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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:54 UTC

HMDB ID

HMDB0015215

Secondary Accession Numbers

HMDB15215

Metabolite Identification

Common Name

Orlistat

Description

Orlistat is a drug designed to treat obesity. Its primary function is preventing the absorption of fats from the human diet, thereby reducing caloric intake. Orlistat works by inhibiting pancreatic lipase, an enzyme that breaks down triglycerides in the intestine. Without this enzyme, triglycerides from the diet are prevented from being hydrolyzed into absorbable free fatty acids and are excreted undigested.

Structure

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

1083
  Mrv0541 02231215142D          

 35 35  0  0  1  0            999 V2000
    6.6160   -0.3494    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5796   -2.1277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2076    0.2340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5901   -1.1172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1267   -3.6643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7568   -2.2840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6160   -1.1744    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7909   -1.1744    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.6500   -2.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.3402   -2.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2620    4.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
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 27 32  1  0  0  0  0
 28 30  1  0  0  0  0
 30 33  1  0  0  0  0
 33 35  1  0  0  0  0
M  END

HMDB0015215
     RDKit          3D
Orlistat
 88 88  0  0  0  0  0  0  0  0999 V2000
    8.6452    0.1102    1.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

1083
  Mrv0541 02231215142D          

 35 35  0  0  1  0            999 V2000
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    1.6500   -2.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2515    3.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3661   -2.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7359   -4.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0485    3.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3402   -2.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2620    4.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 12  1  0  0  0  0
 11  2  1  6  0  0  0
  2 21  1  0  0  0  0
  3 12  2  0  0  0  0
  4 21  2  0  0  0  0
  5 34  2  0  0  0  0
 22  6  1  1  0  0  0
  6 34  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  1  0  0  0
  8 10  1  6  0  0  0
  8 12  1  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 13  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 24  1  0  0  0  0
 20 23  1  0  0  0  0
 21 22  1  0  0  0  0
 22 25  1  0  0  0  0
 23 26  1  0  0  0  0
 24 29  1  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
 27 31  1  0  0  0  0
 27 32  1  0  0  0  0
 28 30  1  0  0  0  0
 30 33  1  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015215

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H53NO5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h22-27H,5-21H2,1-4H3,(H,30,31)/t24-,25-,26-,27-/m0/s1

> <INCHI_KEY>
AHLBNYSZXLDEJQ-FWEHEUNISA-N

> <FORMULA>
C29H53NO5

> <MOLECULAR_WEIGHT>
495.7348

> <EXACT_MASS>
495.392373811

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
61.11855493108451

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methylpentanoate

> <ALOGPS_LOGP>
7.61

> <JCHEM_LOGP>
8.106577767000001

> <ALOGPS_LOGS>
-6.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.743767089986566

> <JCHEM_PKA_STRONGEST_BASIC>
-0.911687162329263

> <JCHEM_POLAR_SURFACE_AREA>
81.7

> <JCHEM_REFRACTIVITY>
139.9443

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.19e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
orlistat

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015215
     RDKit          3D
Orlistat
 88 88  0  0  0  0  0  0  0  0999 V2000
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   -2.1118   -2.0262   -0.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1358   -3.6042   -1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4557   -2.0176   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9515   -2.5770    0.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1611   -6.5509   -1.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8576   -6.6151   -2.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3760    4.0826    1.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8266    4.8666    1.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0069    5.2165   -0.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  9 10  1  0
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 11 12  1  0
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 12 25  1  0
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 34 35  2  0
 18 14  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
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  3 41  1  0
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  8 51  1  0
  8 52  1  0
  9 53  1  0
  9 54  1  0
 10 55  1  0
 10 56  1  0
 11 57  1  0
 11 58  1  0
 12 59  1  6
 13 60  1  0
 13 61  1  0
 14 62  1  1
 18 63  1  6
 19 64  1  0
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 20 66  1  0
 20 67  1  0
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 21 69  1  0
 22 70  1  0
 22 71  1  0
 23 72  1  0
 23 73  1  0
 24 74  1  0
 24 75  1  0
 24 76  1  0
 28 77  1  1
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 31 81  1  0
 31 82  1  0
 31 83  1  0
 32 84  1  0
 32 85  1  0
 32 86  1  0
 33 87  1  0
 34 88  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1083                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      12.350  -0.652   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      16.015  -3.972   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.721   0.437   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      17.902  -2.085   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      20.770  -6.840   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      20.079  -4.263   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      12.350  -2.192   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.810  -2.192   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.439  -3.281   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.721  -3.281   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.926  -2.883   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.810  -0.652   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.325  -1.395   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.233  -2.883   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.813  -0.996   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.144  -3.972   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.211   0.491   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.699   0.890   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.657  -3.573   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.097   2.377   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.503  -3.573   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.592  -4.662   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.585   2.776   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.568  -4.662   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.193  -6.150   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      20.983   4.263   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.706  -6.548   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      22.471   4.662   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.080  -4.263   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      22.869   6.150   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.617  -5.459   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.307  -8.036   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      24.357   6.548   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      21.168  -5.352   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      24.756   8.036   0.000  0.00  0.00           C+0
CONECT    1    7   12                                                       
CONECT    2   11   21                                                       
CONECT    3   12                                                            
CONECT    4   21                                                            
CONECT    5   34                                                            
CONECT    6   22   34                                                       
CONECT    7    1    8    9                                                  
CONECT    8    7   10   12                                                  
CONECT    9    7   11                                                       
CONECT   10    8   14                                                       
CONECT   11    2    9   13                                                  
CONECT   12    1    3    8                                                  
CONECT   13   11   15                                                       
CONECT   14   10   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   19                                                       
CONECT   17   15   18                                                       
CONECT   18   17   20                                                       
CONECT   19   16   24                                                       
CONECT   20   18   23                                                       
CONECT   21    2    4   22                                                  
CONECT   22    6   21   25                                                  
CONECT   23   20   26                                                       
CONECT   24   19   29                                                       
CONECT   25   22   27                                                       
CONECT   26   23   28                                                       
CONECT   27   25   31   32                                                  
CONECT   28   26   30                                                       
CONECT   29   24                                                            
CONECT   30   28   33                                                       
CONECT   31   27                                                            
CONECT   32   27                                                            
CONECT   33   30   35                                                       
CONECT   34    5    6                                                       
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   70    0
END

COMPND    HMDB0015215
HETATM    1  C1  UNL     1       8.645   0.110   1.534  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.562  -1.146   0.723  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.197  -1.387   0.138  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.148  -1.505   1.237  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.802  -1.764   0.644  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.676  -1.897   1.605  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.425  -0.692   2.448  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.279  -0.840   3.411  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.973  -1.126   2.699  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.613  -0.024   1.727  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.719  -0.445   1.090  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.150   0.590   0.057  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.444   0.153  -0.541  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.280  -1.195  -1.198  1.00  0.00           C  
HETATM   15  O1  UNL     1      -1.335  -1.259  -2.228  1.00  0.00           O  
HETATM   16  C15 UNL     1      -2.182  -1.741  -3.215  1.00  0.00           C  
HETATM   17  O2  UNL     1      -1.956  -2.153  -4.377  1.00  0.00           O  
HETATM   18  C16 UNL     1      -3.300  -1.521  -2.261  1.00  0.00           C  
HETATM   19  C17 UNL     1      -3.977  -2.855  -1.967  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.691  -2.829  -0.641  1.00  0.00           C  
HETATM   21  C19 UNL     1      -5.323  -4.175  -0.403  1.00  0.00           C  
HETATM   22  C20 UNL     1      -6.308  -4.467  -1.499  1.00  0.00           C  
HETATM   23  C21 UNL     1      -6.979  -5.835  -1.272  1.00  0.00           C  
HETATM   24  C22 UNL     1      -7.949  -6.088  -2.402  1.00  0.00           C  
HETATM   25  O3  UNL     1      -1.140   1.884   0.594  1.00  0.00           O  
HETATM   26  C23 UNL     1      -0.140   2.775   0.231  1.00  0.00           C  
HETATM   27  O4  UNL     1       0.728   2.373  -0.572  1.00  0.00           O  
HETATM   28  C24 UNL     1      -0.049   4.171   0.751  1.00  0.00           C  
HETATM   29  C25 UNL     1      -0.984   5.071   0.020  1.00  0.00           C  
HETATM   30  C26 UNL     1      -1.017   6.486   0.446  1.00  0.00           C  
HETATM   31  C27 UNL     1       0.246   7.267   0.352  1.00  0.00           C  
HETATM   32  C28 UNL     1      -2.087   7.284  -0.308  1.00  0.00           C  
HETATM   33  N1  UNL     1       1.292   4.651   0.672  1.00  0.00           N  
HETATM   34  C29 UNL     1       1.964   4.848  -0.546  1.00  0.00           C  
HETATM   35  O5  UNL     1       1.414   4.616  -1.640  1.00  0.00           O  
HETATM   36  H1  UNL     1       8.697  -0.128   2.636  1.00  0.00           H  
HETATM   37  H2  UNL     1       9.577   0.684   1.325  1.00  0.00           H  
HETATM   38  H3  UNL     1       7.772   0.774   1.415  1.00  0.00           H  
HETATM   39  H4  UNL     1       9.310  -1.089  -0.099  1.00  0.00           H  
HETATM   40  H5  UNL     1       8.798  -2.011   1.395  1.00  0.00           H  
HETATM   41  H6  UNL     1       6.936  -0.477  -0.444  1.00  0.00           H  
HETATM   42  H7  UNL     1       7.198  -2.298  -0.466  1.00  0.00           H  
HETATM   43  H8  UNL     1       6.198  -0.571   1.832  1.00  0.00           H  
HETATM   44  H9  UNL     1       6.485  -2.319   1.909  1.00  0.00           H  
HETATM   45  H10 UNL     1       4.602  -1.027  -0.172  1.00  0.00           H  
HETATM   46  H11 UNL     1       4.881  -2.771   0.123  1.00  0.00           H  
HETATM   47  H12 UNL     1       2.744  -2.075   0.993  1.00  0.00           H  
HETATM   48  H13 UNL     1       3.813  -2.826   2.194  1.00  0.00           H  
HETATM   49  H14 UNL     1       3.226   0.207   1.833  1.00  0.00           H  
HETATM   50  H15 UNL     1       4.323  -0.421   3.066  1.00  0.00           H  
HETATM   51  H16 UNL     1       2.422  -1.643   4.144  1.00  0.00           H  
HETATM   52  H17 UNL     1       2.173   0.126   3.931  1.00  0.00           H  
HETATM   53  H18 UNL     1       0.148  -1.279   3.421  1.00  0.00           H  
HETATM   54  H19 UNL     1       1.103  -2.113   2.195  1.00  0.00           H  
HETATM   55  H20 UNL     1       0.468   0.891   2.340  1.00  0.00           H  
HETATM   56  H21 UNL     1       1.387   0.109   0.954  1.00  0.00           H  
HETATM   57  H22 UNL     1      -1.437  -0.513   1.927  1.00  0.00           H  
HETATM   58  H23 UNL     1      -0.526  -1.430   0.638  1.00  0.00           H  
HETATM   59  H24 UNL     1      -0.344   0.506  -0.730  1.00  0.00           H  
HETATM   60  H25 UNL     1      -2.914   0.848  -1.235  1.00  0.00           H  
HETATM   61  H26 UNL     1      -3.193   0.014   0.296  1.00  0.00           H  
HETATM   62  H27 UNL     1      -2.112  -2.026  -0.477  1.00  0.00           H  
HETATM   63  H28 UNL     1      -3.994  -0.710  -2.527  1.00  0.00           H  
HETATM   64  H29 UNL     1      -4.627  -3.046  -2.837  1.00  0.00           H  
HETATM   65  H30 UNL     1      -3.136  -3.604  -1.886  1.00  0.00           H  
HETATM   66  H31 UNL     1      -5.456  -2.018  -0.694  1.00  0.00           H  
HETATM   67  H32 UNL     1      -3.952  -2.577   0.163  1.00  0.00           H  
HETATM   68  H33 UNL     1      -4.492  -4.925  -0.434  1.00  0.00           H  
HETATM   69  H34 UNL     1      -5.827  -4.151   0.585  1.00  0.00           H  
HETATM   70  H35 UNL     1      -7.106  -3.710  -1.549  1.00  0.00           H  
HETATM   71  H36 UNL     1      -5.822  -4.583  -2.496  1.00  0.00           H  
HETATM   72  H37 UNL     1      -7.528  -5.815  -0.303  1.00  0.00           H  
HETATM   73  H38 UNL     1      -6.161  -6.551  -1.214  1.00  0.00           H  
HETATM   74  H39 UNL     1      -8.858  -6.615  -2.033  1.00  0.00           H  
HETATM   75  H40 UNL     1      -7.426  -6.695  -3.179  1.00  0.00           H  
HETATM   76  H41 UNL     1      -8.191  -5.114  -2.870  1.00  0.00           H  
HETATM   77  H42 UNL     1      -0.376   4.083   1.839  1.00  0.00           H  
HETATM   78  H43 UNL     1      -0.746   5.050  -1.065  1.00  0.00           H  
HETATM   79  H44 UNL     1      -2.047   4.672   0.087  1.00  0.00           H  
HETATM   80  H45 UNL     1      -1.343   6.531   1.530  1.00  0.00           H  
HETATM   81  H46 UNL     1       1.032   7.023   1.077  1.00  0.00           H  
HETATM   82  H47 UNL     1      -0.044   8.336   0.630  1.00  0.00           H  
HETATM   83  H48 UNL     1       0.604   7.370  -0.703  1.00  0.00           H  
HETATM   84  H49 UNL     1      -2.301   8.250   0.217  1.00  0.00           H  
HETATM   85  H50 UNL     1      -1.701   7.503  -1.341  1.00  0.00           H  
HETATM   86  H51 UNL     1      -3.028   6.734  -0.408  1.00  0.00           H  
HETATM   87  H52 UNL     1       1.827   4.867   1.585  1.00  0.00           H  
HETATM   88  H53 UNL     1       3.007   5.217  -0.581  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3   39   40
CONECT    3    4   41   42
CONECT    4    5   43   44
CONECT    5    6   45   46
CONECT    6    7   47   48
CONECT    7    8   49   50
CONECT    8    9   51   52
CONECT    9   10   53   54
CONECT   10   11   55   56
CONECT   11   12   57   58
CONECT   12   13   25   59
CONECT   13   14   60   61
CONECT   14   15   18   62
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19   63
CONECT   19   20   64   65
CONECT   20   21   66   67
CONECT   21   22   68   69
CONECT   22   23   70   71
CONECT   23   24   72   73
CONECT   24   74   75   76
CONECT   25   26
CONECT   26   27   27   28
CONECT   28   29   33   77
CONECT   29   30   78   79
CONECT   30   31   32   80
CONECT   31   81   82   83
CONECT   32   84   85   86
CONECT   33   34   87
CONECT   34   35   35   88
END

HMDB0015215
     RDKit          3D
Orlistat
 88 88  0  0  0  0  0  0  0  0999 V2000
    8.6452    0.1102    1.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5623   -1.1460    0.7229 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1971   -1.3866    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1477   -1.5049    1.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8023   -1.7644    0.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6756   -1.8968    1.6052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4252   -0.6922    2.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2787   -0.8402    3.4107 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9731   -1.1255    2.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6134   -0.0243    1.7273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7195   -0.4446    1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495    0.5899    0.0574 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4442    0.1530   -0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2799   -1.1950   -1.1978 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3348   -1.2588   -2.2283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1817   -1.7411   -3.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9559   -2.1534   -4.3767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3002   -1.5210   -2.2606 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9766   -2.8548   -1.9665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6910   -2.8286   -0.6410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3234   -4.1754   -0.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3078   -4.4668   -1.4986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9786   -5.8346   -1.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9494   -6.0879   -2.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1397    1.8838    0.5937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1399    2.7754    0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7281    2.3727   -0.5723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0491    4.1709    0.7505 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9835    5.0711    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0169    6.4862    0.4463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2465    7.2673    0.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0875    7.2842   -0.3083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917    4.6507    0.6719 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9644    4.8479   -0.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139    4.6164   -1.6396 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6969   -0.1281    2.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5775    0.6839    1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7716    0.7736    1.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3099   -1.0887   -0.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7976   -2.0109    1.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9355   -0.4766   -0.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1976   -2.2983   -0.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1983   -0.5710    1.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4846   -2.3186    1.9089 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6020   -1.0273   -0.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8813   -2.7713    0.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7437   -2.0752    0.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8135   -2.8260    2.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2257    0.2073    1.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3232   -0.4205    3.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4219   -1.6432    4.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1732    0.1261    3.9313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1478   -1.2788    3.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1034   -2.1134    2.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4684    0.8914    2.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875    0.1088    0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4374   -0.5129    1.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5262   -1.4302    0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3444    0.5063   -0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9136    0.8476   -1.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1933    0.0141    0.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1118   -2.0262   -0.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9940   -0.7100   -2.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6271   -3.0458   -2.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1358   -3.6042   -1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4557   -2.0176   -0.6935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9515   -2.5770    0.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4922   -4.9254   -0.4337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8266   -4.1513    0.5853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1056   -3.7102   -1.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8218   -4.5827   -2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5284   -5.8147   -0.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1611   -6.5509   -1.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8576   -6.6151   -2.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4261   -6.6948   -3.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1905   -5.1143   -2.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3760    4.0826    1.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7463    5.0503   -1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0471    4.6719    0.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3430    6.5307    1.5303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0317    7.0227    1.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0442    8.3363    0.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043    7.3704   -0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3009    8.2499    0.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7007    7.5033   -1.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0277    6.7341   -0.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8266    4.8666    1.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0069    5.2165   -0.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 12 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 28 33  1  0
 33 34  1  0
 34 35  2  0
 18 14  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  2 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
  6 47  1  0
  6 48  1  0
  7 49  1  0
  7 50  1  0
  8 51  1  0
  8 52  1  0
  9 53  1  0
  9 54  1  0
 10 55  1  0
 10 56  1  0
 11 57  1  0
 11 58  1  0
 12 59  1  6
 13 60  1  0
 13 61  1  0
 14 62  1  1
 18 63  1  6
 19 64  1  0
 19 65  1  0
 20 66  1  0
 20 67  1  0
 21 68  1  0
 21 69  1  0
 22 70  1  0
 22 71  1  0
 23 72  1  0
 23 73  1  0
 24 74  1  0
 24 75  1  0
 24 76  1  0
 28 77  1  1
 29 78  1  0
 29 79  1  0
 30 80  1  0
 31 81  1  0
 31 82  1  0
 31 83  1  0
 32 84  1  0
 32 85  1  0
 32 86  1  0
 33 87  1  0
 34 88  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Tetrahydrolipostatin	ChEBI
(2S)-2-Formamido-4-methylpentanoic acid [(2S)-1-[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]tridecan-2-yl] ester	ChEBI
Alli	ChEBI
N-Formyl-L-leucine (1S)-1-{[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl}dodecyl ester	ChEBI
Orlipastat	ChEBI
Orlistatum	ChEBI
Ro-18-0647	ChEBI
Xenical	ChEBI
(2S)-2-Formamido-4-methylpentanoate [(2S)-1-[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]tridecan-2-yl] ester	Generator
(-)-Tetrahydrolipstatin	HMDB
Tetrahydrolipstatin	HMDB
Roche brand OF orlistat	HMDB
THLP	HMDB
1-((3-Hexyl-4-oxo-2-oxetanyl)methyl)dodecyl-2-formamido-4-methylvalerate	HMDB
GlaxoSmithKline brand OF orlistat	HMDB
Hoffmann-la roche brand OF orlistat	HMDB
Tetrahydrolipastatin	HMDB

Chemical Formula

C₂₉H₅₃NO₅

Average Molecular Weight

495.7348

Monoisotopic Molecular Weight

495.392373811

IUPAC Name

(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methylpentanoate

Traditional Name

orlistat

CAS Registry Number

96829-58-2

SMILES

CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O

InChI Identifier

InChI=1S/C29H53NO5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h22-27H,5-21H2,1-4H3,(H,30,31)/t24-,25-,26-,27-/m0/s1

InChI Key

AHLBNYSZXLDEJQ-FWEHEUNISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Leucine and derivatives

Alternative Parents

Substituents

Leucine or derivatives
Alpha-amino acid ester
N-formyl-alpha amino acid or derivatives
N-formyl-alpha-amino acid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Beta_propiolactone
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Oxetane
Lactone
Oxacycle
Organoheterocyclic compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

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

Source

Exogenous

Exogenous (HMDB: HMDB0015215)

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	9.2e-05 g/L	Not Available
LogP	8.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	9.2e-05 g/L	ALOGPS
logP	7.61	ALOGPS
logP	8.11	ChemAxon
logS	-6.7	ALOGPS
pKa (Strongest Acidic)	12.74	ChemAxon
pKa (Strongest Basic)	-0.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	81.7 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	139.94 m³·mol⁻¹	ChemAxon
Polarizability	61.12 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	221.505	31661259
DarkChem	[M-H]-	221.642	31661259
DeepCCS	[M+H]+	240.902	30932474
DeepCCS	[M-H]-	238.506	30932474
DeepCCS	[M-2H]-	271.391	30932474
DeepCCS	[M+Na]+	246.815	30932474
AllCCS	[M+H]+	233.3	32859911
AllCCS	[M+H-H2O]+	231.8	32859911
AllCCS	[M+NH4]+	234.7	32859911
AllCCS	[M+Na]+	235.1	32859911
AllCCS	[M-H]-	224.2	32859911
AllCCS	[M+Na-2H]-	227.7	32859911
AllCCS	[M+HCOO]-	231.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Orlistat	CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O	3916.0	Standard polar	33892256
Orlistat	CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O	3152.5	Standard non polar	33892256
Orlistat	CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O	3420.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Orlistat,1TMS,isomer #1	CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)N(C=O)[Si](C)(C)C	3333.9	Semi standard non polar	33892256
Orlistat,1TMS,isomer #1	CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)N(C=O)[Si](C)(C)C	3271.3	Standard non polar	33892256
Orlistat,1TMS,isomer #1	CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)N(C=O)[Si](C)(C)C	3906.7	Standard polar	33892256
Orlistat,1TBDMS,isomer #1	CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)N(C=O)[Si](C)(C)C(C)(C)C	3543.4	Semi standard non polar	33892256
Orlistat,1TBDMS,isomer #1	CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)N(C=O)[Si](C)(C)C(C)(C)C	3418.5	Standard non polar	33892256
Orlistat,1TBDMS,isomer #1	CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)N(C=O)[Si](C)(C)C(C)(C)C	3968.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Orlistat GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-2902200000-dfdc46fddbbd1d2170e0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Orlistat GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Orlistat GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat LC-ESI-qTof , Positive-QTOF	splash10-001i-0000190000-0f2b7ec7f6bc7f95ba46	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat LC-ESI-qTof , Positive-QTOF	splash10-001i-0000390000-65e16678dbfdcc1c64fd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat LC-ESI-qTof , Positive-QTOF	splash10-00di-0001190000-27c5d161a5754e1434f4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat LC-ESI-qTof , Positive-QTOF	splash10-00di-0001190000-27c5d161a5754e1434f4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat LC-ESI-qTof , Positive-QTOF	splash10-0pb9-0971000000-b771a74c99af15873a47	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat LC-ESI-qTof , Positive-QTOF	splash10-0pb9-0971000000-b771a74c99af15873a47	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat 50V, Positive-QTOF	splash10-00ps-0394000000-a7e235f00f39832cb26b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat 40V, Positive-QTOF	splash10-0bti-0289000000-1db53b3f6bf551f35934	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat 35V, Negative-QTOF	splash10-052o-0922300000-3340cd8d705353e68b6a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat 10V, Negative-QTOF	splash10-0a4i-0900000000-b8cb3b916515e9d87eeb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat 35V, Positive-QTOF	splash10-02t9-8904000000-d71719418cae9e9993cd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat 30V, Positive-QTOF	splash10-08fr-0459000000-2afd07b05b6499ee680b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat 20V, Positive-QTOF	splash10-02tl-0859400000-c74907b45c6c88f27dbf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat 35V, Positive-QTOF	splash10-03xr-2914000000-c9c25c9d546bc7dd3cf1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat 10V, Positive-QTOF	splash10-0002-0105900000-34995f5e283fa1168b24	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat 30V, Positive-QTOF	splash10-08fr-0459000000-c1482a9118d79780ad8f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat 40V, Positive-QTOF	splash10-0bti-0289000000-47f99f82e0bf6c110477	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat 40V, Negative-QTOF	splash10-0a4i-0900000000-4a9952eba82d4734c89c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Orlistat 50V, Positive-QTOF	splash10-00ps-0394000000-4e5093c320f2bd221805	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orlistat 10V, Positive-QTOF	splash10-014j-0201900000-f738d9eb60da2cb3f8b2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orlistat 20V, Positive-QTOF	splash10-0btd-4903200000-880d8bcbe0e86c1dedee	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orlistat 40V, Positive-QTOF	splash10-0a4m-9300100000-59ee07367048664d1aea	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orlistat 10V, Negative-QTOF	splash10-0udi-2103900000-12eb6aa4152fd723fd4c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orlistat 20V, Negative-QTOF	splash10-0zfu-7508900000-d827e3d71bdc755b28a0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Orlistat 40V, Negative-QTOF	splash10-002f-9315000000-4c6b30daf1a2bd6ffaf8	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
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 DB01083	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01083	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01083

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2298564

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Orlistat

METLIN ID

Not Available

PubChem Compound

3034010

PDB ID

Not Available

ChEBI ID

94686

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

Drew BS, Dixon AF, Dixon JB: Obesity management: update on orlistat. Vasc Health Risk Manag. 2007;3(6):817-21. [PubMed:18200802 ]
Wong NN, Cheng-Lai A: Orlistat. Heart Dis. 2000 Mar-Apr;2(2):174-81. [PubMed:11728255 ]
Curran MP, Scott LJ: Orlistat: a review of its use in the management of patients with obesity. Drugs. 2004;64(24):2845-64. [PubMed:15563254 ]
Ballinger A, Peikin SR: Orlistat: its current status as an anti-obesity drug. Eur J Pharmacol. 2002 Apr 12;440(2-3):109-17. [PubMed:12007529 ]
Menendez JA, Vellon L, Lupu R: Antitumoral actions of the anti-obesity drug orlistat (XenicalTM) in breast cancer cells: blockade of cell cycle progression, promotion of apoptotic cell death and PEA3-mediated transcriptional repression of Her2/neu (erbB-2) oncogene. Ann Oncol. 2005 Aug;16(8):1253-67. Epub 2005 May 3. [PubMed:15870086 ]
Hvizdos KM, Markham A: Orlistat: a review of its use in the management of obesity. Drugs. 1999 Oct;58(4):743-60. [PubMed:10551441 ]
Lucas KH, Kaplan-Machlis B: Orlistat--a novel weight loss therapy. Ann Pharmacother. 2001 Mar;35(3):314-28. [PubMed:11261530 ]
Torgerson JS, Hauptman J, Boldrin MN, Sjostrom L: XENical in the prevention of diabetes in obese subjects (XENDOS) study: a randomized study of orlistat as an adjunct to lifestyle changes for the prevention of type 2 diabetes in obese patients. Diabetes Care. 2004 Jan;27(1):155-61. [PubMed:14693982 ]
Garcia SB, Barros LT, Turatti A, Martinello F, Modiano P, Ribeiro-Silva A, Vespucio MV, Uyemura SA: The anti-obesity agent Orlistat is associated to increase in colonic preneoplastic markers in rats treated with a chemical carcinogen. Cancer Lett. 2006 Aug 28;240(2):221-4. Epub 2005 Dec 27. [PubMed:16377080 ]
Mancini MC, Halpern A: Pharmacological treatment of obesity. Arq Bras Endocrinol Metabol. 2006 Apr;50(2):377-89. Epub 2006 May 23. [PubMed:16767304 ]

Enzymes

Enzyme Details

1. Fatty acid synthase

General function:: Involved in transferase activity
Specific function:: Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:: FASN
Uniprot ID:: P49327
Molecular weight:: 273424.06

References

Kridel SJ, Axelrod F, Rozenkrantz N, Smith JW: Orlistat is a novel inhibitor of fatty acid synthase with antitumor activity. Cancer Res. 2004 Mar 15;64(6):2070-5. [PubMed:15026345 ]
Knowles LM, Axelrod F, Browne CD, Smith JW: A fatty acid synthase blockade induces tumor cell-cycle arrest by down-regulating Skp2. J Biol Chem. 2004 Jul 16;279(29):30540-5. Epub 2004 May 11. [PubMed:15138278 ]
Menendez JA, Vellon L, Lupu R: Antitumoral actions of the anti-obesity drug orlistat (XenicalTM) in breast cancer cells: blockade of cell cycle progression, promotion of apoptotic cell death and PEA3-mediated transcriptional repression of Her2/neu (erbB-2) oncogene. Ann Oncol. 2005 Aug;16(8):1253-67. Epub 2005 May 3. [PubMed:15870086 ]
Kremer L, de Chastellier C, Dobson G, Gibson KJ, Bifani P, Balor S, Gorvel JP, Locht C, Minnikin DE, Besra GS: Identification and structural characterization of an unusual mycobacterial monomeromycolyl-diacylglycerol. Mol Microbiol. 2005 Aug;57(4):1113-26. [PubMed:16091048 ]
Purohit VC, Richardson RD, Smith JW, Romo D: Practical, catalytic, asymmetric synthesis of beta-lactones via a sequential ketene dimerization/hydrogenation process: inhibitors of the thioesterase domain of fatty acid synthase. J Org Chem. 2006 Jun 9;71(12):4549-58. [PubMed:16749788 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Cytosolic phospholipase A2

General function:: Involved in metabolic process
Specific function:: Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:: PLA2G4A
Uniprot ID:: P47712
Molecular weight:: 85210.19

References

Filippatos TD, Gazi IF, Liberopoulos EN, Athyros VG, Elisaf MS, Tselepis AD, Kiortsis DN: The effect of orlistat and fenofibrate, alone or in combination, on small dense LDL and lipoprotein-associated phospholipase A2 in obese patients with metabolic syndrome. Atherosclerosis. 2007 Aug;193(2):428-37. Epub 2006 Sep 5. [PubMed:16911813 ]

Enzyme Details

3. Pancreatic triacylglycerol lipase

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: PNLIP
Uniprot ID:: P16233
Molecular weight:: 51156.48

References

Uusitupa M: New aspects in the management of obesity: operation and the impact of lipase inhibitors. Curr Opin Lipidol. 1999 Feb;10(1):3-7. [PubMed:10095983 ]
Leonhardt M, Hrupka B, Langhans W: New approaches in the pharmacological treatment of obesity. Eur J Nutr. 1999 Feb;38(1):1-13. [PubMed:10338682 ]
Bray GA: Drug treatment of obesity. Baillieres Best Pract Res Clin Endocrinol Metab. 1999 Apr;13(1):131-48. [PubMed:10932681 ]
Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60. [PubMed:11054601 ]
Gomis Barbara R: [Pharmacological treatment of obesity]. Rev Med Univ Navarra. 2004 Apr-Jun;48(2):63-5. [PubMed:15382615 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Drew BS, Dixon AF, Dixon JB: Obesity management: update on orlistat. Vasc Health Risk Manag. 2007;3(6):817-21. [PubMed:18200802 ]
Wong NN, Cheng-Lai A: Orlistat. Heart Dis. 2000 Mar-Apr;2(2):174-81. [PubMed:11728255 ]
Nelson RH, Miles JM: The use of orlistat in the treatment of obesity, dyslipidaemia and Type 2 diabetes. Expert Opin Pharmacother. 2005 Nov;6(14):2483-91. [PubMed:16259579 ]
Heck AM, Yanovski JA, Calis KA: Orlistat, a new lipase inhibitor for the management of obesity. Pharmacotherapy. 2000 Mar;20(3):270-9. [PubMed:10730683 ]
Henness S, Perry CM: Orlistat: a review of its use in the management of obesity. Drugs. 2006;66(12):1625-56. [PubMed:16956313 ]
Ballinger A, Peikin SR: Orlistat: its current status as an anti-obesity drug. Eur J Pharmacol. 2002 Apr 12;440(2-3):109-17. [PubMed:12007529 ]
McNeely W, Benfield P: Orlistat. Drugs. 1998 Aug;56(2):241-9; discussion 250. [PubMed:9711448 ]

Enzyme Details

4. Gastric triacylglycerol lipase

General function:: Involved in lipid metabolic process
Specific function:: Not Available
Gene Name:: LIPF
Uniprot ID:: P07098
Molecular weight:: 45237.375

References

Drew BS, Dixon AF, Dixon JB: Obesity management: update on orlistat. Vasc Health Risk Manag. 2007;3(6):817-21. [PubMed:18200802 ]
Wong NN, Cheng-Lai A: Orlistat. Heart Dis. 2000 Mar-Apr;2(2):174-81. [PubMed:11728255 ]
Bray GA: Lifestyle and pharmacological approaches to weight loss: efficacy and safety. J Clin Endocrinol Metab. 2008 Nov;93(11 Suppl 1):S81-8. doi: 10.1210/jc.2008-1294. [PubMed:18987274 ]
Nelson RH, Miles JM: The use of orlistat in the treatment of obesity, dyslipidaemia and Type 2 diabetes. Expert Opin Pharmacother. 2005 Nov;6(14):2483-91. [PubMed:16259579 ]
Heck AM, Yanovski JA, Calis KA: Orlistat, a new lipase inhibitor for the management of obesity. Pharmacotherapy. 2000 Mar;20(3):270-9. [PubMed:10730683 ]
Henness S, Perry CM: Orlistat: a review of its use in the management of obesity. Drugs. 2006;66(12):1625-56. [PubMed:16956313 ]
Curran MP, Scott LJ: Orlistat: a review of its use in the management of patients with obesity. Drugs. 2004;64(24):2845-64. [PubMed:15563254 ]
Ballinger A, Peikin SR: Orlistat: its current status as an anti-obesity drug. Eur J Pharmacol. 2002 Apr 12;440(2-3):109-17. [PubMed:12007529 ]

Enzyme Details

5. 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

Novotna A, Doricakova A, Vrzal R, Maurel P, Pavek P, Dvorak Z: Investigation of Orlistat effects on PXR activation and CYP3A4 expression in primary human hepatocytes and human intestinal LS174T cells. Eur J Pharm Sci. 2010 Oct 9;41(2):276-80. doi: 10.1016/j.ejps.2010.06.019. Epub 2010 Jul 3. [PubMed:20599501 ]

Showing metabocard for Orlistat (HMDB0015215)

MOL for HMDB0015215 (Orlistat)

3D MOL for HMDB0015215 (Orlistat)

3D SDF for HMDB0015215 (Orlistat)

3D-SDF for HMDB0015215 (Orlistat)

PDB for HMDB0015215 (Orlistat)

3D PDB for HMDB0015215 (Orlistat)

SMILES for HMDB0015215 (Orlistat)

INCHI for HMDB0015215 (Orlistat)

Structure for HMDB0015215 (Orlistat)

3D Structure for HMDB0015215 (Orlistat)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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