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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:42 UTC

HMDB ID

HMDB0014689

Secondary Accession Numbers

HMDB14689

Metabolite Identification

Common Name

Zafirlukast

Description

Zafirlukast is an oral leukotriene receptor antagonist (LTRA) for the maintenance treatment of asthma, often used in conjunction with an inhaled steroid and/or long-acting bronchodilator. It is available as a tablet and is usually dosed twice daily. Another leukotriene receptor antagonist is montelukast (Singulair), which is usually taken just once daily. Zafirlukast blocks the action of the cysteinyl leukotrienes on the CysLT1 receptors, thus reducing constriction of the airways, build-up of mucus in the lungs and inflammation of the breathing passages.

Structure

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

549
  Mrv0541 02231214462D          

 41 45  0  0  0  0            999 V2000
   12.5724    1.7033    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703   -0.5547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -1.7922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7922    1.6368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0598    0.1349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7425    0.8961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4023    2.5106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0233   -2.0436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0993   -0.5547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7651    1.5332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558   -0.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2021   -0.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695   -1.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3847   -0.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.9942    2.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
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 35 39  1  0  0  0  0
 37 40  1  0  0  0  0
 38 41  1  0  0  0  0
 40 41  2  0  0  0  0
M  END

HMDB0014689
     RDKit          3D
Zafirlukast
 74 78  0  0  0  0  0  0  0  0999 V2000
    3.0010   -3.8893   -2.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
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 40 74  1  0
M  END

549
  Mrv0541 02231214462D          

 41 45  0  0  0  0            999 V2000
   12.5724    1.7033    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    9.0486    2.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6360    2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7380    1.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6743    0.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4433    2.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9942    2.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  1  7  2  0  0  0  0
  1 10  1  0  0  0  0
  1 34  1  0  0  0  0
  2 11  1  0  0  0  0
  2 16  1  0  0  0  0
  3 16  2  0  0  0  0
  4 28  1  0  0  0  0
  4 36  1  0  0  0  0
  5 33  2  0  0  0  0
  8 19  1  0  0  0  0
  8 23  1  0  0  0  0
  8 27  1  0  0  0  0
  9 16  1  0  0  0  0
  9 20  1  0  0  0  0
 10 33  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 15  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 17 22  1  0  0  0  0
 18 21  1  0  0  0  0
 18 23  2  0  0  0  0
 19 24  1  0  0  0  0
 20 22  2  0  0  0  0
 20 25  1  0  0  0  0
 21 26  1  0  0  0  0
 24 25  2  0  0  0  0
 26 28  2  0  0  0  0
 26 29  1  0  0  0  0
 28 30  1  0  0  0  0
 29 32  2  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 34 35  1  0  0  0  0
 34 37  2  0  0  0  0
 35 38  2  0  0  0  0
 35 39  1  0  0  0  0
 37 40  1  0  0  0  0
 38 41  1  0  0  0  0
 40 41  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014689

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(CC2=CN(C)C3=C2C=C(NC(=O)OC2CCCC2)C=C3)C=CC(=C1)C(=O)NS(=O)(=O)C1=CC=CC=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C31H33N3O6S/c1-20-8-4-7-11-29(20)41(37,38)33-30(35)22-13-12-21(28(17-22)39-3)16-23-19-34(2)27-15-14-24(18-26(23)27)32-31(36)40-25-9-5-6-10-25/h4,7-8,11-15,17-19,25H,5-6,9-10,16H2,1-3H3,(H,32,36)(H,33,35)

> <INCHI_KEY>
YEEZWCHGZNKEEK-UHFFFAOYSA-N

> <FORMULA>
C31H33N3O6S

> <MOLECULAR_WEIGHT>
575.675

> <EXACT_MASS>
575.209006493

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
62.06178485664529

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
cyclopentyl N-[3-({2-methoxy-4-[(2-methylbenzenesulfonyl)carbamoyl]phenyl}methyl)-1-methyl-1H-indol-5-yl]carbamate

> <ALOGPS_LOGP>
4.84

> <JCHEM_LOGP>
6.403744909

> <ALOGPS_LOGS>
-5.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.933285317986634

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.2852968683587545

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0817440806037872

> <JCHEM_POLAR_SURFACE_AREA>
115.73000000000002

> <JCHEM_REFRACTIVITY>
158.57689999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.62e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zafirlukast

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014689
     RDKit          3D
Zafirlukast
 74 78  0  0  0  0  0  0  0  0999 V2000
    3.0010   -3.8893   -2.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9014   -3.0228   -2.4913 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8330   -1.8005   -1.8382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7942   -1.4141   -0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7735   -0.2252   -0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7797    0.2137    0.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5285    1.1559    1.5190 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0372   -0.4282    0.7329 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2843    0.0455    1.8436 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.7920   -0.0008    3.2620 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4541   -0.9019    1.7334 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8456    1.6612    1.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2915    2.3696    0.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7594    3.6420    0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7434    4.2244    0.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2887    3.4987    2.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7052    0.6360   -0.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7769   -0.9476   -2.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2392   -1.3367   -3.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2131   -2.3414   -2.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2747   -3.6800   -2.9363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3075   -4.2405   -2.3140 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6965   -5.6361   -2.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9365   -3.3153   -1.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0501   -3.3904   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4734   -2.2112   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8242   -1.0188   -0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2769    0.1579    0.2973 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5599    0.3586    0.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4565   -0.4810    0.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8902    1.5667    1.3957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1686    1.8544    1.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1829    2.3651    3.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4540    3.6612    3.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7243    4.1536    1.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6307    3.0897    1.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7020   -0.9704   -1.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2727   -2.1060   -1.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9597   -3.3836   -2.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9968   -4.1293   -1.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9602   -4.7974   -2.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6097   -2.1036   -0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2257   -1.1991    0.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5165    1.9748   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3067    4.1897   -0.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0956    5.2375    0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0599    3.9597    2.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6686    1.1533    4.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8749    0.5381    2.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1941    2.0441    3.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6585    1.5803   -0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0801    0.9439   -1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7371   -0.4049   -3.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2932   -1.7317   -4.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5613   -4.1937   -3.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5883   -5.9485   -3.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0220   -6.2240   -1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7540   -5.7506   -2.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5617   -4.3209   -0.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3472   -2.3566    0.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5950    0.9743    0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8842    1.0171    1.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7859    1.6689    4.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2513    2.6022    3.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3489    3.4723    3.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8459    4.3525    3.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7737    4.1204    1.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2067    5.1485    1.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6681    3.3434    1.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4212    3.0076    0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2255    0.0009   -1.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
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 13 14  1  0
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 16 17  2  0
 17 18  1  0
  5 19  2  0
 19 20  1  0
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 29 30  2  0
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 31 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 30 40  1  0
 40 41  2  0
 21  3  1  0
 41 23  1  0
 17 12  1  0
 41 27  1  0
 39 35  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  4 45  1  0
  8 46  1  0
 13 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
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 22 56  1  0
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 26 59  1  0
 26 60  1  0
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 28 62  1  0
 29 63  1  0
 31 64  1  0
 35 65  1  0
 36 66  1  0
 36 67  1  0
 37 68  1  0
 37 69  1  0
 38 70  1  0
 38 71  1  0
 39 72  1  0
 39 73  1  0
 40 74  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 549                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      23.468   3.179   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       6.851  -1.035   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.185  -3.345   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      16.412   3.055   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      22.512   0.252   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      23.786   1.673   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      23.151   4.686   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      14.977  -3.815   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       9.519  -1.035   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      21.962   2.862   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       5.517  -1.805   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.111  -1.179   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.356  -3.337   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -2.323   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.850  -3.657   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.185  -1.805   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.520  -1.805   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.977  -1.336   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.520  -3.345   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.852  -1.805   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.455   0.128   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.186  -1.035   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.876  -2.575   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.186  -4.115   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.852  -3.345   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.962   0.445   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.455  -5.278   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.441   1.909   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.991  -0.701   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.948   2.227   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      19.976   1.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      19.498  -0.383   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      21.483   1.398   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      24.975   3.497   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      26.004   2.351   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.891   4.519   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      25.454   4.961   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      27.511   2.668   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      25.525   0.887   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      26.961   5.278   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      27.989   4.132   0.000  0.00  0.00           C+0
CONECT    1    6    7   10   34                                             
CONECT    2   11   16                                                       
CONECT    3   16                                                            
CONECT    4   28   36                                                       
CONECT    5   33                                                            
CONECT    6    1                                                            
CONECT    7    1                                                            
CONECT    8   19   23   27                                                  
CONECT    9   16   20                                                       
CONECT   10    1   33                                                       
CONECT   11    2   12   13                                                  
CONECT   12   11   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   15                                                       
CONECT   15   13   14                                                       
CONECT   16    2    3    9                                                  
CONECT   17   18   19   22                                                  
CONECT   18   17   21   23                                                  
CONECT   19    8   17   24                                                  
CONECT   20    9   22   25                                                  
CONECT   21   18   26                                                       
CONECT   22   17   20                                                       
CONECT   23    8   18                                                       
CONECT   24   19   25                                                       
CONECT   25   20   24                                                       
CONECT   26   21   28   29                                                  
CONECT   27    8                                                            
CONECT   28    4   26   30                                                  
CONECT   29   26   32                                                       
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   29   31                                                       
CONECT   33    5   10   31                                                  
CONECT   34    1   35   37                                                  
CONECT   35   34   38   39                                                  
CONECT   36    4                                                            
CONECT   37   34   40                                                       
CONECT   38   35   41                                                       
CONECT   39   35                                                            
CONECT   40   37   41                                                       
CONECT   41   38   40                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

COMPND    HMDB0014689
HETATM    1  C1  UNL     1       3.001  -3.889  -2.187  1.00  0.00           C  
HETATM    2  O1  UNL     1       1.901  -3.023  -2.491  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.833  -1.800  -1.838  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.794  -1.414  -0.915  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.774  -0.225  -0.246  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.780   0.214   0.716  1.00  0.00           C  
HETATM    7  O2  UNL     1       3.528   1.156   1.519  1.00  0.00           O  
HETATM    8  N1  UNL     1       5.037  -0.428   0.733  1.00  0.00           N  
HETATM    9  S1  UNL     1       6.284   0.046   1.844  1.00  0.00           S  
HETATM   10  O3  UNL     1       5.792  -0.001   3.262  1.00  0.00           O  
HETATM   11  O4  UNL     1       7.454  -0.902   1.733  1.00  0.00           O  
HETATM   12  C6  UNL     1       6.846   1.661   1.510  1.00  0.00           C  
HETATM   13  C7  UNL     1       6.291   2.370   0.473  1.00  0.00           C  
HETATM   14  C8  UNL     1       6.759   3.642   0.243  1.00  0.00           C  
HETATM   15  C9  UNL     1       7.743   4.224   0.997  1.00  0.00           C  
HETATM   16  C10 UNL     1       8.289   3.499   2.034  1.00  0.00           C  
HETATM   17  C11 UNL     1       7.822   2.218   2.271  1.00  0.00           C  
HETATM   18  C12 UNL     1       8.412   1.439   3.392  1.00  0.00           C  
HETATM   19  C13 UNL     1       1.705   0.636  -0.529  1.00  0.00           C  
HETATM   20  C14 UNL     1       0.748   0.261  -1.443  1.00  0.00           C  
HETATM   21  C15 UNL     1       0.777  -0.948  -2.118  1.00  0.00           C  
HETATM   22  C16 UNL     1      -0.239  -1.337  -3.096  1.00  0.00           C  
HETATM   23  C17 UNL     1      -1.213  -2.341  -2.626  1.00  0.00           C  
HETATM   24  C18 UNL     1      -1.275  -3.680  -2.936  1.00  0.00           C  
HETATM   25  N2  UNL     1      -2.308  -4.241  -2.314  1.00  0.00           N  
HETATM   26  C19 UNL     1      -2.696  -5.636  -2.395  1.00  0.00           C  
HETATM   27  C20 UNL     1      -2.937  -3.315  -1.598  1.00  0.00           C  
HETATM   28  C21 UNL     1      -4.050  -3.390  -0.788  1.00  0.00           C  
HETATM   29  C22 UNL     1      -4.473  -2.211  -0.160  1.00  0.00           C  
HETATM   30  C23 UNL     1      -3.824  -1.019  -0.327  1.00  0.00           C  
HETATM   31  N3  UNL     1      -4.277   0.158   0.297  1.00  0.00           N  
HETATM   32  C24 UNL     1      -5.560   0.359   0.784  1.00  0.00           C  
HETATM   33  O5  UNL     1      -6.457  -0.481   0.713  1.00  0.00           O  
HETATM   34  O6  UNL     1      -5.890   1.567   1.396  1.00  0.00           O  
HETATM   35  C25 UNL     1      -7.169   1.854   1.907  1.00  0.00           C  
HETATM   36  C26 UNL     1      -7.183   2.365   3.315  1.00  0.00           C  
HETATM   37  C27 UNL     1      -6.454   3.661   3.207  1.00  0.00           C  
HETATM   38  C28 UNL     1      -6.724   4.154   1.795  1.00  0.00           C  
HETATM   39  C29 UNL     1      -7.631   3.090   1.155  1.00  0.00           C  
HETATM   40  C30 UNL     1      -2.702  -0.970  -1.150  1.00  0.00           C  
HETATM   41  C31 UNL     1      -2.273  -2.106  -1.771  1.00  0.00           C  
HETATM   42  H1  UNL     1       3.960  -3.384  -2.401  1.00  0.00           H  
HETATM   43  H2  UNL     1       2.997  -4.129  -1.098  1.00  0.00           H  
HETATM   44  H3  UNL     1       2.960  -4.797  -2.818  1.00  0.00           H  
HETATM   45  H4  UNL     1       3.610  -2.104  -0.714  1.00  0.00           H  
HETATM   46  H5  UNL     1       5.226  -1.199   0.068  1.00  0.00           H  
HETATM   47  H6  UNL     1       5.517   1.975  -0.163  1.00  0.00           H  
HETATM   48  H7  UNL     1       6.307   4.190  -0.585  1.00  0.00           H  
HETATM   49  H8  UNL     1       8.096   5.237   0.791  1.00  0.00           H  
HETATM   50  H9  UNL     1       9.060   3.960   2.622  1.00  0.00           H  
HETATM   51  H10 UNL     1       7.669   1.153   4.157  1.00  0.00           H  
HETATM   52  H11 UNL     1       8.875   0.538   2.959  1.00  0.00           H  
HETATM   53  H12 UNL     1       9.194   2.044   3.915  1.00  0.00           H  
HETATM   54  H13 UNL     1       1.658   1.580  -0.019  1.00  0.00           H  
HETATM   55  H14 UNL     1      -0.080   0.944  -1.659  1.00  0.00           H  
HETATM   56  H15 UNL     1      -0.737  -0.405  -3.471  1.00  0.00           H  
HETATM   57  H16 UNL     1       0.293  -1.732  -4.009  1.00  0.00           H  
HETATM   58  H17 UNL     1      -0.561  -4.194  -3.605  1.00  0.00           H  
HETATM   59  H18 UNL     1      -2.588  -5.948  -3.457  1.00  0.00           H  
HETATM   60  H19 UNL     1      -2.022  -6.224  -1.737  1.00  0.00           H  
HETATM   61  H20 UNL     1      -3.754  -5.751  -2.075  1.00  0.00           H  
HETATM   62  H21 UNL     1      -4.562  -4.321  -0.654  1.00  0.00           H  
HETATM   63  H22 UNL     1      -5.347  -2.357   0.468  1.00  0.00           H  
HETATM   64  H23 UNL     1      -3.595   0.974   0.416  1.00  0.00           H  
HETATM   65  H24 UNL     1      -7.884   1.017   1.751  1.00  0.00           H  
HETATM   66  H25 UNL     1      -6.786   1.669   4.063  1.00  0.00           H  
HETATM   67  H26 UNL     1      -8.251   2.602   3.552  1.00  0.00           H  
HETATM   68  H27 UNL     1      -5.349   3.472   3.345  1.00  0.00           H  
HETATM   69  H28 UNL     1      -6.846   4.353   3.979  1.00  0.00           H  
HETATM   70  H29 UNL     1      -5.774   4.120   1.200  1.00  0.00           H  
HETATM   71  H30 UNL     1      -7.207   5.149   1.781  1.00  0.00           H  
HETATM   72  H31 UNL     1      -8.668   3.343   1.407  1.00  0.00           H  
HETATM   73  H32 UNL     1      -7.421   3.008   0.069  1.00  0.00           H  
HETATM   74  H33 UNL     1      -2.225   0.001  -1.249  1.00  0.00           H  
CONECT    1    2   42   43   44
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   45
CONECT    5    6   19   19
CONECT    6    7    7    8
CONECT    8    9   46
CONECT    9   10   10   11   11
CONECT    9   12
CONECT   12   13   13   17
CONECT   13   14   47
CONECT   14   15   15   48
CONECT   15   16   49
CONECT   16   17   17   50
CONECT   17   18
CONECT   18   51   52   53
CONECT   19   20   54
CONECT   20   21   21   55
CONECT   21   22
CONECT   22   23   56   57
CONECT   23   24   24   41
CONECT   24   25   58
CONECT   25   26   27
CONECT   26   59   60   61
CONECT   27   28   28   41
CONECT   28   29   62
CONECT   29   30   30   63
CONECT   30   31   40
CONECT   31   32   64
CONECT   32   33   33   34
CONECT   34   35
CONECT   35   36   39   65
CONECT   36   37   66   67
CONECT   37   38   68   69
CONECT   38   39   70   71
CONECT   39   72   73
CONECT   40   41   41   74
END

HMDB0014689
     RDKit          3D
Zafirlukast
 74 78  0  0  0  0  0  0  0  0999 V2000
    3.0010   -3.8893   -2.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9014   -3.0228   -2.4913 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8330   -1.8005   -1.8382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7942   -1.4141   -0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7735   -0.2252   -0.2458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7797    0.2137    0.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5285    1.1559    1.5190 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0372   -0.4282    0.7329 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2843    0.0455    1.8436 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.7920   -0.0008    3.2620 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4541   -0.9019    1.7334 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8456    1.6612    1.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2915    2.3696    0.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7594    3.6420    0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7434    4.2244    0.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2887    3.4987    2.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8222    2.2180    2.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4117    1.4393    3.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7052    0.6360   -0.5292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7482    0.2610   -1.4434 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7769   -0.9476   -2.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2392   -1.3367   -3.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2131   -2.3414   -2.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2747   -3.6800   -2.9363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3075   -4.2405   -2.3140 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6965   -5.6361   -2.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9365   -3.3153   -1.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0501   -3.3904   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4734   -2.2112   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8242   -1.0188   -0.3273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2769    0.1579    0.2973 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5599    0.3586    0.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4565   -0.4810    0.7128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8902    1.5667    1.3957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1686    1.8544    1.9075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1829    2.3651    3.3154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4540    3.6612    3.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7243    4.1536    1.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6307    3.0897    1.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7020   -0.9704   -1.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2727   -2.1060   -1.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9597   -3.3836   -2.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9968   -4.1293   -1.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9602   -4.7974   -2.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6097   -2.1036   -0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2257   -1.1991    0.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5165    1.9748   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3067    4.1897   -0.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0956    5.2375    0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0599    3.9597    2.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6686    1.1533    4.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8749    0.5381    2.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1941    2.0441    3.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6585    1.5803   -0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0801    0.9439   -1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7371   -0.4049   -3.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2932   -1.7317   -4.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5613   -4.1937   -3.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5883   -5.9485   -3.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0220   -6.2240   -1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7540   -5.7506   -2.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5617   -4.3209   -0.6537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3472   -2.3566    0.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5950    0.9743    0.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8842    1.0171    1.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7859    1.6689    4.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2513    2.6022    3.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3489    3.4723    3.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8459    4.3525    3.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7737    4.1204    1.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2067    5.1485    1.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6681    3.3434    1.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4212    3.0076    0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2255    0.0009   -1.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  2  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
  5 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 30 40  1  0
 40 41  2  0
 21  3  1  0
 41 23  1  0
 17 12  1  0
 41 27  1  0
 39 35  1  0
  1 42  1  0
  1 43  1  0
  1 44  1  0
  4 45  1  0
  8 46  1  0
 13 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 20 55  1  0
 22 56  1  0
 22 57  1  0
 24 58  1  0
 26 59  1  0
 26 60  1  0
 26 61  1  0
 28 62  1  0
 29 63  1  0
 31 64  1  0
 35 65  1  0
 36 66  1  0
 36 67  1  0
 37 68  1  0
 37 69  1  0
 38 70  1  0
 38 71  1  0
 39 72  1  0
 39 73  1  0
 40 74  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(5-Cyclopentyloxycarbonylamino-1-methyl-1H-indol-3-ylmethyl)-3-methoxy-N-O-tolylsulfonylbenzamide	ChEBI
Accolate	ChEBI
Cyclopentyl 3-(2-methoxy-4-((O-tolylsulfonyl)carbamoyl)benzyl)-1-methylindole-5-carbamate	ChEBI
4-(5-Cyclopentyloxycarbonylamino-1-methyl-1H-indol-3-ylmethyl)-3-methoxy-N-O-tolylsulphonylbenzamide	Generator
Accolic acid	Generator
Cyclopentyl 3-(2-methoxy-4-((O-tolylsulfonyl)carbamoyl)benzyl)-1-methylindole-5-carbamic acid	Generator
Cyclopentyl 3-(2-methoxy-4-((O-tolylsulphonyl)carbamoyl)benzyl)-1-methylindole-5-carbamate	Generator
Cyclopentyl 3-(2-methoxy-4-((O-tolylsulphonyl)carbamoyl)benzyl)-1-methylindole-5-carbamic acid	Generator
Aeronix	HMDB
4-(5-Cyclopentyloxycarbonylamino-2-methylindol-3-yl-methyl)-3-methoxy-N-O-tolylsulfonylbenzamide	HMDB
Olmoran	HMDB

Chemical Formula

C₃₁H₃₃N₃O₆S

Average Molecular Weight

575.675

Monoisotopic Molecular Weight

575.209006493

IUPAC Name

cyclopentyl N-[3-({2-methoxy-4-[(2-methylbenzenesulfonyl)carbamoyl]phenyl}methyl)-1-methyl-1H-indol-5-yl]carbamate

Traditional Name

zafirlukast

CAS Registry Number

107753-78-6

SMILES

COC1=C(CC2=CN(C)C3=C2C=C(NC(=O)OC2CCCC2)C=C3)C=CC(=C1)C(=O)NS(=O)(=O)C1=CC=CC=C1C

InChI Identifier

InChI=1S/C31H33N3O6S/c1-20-8-4-7-11-29(20)41(37,38)33-30(35)22-13-12-21(28(17-22)39-3)16-23-19-34(2)27-15-14-24(18-26(23)27)32-31(36)40-25-9-5-6-10-25/h4,7-8,11-15,17-19,25H,5-6,9-10,16H2,1-3H3,(H,32,36)(H,33,35)

InChI Key

YEEZWCHGZNKEEK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Benzenesulfonamides

Alternative Parents

Substituents

Benzenesulfonamide
N-alkylindole
3-alkylindole
Benzoic acid or derivatives
Benzenesulfonyl group
Indole
Indole or derivatives
Phenoxy compound
Anisole
Benzoyl
Methoxybenzene
Phenol ether
Alkyl aryl ether
Toluene
N-methylpyrrole
Substituted pyrrole
Heteroaromatic compound
Aminosulfonyl compound
Pyrrole
Carbamic acid ester
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Carbonic acid derivative
Organoheterocyclic compound
Azacycle
Ether
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organosulfur compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbamate ester (CHEBI:10100 )
sulfonamide (CHEBI:10100 )
indoles (CHEBI:10100 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014689)
Membrane (HMDB: HMDB0014689)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	139 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00096 g/L	Not Available
LogP	5.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00096 g/L	ALOGPS
logP	4.84	ALOGPS
logP	6.4	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	4.29	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	115.73 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	158.58 m³·mol⁻¹	ChemAxon
Polarizability	62.06 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
DarkChem	[M+H]+	233.197	31661259
DarkChem	[M-H]-	229.102	31661259
DeepCCS	[M+H]+	228.705	30932474
DeepCCS	[M-H]-	226.522	30932474
DeepCCS	[M-2H]-	259.763	30932474
DeepCCS	[M+Na]+	234.618	30932474
AllCCS	[M+H]+	236.4	32859911
AllCCS	[M+H-H2O]+	235.0	32859911
AllCCS	[M+NH4]+	237.7	32859911
AllCCS	[M+Na]+	238.0	32859911
AllCCS	[M-H]-	225.7	32859911
AllCCS	[M+Na-2H]-	227.7	32859911
AllCCS	[M+HCOO]-	230.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zafirlukast	COC1=C(CC2=CN(C)C3=C2C=C(NC(=O)OC2CCCC2)C=C3)C=CC(=C1)C(=O)NS(=O)(=O)C1=CC=CC=C1C	6651.5	Standard polar	33892256
Zafirlukast	COC1=C(CC2=CN(C)C3=C2C=C(NC(=O)OC2CCCC2)C=C3)C=CC(=C1)C(=O)NS(=O)(=O)C1=CC=CC=C1C	4481.7	Standard non polar	33892256
Zafirlukast	COC1=C(CC2=CN(C)C3=C2C=C(NC(=O)OC2CCCC2)C=C3)C=CC(=C1)C(=O)NS(=O)(=O)C1=CC=CC=C1C	5144.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Zafirlukast,1TMS,isomer #1	COC1=CC(C(=O)NS(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(N(C(=O)OC3CCCC3)[Si](C)(C)C)C=C12	4791.0	Semi standard non polar	33892256
Zafirlukast,1TMS,isomer #1	COC1=CC(C(=O)NS(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(N(C(=O)OC3CCCC3)[Si](C)(C)C)C=C12	4388.7	Standard non polar	33892256
Zafirlukast,1TMS,isomer #1	COC1=CC(C(=O)NS(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(N(C(=O)OC3CCCC3)[Si](C)(C)C)C=C12	6036.4	Standard polar	33892256
Zafirlukast,1TMS,isomer #2	COC1=CC(C(=O)N([Si](C)(C)C)S(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(NC(=O)OC3CCCC3)C=C12	4883.2	Semi standard non polar	33892256
Zafirlukast,1TMS,isomer #2	COC1=CC(C(=O)N([Si](C)(C)C)S(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(NC(=O)OC3CCCC3)C=C12	4371.1	Standard non polar	33892256
Zafirlukast,1TMS,isomer #2	COC1=CC(C(=O)N([Si](C)(C)C)S(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(NC(=O)OC3CCCC3)C=C12	6198.4	Standard polar	33892256
Zafirlukast,2TMS,isomer #1	COC1=CC(C(=O)N([Si](C)(C)C)S(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(N(C(=O)OC3CCCC3)[Si](C)(C)C)C=C12	4560.9	Semi standard non polar	33892256
Zafirlukast,2TMS,isomer #1	COC1=CC(C(=O)N([Si](C)(C)C)S(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(N(C(=O)OC3CCCC3)[Si](C)(C)C)C=C12	4449.0	Standard non polar	33892256
Zafirlukast,2TMS,isomer #1	COC1=CC(C(=O)N([Si](C)(C)C)S(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(N(C(=O)OC3CCCC3)[Si](C)(C)C)C=C12	5812.3	Standard polar	33892256
Zafirlukast,1TBDMS,isomer #1	COC1=CC(C(=O)NS(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(N(C(=O)OC3CCCC3)[Si](C)(C)C(C)(C)C)C=C12	5064.3	Semi standard non polar	33892256
Zafirlukast,1TBDMS,isomer #1	COC1=CC(C(=O)NS(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(N(C(=O)OC3CCCC3)[Si](C)(C)C(C)(C)C)C=C12	4594.8	Standard non polar	33892256
Zafirlukast,1TBDMS,isomer #1	COC1=CC(C(=O)NS(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(N(C(=O)OC3CCCC3)[Si](C)(C)C(C)(C)C)C=C12	6023.1	Standard polar	33892256
Zafirlukast,1TBDMS,isomer #2	COC1=CC(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(NC(=O)OC3CCCC3)C=C12	5124.4	Semi standard non polar	33892256
Zafirlukast,1TBDMS,isomer #2	COC1=CC(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(NC(=O)OC3CCCC3)C=C12	4582.7	Standard non polar	33892256
Zafirlukast,1TBDMS,isomer #2	COC1=CC(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(NC(=O)OC3CCCC3)C=C12	6163.3	Standard polar	33892256
Zafirlukast,2TBDMS,isomer #1	COC1=CC(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(N(C(=O)OC3CCCC3)[Si](C)(C)C(C)(C)C)C=C12	5070.0	Semi standard non polar	33892256
Zafirlukast,2TBDMS,isomer #1	COC1=CC(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(N(C(=O)OC3CCCC3)[Si](C)(C)C(C)(C)C)C=C12	4867.1	Standard non polar	33892256
Zafirlukast,2TBDMS,isomer #1	COC1=CC(C(=O)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=CC=C2C)=CC=C1CC1=CN(C)C2=CC=C(N(C(=O)OC3CCCC3)[Si](C)(C)C(C)(C)C)C=C12	5781.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Zafirlukast GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9330620000-fc40738dd1a7e2c81dc5	2017-09-01	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zafirlukast 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 - Zafirlukast 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 - Zafirlukast LC-ESI-qTof , Positive-QTOF	splash10-0292-0940000000-f369442eba5344b3ecb4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zafirlukast LC-ESI-qTof , Positive-QTOF	splash10-0292-0940000000-f369442eba5344b3ecb4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zafirlukast , positive-QTOF	splash10-0002-0003191000-ba3996913abfda3b22c4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zafirlukast , positive-QTOF	splash10-0a4r-0259300000-1440474b4cb47824c9f2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zafirlukast , positive-QTOF	splash10-0002-0001191000-58bcdb71b459847fc794	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zafirlukast , positive-QTOF	splash10-0ap0-0149300000-896e679131032968db95	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zafirlukast 35V, Positive-QTOF	splash10-000i-0029300000-c82ecc534ef9c1eb1c1f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Zafirlukast 35V, Negative-QTOF	splash10-00di-0000090000-e0b91fc76d38f979ecca	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zafirlukast 10V, Positive-QTOF	splash10-002r-9110380000-9e5c8dd5fdec56391e67	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zafirlukast 20V, Positive-QTOF	splash10-000i-9012110000-e33cb25b1e67d0d2bf04	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zafirlukast 40V, Positive-QTOF	splash10-0006-9021000000-1a28cc2a5255b3c26347	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zafirlukast 10V, Negative-QTOF	splash10-000i-3000940000-d189a5e1b668abe5609e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zafirlukast 20V, Negative-QTOF	splash10-000i-7511930000-ba1443db38e17f7c56c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zafirlukast 40V, Negative-QTOF	splash10-000m-9601600000-7d2519b7cb04660b56f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zafirlukast 10V, Positive-QTOF	splash10-052r-0008290000-74ba6045634101ef1590	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zafirlukast 20V, Positive-QTOF	splash10-052o-9217440000-736a786992f3e2189ffd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zafirlukast 40V, Positive-QTOF	splash10-00ou-9051430000-b689491e7cebb735e1b3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zafirlukast 10V, Negative-QTOF	splash10-00di-0000090000-08c3cf635346a0e9b809	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zafirlukast 20V, Negative-QTOF	splash10-00dl-7300490000-1baf05db9dff2aaf16ea	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zafirlukast 40V, Negative-QTOF	splash10-00di-4201390000-a227805ba727dea02ed8	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 DB00549	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00549	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00549

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5515

KEGG Compound ID

C07206

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Zafirlukast

METLIN ID

Not Available

PubChem Compound

5717

PDB ID

Not Available

ChEBI ID

10100

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. 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

2. Cytochrome P450 3A4

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

References

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

Enzyme Details

3. 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 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2C19

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

References

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

Enzyme Details

5. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

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

Enzyme Details

6. Cytochrome P450 2D6

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

References

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

Enzyme Details

7. Cytochrome P450 1A2

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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

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

Enzyme Details

8. 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

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

9. 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

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Cazzola M, Boveri B, Carlucci P, Santus P, DiMarco F, Centanni S, Allegra L: Lung function improvement in smokers suffering from COPD with zafirlukast, a CysLT(1)-receptor antagonist. Pulm Pharmacol Ther. 2000;13(6):301-5. [PubMed:11061985 ]
Murata Y, Sugimoto O: [Zafirlukast (Accolate): a review of its pharmacological and clinical profile]. Nihon Yakurigaku Zasshi. 2002 Apr;119(4):247-58. [PubMed:11979731 ]
Wang S, Gustafson E, Pang L, Qiao X, Behan J, Maguire M, Bayne M, Laz T: A novel hepatointestinal leukotriene B4 receptor. Cloning and functional characterization. J Biol Chem. 2000 Dec 29;275(52):40686-94. [PubMed:11006272 ]
O'Byrne PM: Leukotrienes in the pathogenesis of asthma. Chest. 1997 Feb;111(2 Suppl):27S-34S. [PubMed:9042024 ]
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Showing metabocard for Zafirlukast (HMDB0014689)

MOL for HMDB0014689 (Zafirlukast)

3D MOL for HMDB0014689 (Zafirlukast)

3D SDF for HMDB0014689 (Zafirlukast)

3D-SDF for HMDB0014689 (Zafirlukast)

PDB for HMDB0014689 (Zafirlukast)

3D PDB for HMDB0014689 (Zafirlukast)

SMILES for HMDB0014689 (Zafirlukast)

INCHI for HMDB0014689 (Zafirlukast)

Structure for HMDB0014689 (Zafirlukast)

3D Structure for HMDB0014689 (Zafirlukast)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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