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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (10) Show 10 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:51 UTC

HMDB ID

HMDB0015056

Secondary Accession Numbers

HMDB15056

Metabolite Identification

Common Name

Ketotifen

Description

Ketotifen is only found in individuals that have used or taken this drug. It is a cycloheptathiophene blocker of histamine H1 receptors and release of inflammatory mediators. It has been proposed for the treatment of asthma, rhinitis, skin allergies, and anaphylaxis. [PubChem]Ketotifen is a relatively selective, non-competitive histamine antagonist (H1-receptor) and mast cell stabilizer. Ketotifen inhibits the release of mediators from mast cells involved in hypersensitivity reactions. Decreased chemotaxis and activation of eosinophils have also been demonstrated. Ketotifen also inhibits cAMP phosphodiesterase. Properties of ketotifen which may contribute to its antiallergic activity and its ability to affect the underlying pathology of asthma include inhibition of the development of airway hyper-reactivity associated with activation of platelets by PAF (Platelet Activating Factor), inhibition of PAF-induced accumulation of eosinophils and platelets in the airways, suppression of the priming of eosinophils by human recombinant cytokines and antagonism of bronchoconstriction due to leukotrienes. Ketotifen inhibits of the release of allergic mediators such as histamine, leukotrienes C4 and D4(SRS-A) and PAF.

Structure

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

HMDB0015056
     RDKit          3D
Ketotifen
 41 44  0  0  0  0  0  0  0  0999 V2000
    4.4900   -0.2330   -0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022   -0.1123    0.8003 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8549    1.1650    0.8324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    1.2783   -0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6563    0.2411    0.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5798    0.2983   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4270   -0.8326    0.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765   -2.0395   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5142   -3.2196    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7492   -3.2176    0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2984   -2.0191    1.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6679   -0.8176    0.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4741    0.3087    1.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3432    1.5683    0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2275    2.4242    0.7762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3509    2.0680   -0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973    3.4751   -1.4027 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0356    3.3673   -2.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622    2.2321   -1.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1349    1.5511   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1832   -0.7712    1.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667   -1.2161    0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2603   -0.9506    0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0025   -0.6882   -1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9913    0.7130   -0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5193    1.3808    1.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5940    1.9327    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1578    1.1463   -1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2639    2.2512   -0.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0882   -1.9572   -0.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0202   -4.1260   -0.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2277   -4.1799    0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2782   -2.0632    1.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3809    0.5072    2.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5547   -0.0109    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107    4.0306   -3.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154    1.8855   -2.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3340   -0.2103    2.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5351   -1.5460    1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906   -1.9991    1.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5962   -1.6148   -0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
  5 21  1  0
 21 22  1  0
 22  2  1  0
 20  6  1  0
 12  7  1  0
 20 16  2  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 18 36  1  0
 19 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
M  END

920
  Mrv0541 02231215062D          

 22 25  0  0  0  0            999 V2000
    1.9717    1.6084    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9451    2.9253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7156   -2.1003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7156   -0.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4301   -0.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0012   -0.8628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4301   -1.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0012   -1.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7156    0.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4590    0.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9723    0.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6425    1.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7156   -2.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7887    1.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1281    2.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031    2.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0798    0.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2671    0.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4597    1.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9029    0.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0941    1.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 20  1  0  0  0  0
  2 16  2  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3 13  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  9  2  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 17  2  0  0  0  0
 11 14  2  0  0  0  0
 11 18  1  0  0  0  0
 12 15  1  0  0  0  0
 12 19  2  0  0  0  0
 14 16  1  0  0  0  0
 15 16  1  0  0  0  0
 17 21  1  0  0  0  0
 18 20  2  0  0  0  0
 19 22  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015056

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC(CC1)=C1C2=C(SC=C2)C(=O)CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H19NOS/c1-20-9-6-13(7-10-20)18-15-5-3-2-4-14(15)12-17(21)19-16(18)8-11-22-19/h2-5,8,11H,6-7,9-10,12H2,1H3

> <INCHI_KEY>
ZCVMWBYGMWKGHF-UHFFFAOYSA-N

> <FORMULA>
C19H19NOS

> <MOLECULAR_WEIGHT>
309.425

> <EXACT_MASS>
309.118734925

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.61451824356662

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(1-methylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.0³,⁷]tetradeca-1(14),3(7),4,10,12-pentaen-8-one

> <ALOGPS_LOGP>
3.49

> <JCHEM_LOGP>
3.3478693229999994

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.299357282643564

> <JCHEM_PKA_STRONGEST_BASIC>
7.145918672338627

> <JCHEM_POLAR_SURFACE_AREA>
20.310000000000002

> <JCHEM_REFRACTIVITY>
101.73400000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.87e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ketotifen

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015056
     RDKit          3D
Ketotifen
 41 44  0  0  0  0  0  0  0  0999 V2000
    4.4900   -0.2330   -0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022   -0.1123    0.8003 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8549    1.1650    0.8324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    1.2783   -0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6563    0.2411    0.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5798    0.2983   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4270   -0.8326    0.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765   -2.0395   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5142   -3.2196    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7492   -3.2176    0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2984   -2.0191    1.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6679   -0.8176    0.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4741    0.3087    1.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3432    1.5683    0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2275    2.4242    0.7762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3509    2.0680   -0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973    3.4751   -1.4027 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0356    3.3673   -2.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622    2.2321   -1.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1349    1.5511   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1832   -0.7712    1.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667   -1.2161    0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2603   -0.9506    0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0025   -0.6882   -1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9913    0.7130   -0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5193    1.3808    1.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5940    1.9327    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1578    1.1463   -1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2639    2.2512   -0.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0882   -1.9572   -0.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0202   -4.1260   -0.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2277   -4.1799    0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2782   -2.0632    1.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3809    0.5072    2.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5547   -0.0109    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107    4.0306   -3.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154    1.8855   -2.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3340   -0.2103    2.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5351   -1.5460    1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906   -1.9991    1.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5962   -1.6148   -0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
  5 21  1  0
 21 22  1  0
 22  2  1  0
 20  6  1  0
 12  7  1  0
 20 16  2  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 18 36  1  0
 19 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 920                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       3.681   3.002   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       5.498   5.461   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       6.936  -3.921   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       6.936  -0.841   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.270  -1.611   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.602  -1.611   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.270  -3.151   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.602  -3.151   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.936   0.699   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.323   1.368   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.548   1.368   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.666   2.869   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.936  -5.461   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.206   2.869   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.706   4.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.166   4.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.482   0.259   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.232   0.586   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.191   3.365   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080   1.594   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.019   0.719   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.376   2.283   0.000  0.00  0.00           C+0
CONECT    1   14   20                                                       
CONECT    2   16                                                            
CONECT    3    7    8   13                                                  
CONECT    4    5    6    9                                                  
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    3    5                                                       
CONECT    8    3    6                                                       
CONECT    9    4   10   11                                                  
CONECT   10    9   12   17                                                  
CONECT   11    9   14   18                                                  
CONECT   12   10   15   19                                                  
CONECT   13    3                                                            
CONECT   14    1   11   16                                                  
CONECT   15   12   16                                                       
CONECT   16    2   14   15                                                  
CONECT   17   10   21                                                       
CONECT   18   11   20                                                       
CONECT   19   12   22                                                       
CONECT   20    1   18                                                       
CONECT   21   17   22                                                       
CONECT   22   19   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0015056
HETATM    1  C1  UNL     1       4.490  -0.233  -0.247  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.502  -0.112   0.800  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.855   1.165   0.832  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.709   1.278  -0.161  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.656   0.241   0.143  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.580   0.298  -0.194  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.427  -0.833   0.181  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.877  -2.040  -0.190  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.514  -3.220   0.047  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.749  -3.218   0.675  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.298  -2.019   1.041  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.668  -0.818   0.810  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.474   0.309   1.265  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.343   1.568   0.545  1.00  0.00           C  
HETATM   15  O1  UNL     1      -4.228   2.424   0.776  1.00  0.00           O  
HETATM   16  C14 UNL     1      -2.351   2.068  -0.436  1.00  0.00           C  
HETATM   17  S1  UNL     1      -2.497   3.475  -1.403  1.00  0.00           S  
HETATM   18  C15 UNL     1      -1.036   3.367  -2.264  1.00  0.00           C  
HETATM   19  C16 UNL     1      -0.462   2.232  -1.778  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.135   1.551  -0.828  1.00  0.00           C  
HETATM   21  C18 UNL     1       1.183  -0.771   1.089  1.00  0.00           C  
HETATM   22  C19 UNL     1       2.567  -1.216   0.714  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.260  -0.951   0.108  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.002  -0.688  -1.131  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.991   0.713  -0.472  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.519   1.381   1.850  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.594   1.933   0.541  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.158   1.146  -1.161  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.264   2.251  -0.046  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.088  -1.957  -0.707  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.020  -4.126  -0.270  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.228  -4.180   0.847  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.278  -2.063   1.535  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.381   0.507   2.361  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.555  -0.011   1.154  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.611   4.031  -3.038  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.515   1.886  -2.196  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.334  -0.210   2.100  1.00  0.00           H  
HETATM   39  H17 UNL     1       0.535  -1.546   1.347  1.00  0.00           H  
HETATM   40  H18 UNL     1       2.891  -1.999   1.411  1.00  0.00           H  
HETATM   41  H19 UNL     1       2.596  -1.615  -0.308  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   22
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6    6   21
CONECT    6    7   20
CONECT    7    8    8   12
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11   32
CONECT   11   12   12   33
CONECT   12   13
CONECT   13   14   34   35
CONECT   14   15   15   16
CONECT   16   17   20   20
CONECT   17   18
CONECT   18   19   19   36
CONECT   19   20   37
CONECT   21   22   38   39
CONECT   22   40   41
END

HMDB0015056
     RDKit          3D
Ketotifen
 41 44  0  0  0  0  0  0  0  0999 V2000
    4.4900   -0.2330   -0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022   -0.1123    0.8003 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8549    1.1650    0.8324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    1.2783   -0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6563    0.2411    0.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5798    0.2983   -0.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4270   -0.8326    0.1808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8765   -2.0395   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5142   -3.2196    0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7492   -3.2176    0.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2984   -2.0191    1.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6679   -0.8176    0.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4741    0.3087    1.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3432    1.5683    0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2275    2.4242    0.7762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3509    2.0680   -0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4973    3.4751   -1.4027 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0356    3.3673   -2.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4622    2.2321   -1.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1349    1.5511   -0.8277 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1832   -0.7712    1.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667   -1.2161    0.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2603   -0.9506    0.1078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0025   -0.6882   -1.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9913    0.7130   -0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5193    1.3808    1.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5940    1.9327    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1578    1.1463   -1.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2639    2.2512   -0.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0882   -1.9572   -0.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0202   -4.1260   -0.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2277   -4.1799    0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2782   -2.0632    1.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3809    0.5072    2.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5547   -0.0109    1.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6107    4.0306   -3.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5154    1.8855   -2.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3340   -0.2103    2.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5351   -1.5460    1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8906   -1.9991    1.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5962   -1.6148   -0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
  5 21  1  0
 21 22  1  0
 22  2  1  0
 20  6  1  0
 12  7  1  0
 20 16  2  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 18 36  1  0
 19 37  1  0
 21 38  1  0
 21 39  1  0
 22 40  1  0
 22 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10-(1-Methyl-4-piperidinylidene)-5H-benzo[1,2]cyclohepta[3,4-b]thiophen-4-one	ChEBI
Ketotifene	ChEBI
Ketotifeno	ChEBI
Ketotifenum	ChEBI
Alaway	Kegg
Ketotifen fumarate	HMDB
Ketotifene fumarate	HMDB
Fumarate, ketotifen	HMDB
Ketotiphen	HMDB
Ketotiphene	HMDB
Zaditen	HMDB
4,9-Dihydro-4-(1-methyl-4-piperidylidene)-10H-benzo(4,5)-cyclohepta(1,2-b)thiophen-10-one	HMDB

Chemical Formula

C₁₉H₁₉NOS

Average Molecular Weight

309.425

Monoisotopic Molecular Weight

309.118734925

IUPAC Name

2-(1-methylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.0³,⁷]tetradeca-1(14),3(7),4,10,12-pentaen-8-one

Traditional Name

ketotifen

CAS Registry Number

34580-14-8

SMILES

CN1CCC(CC1)=C1C2=C(SC=C2)C(=O)CC2=CC=CC=C12

InChI Identifier

InChI=1S/C19H19NOS/c1-20-9-6-13(7-10-20)18-15-5-3-2-4-14(15)12-17(21)19-16(18)8-11-22-19/h2-5,8,11H,6-7,9-10,12H2,1H3

InChI Key

ZCVMWBYGMWKGHF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloheptathiophenes. These are polycyclic compounds containing a thiophene ring fused to a 7 member carbocyclic moiety. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Cycloheptathiophenes

Sub Class

Not Available

Direct Parent

Cycloheptathiophenes

Alternative Parents

Substituents

Cycloheptathiophene
Aryl alkyl ketone
Aryl ketone
Piperidine
Benzenoid
Thiophene
Heteroaromatic compound
Ketone
Tertiary amine
Tertiary aliphatic amine
Azacycle
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015056)
Membrane (HMDB: HMDB0015056)

Source

Exogenous

Exogenous (HMDB: HMDB0015056)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Ketotifen H1-Antihistamine Action (PathBank: SMP0059868)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	191 °C (fumarate salt)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0079 g/L	Not Available
LogP	2.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	177.128	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000990

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0079 g/L	ALOGPS
logP	3.49	ALOGPS
logP	3.35	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	12.3	ChemAxon
pKa (Strongest Basic)	7.15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	101.73 m³·mol⁻¹	ChemAxon
Polarizability	34.61 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	172.864	31661259
DarkChem	[M-H]-	169.319	31661259
DeepCCS	[M-2H]-	202.312	30932474
DeepCCS	[M+Na]+	177.877	30932474
AllCCS	[M+H]+	172.8	32859911
AllCCS	[M+H-H2O]+	169.5	32859911
AllCCS	[M+NH4]+	175.9	32859911
AllCCS	[M+Na]+	176.8	32859911
AllCCS	[M-H]-	178.2	32859911
AllCCS	[M+Na-2H]-	177.6	32859911
AllCCS	[M+HCOO]-	177.0	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.	6.43 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6347 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.75 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1114.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	243.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	160.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	186.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	94.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	306.7 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	359.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	687.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	833.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	272.5 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	933.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	225.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	289.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	500.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	483.1 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	59.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ketotifen	CN1CCC(CC1)=C1C2=C(SC=C2)C(=O)CC2=CC=CC=C12	3818.7	Standard polar	33892256
Ketotifen	CN1CCC(CC1)=C1C2=C(SC=C2)C(=O)CC2=CC=CC=C12	2620.8	Standard non polar	33892256
Ketotifen	CN1CCC(CC1)=C1C2=C(SC=C2)C(=O)CC2=CC=CC=C12	2750.6	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 - Ketotifen GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f7k-1390000000-6db4be150fa1cfb3f6ab	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ketotifen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ketotifen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ketotifen 35V, Positive-QTOF	splash10-03dj-7029000000-c3d9a1eaad92426878c8	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketotifen 10V, Positive-QTOF	splash10-03di-1049000000-d6f913b65f74f32c4e40	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketotifen 20V, Positive-QTOF	splash10-03di-3596000000-3bf4c9440bb74daa21de	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketotifen 40V, Positive-QTOF	splash10-03xu-5590000000-eaa341611f9d8f05b26a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketotifen 10V, Negative-QTOF	splash10-0a4i-0019000000-5e8d8103685306cf139c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketotifen 20V, Negative-QTOF	splash10-0a4i-1059000000-1e72a4b45cb2dfd7ec30	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketotifen 40V, Negative-QTOF	splash10-052f-9030000000-337f8e348bb65d9aa81f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketotifen 10V, Positive-QTOF	splash10-03di-0009000000-c3dc11361445a69aa787	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketotifen 20V, Positive-QTOF	splash10-03di-0009000000-c3dc11361445a69aa787	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketotifen 40V, Positive-QTOF	splash10-11ou-3091000000-a9fe010a226e84ea6445	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketotifen 10V, Negative-QTOF	splash10-0a4i-0009000000-8fa28bced3a8b154afb3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketotifen 20V, Negative-QTOF	splash10-0a4i-0029000000-3597e359772457e300ab	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ketotifen 40V, Negative-QTOF	splash10-0a4i-0096000000-04b0eb63f2d1f82a3466	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Ketotifen H1-Antihistamine Action		Not Available

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 DB00920	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00920	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00920

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3695

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ketotifen

METLIN ID

Not Available

PubChem Compound

3827

PDB ID

Not Available

ChEBI ID

92511

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. High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in maintaining basal levels of the cyclic nucleotide and/or in the cAMP regulation of germ cell development.
Gene Name:: PDE8A
Uniprot ID:: O60658
Molecular weight:: 86047.88

References

Castillo JG, Gamboa PM, Garcia BE, Oehling A: Effect of ketotifen on phosphodiesterase activity from asthmatic individuals. Allergol Immunopathol (Madr). 1990 Jul-Aug;18(4):197-201. [PubMed:1702263 ]

Enzyme Details

2. High affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A

General function:: Involved in 3',5'-cyclic-AMP phosphodiesterase activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May have a role in muscle signal transduction.
Gene Name:: PDE7A
Uniprot ID:: Q13946
Molecular weight:: 55504.475

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

3. cAMP-specific 3',5'-cyclic phosphodiesterase 4B

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in mediating central nervous system effects of therapeutic agents ranging from antidepressants to antiasthmatic and anti-inflammatory agents.
Gene Name:: PDE4B
Uniprot ID:: Q07343
Molecular weight:: 64351.765

References

Castillo JG, Gamboa PM, Garcia BE, Oehling A: Effect of ketotifen on phosphodiesterase activity from asthmatic individuals. Allergol Immunopathol (Madr). 1990 Jul-Aug;18(4):197-201. [PubMed:1702263 ]
Huang Z, Liu S, Zhang L, Salem M, Greig GM, Chan CC, Natsumeda Y, Noguchi K: Preferential inhibition of human phosphodiesterase 4 by ibudilast. Life Sci. 2006 May 1;78(23):2663-8. Epub 2005 Nov 28. [PubMed:16313925 ]

Enzyme Details

4. cAMP-specific 3',5'-cyclic phosphodiesterase 7B

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in the control of cAMP-mediated neural activity and cAMP metabolism in the brain.
Gene Name:: PDE7B
Uniprot ID:: Q9NP56
Molecular weight:: 51834.855

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

5. High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8B

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in specific signaling in the thyroid gland.
Gene Name:: PDE8B
Uniprot ID:: O95263
Molecular weight:: 87973.225

References

Castillo JG, Gamboa PM, Garcia BE, Oehling A: Effect of ketotifen on phosphodiesterase activity from asthmatic individuals. Allergol Immunopathol (Madr). 1990 Jul-Aug;18(4):197-201. [PubMed:1702263 ]

Enzyme Details

6. cAMP-specific 3',5'-cyclic phosphodiesterase 4C

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name:: PDE4C
Uniprot ID:: Q08493
Molecular weight:: 79900.795

References

Castillo JG, Gamboa PM, Garcia BE, Oehling A: Effect of ketotifen on phosphodiesterase activity from asthmatic individuals. Allergol Immunopathol (Madr). 1990 Jul-Aug;18(4):197-201. [PubMed:1702263 ]
Huang Z, Liu S, Zhang L, Salem M, Greig GM, Chan CC, Natsumeda Y, Noguchi K: Preferential inhibition of human phosphodiesterase 4 by ibudilast. Life Sci. 2006 May 1;78(23):2663-8. Epub 2005 Nov 28. [PubMed:16313925 ]

Enzyme Details

7. cAMP-specific 3',5'-cyclic phosphodiesterase 4D

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name:: PDE4D
Uniprot ID:: Q08499
Molecular weight:: 91114.1

References

Castillo JG, Gamboa PM, Garcia BE, Oehling A: Effect of ketotifen on phosphodiesterase activity from asthmatic individuals. Allergol Immunopathol (Madr). 1990 Jul-Aug;18(4):197-201. [PubMed:1702263 ]
Huang Z, Liu S, Zhang L, Salem M, Greig GM, Chan CC, Natsumeda Y, Noguchi K: Preferential inhibition of human phosphodiesterase 4 by ibudilast. Life Sci. 2006 May 1;78(23):2663-8. Epub 2005 Nov 28. [PubMed:16313925 ]

Enzyme Details

8. cAMP-specific 3',5'-cyclic phosphodiesterase 4A

General function:: Involved in 3',5'-cyclic-nucleotide phosphodiesterase activity
Specific function:: Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
Gene Name:: PDE4A
Uniprot ID:: P27815
Molecular weight:: 98142.155

References

Castillo JG, Gamboa PM, Garcia BE, Oehling A: Effect of ketotifen on phosphodiesterase activity from asthmatic individuals. Allergol Immunopathol (Madr). 1990 Jul-Aug;18(4):197-201. [PubMed:1702263 ]
Huang Z, Liu S, Zhang L, Salem M, Greig GM, Chan CC, Natsumeda Y, Noguchi K: Preferential inhibition of human phosphodiesterase 4 by ibudilast. Life Sci. 2006 May 1;78(23):2663-8. Epub 2005 Nov 28. [PubMed:16313925 ]

Enzyme Details

9. 6-phosphogluconate dehydrogenase, decarboxylating

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative decarboxylation of 6-phosphogluconate to ribulose 5-phosphate and CO(2), with concomitant reduction of NADP to NADPH (By similarity).
Gene Name:: PGD
Uniprot ID:: P52209
Molecular weight:: 53139.56

References

Akkemik E, Budak H, Ciftci M: Effects of some drugs on human erythrocyte 6-phosphogluconate dehydrogenase: an in vitro study. J Enzyme Inhib Med Chem. 2010 Aug;25(4):476-9. doi: 10.3109/14756360903257900. [PubMed:20235752 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

10. Histamine H1 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:: HRH1
Uniprot ID:: P35367
Molecular weight:: 55783.6

References

Mita H, Shida T: Comparison of anti-allergic activities of the histamine H1 receptor antagonists epinastine, ketotifen and oxatomide in human leukocytes. Arzneimittelforschung. 1995 Jan;45(1):36-40. [PubMed:7893266 ]
Okabe S, Nakaji S, Tachibana M: Effect of ketotifen on acute gastric lesions and gastric secretion in rats. Jpn J Pharmacol. 1992 Jun;59(2):251-4. [PubMed:1434122 ]
Hashimoto T, Ohata H, Honda K: Lysophosphatidic acid (LPA) induces plasma exudation and histamine release in mice via LPA receptors. J Pharmacol Sci. 2006 Jan;100(1):82-7. Epub 2006 Jan 11. [PubMed:16404130 ]
Ito K, Sakamoto T, Hayashi Y, Morishita M, Shibata E, Sakai K, Takeuchi Y, Torii S: Role of tachykinin and bradykinin receptors and mast cells in gaseous formaldehyde-induced airway microvascular leakage in rats. Eur J Pharmacol. 1996 Jul 4;307(3):291-8. [PubMed:8836617 ]
Yokoyama H, Iinuma K, Yanai K, Watanabe T, Sakurai E, Onodera K: Proconvulsant effect of ketotifen, a histamine H1 antagonist, confirmed by the use of d-chlorpheniramine with monitoring electroencephalography. Methods Find Exp Clin Pharmacol. 1993 Apr;15(3):183-8. [PubMed:8101246 ]
Werner-Klein M, Goggel R, Westhof A, Erb KJ: Development and characterisation of a novel and rapid lung eosinophil influx model in the rat. Pulm Pharmacol Ther. 2008 Aug;21(4):648-56. doi: 10.1016/j.pupt.2008.03.002. Epub 2008 Apr 7. [PubMed:18490184 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Ketotifen (HMDB0015056)

MOL for HMDB0015056 (Ketotifen)

3D MOL for HMDB0015056 (Ketotifen)

3D SDF for HMDB0015056 (Ketotifen)

3D-SDF for HMDB0015056 (Ketotifen)

PDB for HMDB0015056 (Ketotifen)

3D PDB for HMDB0015056 (Ketotifen)

SMILES for HMDB0015056 (Ketotifen)

INCHI for HMDB0015056 (Ketotifen)

Structure for HMDB0015056 (Ketotifen)

3D Structure for HMDB0015056 (Ketotifen)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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