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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 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

HMDB0015070

Secondary Accession Numbers

HMDB15070

Metabolite Identification

Common Name

Oxymetazoline

Description

Oxymetazoline is only found in individuals that have used or taken this drug. It is a direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1251)Oxymetazoline is a direct acting sympathomimetic amine, which acts on alpha-adrenergic receptors in the arterioles of the conjunctiva and nasal mucosa. It produces vasoconstriction, resulting in decreased conjunctival congestion in ophthalmic. In nasal it produces constriction, resulting in decreased blood flow and decreased nasal congestion.

Structure

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

HMDB0015070
     RDKit          3D
Oxymetazoline
 43 44  0  0  0  0  0  0  0  0999 V2000
    0.8970   -2.6601   -0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -1.4589    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1169   -1.2693   -0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203   -0.1889    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2590    0.0351   -0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3195    1.3648   -0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6982   -1.0647   -1.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1639    0.0597    0.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2144    0.7120    1.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9461    1.8050    1.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1229    0.5066    1.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6826    1.5388    2.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8458   -0.5711    0.9218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621   -0.7229    1.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2021   -0.0770    0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1911    0.6361    0.7121 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853    1.1760   -0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4688    0.4793   -1.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2298   -0.0986   -1.1042 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1250   -3.4370   -0.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4621   -3.2204    0.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4576   -2.4553   -1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967   -1.9803   -0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3414    1.6043   -1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5514    2.1704   -0.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1282    1.3241   -1.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7467   -0.8243   -1.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0986   -1.0824   -2.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6165   -2.0621   -0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0871   -0.4664    0.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5875   -0.3554    1.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4375    1.0980    1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5875    2.5033    2.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7310    2.5249    1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0604    1.6899    3.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142    1.2879    2.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637   -0.4171    2.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765   -1.8180    1.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0712    0.9979   -0.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7728    2.2802   -0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2003   -0.3103   -1.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2920    1.1972   -2.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5018   -0.4510   -1.7312 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
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 13  2  1  0
 19 15  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
M  END

935
  Mrv0541 02231215072D          

 19 20  0  0  0  0            999 V2000
    2.0930    1.2002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3227   -2.5079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9902   -1.3519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    2.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    2.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3470    2.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6970    2.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1297   -2.6794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5422   -1.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2 15  1  0  0  0  0
  2 18  1  0  0  0  0
  3 15  2  0  0  0  0
  3 19  1  0  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  4 13  1  0  0  0  0
  5  7  2  0  0  0  0
  5 10  1  0  0  0  0
  6  8  2  0  0  0  0
  6  9  1  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  2  0  0  0  0
  9 17  1  0  0  0  0
 14 15  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015070

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H24N2O/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14/h8,19H,6-7,9H2,1-5H3,(H,17,18)

> <INCHI_KEY>
WYWIFABBXFUGLM-UHFFFAOYSA-N

> <FORMULA>
C16H24N2O

> <MOLECULAR_WEIGHT>
260.3746

> <EXACT_MASS>
260.1888634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.64030111183132

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol

> <ALOGPS_LOGP>
3.70

> <JCHEM_LOGP>
3.032315205208703

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.906928467098338

> <JCHEM_PKA_STRONGEST_BASIC>
10.149300298695183

> <JCHEM_POLAR_SURFACE_AREA>
44.62

> <JCHEM_REFRACTIVITY>
79.79849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oxymetazoline

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015070
     RDKit          3D
Oxymetazoline
 43 44  0  0  0  0  0  0  0  0999 V2000
    0.8970   -2.6601   -0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -1.4589    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1169   -1.2693   -0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203   -0.1889    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2590    0.0351   -0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3195    1.3648   -0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6982   -1.0647   -1.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1639    0.0597    0.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2144    0.7120    1.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9461    1.8050    1.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1229    0.5066    1.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6826    1.5388    2.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8458   -0.5711    0.9218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621   -0.7229    1.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2021   -0.0770    0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1911    0.6361    0.7121 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853    1.1760   -0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4688    0.4793   -1.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2298   -0.0986   -1.1042 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1250   -3.4370   -0.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4621   -3.2204    0.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4576   -2.4553   -1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967   -1.9803   -0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3414    1.6043   -1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5514    2.1704   -0.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1282    1.3241   -1.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7467   -0.8243   -1.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0986   -1.0824   -2.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6165   -2.0621   -0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0871   -0.4664    0.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5875   -0.3554    1.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4375    1.0980    1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5875    2.5033    2.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7310    2.5249    1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0604    1.6899    3.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142    1.2879    2.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637   -0.4171    2.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765   -1.8180    1.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0712    0.9979   -0.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7728    2.2802   -0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2003   -0.3103   -1.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2920    1.1972   -2.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5018   -0.4510   -1.7312 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
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 13  2  1  0
 19 15  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 935                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.907   2.240   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       8.069  -4.681   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       9.315  -2.524   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       6.574   3.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.574   2.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.574  -0.840   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.241   1.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.241  -0.070   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.908  -0.070   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.908   1.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.574   5.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.114   3.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.034   3.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.574  -2.380   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.908  -3.150   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.907  -0.840   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.242  -0.840   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.575  -5.002   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.345  -3.668   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2   15   18                                                       
CONECT    3   15   19                                                       
CONECT    4    5   11   12   13                                             
CONECT    5    4    7   10                                                  
CONECT    6    8    9   14                                                  
CONECT    7    1    5    8                                                  
CONECT    8    6    7   16                                                  
CONECT    9    6   10   17                                                  
CONECT   10    5    9                                                       
CONECT   11    4                                                            
CONECT   12    4                                                            
CONECT   13    4                                                            
CONECT   14    6   15                                                       
CONECT   15    2    3   14                                                  
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18    2   19                                                       
CONECT   19    3   18                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0015070
HETATM    1  C1  UNL     1       0.897  -2.660  -0.405  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.222  -1.459   0.086  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.117  -1.269  -0.294  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.820  -0.189   0.170  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.259   0.035  -0.234  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.320   1.365  -0.943  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.698  -1.065  -1.147  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.164   0.060   0.977  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.214   0.712   1.010  1.00  0.00           C  
HETATM   10  O1  UNL     1      -1.946   1.805   1.474  1.00  0.00           O  
HETATM   11  C10 UNL     1       0.123   0.507   1.377  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.683   1.539   2.285  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.846  -0.571   0.922  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.262  -0.723   1.259  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.202  -0.077   0.300  1.00  0.00           C  
HETATM   16  N1  UNL     1       4.191   0.636   0.712  1.00  0.00           N  
HETATM   17  C15 UNL     1       4.985   1.176  -0.352  1.00  0.00           C  
HETATM   18  C16 UNL     1       4.469   0.479  -1.584  1.00  0.00           C  
HETATM   19  N2  UNL     1       3.230  -0.099  -1.104  1.00  0.00           N  
HETATM   20  H1  UNL     1       0.125  -3.437  -0.736  1.00  0.00           H  
HETATM   21  H2  UNL     1       1.462  -3.220   0.374  1.00  0.00           H  
HETATM   22  H3  UNL     1       1.458  -2.455  -1.323  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.597  -1.980  -0.955  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.341   1.604  -1.455  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.551   2.170  -0.218  1.00  0.00           H  
HETATM   26  H7  UNL     1      -4.128   1.324  -1.728  1.00  0.00           H  
HETATM   27  H8  UNL     1      -4.747  -0.824  -1.473  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.099  -1.082  -2.084  1.00  0.00           H  
HETATM   29  H10 UNL     1      -3.617  -2.062  -0.698  1.00  0.00           H  
HETATM   30  H11 UNL     1      -5.087  -0.466   0.737  1.00  0.00           H  
HETATM   31  H12 UNL     1      -3.588  -0.355   1.825  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.437   1.098   1.274  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.588   2.503   2.078  1.00  0.00           H  
HETATM   34  H15 UNL     1       0.731   2.525   1.735  1.00  0.00           H  
HETATM   35  H16 UNL     1      -0.060   1.690   3.129  1.00  0.00           H  
HETATM   36  H17 UNL     1       1.614   1.288   2.774  1.00  0.00           H  
HETATM   37  H18 UNL     1       2.464  -0.417   2.289  1.00  0.00           H  
HETATM   38  H19 UNL     1       2.576  -1.818   1.239  1.00  0.00           H  
HETATM   39  H20 UNL     1       6.071   0.998  -0.194  1.00  0.00           H  
HETATM   40  H21 UNL     1       4.773   2.280  -0.370  1.00  0.00           H  
HETATM   41  H22 UNL     1       5.200  -0.310  -1.876  1.00  0.00           H  
HETATM   42  H23 UNL     1       4.292   1.197  -2.416  1.00  0.00           H  
HETATM   43  H24 UNL     1       2.502  -0.451  -1.731  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3   13
CONECT    3    4   23
CONECT    4    5    9    9
CONECT    5    6    7    8
CONECT    6   24   25   26
CONECT    7   27   28   29
CONECT    8   30   31   32
CONECT    9   10   11
CONECT   10   33
CONECT   11   12   13   13
CONECT   12   34   35   36
CONECT   13   14
CONECT   14   15   37   38
CONECT   15   16   16   19
CONECT   16   17
CONECT   17   18   39   40
CONECT   18   19   41   42
CONECT   19   43
END

HMDB0015070
     RDKit          3D
Oxymetazoline
 43 44  0  0  0  0  0  0  0  0999 V2000
    0.8970   -2.6601   -0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -1.4589    0.0863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1169   -1.2693   -0.2944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203   -0.1889    0.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2590    0.0351   -0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3195    1.3648   -0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6982   -1.0647   -1.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1639    0.0597    0.9774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2144    0.7120    1.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9461    1.8050    1.4735 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1229    0.5066    1.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6826    1.5388    2.2846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8458   -0.5711    0.9218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621   -0.7229    1.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2021   -0.0770    0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1911    0.6361    0.7121 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853    1.1760   -0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4688    0.4793   -1.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2298   -0.0986   -1.1042 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1250   -3.4370   -0.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4621   -3.2204    0.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4576   -2.4553   -1.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967   -1.9803   -0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3414    1.6043   -1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5514    2.1704   -0.2179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1282    1.3241   -1.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7467   -0.8243   -1.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0986   -1.0824   -2.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6165   -2.0621   -0.6978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0871   -0.4664    0.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5875   -0.3554    1.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4375    1.0980    1.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5875    2.5033    2.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7310    2.5249    1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0604    1.6899    3.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6142    1.2879    2.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637   -0.4171    2.2891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765   -1.8180    1.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0712    0.9979   -0.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7728    2.2802   -0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2003   -0.3103   -1.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2920    1.1972   -2.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5018   -0.4510   -1.7312 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
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 13  2  1  0
 19 15  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(4-Tert-butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazoline	ChEBI
3-[(4,5-Dihydro-1H-imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethylphenol	ChEBI
6-t-Butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol	ChEBI
6-Tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol	ChEBI
Oxymetazolina	ChEBI
Oxymetazolinum	ChEBI
Afrin	Kegg
Operil	Kegg
Oximetazolinum	HMDB
Oxymetazoline hydrochloride crystalline	HMDB
Oxymethazoline	HMDB
Oxymetozoline	HMDB
Hydrochloride, oxymetazoline	HMDB
Oxymetazoline hydrochloride	HMDB

Chemical Formula

C₁₆H₂₄N₂O

Average Molecular Weight

260.3746

Monoisotopic Molecular Weight

260.1888634

IUPAC Name

6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol

Traditional Name

oxymetazoline

CAS Registry Number

1491-59-4

SMILES

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

InChI Identifier

InChI=1S/C16H24N2O/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14/h8,19H,6-7,9H2,1-5H3,(H,17,18)

InChI Key

WYWIFABBXFUGLM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xylenols. These are aromatic compounds that contain a xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups, and at least one hydroxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Xylenes

Direct Parent

Xylenols

Alternative Parents

Substituents

Xylenol
Phenylpropane
M-xylene
O-cresol
P-cresol
Phenol
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
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

phenols (CHEBI:7862 )
carboxamidine (CHEBI:7862 )
imidazolines (CHEBI:7862 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	182 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.052 g/L	Not Available
LogP	3.4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	169.894	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000752

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.052 g/L	ALOGPS
logP	3.7	ALOGPS
logP	3.03	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	10.91	ChemAxon
pKa (Strongest Basic)	10.15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	44.62 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.8 m³·mol⁻¹	ChemAxon
Polarizability	30.64 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	163.783	31661259
DarkChem	[M-H]-	160.746	31661259
DeepCCS	[M+H]+	165.52	30932474
DeepCCS	[M-H]-	163.162	30932474
DeepCCS	[M-2H]-	196.048	30932474
DeepCCS	[M+Na]+	171.614	30932474
AllCCS	[M+H]+	159.7	32859911
AllCCS	[M+H-H2O]+	156.1	32859911
AllCCS	[M+NH4]+	163.1	32859911
AllCCS	[M+Na]+	164.1	32859911
AllCCS	[M-H]-	170.8	32859911
AllCCS	[M+Na-2H]-	171.1	32859911
AllCCS	[M+HCOO]-	171.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oxymetazoline	CC1=CC(=C(O)C(C)=C1CC1=NCCN1)C(C)(C)C	2892.6	Standard polar	33892256
Oxymetazoline	CC1=CC(=C(O)C(C)=C1CC1=NCCN1)C(C)(C)C	2208.5	Standard non polar	33892256
Oxymetazoline	CC1=CC(=C(O)C(C)=C1CC1=NCCN1)C(C)(C)C	2302.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Oxymetazoline,1TMS,isomer #1	CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C(C)=C1CC1=NCCN1	2273.3	Semi standard non polar	33892256
Oxymetazoline,1TMS,isomer #2	CC1=CC(C(C)(C)C)=C(O)C(C)=C1CC1=NCCN1[Si](C)(C)C	2253.1	Semi standard non polar	33892256
Oxymetazoline,2TMS,isomer #1	CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C(C)=C1CC1=NCCN1[Si](C)(C)C	2306.3	Semi standard non polar	33892256
Oxymetazoline,2TMS,isomer #1	CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C(C)=C1CC1=NCCN1[Si](C)(C)C	2353.1	Standard non polar	33892256
Oxymetazoline,2TMS,isomer #1	CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C)C(C)=C1CC1=NCCN1[Si](C)(C)C	2969.1	Standard polar	33892256
Oxymetazoline,1TBDMS,isomer #1	CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C)=C1CC1=NCCN1	2474.5	Semi standard non polar	33892256
Oxymetazoline,1TBDMS,isomer #2	CC1=CC(C(C)(C)C)=C(O)C(C)=C1CC1=NCCN1[Si](C)(C)C(C)(C)C	2501.8	Semi standard non polar	33892256
Oxymetazoline,2TBDMS,isomer #1	CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C)=C1CC1=NCCN1[Si](C)(C)C(C)(C)C	2704.2	Semi standard non polar	33892256
Oxymetazoline,2TBDMS,isomer #1	CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C)=C1CC1=NCCN1[Si](C)(C)C(C)(C)C	2790.0	Standard non polar	33892256
Oxymetazoline,2TBDMS,isomer #1	CC1=CC(C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(C)=C1CC1=NCCN1[Si](C)(C)C(C)(C)C	3097.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Oxymetazoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-004m-3970000000-ee2ec321a55bc78173e1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxymetazoline GC-MS (1 TMS) - 70eV, Positive	splash10-01di-9847000000-0444f6bbf25ec5a41405	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oxymetazoline 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 - Oxymetazoline 10V, Positive-QTOF	splash10-03di-0090000000-c488f3b0f9552a4b7dfc	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymetazoline 20V, Positive-QTOF	splash10-03di-1290000000-a18cdab404c55b4e4497	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymetazoline 40V, Positive-QTOF	splash10-0006-7960000000-1c8f2a11df7638b325df	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymetazoline 10V, Negative-QTOF	splash10-0a4i-0090000000-fd2fa239fe46b8ca41c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymetazoline 20V, Negative-QTOF	splash10-0a4i-1090000000-0e91b1578606ee50752f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymetazoline 40V, Negative-QTOF	splash10-01r6-4890000000-3e6c50f85057e4ad43d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymetazoline 10V, Positive-QTOF	splash10-03di-0190000000-d99fec2889c2b1f7a321	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymetazoline 20V, Positive-QTOF	splash10-03dr-1970000000-c0fcd30c275a95baee23	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymetazoline 40V, Positive-QTOF	splash10-0596-6910000000-b96b7ef48bcbbf6173b0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymetazoline 10V, Negative-QTOF	splash10-0a4i-0090000000-7c4aa654b272455d2904	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymetazoline 20V, Negative-QTOF	splash10-0a6r-0970000000-1e55ae3560aa333e78fa	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oxymetazoline 40V, Negative-QTOF	splash10-00ac-0930000000-4066d357ff89a3ee1206	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 DB00935	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00935	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00935

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4475

KEGG Compound ID

C07363

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oxymetazoline

METLIN ID

Not Available

PubChem Compound

4636

PDB ID

Not Available

ChEBI ID

7862

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. 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

MacKinnon AC, Kilpatrick AT, Kenny BA, Spedding M, Brown CM: [3H]-RS-15385-197, a selective and high affinity radioligand for alpha 2-adrenoceptors: implications for receptor classification. Br J Pharmacol. 1992 Aug;106(4):1011-8. [PubMed:1327384 ]
Mitrani P, Srinivasan M, Dodds C, Patel MS: Role of the autonomic nervous system in the development of hyperinsulinemia by high-carbohydrate formula feeding to neonatal rats. Am J Physiol Endocrinol Metab. 2007 Apr;292(4):E1069-78. Epub 2006 Dec 12. [PubMed:17164433 ]
Lepretre N, Mironneau J: Alpha 2-adrenoceptors activate dihydropyridine-sensitive calcium channels via Gi-proteins and protein kinase C in rat portal vein myocytes. Pflugers Arch. 1994 Dec;429(2):253-61. [PubMed:7892112 ]

Enzyme Details

2. 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 ]
Deplanne V, Galzin AM: Functional characterization of alpha-1-adrenoceptor subtypes in the prostatic urethra and trigone of male rabbit. J Pharmacol Exp Ther. 1996 Aug;278(2):527-34. [PubMed:8768700 ]
Shibata K, Taketani K: [Excitatory effect of noradrenaline on rat airway parasympathetic ganglion neurons]. Fukuoka Igaku Zasshi. 2001 Nov;92(11):377-83. [PubMed:11774707 ]
Furukawa K, Rosario DJ, Smith DJ, Chapple CR, Uchiyama T, Chess-Williams R: Alpha 1A-adrenoceptor-mediated contractile responses of the human vas deferens. Br J Pharmacol. 1995 Sep;116(1):1605-10. [PubMed:8564226 ]
Gonzalez-Espinosa C, Romero-Avila MT, Mora-Rodriguez DM, Gonzalez-Espinosa D, Garcia-Sainz JA: Molecular cloning and functional expression of the guinea pig alpha(1a)-adrenoceptor. Eur J Pharmacol. 2001 Aug 31;426(3):147-55. [PubMed:11527538 ]

Showing metabocard for Oxymetazoline (HMDB0015070)

MOL for HMDB0015070 (Oxymetazoline)

3D MOL for HMDB0015070 (Oxymetazoline)

3D SDF for HMDB0015070 (Oxymetazoline)

3D-SDF for HMDB0015070 (Oxymetazoline)

PDB for HMDB0015070 (Oxymetazoline)

3D PDB for HMDB0015070 (Oxymetazoline)

SMILES for HMDB0015070 (Oxymetazoline)

INCHI for HMDB0015070 (Oxymetazoline)

Structure for HMDB0015070 (Oxymetazoline)

3D Structure for HMDB0015070 (Oxymetazoline)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References