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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:54 UTC

HMDB ID

HMDB0015216

Secondary Accession Numbers

HMDB15216

Metabolite Identification

Common Name

Emedastine

Description

Emedastine is only found in individuals that have used or taken this drug. It is an antihistamine used in eye drops to treat allergic conjunctivitis. [Wikipedia ]Emedastine is a relatively selective, histamine H₁ antagonist. In vitro examinations of emedastine's affinity for histamine receptors demonstrate relative selectivity for the H₁ histamine receptor. In vivo studies have shown concentration-dependent inhibition of histamine-stimulated vascular permeability in the conjunctiva following topical ocular administration. Emedastine appears to be devoid of effects on adrenergic, dopaminergic and serotonin receptors.

Structure

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

HMDB0015216
     RDKit          3D
Emedastine
 48 50  0  0  0  0  0  0  0  0999 V2000
    5.2365   -2.6233   -0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2778   -1.4322   -0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1487   -1.8442    0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2659   -0.7876    0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951   -0.1952   -0.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662    0.8932   -0.3165 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4826    0.7508   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -0.4510   -0.3233 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6281   -0.7957   -1.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9310   -0.0375   -1.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8572   -0.3863   -0.7685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6122   -1.6746   -0.2064 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9094   -2.2817    0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550   -1.6790    1.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4591   -1.1590    0.8985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    1.9949    0.0684 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0334    2.8952    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0719    4.2639    0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2765    4.9294    0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4412    4.2068    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3815    2.8645   -0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1928    2.1822   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8435   -2.6533    0.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8856   -2.4844   -1.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6156   -3.5133   -0.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0629   -1.1511   -1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7634   -0.6225    0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3981   -1.1210    1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7495    0.0075    1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6698    0.2771   -1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3063   -0.9763   -1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8406   -1.8737   -1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9177   -0.4597   -2.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770    1.0429   -1.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148   -0.3629   -2.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8837   -0.3943   -1.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8866    0.3960    0.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2583   -2.9337   -0.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8698   -2.8627    1.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6813   -1.4948    0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4003   -1.0240    1.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8559   -2.7198    1.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7696   -2.0540    0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1480   -0.5655    1.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8161    4.8420    0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3483    5.9986    0.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3948    4.7514    0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3058    2.3178   -0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  7 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  6  1  0
 15  8  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
M  END

1084
  Mrv0541 02231215142D          

 22 24  0  0  1  0            999 V2000
    3.8213    1.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1662   -1.6589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9735   -2.0714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -0.9950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -2.3228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5242   -0.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5242   -2.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3285   -0.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3285   -2.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9735   -1.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3412   -1.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -0.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7168   -2.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5650    0.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.2464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2703    1.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5266    2.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  1 21  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  2 11  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  3 15  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 11  2  0  0  0  0
  5 14  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 12 14  1  0  0  0  0
 12 17  2  0  0  0  0
 13 16  1  0  0  0  0
 14 18  2  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 19 20  2  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015216

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOCCN1C(=NC2=CC=CC=C12)N1CCCN(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C17H26N4O/c1-3-22-14-13-21-16-8-5-4-7-15(16)18-17(21)20-10-6-9-19(2)11-12-20/h4-5,7-8H,3,6,9-14H2,1-2H3

> <INCHI_KEY>
KBUZBQVCBVDWKX-UHFFFAOYSA-N

> <FORMULA>
C17H26N4O

> <MOLECULAR_WEIGHT>
302.4145

> <EXACT_MASS>
302.210661474

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
35.494199576355825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)-1H-1,3-benzodiazole

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
2.4923856926666663

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.680268990788557

> <JCHEM_POLAR_SURFACE_AREA>
33.53

> <JCHEM_REFRACTIVITY>
90.47470000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
emedastine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015216
     RDKit          3D
Emedastine
 48 50  0  0  0  0  0  0  0  0999 V2000
    5.2365   -2.6233   -0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2778   -1.4322   -0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1487   -1.8442    0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2659   -0.7876    0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951   -0.1952   -0.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662    0.8932   -0.3165 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4826    0.7508   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -0.4510   -0.3233 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6281   -0.7957   -1.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9310   -0.0375   -1.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8572   -0.3863   -0.7685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6122   -1.6746   -0.2064 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9094   -2.2817    0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550   -1.6790    1.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4591   -1.1590    0.8985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    1.9949    0.0684 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0334    2.8952    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0719    4.2639    0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2765    4.9294    0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4412    4.2068    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3815    2.8645   -0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1928    2.1822   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8435   -2.6533    0.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8856   -2.4844   -1.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6156   -3.5133   -0.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0629   -1.1511   -1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7634   -0.6225    0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3981   -1.1210    1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7495    0.0075    1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6698    0.2771   -1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3063   -0.9763   -1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8406   -1.8737   -1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9177   -0.4597   -2.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770    1.0429   -1.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148   -0.3629   -2.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8837   -0.3943   -1.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8866    0.3960    0.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2583   -2.9337   -0.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8698   -2.8627    1.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6813   -1.4948    0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4003   -1.0240    1.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8559   -2.7198    1.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7696   -2.0540    0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1480   -0.5655    1.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8161    4.8420    0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3483    5.9986    0.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3948    4.7514    0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3058    2.3178   -0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  7 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  6  1  0
 15  8  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1084                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.133   2.217   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       9.644  -3.097   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      13.017  -3.867   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       7.205  -1.857   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.205  -4.336   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      10.312  -1.709   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.312  -4.484   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.813  -1.366   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.813  -4.827   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.017  -2.327   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.104  -3.097   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -2.327   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.683  -0.393   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748  -3.867   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.405  -4.535   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.655   0.753   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -1.556   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414  -4.637   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.080  -2.327   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080  -3.867   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.105   3.363   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.583   4.827   0.000  0.00  0.00           C+0
CONECT    1   16   21                                                       
CONECT    2    6    7   11                                                  
CONECT    3    9   10   15                                                  
CONECT    4   11   12   13                                                  
CONECT    5   11   14                                                       
CONECT    6    2    8                                                       
CONECT    7    2    9                                                       
CONECT    8    6   10                                                       
CONECT    9    3    7                                                       
CONECT   10    3    8                                                       
CONECT   11    2    4    5                                                  
CONECT   12    4   14   17                                                  
CONECT   13    4   16                                                       
CONECT   14    5   12   18                                                  
CONECT   15    3                                                            
CONECT   16    1   13                                                       
CONECT   17   12   19                                                       
CONECT   18   14   20                                                       
CONECT   19   17   20                                                       
CONECT   20   18   19                                                       
CONECT   21    1   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0015216
HETATM    1  C1  UNL     1       5.236  -2.623  -0.211  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.278  -1.432  -0.102  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.149  -1.844   0.566  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.266  -0.788   0.702  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.795  -0.195  -0.603  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.866   0.893  -0.316  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.483   0.751  -0.196  1.00  0.00           C  
HETATM    8  N2  UNL     1      -1.218  -0.451  -0.323  1.00  0.00           N  
HETATM    9  C6  UNL     1      -1.628  -0.796  -1.651  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.931  -0.037  -1.912  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.857  -0.386  -0.768  1.00  0.00           C  
HETATM   12  N3  UNL     1      -3.612  -1.675  -0.206  1.00  0.00           N  
HETATM   13  C9  UNL     1      -4.909  -2.282   0.110  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.855  -1.679   1.016  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.459  -1.159   0.898  1.00  0.00           C  
HETATM   16  N4  UNL     1      -0.958   1.995   0.068  1.00  0.00           N  
HETATM   17  C12 UNL     1       0.033   2.895   0.117  1.00  0.00           C  
HETATM   18  C13 UNL     1       0.072   4.264   0.348  1.00  0.00           C  
HETATM   19  C14 UNL     1       1.276   4.929   0.334  1.00  0.00           C  
HETATM   20  C15 UNL     1       2.441   4.207   0.085  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.381   2.865  -0.140  1.00  0.00           C  
HETATM   22  C17 UNL     1       1.193   2.182  -0.130  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.843  -2.653   0.732  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.886  -2.484  -1.104  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.616  -3.513  -0.339  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.063  -1.151  -1.155  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.763  -0.623   0.473  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.398  -1.121   1.326  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.749   0.008   1.347  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.670   0.277  -1.098  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.306  -0.976  -1.185  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.841  -1.874  -1.696  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.918  -0.460  -2.433  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.777   1.043  -1.932  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.315  -0.363  -2.894  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.884  -0.394  -1.216  1.00  0.00           H  
HETATM   37  H15 UNL     1      -3.887   0.396   0.014  1.00  0.00           H  
HETATM   38  H16 UNL     1      -5.258  -2.934  -0.696  1.00  0.00           H  
HETATM   39  H17 UNL     1      -4.870  -2.863   1.054  1.00  0.00           H  
HETATM   40  H18 UNL     1      -5.681  -1.495   0.273  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.400  -1.024   1.751  1.00  0.00           H  
HETATM   42  H20 UNL     1      -2.856  -2.720   1.402  1.00  0.00           H  
HETATM   43  H21 UNL     1      -0.770  -2.054   0.903  1.00  0.00           H  
HETATM   44  H22 UNL     1      -1.148  -0.566   1.784  1.00  0.00           H  
HETATM   45  H23 UNL     1      -0.816   4.842   0.543  1.00  0.00           H  
HETATM   46  H24 UNL     1       1.348   5.999   0.510  1.00  0.00           H  
HETATM   47  H25 UNL     1       3.395   4.751   0.076  1.00  0.00           H  
HETATM   48  H26 UNL     1       3.306   2.318  -0.333  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   22
CONECT    7    8   16   16
CONECT    8    9   15
CONECT    9   10   32   33
CONECT   10   11   34   35
CONECT   11   12   36   37
CONECT   12   13   14
CONECT   13   38   39   40
CONECT   14   15   41   42
CONECT   15   43   44
CONECT   16   17
CONECT   17   18   18   22
CONECT   18   19   45
CONECT   19   20   20   46
CONECT   20   21   47
CONECT   21   22   22   48
END

HMDB0015216
     RDKit          3D
Emedastine
 48 50  0  0  0  0  0  0  0  0999 V2000
    5.2365   -2.6233   -0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2778   -1.4322   -0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1487   -1.8442    0.5661 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2659   -0.7876    0.7017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7951   -0.1952   -0.6028 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8662    0.8932   -0.3165 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4826    0.7508   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -0.4510   -0.3233 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6281   -0.7957   -1.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9310   -0.0375   -1.9122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8572   -0.3863   -0.7685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6122   -1.6746   -0.2064 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9094   -2.2817    0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8550   -1.6790    1.0159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4591   -1.1590    0.8985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9584    1.9949    0.0684 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0334    2.8952    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0719    4.2639    0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2765    4.9294    0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4412    4.2068    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3815    2.8645   -0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1928    2.1822   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8435   -2.6533    0.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8856   -2.4844   -1.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6156   -3.5133   -0.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0629   -1.1511   -1.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7634   -0.6225    0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3981   -1.1210    1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7495    0.0075    1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6698    0.2771   -1.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3063   -0.9763   -1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8406   -1.8737   -1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9177   -0.4597   -2.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770    1.0429   -1.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148   -0.3629   -2.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8837   -0.3943   -1.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8866    0.3960    0.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2583   -2.9337   -0.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8698   -2.8627    1.0542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6813   -1.4948    0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4003   -1.0240    1.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8559   -2.7198    1.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7696   -2.0540    0.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1480   -0.5655    1.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8161    4.8420    0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3483    5.9986    0.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3948    4.7514    0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3058    2.3178   -0.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  7 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22  6  1  0
 15  8  1  0
 22 17  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 13 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(2-Ethoxy-ethyl)-2-(4-methyl-[1,4]diazepan-1-yl)-1H-benzoimidazole	ChEBI
1-(2-Ethoxyethyl)-2-(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)benzimidazole	ChEBI
1-[2-(Ethoxy)ethyl]-2-(4-methyl-1-homopiperazinyl)benzimidazole	ChEBI
Emedastina	ChEBI
Emedastinum	ChEBI
Emadine	Kegg
Emedastine difumarate	HMDB
1-(2-Ethoxyethyl)-2-(4-methyl-1-homopiperazinyl)benzimidazole difumarate	HMDB

Chemical Formula

C₁₇H₂₆N₄O

Average Molecular Weight

302.4145

Monoisotopic Molecular Weight

302.210661474

IUPAC Name

1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)-1H-1,3-benzodiazole

Traditional Name

emedastine

CAS Registry Number

87233-61-2

SMILES

CCOCCN1C(=NC2=CC=CC=C12)N1CCCN(C)CC1

InChI Identifier

InChI=1S/C17H26N4O/c1-3-22-14-13-21-16-8-5-4-7-15(16)18-17(21)20-10-6-9-19(2)11-12-20/h4-5,7-8H,3,6,9-14H2,1-2H3

InChI Key

KBUZBQVCBVDWKX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzimidazoles

Sub Class

Not Available

Direct Parent

Benzimidazoles

Alternative Parents

Substituents

Benzimidazole
Dialkylarylamine
Diazepane
1,4-diazepane
Aminoimidazole
N-substituted imidazole
Benzenoid
Imidazole
Azole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Ether
Dialkyl ether
Azacycle
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzimidazoles (CHEBI:4779 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015216)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Emedastine H1-Antihistamine Action (PathBank: SMP0061040)

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	1.44 g/L	Not Available
LogP	2.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.44 g/L	ALOGPS
logP	2.91	ALOGPS
logP	2.49	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	8.68	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	33.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	90.47 m³·mol⁻¹	ChemAxon
Polarizability	35.49 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]+	170.0	31661259
DarkChem	[M-H]-	168.618	31661259
DeepCCS	[M-2H]-	202.105	30932474
DeepCCS	[M+Na]+	177.67	30932474
AllCCS	[M+H]+	172.4	32859911
AllCCS	[M+H-H2O]+	169.2	32859911
AllCCS	[M+NH4]+	175.4	32859911
AllCCS	[M+Na]+	176.2	32859911
AllCCS	[M-H]-	176.2	32859911
AllCCS	[M+Na-2H]-	176.3	32859911
AllCCS	[M+HCOO]-	176.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Emedastine	CCOCCN1C(=NC2=CC=CC=C12)N1CCCN(C)CC1	3426.8	Standard polar	33892256
Emedastine	CCOCCN1C(=NC2=CC=CC=C12)N1CCCN(C)CC1	2357.8	Standard non polar	33892256
Emedastine	CCOCCN1C(=NC2=CC=CC=C12)N1CCCN(C)CC1	2466.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Emedastine GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-7290000000-403c6f7ea26245b8aa3d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Emedastine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Emedastine 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 - Emedastine 10V, Positive-QTOF	splash10-0udi-0039000000-88d0f578474ee13848dd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emedastine 20V, Positive-QTOF	splash10-0zgi-2093000000-4d49f8e693f1a29a4340	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emedastine 40V, Positive-QTOF	splash10-00sr-9330000000-ce0a5d1ce6666a00db17	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emedastine 10V, Negative-QTOF	splash10-0udi-1059000000-2069d9730b3ab025cd02	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emedastine 20V, Negative-QTOF	splash10-0fb9-1193000000-10c8f72e647d91eca02d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emedastine 40V, Negative-QTOF	splash10-114i-2790000000-42ba1c4128b01cda2e12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emedastine 10V, Positive-QTOF	splash10-0udi-0029000000-8a6a03ec309aee4a5b69	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emedastine 20V, Positive-QTOF	splash10-0zfr-0098000000-692570c2a4d37d1a187a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emedastine 40V, Positive-QTOF	splash10-07fs-1940000000-114d05222c09f73f0b98	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emedastine 10V, Negative-QTOF	splash10-0udi-0059000000-3fcac4e0104dba0e140d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emedastine 20V, Negative-QTOF	splash10-0gvo-0394000000-c3934240bec1a912f7c6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Emedastine 40V, Negative-QTOF	splash10-0hji-0980000000-8d2c0ee402a42d3bd4c3	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01084	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01084	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01084

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3106

KEGG Compound ID

C07785

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Emedastine

METLIN ID

Not Available

PubChem Compound

3219

PDB ID

Not Available

ChEBI ID

4779

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. Histamine H1 receptor

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

References

Sharif NA, Su SX, Yanni JM: Emedastine: a potent, high affinity histamine H1-receptor-selective antagonist for ocular use: receptor binding and second messenger studies. J Ocul Pharmacol. 1994 Winter;10(4):653-64. [PubMed:7714409 ]
Yanni JM, Stephens DJ, Parnell DW, Spellman JM: Preclinical efficacy of emedastine, a potent, selective histamine H1 antagonist for topical ocular use. J Ocul Pharmacol. 1994 Winter;10(4):665-75. [PubMed:7714410 ]
Inagaki N, Sakurai T, Abe T, Musoh K, Kawasaki H, Tsunematsu M, Nagai H: Characterization of antihistamines using biphasic cutaneous reaction in BALB/c mice. Life Sci. 1998;63(11):PL 145-50. [PubMed:9747899 ]
Murota H, Katayama I: Emedastine difumarate: a review of its potential ameliorating effect for tissue remodeling in allergic diseases. Expert Opin Pharmacother. 2009 Aug;10(11):1859-67. doi: 10.1517/14656560903078410. [PubMed:19558341 ]
Corrado ME, Radicioni MM, Hartwig J, Assandri A, Oldeman HG, Mion A: Clinical study of the therapeutic efficacy and safety of emedastine difumarate versus terfenadine in the treatment of seasonal allergic rhinitis. Arzneimittelforschung. 2004;54(10):660-5. [PubMed:15553105 ]
Murota H, Bae S, Hamasaki Y, Maruyama R, Katayama I: Emedastine difumarate inhibits histamine-induced collagen synthesis in dermal fibroblasts. J Investig Allergol Clin Immunol. 2008;18(4):245-52. [PubMed:18714531 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Emedastine (HMDB0015216)

MOL for HMDB0015216 (Emedastine)

3D MOL for HMDB0015216 (Emedastine)

3D SDF for HMDB0015216 (Emedastine)

3D-SDF for HMDB0015216 (Emedastine)

PDB for HMDB0015216 (Emedastine)

3D PDB for HMDB0015216 (Emedastine)

SMILES for HMDB0015216 (Emedastine)

INCHI for HMDB0015216 (Emedastine)

Structure for HMDB0015216 (Emedastine)

3D Structure for HMDB0015216 (Emedastine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References