  9  1  1  0  0  0
  9 20  1  0  0  0  0
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 29 33  1  0  0  0  0
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 31 36  1  0  0  0  0
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 33 35  2  0  0  0  0
 34 35  1  0  0  0  0
 36 38  2  0  0  0  0
 37 38  1  0  0  0  0
M  END

HMDB0015393
     RDKit          3D
Darunavir
 75 78  0  0  0  0  0  0  0  0999 V2000
   -3.7398    0.5877    2.7646 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8247    3.5533   -0.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5814    3.6399   -0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
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 38 75  1  0
M  END

1264
  Mrv0541 02231215222D          

 40 43  0  0  1  0            999 V2000
    5.2174    1.5520    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.7471   -4.4910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6654    0.9388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2021   -0.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6501   -1.3421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1285    2.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0666    3.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8736    3.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5327   -2.7509    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5327   -4.8961    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  1  8  2  0  0  0  0
  1 10  1  0  0  0  0
  1 26  1  0  0  0  0
  2 13  1  0  0  0  0
  2 16  1  0  0  0  0
  3 13  1  0  0  0  0
  3 17  1  0  0  0  0
 14  4  1  6  0  0  0
  4 20  1  0  0  0  0
 19  5  1  6  0  0  0
  6 20  2  0  0  0  0
 18  9  1  1  0  0  0
  9 20  1  0  0  0  0
 10 21  1  0  0  0  0
 10 23  1  0  0  0  0
 11 38  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 12 39  1  1  0  0  0
 13 40  1  1  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 22  1  0  0  0  0
 19 21  1  0  0  0  0
 22 25  1  0  0  0  0
 23 24  1  0  0  0  0
 24 27  1  0  0  0  0
 24 28  1  0  0  0  0
 25 29  2  0  0  0  0
 25 30  1  0  0  0  0
 26 31  2  0  0  0  0
 26 32  1  0  0  0  0
 29 33  1  0  0  0  0
 30 34  2  0  0  0  0
 31 36  1  0  0  0  0
 32 37  2  0  0  0  0
 33 35  2  0  0  0  0
 34 35  1  0  0  0  0
 36 38  2  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015393

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCO[C@]1([H])OC[C@@H]2OC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](O)CN(CC(C)C)S(=O)(=O)C1=CC=C(N)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H37N3O7S/c1-18(2)15-30(38(33,34)21-10-8-20(28)9-11-21)16-24(31)23(14-19-6-4-3-5-7-19)29-27(32)37-25-17-36-26-22(25)12-13-35-26/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32)/t22-,23-,24+,25-,26+/m0/s1

> <INCHI_KEY>
CJBJHOAVZSMMDJ-HEXNFIEUSA-N

> <FORMULA>
C27H37N3O7S

> <MOLECULAR_WEIGHT>
547.664

> <EXACT_MASS>
547.235221243

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
57.241741627684895

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate

> <ALOGPS_LOGP>
1.76

> <JCHEM_LOGP>
2.8168176063333332

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.23135852263432

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.588299257233068

> <JCHEM_PKA_STRONGEST_BASIC>
2.3863099633984333

> <JCHEM_POLAR_SURFACE_AREA>
140.42

> <JCHEM_REFRACTIVITY>
142.3406

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
darunavir

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015393
     RDKit          3D
Darunavir
 75 78  0  0  0  0  0  0  0  0999 V2000
   -3.7398    0.5877    2.7646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1690   -0.7658    2.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8149   -1.7429    3.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916   -1.1899    1.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6407   -0.3316    0.1059 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6584   -1.0572   -0.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3648   -0.2892   -0.7529 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1100   -0.1598    0.5469 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6835   -0.9743   -1.6421 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8549   -2.4084   -1.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8879   -3.0912   -1.9657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2183   -3.0498   -1.6815 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1134   -3.6802   -2.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6576   -4.3591   -3.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3122   -4.4128   -3.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4230   -3.7725   -3.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8885   -0.2898   -1.7138 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0599    0.3756   -1.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7910    0.6110   -2.7922 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6770    0.9501   -0.6249 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8766    1.6371   -0.6273 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8019    3.0839   -0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2833    3.1430    1.0614 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3818    2.2795    1.0624 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6697    1.8104    2.3135 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9229    0.6736    2.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5961    0.0476    1.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9557    1.0940    0.2215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6369    0.5601   -0.9376 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.3970   -0.4548   -1.7967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7471    1.2920   -1.9204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7228    1.6689   -0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0231    1.3015    0.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9009    2.1903    0.6978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5284    3.4832    0.9935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4402    4.4084    1.6026 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2358    3.8620    0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3627    2.9784    0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8344    0.6167    2.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2409    1.3999    2.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6158    0.7561    3.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0813   -0.7610    2.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3930   -2.7479    3.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6319   -1.3601    4.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9161   -1.8349    3.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3871   -1.1872    0.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9945   -2.2588    0.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0446   -1.1658   -1.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5516   -2.0940   -0.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586    0.7450   -1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1111   -0.9983    1.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1558   -1.1439   -2.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1169   -2.4567   -0.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0874   -2.9559   -1.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5299   -2.4913   -0.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1684   -3.6482   -2.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3563   -4.8703   -4.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9798   -4.9600   -4.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3492   -3.8084   -3.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9697   -0.5653   -3.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2626    1.6198   -1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8247    3.5533   -0.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5814    3.6399   -0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2289    2.8129    0.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0281    0.9042    3.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5741   -0.0358    3.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5509   -0.3166    1.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2335   -0.8781    1.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8328    0.7403   -0.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3087    0.2807   -0.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9178    1.8971    0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0268    4.9986    1.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4604    4.4352    2.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9489    4.8683    0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3456    3.2612   -0.1500 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
 25 26  1  0
 26 27  1  0
 27 28  1  0
  5 29  1  0
 29 30  2  0
 29 31  2  0
 29 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 35 37  1  0
 37 38  2  0
 16 11  1  0
 28 21  1  0
 38 32  1  0
 28 24  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  0
  3 43  1  0
  3 44  1  0
  3 45  1  0
  4 46  1  0
  4 47  1  0
  6 48  1  0
  6 49  1  0
  7 50  1  6
  8 51  1  0
  9 52  1  6
 10 53  1  0
 10 54  1  0
 12 55  1  0
 13 56  1  0
 14 57  1  0
 15 58  1  0
 16 59  1  0
 17 60  1  0
 21 61  1  6
 22 62  1  0
 22 63  1  0
 24 64  1  6
 26 65  1  0
 26 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  6
 33 70  1  0
 34 71  1  0
 36 72  1  0
 36 73  1  0
 37 74  1  0
 38 75  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1264                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       9.739   2.897   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      12.595  -8.383   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      15.517  -8.376   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.119  -4.426   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.648  -0.536   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       9.582  -5.251   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      10.884   1.866   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       8.595   3.927   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      10.136  -2.642   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       8.709   1.752   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      13.861   7.475   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      14.059  -6.367   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.059  -7.907   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.595  -5.891   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.517  -5.898   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.689  -7.137   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.415  -7.137   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.630  -2.321   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.154  -0.857   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.612  -4.106   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.185   0.288   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.599  -3.466   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.202   2.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.726   3.537   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.093  -3.146   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.770   4.042   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.757   4.682   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.220   3.858   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.063  -4.290   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.617  -1.681   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.276   3.721   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.294   5.506   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.556  -3.970   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.111  -1.361   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.080  -2.505   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.307   4.866   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.324   6.651   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      12.831   6.330   0.000  0.00  0.00           C+0
HETATM   39  H   UNK     0      14.061  -5.135   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0      14.061  -9.139   0.000  0.00  0.00           H+0
CONECT    1    7    8   10   26                                             
CONECT    2   13   16                                                       
CONECT    3   13   17                                                       
CONECT    4   14   20                                                       
CONECT    5   19                                                            
CONECT    6   20                                                            
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9   18   20                                                       
CONECT   10    1   21   23                                                  
CONECT   11   38                                                            
CONECT   12   13   14   15   39                                             
CONECT   13    2    3   12   40                                             
CONECT   14    4   12   16                                                  
CONECT   15   12   17                                                       
CONECT   16    2   14                                                       
CONECT   17    3   15                                                       
CONECT   18    9   19   22                                                  
CONECT   19    5   18   21                                                  
CONECT   20    4    6    9                                                  
CONECT   21   10   19                                                       
CONECT   22   18   25                                                       
CONECT   23   10   24                                                       
CONECT   24   23   27   28                                                  
CONECT   25   22   29   30                                                  
CONECT   26    1   31   32                                                  
CONECT   27   24                                                            
CONECT   28   24                                                            
CONECT   29   25   33                                                       
CONECT   30   25   34                                                       
CONECT   31   26   36                                                       
CONECT   32   26   37                                                       
CONECT   33   29   35                                                       
CONECT   34   30   35                                                       
CONECT   35   33   34                                                       
CONECT   36   31   38                                                       
CONECT   37   32   38                                                       
CONECT   38   11   36   37                                                  
CONECT   39   12                                                            
CONECT   40   13                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

COMPND    HMDB0015393
HETATM    1  C1  UNL     1      -3.740   0.588   2.765  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.169  -0.766   2.462  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.815  -1.743   3.425  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.292  -1.190   1.042  1.00  0.00           C  
HETATM    5  N1  UNL     1      -2.641  -0.332   0.106  1.00  0.00           N  
HETATM    6  C5  UNL     1      -1.658  -1.057  -0.696  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.365  -0.289  -0.753  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.110  -0.160   0.547  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.684  -0.974  -1.642  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.855  -2.408  -1.104  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.888  -3.091  -1.966  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.218  -3.050  -1.682  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.113  -3.680  -2.496  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.658  -4.359  -3.609  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.312  -4.413  -3.915  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.423  -3.772  -3.084  1.00  0.00           C  
HETATM   17  N2  UNL     1       1.889  -0.290  -1.714  1.00  0.00           N  
HETATM   18  C15 UNL     1       3.060   0.376  -1.784  1.00  0.00           C  
HETATM   19  O2  UNL     1       3.791   0.611  -2.792  1.00  0.00           O  
HETATM   20  O3  UNL     1       3.677   0.950  -0.625  1.00  0.00           O  
HETATM   21  C16 UNL     1       4.877   1.637  -0.627  1.00  0.00           C  
HETATM   22  C17 UNL     1       4.802   3.084  -0.257  1.00  0.00           C  
HETATM   23  O4  UNL     1       5.283   3.143   1.061  1.00  0.00           O  
HETATM   24  C18 UNL     1       6.382   2.279   1.062  1.00  0.00           C  
HETATM   25  O5  UNL     1       6.670   1.810   2.313  1.00  0.00           O  
HETATM   26  C19 UNL     1       5.923   0.674   2.532  1.00  0.00           C  
HETATM   27  C20 UNL     1       5.596   0.048   1.199  1.00  0.00           C  
HETATM   28  C21 UNL     1       5.956   1.094   0.222  1.00  0.00           C  
HETATM   29  S1  UNL     1      -3.637   0.560  -0.938  1.00  0.00           S  
HETATM   30  O6  UNL     1      -4.397  -0.455  -1.797  1.00  0.00           O  
HETATM   31  O7  UNL     1      -2.747   1.292  -1.920  1.00  0.00           O  
HETATM   32  C22 UNL     1      -4.723   1.669  -0.203  1.00  0.00           C  
HETATM   33  C23 UNL     1      -6.023   1.302   0.113  1.00  0.00           C  
HETATM   34  C24 UNL     1      -6.901   2.190   0.698  1.00  0.00           C  
HETATM   35  C25 UNL     1      -6.528   3.483   0.994  1.00  0.00           C  
HETATM   36  N3  UNL     1      -7.440   4.408   1.603  1.00  0.00           N  
HETATM   37  C26 UNL     1      -5.236   3.862   0.682  1.00  0.00           C  
HETATM   38  C27 UNL     1      -4.363   2.978   0.102  1.00  0.00           C  
HETATM   39  H1  UNL     1      -4.834   0.617   2.616  1.00  0.00           H  
HETATM   40  H2  UNL     1      -3.241   1.400   2.226  1.00  0.00           H  
HETATM   41  H3  UNL     1      -3.616   0.756   3.880  1.00  0.00           H  
HETATM   42  H4  UNL     1      -2.081  -0.761   2.728  1.00  0.00           H  
HETATM   43  H5  UNL     1      -3.393  -2.748   3.374  1.00  0.00           H  
HETATM   44  H6  UNL     1      -3.632  -1.360   4.448  1.00  0.00           H  
HETATM   45  H7  UNL     1      -4.916  -1.835   3.239  1.00  0.00           H  
HETATM   46  H8  UNL     1      -4.387  -1.187   0.741  1.00  0.00           H  
HETATM   47  H9  UNL     1      -2.994  -2.259   0.904  1.00  0.00           H  
HETATM   48  H10 UNL     1      -2.045  -1.166  -1.746  1.00  0.00           H  
HETATM   49  H11 UNL     1      -1.552  -2.094  -0.306  1.00  0.00           H  
HETATM   50  H12 UNL     1      -0.559   0.745  -1.111  1.00  0.00           H  
HETATM   51  H13 UNL     1       0.111  -0.998   1.068  1.00  0.00           H  
HETATM   52  H14 UNL     1       0.156  -1.144  -2.595  1.00  0.00           H  
HETATM   53  H15 UNL     1       1.117  -2.457  -0.059  1.00  0.00           H  
HETATM   54  H16 UNL     1      -0.087  -2.956  -1.280  1.00  0.00           H  
HETATM   55  H17 UNL     1       3.530  -2.491  -0.783  1.00  0.00           H  
HETATM   56  H18 UNL     1       5.168  -3.648  -2.273  1.00  0.00           H  
HETATM   57  H19 UNL     1       4.356  -4.870  -4.274  1.00  0.00           H  
HETATM   58  H20 UNL     1       1.980  -4.960  -4.805  1.00  0.00           H  
HETATM   59  H21 UNL     1       0.349  -3.808  -3.317  1.00  0.00           H  
HETATM   60  H22 UNL     1       1.970  -0.565  -3.041  1.00  0.00           H  
HETATM   61  H23 UNL     1       5.263   1.620  -1.693  1.00  0.00           H  
HETATM   62  H24 UNL     1       3.825   3.553  -0.362  1.00  0.00           H  
HETATM   63  H25 UNL     1       5.581   3.640  -0.847  1.00  0.00           H  
HETATM   64  H26 UNL     1       7.229   2.813   0.621  1.00  0.00           H  
HETATM   65  H27 UNL     1       5.028   0.904   3.150  1.00  0.00           H  
HETATM   66  H28 UNL     1       6.574  -0.036   3.129  1.00  0.00           H  
HETATM   67  H29 UNL     1       4.551  -0.317   1.127  1.00  0.00           H  
HETATM   68  H30 UNL     1       6.234  -0.878   1.070  1.00  0.00           H  
HETATM   69  H31 UNL     1       6.833   0.740  -0.378  1.00  0.00           H  
HETATM   70  H32 UNL     1      -6.309   0.281  -0.121  1.00  0.00           H  
HETATM   71  H33 UNL     1      -7.918   1.897   0.942  1.00  0.00           H  
HETATM   72  H34 UNL     1      -8.027   4.999   1.002  1.00  0.00           H  
HETATM   73  H35 UNL     1      -7.460   4.435   2.637  1.00  0.00           H  
HETATM   74  H36 UNL     1      -4.949   4.868   0.911  1.00  0.00           H  
HETATM   75  H37 UNL     1      -3.346   3.261  -0.150  1.00  0.00           H  
CONECT    1    2   39   40   41
CONECT    2    3    4   42
CONECT    3   43   44   45
CONECT    4    5   46   47
CONECT    5    6   29
CONECT    6    7   48   49
CONECT    7    8    9   50
CONECT    8   51
CONECT    9   10   17   52
CONECT   10   11   53   54
CONECT   11   12   12   16
CONECT   12   13   55
CONECT   13   14   14   56
CONECT   14   15   57
CONECT   15   16   16   58
CONECT   16   59
CONECT   17   18   60
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   28   61
CONECT   22   23   62   63
CONECT   23   24
CONECT   24   25   28   64
CONECT   25   26
CONECT   26   27   65   66
CONECT   27   28   67   68
CONECT   28   69
CONECT   29   30   30   31   31
CONECT   29   32
CONECT   32   33   33   38
CONECT   33   34   70
CONECT   34   35   35   71
CONECT   35   36   37
CONECT   36   72   73
CONECT   37   38   38   74
CONECT   38   75
END

HMDB0015393
     RDKit          3D
Darunavir
 75 78  0  0  0  0  0  0  0  0999 V2000
   -3.7398    0.5877    2.7646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1690   -0.7658    2.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8149   -1.7429    3.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2916   -1.1899    1.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6407   -0.3316    0.1059 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6584   -1.0572   -0.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3648   -0.2892   -0.7529 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1100   -0.1598    0.5469 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6835   -0.9743   -1.6421 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8549   -2.4084   -1.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8879   -3.0912   -1.9657 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2183   -3.0498   -1.6815 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1134   -3.6802   -2.4964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6576   -4.3591   -3.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3122   -4.4128   -3.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4230   -3.7725   -3.0836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8885   -0.2898   -1.7138 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0599    0.3756   -1.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7910    0.6110   -2.7922 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6770    0.9501   -0.6249 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8766    1.6371   -0.6273 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8019    3.0839   -0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2833    3.1430    1.0614 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3818    2.2795    1.0624 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6697    1.8104    2.3135 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9229    0.6736    2.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5961    0.0476    1.1994 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9557    1.0940    0.2215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6369    0.5601   -0.9376 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.3970   -0.4548   -1.7967 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7471    1.2920   -1.9204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7228    1.6689   -0.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0231    1.3015    0.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9009    2.1903    0.6978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5284    3.4832    0.9935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4402    4.4084    1.6026 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2358    3.8620    0.6822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3627    2.9784    0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8344    0.6167    2.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2409    1.3999    2.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6158    0.7561    3.8797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0813   -0.7610    2.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3930   -2.7479    3.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6319   -1.3601    4.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9161   -1.8349    3.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3871   -1.1872    0.7406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9945   -2.2588    0.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0446   -1.1658   -1.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5516   -2.0940   -0.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586    0.7450   -1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1111   -0.9983    1.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1558   -1.1439   -2.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1169   -2.4567   -0.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0874   -2.9559   -1.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5299   -2.4913   -0.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1684   -3.6482   -2.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3563   -4.8703   -4.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9798   -4.9600   -4.8045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3492   -3.8084   -3.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9697   -0.5653   -3.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2626    1.6198   -1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8247    3.5533   -0.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5814    3.6399   -0.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2289    2.8129    0.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0281    0.9042    3.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5741   -0.0358    3.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5509   -0.3166    1.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2335   -0.8781    1.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8328    0.7403   -0.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3087    0.2807   -0.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9178    1.8971    0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0268    4.9986    1.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4604    4.4352    2.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9489    4.8683    0.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3456    3.2612   -0.1500 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
 25 26  1  0
 26 27  1  0
 27 28  1  0
  5 29  1  0
 29 30  2  0
 29 31  2  0
 29 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 35 37  1  0
 37 38  2  0
 16 11  1  0
 28 21  1  0
 38 32  1  0
 28 24  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  0
  3 43  1  0
  3 44  1  0
  3 45  1  0
  4 46  1  0
  4 47  1  0
  6 48  1  0
  6 49  1  0
  7 50  1  6
  8 51  1  0
  9 52  1  6
 10 53  1  0
 10 54  1  0
 12 55  1  0
 13 56  1  0
 14 57  1  0
 15 58  1  0
 16 59  1  0
 17 60  1  0
 21 61  1  6
 22 62  1  0
 22 63  1  0
 24 64  1  6
 26 65  1  0
 26 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  6
 33 70  1  0
 34 71  1  0
 36 72  1  0
 36 73  1  0
 37 74  1  0
 38 75  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N(1)-isobutylsulfanilamido)propyl)carbamate	ChEBI
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl(1S,2R)-3-[[(4-aminophenyl)sulfonyl](isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamATE	ChEBI
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate	ChEBI
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-neopentylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate	ChEBI
[(S)-3-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-2-hydroxy-1-((R)-phenylmethyl)-propyl]-carbamic acid (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester	ChEBI
Darunavirum	ChEBI
N-((1S,2R)-3-(((4-Aminophenyl)sulfonyl)(2-methylpropyl)amino)-2-hydroxy-1-benzylpropyl)((1S,2R,5R)-4,6-dioxabicyclo(3.3.0)oct-2-yloxy)carboxamide	ChEBI
TMC114	ChEBI
{(1S,2R)-3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester	ChEBI
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N(1)-isobutylsulfanilamido)propyl)carbamic acid	Generator
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N(1)-isobutylsulphanilamido)propyl)carbamate	Generator
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl N-((1S,2R)-1-benzyl-2-hydroxy-3-(N(1)-isobutylsulphanilamido)propyl)carbamic acid	Generator
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl(1S,2R)-3-[[(4-aminophenyl)sulfonyl](isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamic acid	Generator
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl(1S,2R)-3-[[(4-aminophenyl)sulphonyl](isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamate	Generator
(3R,3AS,6ar)-hexahydrofuro[2,3-b]furan-3-yl(1S,2R)-3-[[(4-aminophenyl)sulphonyl](isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamic acid	Generator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamic acid	Generator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulphonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate	Generator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-isobutylphenylsulphonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamic acid	Generator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-neopentylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamic acid	Generator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-neopentylphenylsulphonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamate	Generator
(3R,3AS,6ar)-tetrahydro-2H-furo[2,3-b]furan-3-yl (2S,3R)-4-(4-amino-N-neopentylphenylsulphonamido)-3-hydroxy-1-phenylbutan-2-ylcarbamic acid	Generator
[(S)-3-[(4-Amino-benzenesulfonyl)-isobutyl-amino]-2-hydroxy-1-((R)-phenylmethyl)-propyl]-carbamate (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester	Generator
[(S)-3-[(4-Amino-benzenesulphonyl)-isobutyl-amino]-2-hydroxy-1-((R)-phenylmethyl)-propyl]-carbamate (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester	Generator
[(S)-3-[(4-Amino-benzenesulphonyl)-isobutyl-amino]-2-hydroxy-1-((R)-phenylmethyl)-propyl]-carbamic acid (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester	Generator
N-((1S,2R)-3-(((4-Aminophenyl)sulphonyl)(2-methylpropyl)amino)-2-hydroxy-1-benzylpropyl)((1S,2R,5R)-4,6-dioxabicyclo(3.3.0)oct-2-yloxy)carboxamide	Generator
{(1S,2R)-3-[(4-amino-benzenesulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamate (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester	Generator
{(1S,2R)-3-[(4-amino-benzenesulphonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamate (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester	Generator
{(1S,2R)-3-[(4-amino-benzenesulphonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid (3R,3as,6ar)-(hexahydro-furo[2,3-b]furan-3-yl) ester	Generator
AIDS073035	HMDB
TMC-114	HMDB
UIC-94017	HMDB
114, TMC	HMDB
TMC 114	HMDB
Ethanolate, darunavir	HMDB
Darunavir ethanolate	HMDB
Prezista	HMDB

Chemical Formula

C₂₇H₃₇N₃O₇S

Average Molecular Weight

547.664

Monoisotopic Molecular Weight

547.235221243

IUPAC Name

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-aminobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate

Traditional Name

darunavir

CAS Registry Number

206361-99-1

SMILES

[H][C@@]12CCO[C@]1([H])OC[C@@H]2OC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](O)CN(CC(C)C)S(=O)(=O)C1=CC=C(N)C=C1

InChI Identifier

InChI=1S/C27H37N3O7S/c1-18(2)15-30(38(33,34)21-10-8-20(28)9-11-21)16-24(31)23(14-19-6-4-3-5-7-19)29-27(32)37-25-17-36-26-22(25)12-13-35-26/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32)/t22-,23-,24+,25-,26+/m0/s1

InChI Key

CJBJHOAVZSMMDJ-HEXNFIEUSA-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
Furofuran
Aniline or substituted anilines
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Tetrahydrofuran
Carbamic acid ester
Aminosulfonyl compound
Secondary alcohol
Carbonic acid derivative
Oxacycle
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary amine
Organopnictogen compound
Carbonyl group
Amine
Organic nitrogen compound
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbamate ester (CHEBI:367163 )
sulfonamide (CHEBI:367163 )
furofuran (CHEBI:367163 )

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: HMDB0015393)
Membrane (HMDB: HMDB0015393)

Source

Exogenous

Exogenous (HMDB: HMDB0015393)

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	0.067 g/L	Not Available
LogP	1.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.067 g/L	ALOGPS
logP	1.76	ALOGPS
logP	2.82	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.59	ChemAxon
pKa (Strongest Basic)	2.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	140.42 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	142.34 m³·mol⁻¹	ChemAxon
Polarizability	57.24 Å³	ChemAxon
Number of Rings	4	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]+	224.597	31661259
DarkChem	[M-H]-	219.063	31661259
DeepCCS	[M-2H]-	259.359	30932474
DeepCCS	[M+Na]+	233.584	30932474
AllCCS	[M+H]+	226.9	32859911
AllCCS	[M+H-H2O]+	225.4	32859911
AllCCS	[M+NH4]+	228.2	32859911
AllCCS	[M+Na]+	228.6	32859911
AllCCS	[M-H]-	214.0	32859911
AllCCS	[M+Na-2H]-	216.0	32859911
AllCCS	[M+HCOO]-	218.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Darunavir	[H][C@@]12CCO[C@]1([H])OC[C@@H]2OC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](O)CN(CC(C)C)S(=O)(=O)C1=CC=C(N)C=C1	6755.7	Standard polar	33892256
Darunavir	[H][C@@]12CCO[C@]1([H])OC[C@@H]2OC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](O)CN(CC(C)C)S(=O)(=O)C1=CC=C(N)C=C1	4222.9	Standard non polar	33892256
Darunavir	[H][C@@]12CCO[C@]1([H])OC[C@@H]2OC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](O)CN(CC(C)C)S(=O)(=O)C1=CC=C(N)C=C1	4410.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Darunavir,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]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N)C=C1	4384.0	Semi standard non polar	33892256
Darunavir,1TMS,isomer #2	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	4520.7	Semi standard non polar	33892256
Darunavir,1TMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	4233.7	Semi standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	4442.1	Semi standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	4003.1	Standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	5625.1	Standard polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	4218.8	Semi standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	3994.0	Standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	6041.5	Standard polar	33892256
Darunavir,2TMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	4331.4	Semi standard non polar	33892256
Darunavir,2TMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	4094.3	Standard non polar	33892256
Darunavir,2TMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	5722.8	Standard polar	33892256
Darunavir,2TMS,isomer #4	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	4390.9	Semi standard non polar	33892256
Darunavir,2TMS,isomer #4	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	4085.7	Standard non polar	33892256
Darunavir,2TMS,isomer #4	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	5731.7	Standard polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	4319.1	Semi standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	4077.2	Standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C)C=C1	5314.3	Standard polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	4350.5	Semi standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	4087.2	Standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	5299.7	Standard polar	33892256
Darunavir,3TMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	4274.5	Semi standard non polar	33892256
Darunavir,3TMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	4175.1	Standard non polar	33892256
Darunavir,3TMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	5394.2	Standard polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	4291.3	Semi standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	4171.2	Standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C)S(=O)(=O)C1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1	5010.1	Standard polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N)C=C1	4596.3	Semi standard non polar	33892256
Darunavir,1TBDMS,isomer #2	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	4738.2	Semi standard non polar	33892256
Darunavir,1TBDMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	4482.5	Semi standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	4879.0	Semi standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	4444.4	Standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	5617.9	Standard polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	4654.6	Semi standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	4452.8	Standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N)C=C1	5949.3	Standard polar	33892256
Darunavir,2TBDMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	4773.4	Semi standard non polar	33892256
Darunavir,2TBDMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	4536.6	Standard non polar	33892256
Darunavir,2TBDMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	5681.4	Standard polar	33892256
Darunavir,2TBDMS,isomer #4	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4804.0	Semi standard non polar	33892256
Darunavir,2TBDMS,isomer #4	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4517.5	Standard non polar	33892256
Darunavir,2TBDMS,isomer #4	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)NC(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	5664.7	Standard polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	4955.8	Semi standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	4729.1	Standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)[Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC=C(N[Si](C)(C)C(C)(C)C)C=C1	5338.2	Standard polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4944.2	Semi standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	4708.0	Standard non polar	33892256
Darunavir,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]1CO[C@H]2OCC[C@@H]12)S(=O)(=O)C1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1	5290.1	Standard polar	33892256
Darunavir,3TBDMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)[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	4890.5	Semi standard non polar	33892256
Darunavir,3TBDMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)[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	4814.8	Standard non polar	33892256
Darunavir,3TBDMS,isomer #3	CC(C)CN(C[C@@H](O)[C@H](CC1=CC=CC=C1)N(C(=O)O[C@H]1CO[C@H]2OCC[C@@H]12)[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	5366.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Darunavir GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7395120000-9ee6643d8e957bfc6883	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Darunavir GC-MS (1 TMS) - 70eV, Positive	splash10-08i3-8659131000-a5895dfe8fa0c5374f22	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Darunavir GC-MS ("Darunavir,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Darunavir GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Darunavir GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Darunavir GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Darunavir GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Darunavir GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir LC-ESI-QFT , negative-QTOF	splash10-0aor-0900800000-e427a102e3a7551cc732	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir LC-ESI-QFT , negative-QTOF	splash10-0a4i-0900000000-8ab8c2b3421f4a277282	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir LC-ESI-QFT , negative-QTOF	splash10-0a4i-2900000000-eddacc917eaf16abe9d2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir LC-ESI-QFT , negative-QTOF	splash10-0a4i-2900000000-86c785caeafe3b4a10c3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir LC-ESI-QFT , negative-QTOF	splash10-0a4l-5900000000-69bc90a59383cb5a804b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir LC-ESI-QFT , negative-QTOF	splash10-0a4l-8900000000-f481d0932a99692c87d9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir 30V, Negative-QTOF	splash10-0a4i-0900000000-40373637b670c5395ffd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir 15V, Negative-QTOF	splash10-0aor-0900800000-f59913cdbcd62042530a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir 45V, Negative-QTOF	splash10-0a4i-2900000000-10dadadeebe1e6ec0164	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir LC-ESI-QTOF , positive-QTOF	splash10-000g-0009760000-f730e27547a482694ebc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir LC-ESI-QTOF , positive-QTOF	splash10-0006-0009000000-fcd18a6f4e9084f0f8f1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir LC-ESI-QTOF , positive-QTOF	splash10-0006-0469000000-716a2ae87ad9df6765fb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0941000000-5e0dbe51025009642b33	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0910000000-2411514d55bfa3c4e81f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir LC-ESI-QFT , positive-QTOF	splash10-0006-2309000000-e6767f5d8648334c41c9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir LC-ESI-QFT , positive-QTOF	splash10-014i-9621000000-3a7c794f5e3f473b9ad5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir LC-ESI-QFT , positive-QTOF	splash10-014i-9400000000-16b363cdd836532460ce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir LC-ESI-QFT , positive-QTOF	splash10-0a4i-2900000000-98bfa9c688e4cb2dbbc3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir LC-ESI-QFT , positive-QTOF	splash10-0a4l-4900000000-05c5a10ff111a5d1c9bf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir LC-ESI-QFT , positive-QTOF	splash10-052f-6900000000-f59c1c0d97f0a8ab00d7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir 20V, Positive-QTOF	splash10-0006-0009000000-8e1cc4b8ca6f49bcfe56	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir 10V, Positive-QTOF	splash10-000g-0009760000-26cdc56a39511d44e965	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir 15V, Positive-QTOF	splash10-0006-2309000000-b56fe3acae7c21ddaba0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir 40V, Positive-QTOF	splash10-0a4i-0941000000-5e0dbe51025009642b33	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Darunavir 30V, Positive-QTOF	splash10-0006-0469000000-c470e3e505d43b7089af	2021-09-20	HMDB team, MONA	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 DB01264	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01264	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01264

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

184733

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Darunavir

METLIN ID

Not Available

PubChem Compound

213039

PDB ID

017

ChEBI ID

367163

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

Tremblay CL: Combating HIV resistance - focus on darunavir. Ther Clin Risk Manag. 2008 Aug;4(4):759-66. [PubMed:19209258 ]
De Meyer S, Azijn H, Surleraux D, Jochmans D, Tahri A, Pauwels R, Wigerinck P, de Bethune MP: TMC114, a novel human immunodeficiency virus type 1 protease inhibitor active against protease inhibitor-resistant viruses, including a broad range of clinical isolates. Antimicrob Agents Chemother. 2005 Jun;49(6):2314-21. [PubMed:15917527 ]
Kovalevsky AY, Tie Y, Liu F, Boross PI, Wang YF, Leshchenko S, Ghosh AK, Harrison RW, Weber IT: Effectiveness of nonpeptide clinical inhibitor TMC-114 on HIV-1 protease with highly drug resistant mutations D30N, I50V, and L90M. J Med Chem. 2006 Feb 23;49(4):1379-87. [PubMed:16480273 ]
Koh Y, Matsumi S, Das D, Amano M, Davis DA, Li J, Leschenko S, Baldridge A, Shioda T, Yarchoan R, Ghosh AK, Mitsuya H: Potent inhibition of HIV-1 replication by novel non-peptidyl small molecule inhibitors of protease dimerization. J Biol Chem. 2007 Sep 28;282(39):28709-20. Epub 2007 Jul 17. [PubMed:17635930 ]
Back D, Sekar V, Hoetelmans RM: Darunavir: pharmacokinetics and drug interactions. Antivir Ther. 2008;13(1):1-13. [PubMed:18389894 ]
Company Website [Link]
Medilexicon [Link]

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

McKeage K, Perry CM, Keam SJ: Darunavir: a review of its use in the management of HIV infection in adults. Drugs. 2009;69(4):477-503. doi: 10.2165/00003495-200969040-00007. [PubMed:19323590 ]
Tremblay CL: Combating HIV resistance - focus on darunavir. Ther Clin Risk Manag. 2008 Aug;4(4):759-66. [PubMed:19209258 ]

Showing metabocard for Darunavir (HMDB0015393)

MOL for HMDB0015393 (Darunavir)

3D MOL for HMDB0015393 (Darunavir)

3D SDF for HMDB0015393 (Darunavir)

3D-SDF for HMDB0015393 (Darunavir)

PDB for HMDB0015393 (Darunavir)

3D PDB for HMDB0015393 (Darunavir)

SMILES for HMDB0015393 (Darunavir)

INCHI for HMDB0015393 (Darunavir)

Structure for HMDB0015393 (Darunavir)

3D Structure for HMDB0015393 (Darunavir)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References