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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:05 UTC

HMDB ID

HMDB0015693

Secondary Accession Numbers

HMDB15693

Metabolite Identification

Common Name

Tymazoline

Description

Tymazoline is only found in individuals that have used or taken this drug. It is a nasal preparation.Thymazen causes vasoconstriction of the nasal mucosa, reducing congestion and thus the swelling of the mucosa. Also reduces the secretions from the nose. Thymazen acts on alpha-adrenergic receptors, which reduces local inflammation of the nasal mucosa especially if their cause is an allergy.

Structure

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

HMDB0015693
     RDKit          3D
Tymazoline
 37 38  0  0  0  0  0  0  0  0999 V2000
   -2.5272    3.6792    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2577    2.2430    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396    1.3226   -0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9987   -0.0511   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6612   -0.4831   -0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023   -1.9299   -0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2291   -2.5665   -1.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1519   -2.4750    0.9780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6517    0.4291   -0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6335   -0.0094    0.0257 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6684    0.9699    0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0239    0.3562    0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6393   -0.2773   -0.6928 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9431   -0.7168   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8923   -0.5522    1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8665    0.4381    1.4068 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9428    1.7787    0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7250    4.1835    0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4825    3.7278    0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6691    4.2396   -0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2502    1.6754   -0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8461   -0.6983   -0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4149   -2.2550   -0.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3335   -3.6353   -1.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1493   -2.0419   -1.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495   -2.5017   -2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5262   -2.4911    1.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863   -1.9419    1.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4419   -3.5598    0.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625    1.5782    1.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6263    1.6396   -0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7502   -0.0938   -0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0788   -1.7775   -0.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4880   -1.5035    1.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8480   -0.2707    1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7425    1.0987    2.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1263    2.4723    0.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  9 17  2  0
 17  2  1  0
 16 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
M  END

34154
  Mrv0541 02241214202D          

 17 18  0  0  0  0            999 V2000
    3.7935   -0.0160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8405    1.7065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1754    1.7065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 12  1  0  0  0  0
  2  7  1  0  0  0  0
  2 10  1  0  0  0  0
  3  7  2  0  0  0  0
  3 13  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  2  0  0  0  0
  5 11  1  0  0  0  0
  6 14  1  0  0  0  0
  7 12  1  0  0  0  0
 10 13  1  0  0  0  0
 11 16  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015693

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=C(OCC2=NCCN2)C=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H20N2O/c1-10(2)12-5-4-11(3)8-13(12)17-9-14-15-6-7-16-14/h4-5,8,10H,6-7,9H2,1-3H3,(H,15,16)

> <INCHI_KEY>
QRORCRWSRPKEHR-UHFFFAOYSA-N

> <FORMULA>
C14H20N2O

> <MOLECULAR_WEIGHT>
232.3214

> <EXACT_MASS>
232.157563272

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.2930740730135

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[5-methyl-2-(propan-2-yl)phenoxymethyl]-4,5-dihydro-1H-imidazole

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
2.6446344863333335

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.658453260346002

> <JCHEM_POLAR_SURFACE_AREA>
33.62

> <JCHEM_REFRACTIVITY>
69.5415

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tymazoline

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015693
     RDKit          3D
Tymazoline
 37 38  0  0  0  0  0  0  0  0999 V2000
   -2.5272    3.6792    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2577    2.2430    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396    1.3226   -0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9987   -0.0511   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6612   -0.4831   -0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023   -1.9299   -0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2291   -2.5665   -1.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1519   -2.4750    0.9780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6517    0.4291   -0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6335   -0.0094    0.0257 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6684    0.9699    0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0239    0.3562    0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6393   -0.2773   -0.6928 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9431   -0.7168   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8923   -0.5522    1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8665    0.4381    1.4068 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9428    1.7787    0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7250    4.1835    0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4825    3.7278    0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6691    4.2396   -0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2502    1.6754   -0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8461   -0.6983   -0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4149   -2.2550   -0.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3335   -3.6353   -1.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1493   -2.0419   -1.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495   -2.5017   -2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5262   -2.4911    1.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863   -1.9419    1.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4419   -3.5598    0.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625    1.5782    1.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6263    1.6396   -0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7502   -0.0938   -0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0788   -1.7775   -0.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4880   -1.5035    1.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8480   -0.2707    1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7425    1.0987    2.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1263    2.4723    0.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  9 17  2  0
 17  2  1  0
 16 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 34154                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       7.081  -0.030   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       7.169   3.185   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       9.661   3.185   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.414  -1.570   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.747  -2.340   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081  -1.570   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415   2.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080  -2.340   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -0.030   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.645   4.650   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.747  -3.880   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415   0.740   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.185   4.650   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415  -2.340   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.415  -3.880   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081  -4.650   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748  -4.650   0.000  0.00  0.00           C+0
CONECT    1    6   12                                                       
CONECT    2    7   10                                                       
CONECT    3    7   13                                                       
CONECT    4    5    8    9                                                  
CONECT    5    4    6   11                                                  
CONECT    6    1    5   14                                                  
CONECT    7    2    3   12                                                  
CONECT    8    4                                                            
CONECT    9    4                                                            
CONECT   10    2   13                                                       
CONECT   11    5   16                                                       
CONECT   12    1    7                                                       
CONECT   13    3   10                                                       
CONECT   14    6   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   11   15                                                       
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0015693
HETATM    1  C1  UNL     1      -2.527   3.679   0.298  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.258   2.243   0.100  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.240   1.323  -0.112  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.999  -0.051  -0.285  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.661  -0.483  -0.240  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.402  -1.930  -0.287  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.229  -2.567  -1.460  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.152  -2.475   0.978  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.652   0.429  -0.025  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.634  -0.009   0.026  1.00  0.00           O  
HETATM   11  C10 UNL     1       1.668   0.970   0.204  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.024   0.356   0.228  1.00  0.00           C  
HETATM   13  N1  UNL     1       3.639  -0.277  -0.693  1.00  0.00           N  
HETATM   14  C12 UNL     1       4.943  -0.717  -0.258  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.892  -0.552   1.238  1.00  0.00           C  
HETATM   16  N2  UNL     1       3.866   0.438   1.407  1.00  0.00           N  
HETATM   17  C14 UNL     1      -0.943   1.779   0.143  1.00  0.00           C  
HETATM   18  H1  UNL     1      -1.725   4.184   0.883  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.482   3.728   0.888  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.669   4.240  -0.639  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.250   1.675  -0.142  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.846  -0.698  -0.456  1.00  0.00           H  
HETATM   23  H6  UNL     1      -0.415  -2.255  -0.302  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.334  -3.635  -1.227  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.149  -2.042  -1.590  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.550  -2.502  -2.349  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.526  -2.491   1.870  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.086  -1.942   1.119  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.442  -3.560   0.747  1.00  0.00           H  
HETATM   30  H13 UNL     1       1.462   1.578   1.091  1.00  0.00           H  
HETATM   31  H14 UNL     1       1.626   1.640  -0.731  1.00  0.00           H  
HETATM   32  H15 UNL     1       5.750  -0.094  -0.705  1.00  0.00           H  
HETATM   33  H16 UNL     1       5.079  -1.778  -0.550  1.00  0.00           H  
HETATM   34  H17 UNL     1       4.488  -1.504   1.663  1.00  0.00           H  
HETATM   35  H18 UNL     1       5.848  -0.271   1.703  1.00  0.00           H  
HETATM   36  H19 UNL     1       3.743   1.099   2.221  1.00  0.00           H  
HETATM   37  H20 UNL     1      -0.126   2.472   0.315  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   17
CONECT    3    4   21
CONECT    4    5    5   22
CONECT    5    6    9
CONECT    6    7    8   23
CONECT    7   24   25   26
CONECT    8   27   28   29
CONECT    9   10   17   17
CONECT   10   11
CONECT   11   12   30   31
CONECT   12   13   13   16
CONECT   13   14
CONECT   14   15   32   33
CONECT   15   16   34   35
CONECT   16   36
CONECT   17   37
END

HMDB0015693
     RDKit          3D
Tymazoline
 37 38  0  0  0  0  0  0  0  0999 V2000
   -2.5272    3.6792    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2577    2.2430    0.1001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396    1.3226   -0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9987   -0.0511   -0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6612   -0.4831   -0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4023   -1.9299   -0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2291   -2.5665   -1.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1519   -2.4750    0.9780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6517    0.4291   -0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6335   -0.0094    0.0257 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6684    0.9699    0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0239    0.3562    0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6393   -0.2773   -0.6928 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9431   -0.7168   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8923   -0.5522    1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8665    0.4381    1.4068 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9428    1.7787    0.1428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7250    4.1835    0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4825    3.7278    0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6691    4.2396   -0.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2502    1.6754   -0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8461   -0.6983   -0.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4149   -2.2550   -0.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3335   -3.6353   -1.2272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1493   -2.0419   -1.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495   -2.5017   -2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5262   -2.4911    1.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863   -1.9419    1.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4419   -3.5598    0.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625    1.5782    1.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6263    1.6396   -0.7307 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7502   -0.0938   -0.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0788   -1.7775   -0.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4880   -1.5035    1.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8480   -0.2707    1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7425    1.0987    2.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1263    2.4723    0.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  9 17  2  0
 17  2  1  0
 16 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Thymazen	Kegg
Pernazene	HMDB

Chemical Formula

C₁₄H₂₀N₂O

Average Molecular Weight

232.3214

Monoisotopic Molecular Weight

232.157563272

IUPAC Name

2-[5-methyl-2-(propan-2-yl)phenoxymethyl]-4,5-dihydro-1H-imidazole

Traditional Name

tymazoline

CAS Registry Number

24243-97-8

SMILES

CC(C)C1=C(OCC2=NCCN2)C=C(C)C=C1

InChI Identifier

InChI=1S/C14H20N2O/c1-10(2)12-5-4-11(3)8-13(12)17-9-14-15-6-7-16-14/h4-5,8,10H,6-7,9H2,1-3H3,(H,15,16)

InChI Key

QRORCRWSRPKEHR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

P-cymene
Aromatic monoterpenoid
Monocyclic monoterpenoid
Cumene
Phenylpropane
Phenoxy compound
Phenol ether
Alkyl aryl ether
Toluene
Monocyclic benzene moiety
Imidolactam
Benzenoid
2-imidazoline
Azacycle
Organoheterocyclic compound
Carboxylic acid amidine
Organic 1,3-dipolar compound
Ether
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Amidine
Organopnictogen compound
Hydrocarbon derivative
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015693)
Membrane (HMDB: HMDB0015693)

Source

Exogenous

Exogenous (HMDB: HMDB0015693)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	3.2	ALOGPS
logP	2.64	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	7.66	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	33.62 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.54 m³·mol⁻¹	ChemAxon
Polarizability	27.29 Å³	ChemAxon
Number of Rings	2	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]+	155.254	31661259
DarkChem	[M-H]-	154.527	31661259
DeepCCS	[M+H]+	158.181	30932474
DeepCCS	[M-H]-	155.823	30932474
DeepCCS	[M-2H]-	188.772	30932474
DeepCCS	[M+Na]+	164.274	30932474
AllCCS	[M+H]+	151.4	32859911
AllCCS	[M+H-H2O]+	147.3	32859911
AllCCS	[M+NH4]+	155.1	32859911
AllCCS	[M+Na]+	156.2	32859911
AllCCS	[M-H]-	160.3	32859911
AllCCS	[M+Na-2H]-	160.6	32859911
AllCCS	[M+HCOO]-	161.0	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.	2.26 minutes	32390414
Predicted by Siyang on May 30, 2022	12.9336 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.55 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1566.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	334.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	164.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	191.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	127.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	532.4 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	508.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	65.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1042.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	454.1 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	1415.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	332.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	364.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	261.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	122.3 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	7.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tymazoline	CC(C)C1=C(OCC2=NCCN2)C=C(C)C=C1	2652.2	Standard polar	33892256
Tymazoline	CC(C)C1=C(OCC2=NCCN2)C=C(C)C=C1	1869.7	Standard non polar	33892256
Tymazoline	CC(C)C1=C(OCC2=NCCN2)C=C(C)C=C1	1984.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tymazoline,1TMS,isomer #1	CC1=CC=C(C(C)C)C(OCC2=NCCN2[Si](C)(C)C)=C1	2082.0	Semi standard non polar	33892256
Tymazoline,1TMS,isomer #1	CC1=CC=C(C(C)C)C(OCC2=NCCN2[Si](C)(C)C)=C1	2053.7	Standard non polar	33892256
Tymazoline,1TMS,isomer #1	CC1=CC=C(C(C)C)C(OCC2=NCCN2[Si](C)(C)C)=C1	2949.9	Standard polar	33892256
Tymazoline,1TBDMS,isomer #1	CC1=CC=C(C(C)C)C(OCC2=NCCN2[Si](C)(C)C(C)(C)C)=C1	2281.0	Semi standard non polar	33892256
Tymazoline,1TBDMS,isomer #1	CC1=CC=C(C(C)C)C(OCC2=NCCN2[Si](C)(C)C(C)(C)C)=C1	2261.1	Standard non polar	33892256
Tymazoline,1TBDMS,isomer #1	CC1=CC=C(C(C)C)C(OCC2=NCCN2[Si](C)(C)C(C)(C)C)=C1	3033.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tymazoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-3920000000-92ae3f5b46aa597e21f7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tymazoline 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tymazoline 10V, Positive-QTOF	splash10-001i-1290000000-db5a9ec8541b185b8f11	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tymazoline 20V, Positive-QTOF	splash10-001i-8950000000-93a7c77f6f3db3f505bd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tymazoline 40V, Positive-QTOF	splash10-001l-9500000000-ade52867ef4d41e260ca	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tymazoline 10V, Negative-QTOF	splash10-001i-1390000000-25a5b325a1082ed95600	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tymazoline 20V, Negative-QTOF	splash10-0002-1920000000-46d28863dbeb1857d495	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tymazoline 40V, Negative-QTOF	splash10-000t-2900000000-a9965e8cefe865670c57	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tymazoline 10V, Positive-QTOF	splash10-001i-7190000000-887e86891df0299deaca	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tymazoline 20V, Positive-QTOF	splash10-001i-9540000000-194245d58eec3c4ac3d9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tymazoline 40V, Positive-QTOF	splash10-0a4l-9100000000-0e0527fe683390be3525	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tymazoline 10V, Negative-QTOF	splash10-001j-0590000000-cbe0bd2ee0e13aca4417	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tymazoline 20V, Negative-QTOF	splash10-001i-8930000000-9c2049d7051d4c60723b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tymazoline 40V, Negative-QTOF	splash10-000y-6900000000-3d9299fe67b6e0633cd3	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB08803	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB08803	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08803

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

31478

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tymazoline

METLIN ID

Not Available

PubChem Compound

34154

PDB ID

Not Available

ChEBI ID

Not Available

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

Levrier J, Molon-Noblot S, Duval D, Lloyd KG: A new ex vivo method for the study of nasal drops on ciliary function. Fundam Clin Pharmacol. 1989;3(5):471-82. [PubMed:2481638 ]
Lorino AM, Lofaso F, Drogou I, Abi-Nader F, Dahan E, Coste A, Lorino H: Effects of different mechanical treatments on nasal resistance assessed by rhinometry. Chest. 1998 Jul;114(1):166-70. [PubMed:9674465 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Tymazoline (HMDB0015693)

MOL for HMDB0015693 (Tymazoline)

3D MOL for HMDB0015693 (Tymazoline)

3D SDF for HMDB0015693 (Tymazoline)

3D-SDF for HMDB0015693 (Tymazoline)

PDB for HMDB0015693 (Tymazoline)

3D PDB for HMDB0015693 (Tymazoline)

SMILES for HMDB0015693 (Tymazoline)

INCHI for HMDB0015693 (Tymazoline)

Structure for HMDB0015693 (Tymazoline)

3D Structure for HMDB0015693 (Tymazoline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra