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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7)transporters (1) Show 8 proteins XML

enzymes (7)transporters (1) Show 8 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014614

Secondary Accession Numbers

HMDB14614

Metabolite Identification

Common Name

Montelukast

Description

Montelukast is a leukotriene receptor antagonist (LTRA) used for the maintenance treatment of asthma and to relieve symptoms of seasonal allergies. It is usually administered orally. Montelukast blocks the action of leukotriene D4 on the cysteinyl leukotriene receptor CysLT1 in the lungs and bronchial tubes by binding to it. This reduces the bronchoconstriction otherwise caused by the leukotriene, and results in less inflammation. Because of its method of operation, it is not useful for the treatment of acute asthma attacks. Again because of its very specific locus of operation, it does not interact with other allergy medications such as theophylline. Montelukast is marketed in United States and many other countries by Merck & Co. with the brand name Singulair. It is available as oral tablets, chewable tablets, and oral granules. In India and other countries, it is also marketed under the brand name Montair®, produced by Indian company Cipla.

Structure

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

471
  Mrv0541 02231214422D          

 41 45  0  0  1  0            999 V2000
   14.2938   -1.4637    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -1.4438    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8075   -2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3814   -1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 37 39  1  0  0  0  0
 38 40  2  0  0  0  0
 39 41  2  0  0  0  0
 40 41  1  0  0  0  0
M  END

HMDB0014614
     RDKit          3D
Montelukast
 77 81  0  0  0  0  0  0  0  0999 V2000
   -3.4995   -2.1231   -2.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
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 41 77  1  0
M  END

471
  Mrv0541 02231214422D          

 41 45  0  0  1  0            999 V2000
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    3.8240    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6490    0.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9524   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6668   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6668   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0958   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3814    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0958   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8333   -1.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8333    0.2349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5809   -1.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5809   -0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 40  1  0  0  0  0
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  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
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  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
 11 12  1  0  0  0  0
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 21 25  1  0  0  0  0
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 22 25  2  0  0  0  0
 23 29  1  0  0  0  0
 23 30  1  0  0  0  0
 24 27  1  0  0  0  0
 26 31  1  0  0  0  0
 27 31  2  0  0  0  0
 28 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 36  2  0  0  0  0
 35 37  2  0  0  0  0
 35 38  1  0  0  0  0
 36 37  1  0  0  0  0
 37 39  1  0  0  0  0
 38 40  2  0  0  0  0
 39 41  2  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014614

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CC1(CC1)CS[C@H](CCC1=CC=CC=C1C(O)(C)C)C1=CC=CC(\C=C\C2=NC3=C(C=CC(Cl)=C3)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C35H36ClNO3S/c1-34(2,40)30-9-4-3-7-25(30)13-17-32(41-23-35(18-19-35)22-33(38)39)27-8-5-6-24(20-27)10-15-29-16-12-26-11-14-28(36)21-31(26)37-29/h3-12,14-16,20-21,32,40H,13,17-19,22-23H2,1-2H3,(H,38,39)/b15-10+/t32-/m1/s1

> <INCHI_KEY>
UCHDWCPVSPXUMX-TZIWLTJVSA-N

> <FORMULA>
C35H36ClNO3S

> <MOLECULAR_WEIGHT>
586.183

> <EXACT_MASS>
585.21044242

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
66.36450362769538

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[1-({[(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanyl}methyl)cyclopropyl]acetic acid

> <ALOGPS_LOGP>
7.25

> <JCHEM_LOGP>
8.493533064849995

> <ALOGPS_LOGS>
-7.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.603668525945846

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.40060890783993

> <JCHEM_PKA_STRONGEST_BASIC>
3.1215483614005577

> <JCHEM_POLAR_SURFACE_AREA>
70.42

> <JCHEM_REFRACTIVITY>
169.50389999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.20e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
montelukast

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014614
     RDKit          3D
Montelukast
 77 81  0  0  0  0  0  0  0  0999 V2000
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   -5.6637   -1.9654   -1.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8605   -3.9516   -2.2882 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1024    0.1267    0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
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 35 75  1  0
 38 76  1  0
 41 77  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 471                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      26.682  -2.732   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0      10.576  -2.695   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       3.907  -1.925   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.241  -4.235   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.574   1.155   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      21.245  -2.695   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.908  -2.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.138  -4.029   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.678  -4.029   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.242  -1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.574  -1.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.241  -2.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.909  -1.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.909  -0.385   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.243  -2.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.576   0.385   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.577  -1.925   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.243  -4.235   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.576   1.925   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.242   2.695   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.910  -2.695   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.577  -5.005   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.908   1.925   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.909   2.695   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.910  -4.235   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.242   4.235   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.909   4.235   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.244  -1.925   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.138   3.259   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.678   0.591   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.576   5.005   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      18.578  -2.695   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      19.911  -1.925   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      19.911  -0.385   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      22.579  -1.925   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      21.245   0.385   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      22.579  -0.385   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      23.955  -2.748   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      23.955   0.438   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      25.351  -1.957   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      25.351  -0.353   0.000  0.00  0.00           C+0
CONECT    1   40                                                            
CONECT    2   10   13                                                       
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5   23                                                            
CONECT    6   33   35                                                       
CONECT    7    8    9   10   11                                             
CONECT    8    7    9                                                       
CONECT    9    7    8                                                       
CONECT   10    2    7                                                       
CONECT   11    7   12                                                       
CONECT   12    3    4   11                                                  
CONECT   13    2   14   15                                                  
CONECT   14   13   16                                                       
CONECT   15   13   17   18                                                  
CONECT   16   14   19                                                       
CONECT   17   15   21                                                       
CONECT   18   15   22                                                       
CONECT   19   16   20   24                                                  
CONECT   20   19   23   26                                                  
CONECT   21   17   25   28                                                  
CONECT   22   18   25                                                       
CONECT   23    5   20   29   30                                             
CONECT   24   19   27                                                       
CONECT   25   21   22                                                       
CONECT   26   20   31                                                       
CONECT   27   24   31                                                       
CONECT   28   21   32                                                       
CONECT   29   23                                                            
CONECT   30   23                                                            
CONECT   31   26   27                                                       
CONECT   32   28   33                                                       
CONECT   33    6   32   34                                                  
CONECT   34   33   36                                                       
CONECT   35    6   37   38                                                  
CONECT   36   34   37                                                       
CONECT   37   35   36   39                                                  
CONECT   38   35   40                                                       
CONECT   39   37   41                                                       
CONECT   40    1   38   41                                                  
CONECT   41   39   40                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

COMPND    HMDB0014614
HETATM    1  C1  UNL     1      -3.499  -2.123  -2.556  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.409  -2.787  -1.579  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.664  -1.965  -1.325  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.861  -3.952  -2.288  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.822  -3.303  -0.334  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.823  -4.667  -0.043  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.345  -5.196   1.124  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.832  -4.372   2.074  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.800  -3.020   1.850  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.289  -2.489   0.654  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.132  -1.033   0.510  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.787  -0.738  -0.088  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.490   0.710  -0.346  1.00  0.00           C  
HETATM   14  S1  UNL     1      -1.480   1.760   1.103  1.00  0.00           S  
HETATM   15  C13 UNL     1      -2.600   3.167   0.974  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.575   4.015   2.220  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.473   5.259   2.090  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.943   6.092   0.944  1.00  0.00           C  
HETATM   19  O2  UNL     1      -1.911   6.800   1.071  1.00  0.00           O  
HETATM   20  O3  UNL     1      -3.628   6.054  -0.246  1.00  0.00           O  
HETATM   21  C17 UNL     1      -2.515   3.430   3.560  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.335   4.183   2.981  1.00  0.00           C  
HETATM   23  C19 UNL     1      -0.298   0.824  -1.207  1.00  0.00           C  
HETATM   24  C20 UNL     1      -0.448   1.300  -2.508  1.00  0.00           C  
HETATM   25  C21 UNL     1       0.623   1.438  -3.371  1.00  0.00           C  
HETATM   26  C22 UNL     1       1.875   1.101  -2.952  1.00  0.00           C  
HETATM   27  C23 UNL     1       2.078   0.621  -1.671  1.00  0.00           C  
HETATM   28  C24 UNL     1       3.394   0.236  -1.213  1.00  0.00           C  
HETATM   29  C25 UNL     1       3.732  -0.190  -0.035  1.00  0.00           C  
HETATM   30  C26 UNL     1       5.130  -0.553   0.288  1.00  0.00           C  
HETATM   31  C27 UNL     1       5.491  -0.976   1.547  1.00  0.00           C  
HETATM   32  C28 UNL     1       6.811  -1.345   1.816  1.00  0.00           C  
HETATM   33  C29 UNL     1       7.764  -1.282   0.794  1.00  0.00           C  
HETATM   34  C30 UNL     1       9.068  -1.647   0.976  1.00  0.00           C  
HETATM   35  C31 UNL     1      10.000  -1.602  -0.060  1.00  0.00           C  
HETATM   36  C32 UNL     1       9.604  -1.175  -1.306  1.00  0.00           C  
HETATM   37 CL1  UNL     1      10.803  -1.141  -2.602  1.00  0.00          CL  
HETATM   38  C33 UNL     1       8.299  -0.805  -1.498  1.00  0.00           C  
HETATM   39  C34 UNL     1       7.373  -0.856  -0.453  1.00  0.00           C  
HETATM   40  N1  UNL     1       6.086  -0.511  -0.654  1.00  0.00           N  
HETATM   41  C35 UNL     1       0.977   0.498  -0.834  1.00  0.00           C  
HETATM   42  H1  UNL     1      -3.405  -1.040  -2.382  1.00  0.00           H  
HETATM   43  H2  UNL     1      -2.526  -2.633  -2.676  1.00  0.00           H  
HETATM   44  H3  UNL     1      -3.935  -2.170  -3.613  1.00  0.00           H  
HETATM   45  H4  UNL     1      -5.634  -0.966  -1.791  1.00  0.00           H  
HETATM   46  H5  UNL     1      -5.864  -1.932  -0.231  1.00  0.00           H  
HETATM   47  H6  UNL     1      -6.575  -2.473  -1.744  1.00  0.00           H  
HETATM   48  H7  UNL     1      -5.385  -3.615  -3.073  1.00  0.00           H  
HETATM   49  H8  UNL     1      -4.224  -5.329  -0.785  1.00  0.00           H  
HETATM   50  H9  UNL     1      -3.369  -6.280   1.318  1.00  0.00           H  
HETATM   51  H10 UNL     1      -2.462  -4.807   2.988  1.00  0.00           H  
HETATM   52  H11 UNL     1      -2.383  -2.374   2.629  1.00  0.00           H  
HETATM   53  H12 UNL     1      -3.146  -0.561   1.537  1.00  0.00           H  
HETATM   54  H13 UNL     1      -3.902  -0.552  -0.116  1.00  0.00           H  
HETATM   55  H14 UNL     1      -0.971  -1.037   0.678  1.00  0.00           H  
HETATM   56  H15 UNL     1      -1.509  -1.340  -0.956  1.00  0.00           H  
HETATM   57  H16 UNL     1      -2.357   1.136  -0.989  1.00  0.00           H  
HETATM   58  H17 UNL     1      -3.640   2.867   0.769  1.00  0.00           H  
HETATM   59  H18 UNL     1      -2.270   3.782   0.095  1.00  0.00           H  
HETATM   60  H19 UNL     1      -3.403   5.898   2.976  1.00  0.00           H  
HETATM   61  H20 UNL     1      -4.524   4.987   1.891  1.00  0.00           H  
HETATM   62  H21 UNL     1      -3.086   5.973  -1.106  1.00  0.00           H  
HETATM   63  H22 UNL     1      -2.408   2.337   3.744  1.00  0.00           H  
HETATM   64  H23 UNL     1      -3.108   3.924   4.387  1.00  0.00           H  
HETATM   65  H24 UNL     1      -0.412   3.596   2.782  1.00  0.00           H  
HETATM   66  H25 UNL     1      -1.115   5.172   3.482  1.00  0.00           H  
HETATM   67  H26 UNL     1      -1.415   1.590  -2.913  1.00  0.00           H  
HETATM   68  H27 UNL     1       0.478   1.815  -4.394  1.00  0.00           H  
HETATM   69  H28 UNL     1       2.756   1.183  -3.571  1.00  0.00           H  
HETATM   70  H29 UNL     1       4.236   0.306  -1.936  1.00  0.00           H  
HETATM   71  H30 UNL     1       2.981  -0.283   0.730  1.00  0.00           H  
HETATM   72  H31 UNL     1       4.778  -1.034   2.328  1.00  0.00           H  
HETATM   73  H32 UNL     1       7.157  -1.678   2.771  1.00  0.00           H  
HETATM   74  H33 UNL     1       9.364  -1.977   1.952  1.00  0.00           H  
HETATM   75  H34 UNL     1      11.039  -1.900   0.097  1.00  0.00           H  
HETATM   76  H35 UNL     1       7.988  -0.469  -2.473  1.00  0.00           H  
HETATM   77  H36 UNL     1       1.102   0.127   0.188  1.00  0.00           H  
CONECT    1    2   42   43   44
CONECT    2    3    4    5
CONECT    3   45   46   47
CONECT    4   48
CONECT    5    6    6   10
CONECT    6    7   49
CONECT    7    8    8   50
CONECT    8    9   51
CONECT    9   10   10   52
CONECT   10   11
CONECT   11   12   53   54
CONECT   12   13   55   56
CONECT   13   14   23   57
CONECT   14   15
CONECT   15   16   58   59
CONECT   16   17   21   22
CONECT   17   18   60   61
CONECT   18   19   19   20
CONECT   20   62
CONECT   21   22   63   64
CONECT   22   65   66
CONECT   23   24   24   41
CONECT   24   25   67
CONECT   25   26   26   68
CONECT   26   27   69
CONECT   27   28   41   41
CONECT   28   29   29   70
CONECT   29   30   71
CONECT   30   31   31   40
CONECT   31   32   72
CONECT   32   33   33   73
CONECT   33   34   39
CONECT   34   35   35   74
CONECT   35   36   75
CONECT   36   37   38   38
CONECT   38   39   76
CONECT   39   40   40
CONECT   41   77
END

HMDB0014614
     RDKit          3D
Montelukast
 77 81  0  0  0  0  0  0  0  0999 V2000
   -3.4995   -2.1231   -2.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4092   -2.7873   -1.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6637   -1.9654   -1.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8605   -3.9516   -2.2882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8224   -3.3031   -0.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8233   -4.6672   -0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3449   -5.1956    1.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8323   -4.3723    2.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7998   -3.0204    1.8497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2893   -2.4887    0.6545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1317   -1.0334    0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7867   -0.7385   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4898    0.7102   -0.3458 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4795    1.7604    1.1033 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6002    3.1669    0.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5747    4.0153    2.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4731    5.2586    2.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9435    6.0917    0.9445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9105    6.7997    1.0714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6276    6.0537   -0.2464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5146    3.4295    3.5597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3354    4.1833    2.9809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2984    0.8238   -1.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4480    1.3003   -2.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6227    1.4381   -3.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8749    1.1008   -2.9517 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0784    0.6207   -1.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3944    0.2363   -1.2132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7322   -0.1898   -0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1298   -0.5531    0.2885 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4914   -0.9763    1.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8115   -1.3446    1.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7640   -1.2824    0.7936 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0676   -1.6471    0.9755 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9997   -1.6020   -0.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6045   -1.1749   -1.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8030   -1.1411   -2.6021 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.2990   -0.8047   -1.4982 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3725   -0.8556   -0.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0863   -0.5110   -0.6540 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9765    0.4983   -0.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4052   -1.0405   -2.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5261   -2.6330   -2.6756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9346   -2.1695   -3.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6341   -0.9659   -1.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8640   -1.9317   -0.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5754   -2.4734   -1.7436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3849   -3.6152   -3.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2239   -5.3287   -0.7848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3688   -6.2800    1.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4618   -4.8070    2.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3831   -2.3741    2.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1460   -0.5609    1.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9020   -0.5523   -0.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9706   -1.0370    0.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5085   -1.3404   -0.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3572    1.1360   -0.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6401    2.8671    0.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2703    3.7825    0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4034    5.8976    2.9765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5241    4.9873    1.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863    5.9726   -1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4080    2.3370    3.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1081    3.9242    4.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4120    3.5962    2.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1154    5.1717    3.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4150    1.5900   -2.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4779    1.8147   -4.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7556    1.1829   -3.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2359    0.3057   -1.9360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9812   -0.2829    0.7300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7784   -1.0337    2.3284 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1575   -1.6777    2.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3640   -1.9772    1.9516 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0386   -1.9002    0.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9879   -0.4695   -2.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1024    0.1267    0.1879 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
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  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  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 13 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 38 39  1  0
 39 40  2  0
 27 41  2  0
 10  5  1  0
 22 16  1  0
 41 23  1  0
 40 30  1  0
 39 33  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  3 45  1  0
  3 46  1  0
  3 47  1  0
  4 48  1  0
  6 49  1  0
  7 50  1  0
  8 51  1  0
  9 52  1  0
 11 53  1  0
 11 54  1  0
 12 55  1  0
 12 56  1  0
 13 57  1  6
 15 58  1  0
 15 59  1  0
 17 60  1  0
 17 61  1  0
 20 62  1  0
 21 63  1  0
 21 64  1  0
 22 65  1  0
 22 66  1  0
 24 67  1  0
 25 68  1  0
 26 69  1  0
 28 70  1  0
 29 71  1  0
 31 72  1  0
 32 73  1  0
 34 74  1  0
 35 75  1  0
 38 76  1  0
 41 77  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(R-(e))-1-(((1-(3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetic acid	ChEBI
1-[[[(1 R)-1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl] phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]sulfanyl]methyl]cyclopropaneacetic acid	ChEBI
Brondilat	Kegg
(R-(e))-1-(((1-(3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetate	Generator
1-[[[(1 R)-1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl] phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]sulfanyl]methyl]cyclopropaneacetate	Generator
1-[[[(1 R)-1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl] phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]sulphanyl]methyl]cyclopropaneacetate	Generator
1-[[[(1 R)-1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl] phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]sulphanyl]methyl]cyclopropaneacetic acid	Generator
Merck brand OF montelukast sodium	HMDB
Singulair	HMDB
Montelukast sodium	HMDB
Sodium 1-(((1-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropylacetate	HMDB
Cahill may roberts brand OF montelukast sodium	HMDB
Merck frosst brand OF montelukast sodium	HMDB
Merck sharp and dohme brand OF montelukast sodium	HMDB

Chemical Formula

C₃₅H₃₆ClNO₃S

Average Molecular Weight

586.183

Monoisotopic Molecular Weight

585.21044242

IUPAC Name

2-[1-({[(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanyl}methyl)cyclopropyl]acetic acid

Traditional Name

montelukast

CAS Registry Number

158966-92-8

SMILES

OC(=O)CC1(CC1)CS[C@H](CCC1=CC=CC=C1C(O)(C)C)C1=CC=CC(\C=C\C2=NC3=C(C=CC(Cl)=C3)C=C2)=C1

InChI Identifier

InChI=1S/C35H36ClNO3S/c1-34(2,40)30-9-4-3-7-25(30)13-17-32(41-23-35(18-19-35)22-33(38)39)27-8-5-6-24(20-27)10-15-29-16-12-26-11-14-28(36)21-31(26)37-29/h3-12,14-16,20-21,32,40H,13,17-19,22-23H2,1-2H3,(H,38,39)/b15-10+/t32-/m1/s1

InChI Key

UCHDWCPVSPXUMX-TZIWLTJVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear 1,3-diarylpropanoids. These are organic compounds with a structure based on a C6-C3-C6 skeleton, where the two benzene rings are not linked together.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Not Available

Direct Parent

Linear 1,3-diarylpropanoids

Alternative Parents

Substituents

Linear 1,3-diarylpropanoid
Haloquinoline
Chloroquinoline
Quinoline
Phenylpropane
Styrene
Hydroxy fatty acid
Thia fatty acid
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Pyridine
Fatty acyl
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Thioether
Dialkylthioether
Sulfenyl compound
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Aromatic alcohol
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organosulfur compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinolines (CHEBI:50730 )
monocarboxylic acid (CHEBI:50730 )
aliphatic sulfide (CHEBI:50730 )

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: HMDB0014614)
Membrane (HMDB: HMDB0014614)

Source

Exogenous

Exogenous (HMDB: HMDB0014614)

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	8.2e-06 g/L	Not Available
LogP	7.9	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	243.0	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.2e-06 g/L	ALOGPS
logP	7.25	ALOGPS
logP	8.49	ChemAxon
logS	-7.8	ALOGPS
pKa (Strongest Acidic)	4.4	ChemAxon
pKa (Strongest Basic)	3.12	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.42 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	169.5 m³·mol⁻¹	ChemAxon
Polarizability	66.36 Å³	ChemAxon
Number of Rings	5	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
DeepCCS	[M+H]+	230.213	30932474
DeepCCS	[M-H]-	228.281	30932474
DeepCCS	[M-2H]-	261.52	30932474
DeepCCS	[M+Na]+	236.024	30932474
AllCCS	[M+H]+	244.7	32859911
AllCCS	[M+H-H2O]+	243.2	32859911
AllCCS	[M+NH4]+	246.0	32859911
AllCCS	[M+Na]+	246.4	32859911
AllCCS	[M-H]-	228.9	32859911
AllCCS	[M+Na-2H]-	231.1	32859911
AllCCS	[M+HCOO]-	233.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.43 minutes	32390414
Predicted by Siyang on May 30, 2022	23.7301 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.26 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	40.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	4287.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	544.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	294.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	249.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	659.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1208.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1126.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	96.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2323.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	947.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2407.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	742.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	548.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	238.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	350.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Montelukast	OC(=O)CC1(CC1)CS[C@H](CCC1=CC=CC=C1C(O)(C)C)C1=CC=CC(\C=C\C2=NC3=C(C=CC(Cl)=C3)C=C2)=C1	6300.0	Standard polar	33892256
Montelukast	OC(=O)CC1(CC1)CS[C@H](CCC1=CC=CC=C1C(O)(C)C)C1=CC=CC(\C=C\C2=NC3=C(C=CC(Cl)=C3)C=C2)=C1	4444.9	Standard non polar	33892256
Montelukast	OC(=O)CC1(CC1)CS[C@H](CCC1=CC=CC=C1C(O)(C)C)C1=CC=CC(\C=C\C2=NC3=C(C=CC(Cl)=C3)C=C2)=C1	5064.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Montelukast,1TMS,isomer #1	CC(C)(O)C1=CC=CC=C1CC[C@@H](SCC1(CC(=O)O[Si](C)(C)C)CC1)C1=CC=CC(/C=C/C2=CC=C3C=CC(Cl)=CC3=N2)=C1	4875.9	Semi standard non polar	33892256
Montelukast,1TMS,isomer #2	CC(C)(O[Si](C)(C)C)C1=CC=CC=C1CC[C@@H](SCC1(CC(=O)O)CC1)C1=CC=CC(/C=C/C2=CC=C3C=CC(Cl)=CC3=N2)=C1	4938.5	Semi standard non polar	33892256
Montelukast,2TMS,isomer #1	CC(C)(O[Si](C)(C)C)C1=CC=CC=C1CC[C@@H](SCC1(CC(=O)O[Si](C)(C)C)CC1)C1=CC=CC(/C=C/C2=CC=C3C=CC(Cl)=CC3=N2)=C1	4827.1	Semi standard non polar	33892256
Montelukast,1TBDMS,isomer #1	CC(C)(O)C1=CC=CC=C1CC[C@@H](SCC1(CC(=O)O[Si](C)(C)C(C)(C)C)CC1)C1=CC=CC(/C=C/C2=CC=C3C=CC(Cl)=CC3=N2)=C1	5128.4	Semi standard non polar	33892256
Montelukast,1TBDMS,isomer #2	CC(C)(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1CC[C@@H](SCC1(CC(=O)O)CC1)C1=CC=CC(/C=C/C2=CC=C3C=CC(Cl)=CC3=N2)=C1	5189.7	Semi standard non polar	33892256
Montelukast,2TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1CC[C@@H](SCC1(CC(=O)O[Si](C)(C)C(C)(C)C)CC1)C1=CC=CC(/C=C/C2=CC=C3C=CC(Cl)=CC3=N2)=C1	5303.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Montelukast GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-8200940000-737f7d3443710f11b1d1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Montelukast GC-MS (1 TMS) - 70eV, Positive	splash10-000f-6610918000-a8fd6048261f76c14cfe	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Montelukast GC-MS ("Montelukast,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Montelukast GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Montelukast GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Montelukast GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Montelukast GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Montelukast GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Montelukast 10V, Positive-QTOF	splash10-02ti-1200290000-7725c97cf7d6852f1a3a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Montelukast 20V, Positive-QTOF	splash10-03k9-3621890000-f0776c5b36cdf2c178f6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Montelukast 40V, Positive-QTOF	splash10-03di-6759410000-a97710ff6bb5322ea910	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Montelukast 10V, Negative-QTOF	splash10-0fk9-0100940000-4313dcc1630729675404	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Montelukast 20V, Negative-QTOF	splash10-0fk9-1100920000-b4afcd6b4074ff107c2a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Montelukast 40V, Negative-QTOF	splash10-0a4j-8943500000-be069e66cc0c2230329c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Montelukast 10V, Positive-QTOF	splash10-000i-0200190000-fd271d41a440a384395a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Montelukast 20V, Positive-QTOF	splash10-00di-4302950000-5e3aaf420bf5f896e62c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Montelukast 40V, Positive-QTOF	splash10-0f79-6576950000-696368916493bebcb7c5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Montelukast 10V, Negative-QTOF	splash10-001i-0000190000-aec216b4ad3561544634	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Montelukast 20V, Negative-QTOF	splash10-0uk9-1300910000-73c58a5b7f71fb0cf7f1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Montelukast 40V, Negative-QTOF	splash10-0gz9-4512930000-9b36ec7bf9f131bb7cc4	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00471	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00471	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00471

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4444507

KEGG Compound ID

C07482

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Montelukast

METLIN ID

Not Available

PubChem Compound

5281040

PDB ID

MTK

ChEBI ID

50730

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Arachidonate 5-lipoxygenase

General function:: Involved in metal ion binding
Specific function:: Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:: ALOX5
Uniprot ID:: P09917
Molecular weight:: 77982.595

References

Ramires R, Caiaffa MF, Tursi A, Haeggstrom JZ, Macchia L: Novel inhibitory effect on 5-lipoxygenase activity by the anti-asthma drug montelukast. Biochem Biophys Res Commun. 2004 Nov 12;324(2):815-21. [PubMed:15474500 ]

Enzyme Details

2. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

3. Cytochrome P450 3A4

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

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

4. Cytochrome P450 2C9

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

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

5. Cytochrome P450 2C8

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

References

Schoch GA, Yano JK, Sansen S, Dansette PM, Stout CD, Johnson EF: Determinants of cytochrome P450 2C8 substrate binding: structures of complexes with montelukast, troglitazone, felodipine, and 9-cis-retinoic acid. J Biol Chem. 2008 Jun 20;283(25):17227-37. doi: 10.1074/jbc.M802180200. Epub 2008 Apr 15. [PubMed:18413310 ]
Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 2A6

General function:: Involved in monooxygenase activity
Specific function:: Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:: CYP2A6
Uniprot ID:: P11509
Molecular weight:: 56517.005

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

7. Cysteinyl leukotriene receptor 1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for cysteinyl leukotrienes mediating bronchoconstriction of individuals with and without asthma. Stimulation by LTD4 results in the contraction and proliferation of smooth muscle, edema, eosinophil migration and damage to the mucus layer in the lung. This response is mediated via a G-protein that activates a phosphatidylinositol-calcium second messenger system. The rank order of affinities for the leukotrienes is LTD4 >> LTE4 = LTC4 >> LTB4
Gene Name:: CYSLTR1
Uniprot ID:: Q9Y271
Molecular weight:: 38540.5

References

Nayak A: A review of montelukast in the treatment of asthma and allergic rhinitis. Expert Opin Pharmacother. 2004 Mar;5(3):679-86. [PubMed:15013935 ]
Zhang YJ, Zhang L, Wang SB, Shen HH, Wei EQ: Montelukast modulates lung CysLT(1) receptor expression and eosinophilic inflammation in asthmatic mice. Acta Pharmacol Sin. 2004 Oct;25(10):1341-6. [PubMed:15456537 ]
Hamacher J, Eichert K, Braun C, Grebe T, Strub A, Lucas R, Eltze M, Wendel A: Montelukast exerts no acute direct effect on NO synthases. Pulm Pharmacol Ther. 2007;20(5):525-33. Epub 2006 May 19. [PubMed:16815057 ]
Langlois A, Ferland C, Tremblay GM, Laviolette M: Montelukast regulates eosinophil protease activity through a leukotriene-independent mechanism. J Allergy Clin Immunol. 2006 Jul;118(1):113-9. Epub 2006 May 19. [PubMed:16815146 ]
Alfieri AB, Tramontana M, Cialdai C, Lecci A, Giuliani S, Crea A, Manzini S, Maggi CA: Heterogeneous effect of leucotriene CysLT1 receptor antagonists on antigen-induced motor and inflammatory responses in guinea-pig airways. Auton Autacoid Pharmacol. 2007 Jan;27(1):39-46. [PubMed:17199874 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 2B1

General function:: Involved in transporter activity
Specific function:: Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost
Gene Name:: SLCO2B1
Uniprot ID:: O94956
Molecular weight:: 76697.9

References

Mougey EB, Feng H, Castro M, Irvin CG, Lima JJ: Absorption of montelukast is transporter mediated: a common variant of OATP2B1 is associated with reduced plasma concentrations and poor response. Pharmacogenet Genomics. 2009 Feb;19(2):129-38. doi: 10.1097/FPC.0b013e32831bd98c. [PubMed:19151602 ]

Showing metabocard for Montelukast (HMDB0014614)

MOL for HMDB0014614 (Montelukast)

3D MOL for HMDB0014614 (Montelukast)

3D SDF for HMDB0014614 (Montelukast)

3D-SDF for HMDB0014614 (Montelukast)

PDB for HMDB0014614 (Montelukast)

3D PDB for HMDB0014614 (Montelukast)

SMILES for HMDB0014614 (Montelukast)

INCHI for HMDB0014614 (Montelukast)

Structure for HMDB0014614 (Montelukast)

3D Structure for HMDB0014614 (Montelukast)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

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Transporters

References