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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 15:16:52 UTC

Update Date

2023-02-21 17:18:33 UTC

HMDB ID

HMDB0015656

Secondary Accession Numbers

HMDB15656

Metabolite Identification

Common Name

Naphazoline

Description

Naphazoline is only found in individuals that have used or taken this drug. It is a rapid acting sympathomimetic vasoconstrictor of occular artierioles. It acts to decrease congestion of the conjunctiva and is found in many over-the-counter eye drops.Naphazoline is a direct acting sympathomimetic drug, which acts on alpha-adrenergic receptors in the arterioles of the nasal mucosa. 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 vasoconstriction means that there is less pressure in the capillaries and less water can filter out, thus less discharge is made.

Structure

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

HMDB0015656
     RDKit          3D
Naphazoline
 30 32  0  0  0  0  0  0  0  0999 V2000
   -3.0979    1.9704    0.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8571    2.1456    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9473    1.1146    0.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2892   -0.1006    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3932   -1.1452    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.0064    0.9328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8941   -0.2485    0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6757    0.2782   -1.0969 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8574    0.9296   -1.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373    0.9131   -0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -0.0147    0.4562 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7802   -2.3396   -0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9972   -2.5485   -0.8243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8914   -1.4992   -0.8480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5476   -0.2816   -0.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4387    0.7545   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8088    2.7656    0.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6372    3.1346    1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0016    1.2838    1.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3984   -2.0198    1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8833   -0.5596    1.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6682    1.9502   -1.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3184    0.3099   -2.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0496    1.9022   -0.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8370    0.4798   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7365   -0.4231    1.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919   -3.1936   -0.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3005   -3.4918   -1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8626   -1.6380   -1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4033    0.5780   -0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  5 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16  1  1  0
 15  4  1  0
 11  7  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  6 20  1  0
  6 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
M  END

Structure #1
  Mrv0541 02241212482D          

 16 18  0  0  0  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0366    4.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4491    3.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2296    4.5330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8971    3.3769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  4  1  0  0  0  0
  2  7  1  0  0  0  0
  3  5  2  0  0  0  0
  3  6  1  0  0  0  0
  4 11  2  0  0  0  0
  5 11  1  0  0  0  0
  6 12  2  0  0  0  0
  7 13  2  0  0  0  0
  8  9  1  0  0  0  0
  8 15  1  0  0  0  0
  9 16  1  0  0  0  0
 10 12  1  0  0  0  0
 10 14  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015656

> <DATABASE_NAME>
hmdb

> <SMILES>
C(C1=NCCN1)C1=CC=CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C14H14N2/c1-2-7-13-11(4-1)5-3-6-12(13)10-14-15-8-9-16-14/h1-7H,8-10H2,(H,15,16)

> <INCHI_KEY>
CNIIGCLFLJGOGP-UHFFFAOYSA-N

> <FORMULA>
C14H14N2

> <MOLECULAR_WEIGHT>
210.2744

> <EXACT_MASS>
210.115698458

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.773655206812087

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
2.1931169496666665

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.190926808201356

> <JCHEM_POLAR_SURFACE_AREA>
24.39

> <JCHEM_REFRACTIVITY>
65.51950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
naphazoline

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015656
     RDKit          3D
Naphazoline
 30 32  0  0  0  0  0  0  0  0999 V2000
   -3.0979    1.9704    0.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8571    2.1456    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9473    1.1146    0.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2892   -0.1006    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3932   -1.1452    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.0064    0.9328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8941   -0.2485    0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6757    0.2782   -1.0969 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8574    0.9296   -1.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373    0.9131   -0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -0.0147    0.4562 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7802   -2.3396   -0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9972   -2.5485   -0.8243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8914   -1.4992   -0.8480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5476   -0.2816   -0.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4387    0.7545   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8088    2.7656    0.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6372    3.1346    1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0016    1.2838    1.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3984   -2.0198    1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8833   -0.5596    1.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6682    1.9502   -1.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3184    0.3099   -2.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0496    1.9022   -0.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8370    0.4798   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7365   -0.4231    1.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919   -3.1936   -0.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3005   -3.4918   -1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8626   -1.6380   -1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4033    0.5780   -0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  5 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16  1  1  0
 15  4  1  0
 11  7  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  6 20  1  0
  6 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.668   8.782   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.438   7.448   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.162   8.462   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       5.408   6.304   0.000  0.00  0.00           N+0
CONECT    1    2    4                                                       
CONECT    2    1    7                                                       
CONECT    3    5    6                                                       
CONECT    4    1   11                                                       
CONECT    5    3   11                                                       
CONECT    6    3   12                                                       
CONECT    7    2   13                                                       
CONECT    8    9   15                                                       
CONECT    9    8   16                                                       
CONECT   10   12   14                                                       
CONECT   11    4    5   13                                                  
CONECT   12    6   10   13                                                  
CONECT   13    7   11   12                                                  
CONECT   14   10   15   16                                                  
CONECT   15    8   14                                                       
CONECT   16    9   14                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0015656
HETATM    1  C1  UNL     1      -3.098   1.970   0.236  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.857   2.146   0.817  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.947   1.115   0.852  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.289  -0.101   0.298  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.393  -1.145   0.324  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.946  -1.006   0.933  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.894  -0.248   0.062  1.00  0.00           C  
HETATM    8  N1  UNL     1       1.676   0.278  -1.097  1.00  0.00           N  
HETATM    9  C8  UNL     1       2.857   0.930  -1.615  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.837   0.913  -0.482  1.00  0.00           C  
HETATM   11  N2  UNL     1       3.241  -0.015   0.456  1.00  0.00           N  
HETATM   12  C10 UNL     1      -0.780  -2.340  -0.241  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.997  -2.549  -0.824  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.891  -1.499  -0.848  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.548  -0.282  -0.293  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.439   0.754  -0.319  1.00  0.00           C  
HETATM   17  H1  UNL     1      -3.809   2.766   0.205  1.00  0.00           H  
HETATM   18  H2  UNL     1      -1.637   3.135   1.244  1.00  0.00           H  
HETATM   19  H3  UNL     1       0.002   1.284   1.309  1.00  0.00           H  
HETATM   20  H4  UNL     1       1.398  -2.020   1.081  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.883  -0.560   1.946  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.668   1.950  -1.991  1.00  0.00           H  
HETATM   23  H7  UNL     1       3.318   0.310  -2.436  1.00  0.00           H  
HETATM   24  H8  UNL     1       4.050   1.902  -0.045  1.00  0.00           H  
HETATM   25  H9  UNL     1       4.837   0.480  -0.781  1.00  0.00           H  
HETATM   26  H10 UNL     1       3.736  -0.423   1.268  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.092  -3.194  -0.238  1.00  0.00           H  
HETATM   28  H12 UNL     1      -2.300  -3.492  -1.270  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.863  -1.638  -1.304  1.00  0.00           H  
HETATM   30  H14 UNL     1      -4.403   0.578  -0.785  1.00  0.00           H  
CONECT    1    2    2   16   17
CONECT    2    3   18
CONECT    3    4    4   19
CONECT    4    5   15
CONECT    5    6   12   12
CONECT    6    7   20   21
CONECT    7    8    8   11
CONECT    8    9
CONECT    9   10   22   23
CONECT   10   11   24   25
CONECT   11   26
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   15   29
CONECT   15   16   16
CONECT   16   30
END

HMDB0015656
     RDKit          3D
Naphazoline
 30 32  0  0  0  0  0  0  0  0999 V2000
   -3.0979    1.9704    0.2355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8571    2.1456    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9473    1.1146    0.8521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2892   -0.1006    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3932   -1.1452    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.0064    0.9328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8941   -0.2485    0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6757    0.2782   -1.0969 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8574    0.9296   -1.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8373    0.9131   -0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405   -0.0147    0.4562 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7802   -2.3396   -0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9972   -2.5485   -0.8243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8914   -1.4992   -0.8480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5476   -0.2816   -0.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4387    0.7545   -0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8088    2.7656    0.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6372    3.1346    1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0016    1.2838    1.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3984   -2.0198    1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8833   -0.5596    1.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6682    1.9502   -1.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3184    0.3099   -2.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0496    1.9022   -0.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8370    0.4798   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7365   -0.4231    1.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919   -3.1936   -0.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3005   -3.4918   -1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8626   -1.6380   -1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4033    0.5780   -0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  5 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16  1  1  0
 15  4  1  0
 11  7  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  6 20  1  0
  6 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Nafazolin	Kegg
AK CON	HMDB
AK-CON	HMDB
Akorn brand OF naphazoline hydrochloride	HMDB
Alcon brand 1 OF naphazoline hydrochloride	HMDB
Alcon brand 2 OF naphazoline hydrochloride	HMDB
Alfa, colirio	HMDB
Bausch and lomb brand 1 OF naphazoline hydrochloride	HMDB
Ciba vision brand 1 OF naphazoline hydrochloride	HMDB
Febena brand OF naphazoline hydrochloride	HMDB
Hydrochloride, naphazoline	HMDB
Idril	HMDB
Iquinosa brand OF naphazoline hydrochloride	HMDB
Naphazoline monohydrochloride	HMDB
Novartis brand 1 OF naphazoline hydrochloride	HMDB
Ross brand OF naphazoline hydrochloride	HMDB
tele Stulln	HMDB
TeleStulln	HMDB
Vasocon regular	HMDB
Abbot brand OF naphazoline hydrochloride	HMDB
Ciba vision brand 2 OF naphazoline hydrochloride	HMDB
Clear eyes	HMDB
Grin brand OF naphazoline hydrochloride	HMDB
Grin, afazol	HMDB
Miraclar	HMDB
Monohydrochloride, naphazoline	HMDB
Naphazoline hydrochloride	HMDB
Naphazoline nitrate	HMDB
Novartis brand 2 OF naphazoline hydrochloride	HMDB
Privine	HMDB
Proculin	HMDB
Warner lambert brand OF naphazoline nitrate	HMDB
Warner-lambert brand OF naphazoline nitrate	HMDB
Winzer brand OF naphazoline hydrochloride	HMDB
Forte, naphcon	HMDB
Afazol grin	HMDB
Albalon	HMDB
Bausch and lomb brand 2 OF naphazoline hydrochloride	HMDB
Chauvin brand OF naphazoline hydrochloride	HMDB
Eyes, clear	HMDB
Nafazair	HMDB
Nitrate, naphazoline	HMDB
Optima brand OF naphazoline hydrochloride	HMDB
Pensa, vasoconstrictor	HMDB
Privin	HMDB
Stulln brand OF naphazoline hydrochloride	HMDB
tele-Stulln	HMDB
VasoNit	HMDB
Vasoclear	HMDB
Vasocon	HMDB
Vasoconstrictor pensa	HMDB
AKCon	HMDB
all Clear	HMDB
Allergan brand OF naphazoline hydrochloride	HMDB
Clear, all	HMDB
Colirio alfa	HMDB
Naphcon	HMDB
Naphcon forte	HMDB
Optazine	HMDB
Regular, vasocon	HMDB
Siozwo	HMDB
Whitehall brand OF naphazoline hydrochloride	HMDB

Chemical Formula

C₁₄H₁₄N₂

Average Molecular Weight

210.2744

Monoisotopic Molecular Weight

210.115698458

IUPAC Name

2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole

Traditional Name

naphazoline

CAS Registry Number

835-31-4

SMILES

C(C1=NCCN1)C1=CC=CC2=CC=CC=C12

InChI Identifier

InChI=1S/C14H14N2/c1-2-7-13-11(4-1)5-3-6-12(13)10-14-15-8-9-16-14/h1-7H,8-10H2,(H,15,16)

InChI Key

CNIIGCLFLJGOGP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Imidolactam
2-imidazoline
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Carboxylic acid amidine
Amidine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015656)

Source

Exogenous

Exogenous (HMDB: HMDB0015656)

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	149.6	30932474
[M+H]+	Not Available	148.543	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000737

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.038 g/L	ALOGPS
logP	3.44	ALOGPS
logP	2.19	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	10.19	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	2	ChemAxon
Refractivity	65.52 m³·mol⁻¹	ChemAxon
Polarizability	23.77 Å³	ChemAxon
Number of Rings	3	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]+	148.749	31661259
DarkChem	[M-H]-	148.669	31661259
DeepCCS	[M-2H]-	176.211	30932474
DeepCCS	[M+Na]+	150.819	30932474
AllCCS	[M+H]+	148.0	32859911
AllCCS	[M+H-H2O]+	143.8	32859911
AllCCS	[M+NH4]+	152.0	32859911
AllCCS	[M+Na]+	153.1	32859911
AllCCS	[M-H]-	153.5	32859911
AllCCS	[M+Na-2H]-	153.3	32859911
AllCCS	[M+HCOO]-	153.1	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.	3.3 minutes	32390414
Predicted by Siyang on May 30, 2022	11.3547 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.9 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	44.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1320.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	322.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	151.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	186.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	89.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	433.2 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	356.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	188.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	736.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	438.7 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	1348.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	249.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	308.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	341.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	206.7 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
Naphazoline	C(C1=NCCN1)C1=CC=CC2=CC=CC=C12	3142.5	Standard polar	33892256
Naphazoline	C(C1=NCCN1)C1=CC=CC2=CC=CC=C12	2042.2	Standard non polar	33892256
Naphazoline	C(C1=NCCN1)C1=CC=CC2=CC=CC=C12	2151.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Naphazoline,1TMS,isomer #1	C[Si](C)(C)N1CCN=C1CC1=CC=CC2=CC=CC=C12	2268.6	Semi standard non polar	33892256
Naphazoline,1TMS,isomer #1	C[Si](C)(C)N1CCN=C1CC1=CC=CC2=CC=CC=C12	2194.1	Standard non polar	33892256
Naphazoline,1TMS,isomer #1	C[Si](C)(C)N1CCN=C1CC1=CC=CC2=CC=CC=C12	3162.5	Standard polar	33892256
Naphazoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1CC1=CC=CC2=CC=CC=C12	2528.5	Semi standard non polar	33892256
Naphazoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1CC1=CC=CC2=CC=CC=C12	2427.6	Standard non polar	33892256
Naphazoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1CC1=CC=CC2=CC=CC=C12	3269.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Naphazoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-2900000000-026b23156746d2a4a1de	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naphazoline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naphazoline 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 - Naphazoline , positive-QTOF	splash10-03di-0390000000-bf587920984867425a82	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphazoline 10V, Positive-QTOF	splash10-03di-0090000000-0076ea45eaeedc60e1fb	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphazoline 20V, Positive-QTOF	splash10-03di-1490000000-9be572c365d8869eec53	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphazoline 40V, Positive-QTOF	splash10-0006-5900000000-b07ec5aa4378446ddd21	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphazoline 10V, Negative-QTOF	splash10-0a4i-0090000000-af432db2e56a6f9aed8d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphazoline 20V, Negative-QTOF	splash10-0a4i-1290000000-46d4b9b044e895d92e64	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphazoline 40V, Negative-QTOF	splash10-00ou-1900000000-8c83d33771f2cc032669	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphazoline 10V, Positive-QTOF	splash10-03di-0090000000-c9f6494c894621a7d1c0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphazoline 20V, Positive-QTOF	splash10-03di-0290000000-2bb6cd3f38dcc7776ea4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphazoline 40V, Positive-QTOF	splash10-002f-0900000000-445b3b85168db2851c1a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphazoline 10V, Negative-QTOF	splash10-0a4i-0090000000-e8abc7c84fa2e857c6c9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphazoline 20V, Negative-QTOF	splash10-0a6r-0790000000-36be1e66b6c2ccbb24fc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphazoline 40V, Negative-QTOF	splash10-0a6u-1960000000-257acbcbef4f826f56d9	2021-10-11	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

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 DB06711	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06711	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06711

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4283

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Naphazoline

METLIN ID

Not Available

PubChem Compound

4436

PDB ID

Not Available

ChEBI ID

142468

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

Piletz JE, Zhu H, Chikkala DN: Comparison of ligand binding affinities at human I1-imidazoline binding sites and the high affinity state of alpha-2 adrenoceptor subtypes. J Pharmacol Exp Ther. 1996 Nov;279(2):694-702. [PubMed:8930173 ]
Fukushima H, Norimoto K, Seki T, Nishiguchi T, Nakamura T, Konobu T, Nishio K, Okuchi K: Acute pulmonary edema associated with naphazoline ingestion. Clin Toxicol (Phila). 2008 Mar;46(3):254-6. [PubMed:17852165 ]
Ogidigben MJ, Chu TC, Potter DE: Naphazoline-induced suppression of aqueous humor pressure and flow: involvement of central and peripheral alpha(2)/I(1) receptors. Exp Eye Res. 2001 Mar;72(3):331-9. [PubMed:11180982 ]

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

Bogacka E: [Decongestants in treatment of nasal obstruction]. Otolaryngol Pol. 1999;53(3):347-52. [PubMed:10481510 ]
Leonardi A: Emerging drugs for ocular allergy. Expert Opin Emerg Drugs. 2005 Aug;10(3):505-20. [PubMed:16083326 ]
Piletz JE, Zhu H, Chikkala DN: Comparison of ligand binding affinities at human I1-imidazoline binding sites and the high affinity state of alpha-2 adrenoceptor subtypes. J Pharmacol Exp Ther. 1996 Nov;279(2):694-702. [PubMed:8930173 ]
Hrometz SL, Edelmann SE, McCune DF, Olges JR, Hadley RW, Perez DM, Piascik MT: Expression of multiple alpha1-adrenoceptors on vascular smooth muscle: correlation with the regulation of contraction. J Pharmacol Exp Ther. 1999 Jul;290(1):452-63. [PubMed:10381812 ]
Kai T: [Effects of topical alpha 1- and beta 2-adrenoceptor stimulants on nasal nitric oxide level]. Nihon Jibiinkoka Gakkai Kaiho. 1999 Jul;102(7):898-906. [PubMed:10459292 ]
Ogidigben MJ, Chu TC, Potter DE: Naphazoline-induced suppression of aqueous humor pressure and flow: involvement of central and peripheral alpha(2)/I(1) receptors. Exp Eye Res. 2001 Mar;72(3):331-9. [PubMed:11180982 ]

Showing metabocard for Naphazoline (HMDB0015656)

MOL for HMDB0015656 (Naphazoline)

3D MOL for HMDB0015656 (Naphazoline)

3D SDF for HMDB0015656 (Naphazoline)

3D-SDF for HMDB0015656 (Naphazoline)

PDB for HMDB0015656 (Naphazoline)

3D PDB for HMDB0015656 (Naphazoline)

SMILES for HMDB0015656 (Naphazoline)

INCHI for HMDB0015656 (Naphazoline)

Structure for HMDB0015656 (Naphazoline)

3D Structure for HMDB0015656 (Naphazoline)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

References

References