Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:03 UTC

HMDB ID

HMDB0015640

Secondary Accession Numbers

HMDB15640

Metabolite Identification

Common Name

Xylometazoline

Description

Xylometazoline, also known as balminil or otrivin mentol, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Xylometazoline is a very strong basic compound (based on its pKa). Xylometazoline is a direct acting sympathomimetic drug, which acts on alpha-adrenergic receptors in the arterioles of the nasal mucosa. Xylometazoline is a direct acting sympathomimetic adrenergic alpha-agonist used to induce systemic vasoconstriction, thereby decreasing nasal congestion. This activates the adrenal system to yield systemic vasoconstrction. In producing vasoconstriction, the result is a decrease in blood flow in the nasal passages and consequently decreased nasal congestion. The sympathomimetic action of xylometazoline constricts the smaller arterioles of the nasal passages, producing a prolonged (8-12 hours) decongesting effect.

Structure

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

HMDB0015640
     RDKit          3D
Xylometazoline
 42 43  0  0  0  0  0  0  0  0999 V2000
    0.9291    2.2820    0.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1383    1.0591    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1849    1.1328    0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9722    0.0227    0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3853    0.1049   -0.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5256    1.1534   -1.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8118   -1.2227   -1.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3167    0.5003    0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4414   -1.1705    0.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1225   -1.2207    0.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3694   -2.5376    1.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6864   -0.1122    0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0518   -0.1623    1.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1174   -0.1629    0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0805   -0.1324   -0.8831 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3968   -0.1565   -1.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2822    0.2827   -0.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4715   -0.2113    0.8032 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3146    3.1693    0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8149    2.2858    1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1459    2.5332   -0.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764    2.0742   -0.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5046    1.0620   -2.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5272    2.1949   -1.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7520    1.0437   -2.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9021   -1.7095   -1.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5450   -1.0766   -1.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2806   -1.8367   -0.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3297    0.5879    0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2336   -0.1647    1.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0201    1.5280    1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1002   -2.0278    0.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1988   -2.9144    0.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3940   -3.3025    1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7424   -2.4399    2.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2101   -1.1217    1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2580    0.6236    2.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6701   -1.1570   -1.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4797    0.5757   -2.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2573   -0.2213   -0.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4269    1.3639   -0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8835   -0.5189    1.7187 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  1  0
  5  6  1  0
  5  7  1  0
  5  8  1  0
  4  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 12  2  1  0
 18 14  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  6 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
M  END


  Mrv0541 02241212362D          

 18 19  0  0  0  0            999 V2000
    3.4656    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6091    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1331    0.5678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8781   -0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0531   -0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7982    0.5678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3235    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0380    3.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7360    2.8132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9110    4.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015640

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(=CC(C)=C1CC1=NCCN1)C(C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C16H24N2/c1-11-8-13(16(3,4)5)9-12(2)14(11)10-15-17-6-7-18-15/h8-9H,6-7,10H2,1-5H3,(H,17,18)

> <INCHI_KEY>
HUCJFAOMUPXHDK-UHFFFAOYSA-N

> <FORMULA>
C16H24N2

> <MOLECULAR_WEIGHT>
244.3752

> <EXACT_MASS>
244.193948778

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
29.8526573853075

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1H-imidazole

> <ALOGPS_LOGP>
4.68

> <JCHEM_LOGP>
3.7755392423333323

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.287868203701459

> <JCHEM_POLAR_SURFACE_AREA>
24.39

> <JCHEM_REFRACTIVITY>
77.81760000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.93e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xylometazoline

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015640
     RDKit          3D
Xylometazoline
 42 43  0  0  0  0  0  0  0  0999 V2000
    0.9291    2.2820    0.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1383    1.0591    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1849    1.1328    0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9722    0.0227    0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3853    0.1049   -0.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5256    1.1534   -1.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8118   -1.2227   -1.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3167    0.5003    0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4414   -1.1705    0.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1225   -1.2207    0.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3694   -2.5376    1.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6864   -0.1122    0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0518   -0.1623    1.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1174   -0.1629    0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0805   -0.1324   -0.8831 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3968   -0.1565   -1.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2822    0.2827   -0.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4715   -0.2113    0.8032 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3146    3.1693    0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8149    2.2858    1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1459    2.5332   -0.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764    2.0742   -0.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5046    1.0620   -2.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5272    2.1949   -1.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7520    1.0437   -2.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9021   -1.7095   -1.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5450   -1.0766   -1.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2806   -1.8367   -0.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3297    0.5879    0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2336   -0.1647    1.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0201    1.5280    1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1002   -2.0278    0.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1988   -2.9144    0.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3940   -3.3025    1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7424   -2.4399    2.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2101   -1.1217    1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2580    0.6236    2.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6701   -1.1570   -1.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4797    0.5757   -2.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2573   -0.2213   -0.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4269    1.3639   -0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8835   -0.5189    1.7187 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  1  0
  5  6  1  0
  5  7  1  0
  5  8  1  0
  4  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 12  2  1  0
 18 14  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  6 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       6.469   6.585   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.803   5.815   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.137   6.585   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.470   5.815   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.470   4.275   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.137   3.505   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.137   1.965   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.803   4.275   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.469   3.505   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.469   1.965   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       7.715   1.060   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       7.239  -0.405   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.699  -0.405   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.223   1.060   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      11.804   6.585   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.138   7.355   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.574   5.251   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.034   7.919   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15    4   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0015640
HETATM    1  C1  UNL     1       0.929   2.282   0.465  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.138   1.059   0.484  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.185   1.133   0.034  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.972   0.023   0.033  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.385   0.105  -0.436  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.526   1.153  -1.515  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.812  -1.223  -1.055  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.317   0.500   0.691  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.441  -1.171   0.485  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.122  -1.221   0.928  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.369  -2.538   1.393  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.686  -0.112   0.935  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.052  -0.162   1.398  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.117  -0.163   0.365  1.00  0.00           C  
HETATM   15  N1  UNL     1       3.081  -0.132  -0.883  1.00  0.00           N  
HETATM   16  C15 UNL     1       4.397  -0.157  -1.452  1.00  0.00           C  
HETATM   17  C16 UNL     1       5.282   0.283  -0.329  1.00  0.00           C  
HETATM   18  N2  UNL     1       4.472  -0.211   0.803  1.00  0.00           N  
HETATM   19  H1  UNL     1       0.315   3.169   0.820  1.00  0.00           H  
HETATM   20  H2  UNL     1       1.815   2.286   1.088  1.00  0.00           H  
HETATM   21  H3  UNL     1       1.146   2.533  -0.615  1.00  0.00           H  
HETATM   22  H4  UNL     1      -1.576   2.074  -0.313  1.00  0.00           H  
HETATM   23  H5  UNL     1      -4.505   1.062  -2.043  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.527   2.195  -1.085  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.752   1.044  -2.268  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.902  -1.710  -1.458  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.545  -1.077  -1.869  1.00  0.00           H  
HETATM   28  H10 UNL     1      -4.281  -1.837  -0.267  1.00  0.00           H  
HETATM   29  H11 UNL     1      -5.330   0.588   0.281  1.00  0.00           H  
HETATM   30  H12 UNL     1      -4.234  -0.165   1.567  1.00  0.00           H  
HETATM   31  H13 UNL     1      -4.020   1.528   1.021  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.100  -2.028   0.467  1.00  0.00           H  
HETATM   33  H15 UNL     1       1.199  -2.914   0.713  1.00  0.00           H  
HETATM   34  H16 UNL     1      -0.394  -3.303   1.400  1.00  0.00           H  
HETATM   35  H17 UNL     1       0.742  -2.440   2.444  1.00  0.00           H  
HETATM   36  H18 UNL     1       2.210  -1.122   1.973  1.00  0.00           H  
HETATM   37  H19 UNL     1       2.258   0.624   2.171  1.00  0.00           H  
HETATM   38  H20 UNL     1       4.670  -1.157  -1.849  1.00  0.00           H  
HETATM   39  H21 UNL     1       4.480   0.576  -2.300  1.00  0.00           H  
HETATM   40  H22 UNL     1       6.257  -0.221  -0.286  1.00  0.00           H  
HETATM   41  H23 UNL     1       5.427   1.364  -0.228  1.00  0.00           H  
HETATM   42  H24 UNL     1       4.883  -0.519   1.719  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   12
CONECT    3    4   22
CONECT    4    5    9    9
CONECT    5    6    7    8
CONECT    6   23   24   25
CONECT    7   26   27   28
CONECT    8   29   30   31
CONECT    9   10   32
CONECT   10   11   12   12
CONECT   11   33   34   35
CONECT   12   13
CONECT   13   14   36   37
CONECT   14   15   15   18
CONECT   15   16
CONECT   16   17   38   39
CONECT   17   18   40   41
CONECT   18   42
END

HMDB0015640
     RDKit          3D
Xylometazoline
 42 43  0  0  0  0  0  0  0  0999 V2000
    0.9291    2.2820    0.4651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1383    1.0591    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1849    1.1328    0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9722    0.0227    0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3853    0.1049   -0.4361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5256    1.1534   -1.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8118   -1.2227   -1.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3167    0.5003    0.6906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4414   -1.1705    0.4849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1225   -1.2207    0.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3694   -2.5376    1.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6864   -0.1122    0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0518   -0.1623    1.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1174   -0.1629    0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0805   -0.1324   -0.8831 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3968   -0.1565   -1.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2822    0.2827   -0.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4715   -0.2113    0.8032 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3146    3.1693    0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8149    2.2858    1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1459    2.5332   -0.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764    2.0742   -0.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5046    1.0620   -2.0434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5272    2.1949   -1.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7520    1.0437   -2.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9021   -1.7095   -1.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5450   -1.0766   -1.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2806   -1.8367   -0.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3297    0.5879    0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2336   -0.1647    1.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0201    1.5280    1.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1002   -2.0278    0.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1988   -2.9144    0.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3940   -3.3025    1.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7424   -2.4399    2.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2101   -1.1217    1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2580    0.6236    2.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6701   -1.1570   -1.8488 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4797    0.5757   -2.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2573   -0.2213   -0.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4269    1.3639   -0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8835   -0.5189    1.7187 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  1  0
  5  6  1  0
  5  7  1  0
  5  8  1  0
  4  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 12  2  1  0
 18 14  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  6 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Balminil	Kegg
Xylomethazoline	HMDB
Amidrin	HMDB
Decongest	HMDB
Gelonasal	HMDB
NasenGel ratiopharm	HMDB
NasenSpray ratiopharm	HMDB
Nasengel al	HMDB
Rapako	HMDB
2-(4'-Tert-butyl-2',6'-dimethylphenylmethyl)imidazoline	HMDB
Balkis	HMDB
Chlorohist-la	HMDB
NasenTropfen ratiopharm	HMDB
Nasenspray al	HMDB
Nasentropfen al	HMDB
Otraspray	HMDB
Otrivin mentol	HMDB
Xylometazoline monohydrochloride	HMDB
Idril N	HMDB
Nasan	HMDB
Stas	HMDB
Idasal	HMDB
Imidin	HMDB
Novorin	HMDB
Otradrops	HMDB
Otriven	HMDB
Otrivin	HMDB
Snup	HMDB
Espa-rhin	HMDB
Schnupfen endrine	HMDB
Xylometazoline hydrochloride	HMDB

Chemical Formula

C₁₆H₂₄N₂

Average Molecular Weight

244.3752

Monoisotopic Molecular Weight

244.193948778

IUPAC Name

2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1H-imidazole

Traditional Name

xylometazoline

CAS Registry Number

526-36-3

SMILES

CC1=CC(=CC(C)=C1CC1=NCCN1)C(C)(C)C

InChI Identifier

InChI=1S/C16H24N2/c1-11-8-13(16(3,4)5)9-12(2)14(11)10-15-17-6-7-18-15/h8-9H,6-7,10H2,1-5H3,(H,17,18)

InChI Key

HUCJFAOMUPXHDK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
M-xylene
Xylene
Imidolactam
2-imidazoline
Amidine
Carboxylic acid amidine
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Organic nitrogen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

alkylbenzene (CHEBI:10082 )

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

Membrane (HMDB: HMDB0015640)
Extracellular (HMDB: HMDB0015640)

Source

Exogenous

Exogenous (HMDB: HMDB0015640)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	131 - 133 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	3.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	170.4	30932474
[M+H]+	Not Available	168.905	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000797

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0089 g/L	ALOGPS
logP	4.68	ALOGPS
logP	3.78	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	10.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	24.39 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	77.82 m³·mol⁻¹	ChemAxon
Polarizability	29.85 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]+	158.756	31661259
DarkChem	[M-H]-	157.855	31661259
DeepCCS	[M+H]+	164.186	30932474
DeepCCS	[M-H]-	161.828	30932474
DeepCCS	[M-2H]-	194.714	30932474
DeepCCS	[M+Na]+	170.279	30932474
AllCCS	[M+H]+	155.6	32859911
AllCCS	[M+H-H2O]+	151.8	32859911
AllCCS	[M+NH4]+	159.1	32859911
AllCCS	[M+Na]+	160.1	32859911
AllCCS	[M-H]-	168.0	32859911
AllCCS	[M+Na-2H]-	168.2	32859911
AllCCS	[M+HCOO]-	168.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.95 minutes	32390414
Predicted by Siyang on May 30, 2022	14.2896 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.42 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1779.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	377.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	191.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	124.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	596.5 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	554.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	68.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1124.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	546.2 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	1527.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	346.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	356.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	221.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	145.1 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	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Xylometazoline	CC1=CC(=CC(C)=C1CC1=NCCN1)C(C)(C)C	2618.5	Standard polar	33892256
Xylometazoline	CC1=CC(=CC(C)=C1CC1=NCCN1)C(C)(C)C	2114.8	Standard non polar	33892256
Xylometazoline	CC1=CC(=CC(C)=C1CC1=NCCN1)C(C)(C)C	2062.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Xylometazoline,1TMS,isomer #1	CC1=CC(C(C)(C)C)=CC(C)=C1CC1=NCCN1[Si](C)(C)C	2075.9	Semi standard non polar	33892256
Xylometazoline,1TMS,isomer #1	CC1=CC(C(C)(C)C)=CC(C)=C1CC1=NCCN1[Si](C)(C)C	2170.5	Standard non polar	33892256
Xylometazoline,1TMS,isomer #1	CC1=CC(C(C)(C)C)=CC(C)=C1CC1=NCCN1[Si](C)(C)C	2804.5	Standard polar	33892256
Xylometazoline,1TBDMS,isomer #1	CC1=CC(C(C)(C)C)=CC(C)=C1CC1=NCCN1[Si](C)(C)C(C)(C)C	2320.1	Semi standard non polar	33892256
Xylometazoline,1TBDMS,isomer #1	CC1=CC(C(C)(C)C)=CC(C)=C1CC1=NCCN1[Si](C)(C)C(C)(C)C	2390.1	Standard non polar	33892256
Xylometazoline,1TBDMS,isomer #1	CC1=CC(C(C)(C)C)=CC(C)=C1CC1=NCCN1[Si](C)(C)C(C)(C)C	2880.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Xylometazoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-05r0-3920000000-c6f0d063c06a4d3ad4d3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xylometazoline 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 - Xylometazoline LC-ESI-QFT , positive-QTOF	splash10-0002-0090000000-c862fcdd09df2d7e84e1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xylometazoline LC-ESI-QFT , positive-QTOF	splash10-0002-0090000000-8a168e444e92aebe729e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xylometazoline LC-ESI-QFT , positive-QTOF	splash10-0002-0190000000-fea379e1a78158c80c57	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xylometazoline LC-ESI-QFT , positive-QTOF	splash10-0002-0490000000-f84be52191db834c336a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xylometazoline LC-ESI-QFT , positive-QTOF	splash10-01s2-1950000000-6ff7d495e9ab66e5291e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xylometazoline LC-ESI-QFT , positive-QTOF	splash10-01ta-1920000000-4fa30a0ba8151f6081f3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xylometazoline 60V, Positive-QTOF	splash10-0002-0390000000-2ef059d0a92ce18944a6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xylometazoline 30V, Positive-QTOF	splash10-0002-0090000000-27ac258267a8ed06cd5d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xylometazoline 45V, Positive-QTOF	splash10-0002-0190000000-1459715c2022eefa3053	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xylometazoline 15V, Positive-QTOF	splash10-0002-0090000000-b599ca261106b80298e7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xylometazoline 75V, Positive-QTOF	splash10-01s2-0950000000-0eed72f909e9ba78cb5a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Xylometazoline 90V, Positive-QTOF	splash10-01ta-1920000000-b4237c6d9bf543a96f83	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xylometazoline 10V, Positive-QTOF	splash10-0002-0190000000-060c2ca9dfe2d240b99e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xylometazoline 20V, Positive-QTOF	splash10-0002-2590000000-a8065812eb0874b9f1af	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xylometazoline 40V, Positive-QTOF	splash10-004l-6930000000-217f14ab6f9450f30df2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xylometazoline 10V, Negative-QTOF	splash10-0006-0090000000-4562776c5453eb7a749b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xylometazoline 20V, Negative-QTOF	splash10-0006-1090000000-ca34d5dc761b0014453c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xylometazoline 40V, Negative-QTOF	splash10-01ta-2930000000-18d8456eb2b8ab553c53	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xylometazoline 10V, Positive-QTOF	splash10-0002-0790000000-dcb6bf9ab3f9e57d62bf	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xylometazoline 20V, Positive-QTOF	splash10-00kk-3940000000-ad26459aa78779495115	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xylometazoline 40V, Positive-QTOF	splash10-014l-4910000000-df3cd18b2754e24a0493	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xylometazoline 10V, Negative-QTOF	splash10-0006-0090000000-b1c2a723e2fe9424a6bb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xylometazoline 20V, Negative-QTOF	splash10-03dl-0940000000-f5976550a896bd4a10fd	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xylometazoline 40V, Negative-QTOF	splash10-0a7i-3960000000-3dcb00e79db17608bd7a	2021-10-11	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 DB06694	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06694	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06694

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5507

KEGG Compound ID

C07913

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Xylometazoline

METLIN ID

Not Available

PubChem Compound

5709

PDB ID

Not Available

ChEBI ID

214810

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

Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735 ]

Enzymes

Enzyme Details

1. Alpha-2A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:: ADRA2A
Uniprot ID:: P08913
Molecular weight:: 48956.3

References

Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735 ]
Petrusewicz J, Kaliszan R: Effect of imidazoline drugs on human blood platelet aggregation. Thromb Haemost. 1985 Dec 17;54(4):784-7. [PubMed:2868542 ]

Enzyme Details

2. Alpha-2B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:: ADRA2B
Uniprot ID:: P18089
Molecular weight:: 49953.1

References

Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735 ]

Enzyme Details

3. Alpha-1A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular weight:: 51486.0

References

Yang HT, Endoh M: (+/-)-tamsulosin, an alpha 1A-adrenoceptor antagonist, inhibits the positive inotropic effect but not the accumulation of inositol phosphates in rabbit heart. Eur J Pharmacol. 1996 Oct 3;312(3):281-91. [PubMed:8894610 ]
Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735 ]

Enzyme Details

4. Alpha-1B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:: ADRA1B
Uniprot ID:: P35368
Molecular weight:: 56835.4

References

Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735 ]

Enzyme Details

5. Alpha-1D adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium
Gene Name:: ADRA1D
Uniprot ID:: P25100
Molecular weight:: 60462.2

References

Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735 ]

Enzyme Details

6. Alpha-2C adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins
Gene Name:: ADRA2C
Uniprot ID:: P18825
Molecular weight:: 49521.6

References

Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735 ]

Showing metabocard for Xylometazoline (HMDB0015640)

MOL for HMDB0015640 (Xylometazoline)

3D MOL for HMDB0015640 (Xylometazoline)

3D SDF for HMDB0015640 (Xylometazoline)

3D-SDF for HMDB0015640 (Xylometazoline)

PDB for HMDB0015640 (Xylometazoline)

3D PDB for HMDB0015640 (Xylometazoline)

SMILES for HMDB0015640 (Xylometazoline)

INCHI for HMDB0015640 (Xylometazoline)

Structure for HMDB0015640 (Xylometazoline)

3D Structure for HMDB0015640 (Xylometazoline)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References