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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-11-21 17:41:24 UTC

Update Date

2022-03-07 03:18:14 UTC

HMDB ID

HMDB0240237

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Mebhydrolin

Description

Mebhydrolin, also known as bexidal or diazolin, belongs to the class of organic compounds known as n-alkylindoles. N-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 1-position. In humans, mebhydrolin is involved in the mebhydrolin h1-antihistamine action pathway. Based on a literature review a small amount of articles have been published on Mebhydrolin.

Structure

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

HMDB0240237
     RDKit          3D
Mebhydrolin
 41 44  0  0  0  0  0  0  0  0999 V2000
   -3.2494   -2.6258   -0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3219   -1.3439    0.3149 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6441   -1.3039    1.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1461   -1.3277    1.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8405   -0.0480    0.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7601    0.4255   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2312    1.5932   -0.7944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7079    2.4973   -1.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9567    3.6084   -2.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2789    3.8148   -1.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463    2.9081   -0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0112    1.7927   -0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2197    0.7797    0.6458 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819    0.5823    1.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4394   -0.2228    0.8237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4296    0.3894    0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4412   -0.3306   -0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4785   -1.7035   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4838   -2.3160    0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4646   -1.5948    0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620   -0.2388   -0.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2255   -2.9191   -0.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745   -2.6739   -1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0680   -3.3838    0.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9083   -0.3675    2.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9628   -2.1756    2.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8389   -2.1584    0.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6324   -1.3644    2.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6737    2.3297   -2.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3849    4.2838   -2.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637    4.6986   -1.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7119    3.0689   -0.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8006    1.5483    1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922    0.0300    2.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4775    1.4619   -0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2103    0.1943   -1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2725   -2.2227   -0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5350   -3.3995    0.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7256   -2.1584    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8836    0.5045   -0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0918   -0.6321   -1.6073 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21  2  1  0
 13  5  1  0
 20 15  1  0
 12  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
M  END

      22530
  Mrv1652311211718412D          

 21 24  0  0  1  0            999 V2000
    3.7934   -0.0575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6129   -1.8022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4608   -0.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -1.3270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2985   -0.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7709   -1.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8784   -0.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.3270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1260   -0.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8158   -1.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2881   -0.3507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1625   -2.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    1.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9738   -1.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7083   -0.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789    2.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    0.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    2.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  9  1  0  0  0  0
  1 10  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  2 13  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  2  0  0  0  0
  9 12  2  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 14 17  2  0  0  0  0
 14 18  1  0  0  0  0
 15 16  2  0  0  0  0
 17 19  1  0  0  0  0
 18 20  2  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240237

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC2=C(C1)C1=CC=CC=C1N2CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H20N2/c1-20-12-11-19-17(14-20)16-9-5-6-10-18(16)21(19)13-15-7-3-2-4-8-15/h2-10H,11-14H2,1H3

> <INCHI_KEY>
FQQIIPAOSKSOJM-UHFFFAOYSA-N

> <FORMULA>
C19H20N2

> <MOLECULAR_WEIGHT>
276.383

> <EXACT_MASS>
276.162648652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
32.54270733603421

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-benzyl-2-methyl-1H,2H,3H,4H,5H-pyrido[4,3-b]indole

> <ALOGPS_LOGP>
3.69

> <JCHEM_LOGP>
3.692741922999999

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.204177901312038

> <JCHEM_POLAR_SURFACE_AREA>
8.17

> <JCHEM_REFRACTIVITY>
88.49400000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mebhydrolin

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0240237
     RDKit          3D
Mebhydrolin
 41 44  0  0  0  0  0  0  0  0999 V2000
   -3.2494   -2.6258   -0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3219   -1.3439    0.3149 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6441   -1.3039    1.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1461   -1.3277    1.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8405   -0.0480    0.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7601    0.4255   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2312    1.5932   -0.7944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7079    2.4973   -1.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9567    3.6084   -2.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2789    3.8148   -1.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463    2.9081   -0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0112    1.7927   -0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2197    0.7797    0.6458 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819    0.5823    1.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4394   -0.2228    0.8237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4296    0.3894    0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4412   -0.3306   -0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4785   -1.7035   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4838   -2.3160    0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4646   -1.5948    0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620   -0.2388   -0.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2255   -2.9191   -0.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745   -2.6739   -1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0680   -3.3838    0.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9083   -0.3675    2.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9628   -2.1756    2.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8389   -2.1584    0.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6324   -1.3644    2.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6737    2.3297   -2.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3849    4.2838   -2.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637    4.6986   -1.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7119    3.0689   -0.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8006    1.5483    1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922    0.0300    2.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4775    1.4619   -0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2103    0.1943   -1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2725   -2.2227   -0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5350   -3.3995    0.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7256   -2.1584    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8836    0.5045   -0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0918   -0.6321   -1.6073 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21  2  1  0
 13  5  1  0
 20 15  1  0
 12  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
M  END

HEADER    PROTEIN                                 21-NOV-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:       22530                                       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-NOV-17         0                                  
HETATM    1  N   UNK     0       7.081  -0.107   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0      10.477  -3.364   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       8.327  -1.012   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.851  -2.477   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.891  -0.655   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.906  -3.686   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.973  -1.838   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.311  -2.477   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.835  -1.012   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081   1.432   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.256  -3.686   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.271  -0.655   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.503  -4.512   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.747   2.202   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.684  -3.364   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.189  -1.838   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.747   3.742   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414   1.432   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414   4.512   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.080   2.202   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.080   3.742   0.000  0.00  0.00           C+0
CONECT    1    3    9   10                                                  
CONECT    2    6    7   13                                                  
CONECT    3    1    4    5                                                  
CONECT    4    3    6    8                                                  
CONECT    5    3    7                                                       
CONECT    6    2    4                                                       
CONECT    7    2    5                                                       
CONECT    8    4    9   11                                                  
CONECT    9    1    8   12                                                  
CONECT   10    1   14                                                       
CONECT   11    8   15                                                       
CONECT   12    9   16                                                       
CONECT   13    2                                                            
CONECT   14   10   17   18                                                  
CONECT   15   11   16                                                       
CONECT   16   12   15                                                       
CONECT   17   14   19                                                       
CONECT   18   14   20                                                       
CONECT   19   17   21                                                       
CONECT   20   18   21                                                       
CONECT   21   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0240237
HETATM    1  C1  UNL     1      -3.249  -2.626  -0.339  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.322  -1.344   0.315  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.644  -1.304   1.580  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.146  -1.328   1.361  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.840  -0.048   0.618  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.760   0.425  -0.264  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.231   1.593  -0.794  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.708   2.497  -1.725  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.957   3.608  -2.083  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.279   3.815  -1.504  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.746   2.908  -0.576  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.011   1.793  -0.207  1.00  0.00           C  
HETATM   13  N2  UNL     1       0.220   0.780   0.646  1.00  0.00           N  
HETATM   14  C12 UNL     1       1.382   0.582   1.467  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.439  -0.223   0.824  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.430   0.389   0.096  1.00  0.00           C  
HETATM   17  C15 UNL     1       4.441  -0.331  -0.525  1.00  0.00           C  
HETATM   18  C16 UNL     1       4.478  -1.704  -0.426  1.00  0.00           C  
HETATM   19  C17 UNL     1       3.484  -2.316   0.304  1.00  0.00           C  
HETATM   20  C18 UNL     1       2.465  -1.595   0.930  1.00  0.00           C  
HETATM   21  C19 UNL     1      -3.062  -0.239  -0.553  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.226  -2.919  -0.808  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.474  -2.674  -1.131  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.068  -3.384   0.466  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.908  -0.368   2.093  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.963  -2.176   2.165  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.839  -2.158   0.701  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.632  -1.364   2.324  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.674   2.330  -2.173  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.385   4.284  -2.821  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.864   4.699  -1.795  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.712   3.069  -0.122  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.801   1.548   1.845  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.092   0.030   2.410  1.00  0.00           H  
HETATM   35  H14 UNL     1       3.477   1.462  -0.032  1.00  0.00           H  
HETATM   36  H15 UNL     1       5.210   0.194  -1.094  1.00  0.00           H  
HETATM   37  H16 UNL     1       5.272  -2.223  -0.918  1.00  0.00           H  
HETATM   38  H17 UNL     1       3.535  -3.400   0.367  1.00  0.00           H  
HETATM   39  H18 UNL     1       1.726  -2.158   1.483  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.884   0.505  -0.497  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.092  -0.632  -1.607  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   21
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6    6   13
CONECT    6    7   21
CONECT    7    8    8   12
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11   31
CONECT   11   12   12   32
CONECT   12   13
CONECT   13   14
CONECT   14   15   33   34
CONECT   15   16   16   20
CONECT   16   17   35
CONECT   17   18   18   36
CONECT   18   19   37
CONECT   19   20   20   38
CONECT   20   39
CONECT   21   40   41
END

HMDB0240237
     RDKit          3D
Mebhydrolin
 41 44  0  0  0  0  0  0  0  0999 V2000
   -3.2494   -2.6258   -0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3219   -1.3439    0.3149 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6441   -1.3039    1.5800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1461   -1.3277    1.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8405   -0.0480    0.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7601    0.4255   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2312    1.5932   -0.7944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7079    2.4973   -1.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9567    3.6084   -2.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2789    3.8148   -1.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7463    2.9081   -0.5764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0112    1.7927   -0.2067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2197    0.7797    0.6458 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819    0.5823    1.4673 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4394   -0.2228    0.8237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4296    0.3894    0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4412   -0.3306   -0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4785   -1.7035   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4838   -2.3160    0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4646   -1.5948    0.9304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0620   -0.2388   -0.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2255   -2.9191   -0.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745   -2.6739   -1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0680   -3.3838    0.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9083   -0.3675    2.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9628   -2.1756    2.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8389   -2.1584    0.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6324   -1.3644    2.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6737    2.3297   -2.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3849    4.2838   -2.8206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637    4.6986   -1.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7119    3.0689   -0.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8006    1.5483    1.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0922    0.0300    2.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4775    1.4619   -0.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2103    0.1943   -1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2725   -2.2227   -0.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5350   -3.3995    0.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7256   -2.1584    1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8836    0.5045   -0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0918   -0.6321   -1.6073 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  6 21  1  0
 21  2  1  0
 13  5  1  0
 20 15  1  0
 12  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 21 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Bexidal	Kegg
Diazolin	HMDB
Diazolinum	HMDB
Fabahistin	HMDB
Incidal	HMDB
Omeril	HMDB
MEBHYDROLIN napadisylATE	HMDB
MEBHYDROLIN napadisylic acid	HMDB
5-Benzyl-1,3,4,5-tetrahydro-2-methyl-2H-pyrido(4,3-b)indole	HMDB
Mebhydroline	HMDB
Mebhydrolin	HMDB

Chemical Formula

C₁₉H₂₀N₂

Average Molecular Weight

276.383

Monoisotopic Molecular Weight

276.162648652

IUPAC Name

5-benzyl-2-methyl-1H,2H,3H,4H,5H-pyrido[4,3-b]indole

Traditional Name

mebhydrolin

CAS Registry Number

524-81-2

SMILES

CN1CCC2=C(C1)C1=CC=CC=C1N2CC1=CC=CC=C1

InChI Identifier

InChI=1S/C19H20N2/c1-20-12-11-19-17(14-20)16-9-5-6-10-18(16)21(19)13-15-7-3-2-4-8-15/h2-10H,11-14H2,1H3

InChI Key

FQQIIPAOSKSOJM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-alkylindoles. N-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

N-alkylindoles

Direct Parent

N-alkylindoles

Alternative Parents

Substituents

N-alkylindole
3-alkylindole
Indole
Aralkylamine
Monocyclic benzene moiety
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Hydrocarbon derivative
Amine
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0240237)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Mebhydrolin H1-Antihistamine Action (PathBank: SMP0061052)

Role

Not Available

Physical Properties

State

Not Available

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]+	Not Available	168.875	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001141

Predicted Molecular Properties

Property	Value	Source
logP	3.69	ALOGPS
logP	3.69	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	7.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	8.17 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	88.49 m³·mol⁻¹	ChemAxon
Polarizability	32.54 Å³	ChemAxon
Number of Rings	4	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]+	164.83	31661259
DarkChem	[M-H]-	165.129	31661259
DeepCCS	[M+H]+	163.692	30932474
DeepCCS	[M-H]-	161.334	30932474
DeepCCS	[M-2H]-	194.22	30932474
DeepCCS	[M+Na]+	169.785	30932474
AllCCS	[M+H]+	166.4	32859911
AllCCS	[M+H-H2O]+	162.8	32859911
AllCCS	[M+NH4]+	169.8	32859911
AllCCS	[M+Na]+	170.8	32859911
AllCCS	[M-H]-	175.4	32859911
AllCCS	[M+Na-2H]-	174.7	32859911
AllCCS	[M+HCOO]-	174.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.92 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0656 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.01 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1356.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	264.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	167.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	186.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	119.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	390.3 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	403.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	615.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	893.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	356.0 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	1124.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	265.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	311.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	316.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	336.5 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	8.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mebhydrolin	CN1CCC2=C(C1)C1=CC=CC=C1N2CC1=CC=CC=C1	3518.4	Standard polar	33892256
Mebhydrolin	CN1CCC2=C(C1)C1=CC=CC=C1N2CC1=CC=CC=C1	2479.6	Standard non polar	33892256
Mebhydrolin	CN1CCC2=C(C1)C1=CC=CC=C1N2CC1=CC=CC=C1	2482.3	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 - Mebhydrolin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9360000000-9002610ba3e228f59aff	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Mebhydrolin 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 - Mebhydrolin 10V, Positive-QTOF	splash10-004i-3090000000-40622525da2ce99796fa	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mebhydrolin 20V, Positive-QTOF	splash10-0006-9060000000-6696356c1054ed8a110d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mebhydrolin 40V, Positive-QTOF	splash10-0006-9000000000-d98d9810eda32a0bbd0a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mebhydrolin 10V, Negative-QTOF	splash10-004i-0190000000-3a3bda3830d86f3d214e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mebhydrolin 20V, Negative-QTOF	splash10-004i-3390000000-22a83e55769bca15edbe	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mebhydrolin 40V, Negative-QTOF	splash10-02vr-2910000000-ea3f90b4d71454e8f193	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mebhydrolin 10V, Negative-QTOF	splash10-004i-0090000000-e86d9a5414dd3e76625b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mebhydrolin 20V, Negative-QTOF	splash10-004i-0190000000-f345a0b2f1d8af6023e5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mebhydrolin 40V, Negative-QTOF	splash10-00dj-1690000000-8af1271e6a2d68401587	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mebhydrolin 10V, Positive-QTOF	splash10-004i-0090000000-5d2789db9f38fbd1411e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mebhydrolin 20V, Positive-QTOF	splash10-004i-2290000000-06c494eafd80be70851a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Mebhydrolin 40V, Positive-QTOF	splash10-0006-9030000000-8984b350cccee3098330	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

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

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13808

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21129

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mebhydrolin

METLIN ID

Not Available

PubChem Compound

22530

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Franks HM, Lawrie M, Schabinsky VV, Starmer GA, Teo RK: Interaction between ethanol and antihistamines: 3. mebhydrolin. Med J Aust. 1981 Oct 31;2(9):477-9. [PubMed:6119605 ]

Showing metabocard for Mebhydrolin (HMDB0240237)

MOL for HMDB0240237 (Mebhydrolin)

3D MOL for HMDB0240237 (Mebhydrolin)

3D SDF for HMDB0240237 (Mebhydrolin)

3D-SDF for HMDB0240237 (Mebhydrolin)

PDB for HMDB0240237 (Mebhydrolin)

3D PDB for HMDB0240237 (Mebhydrolin)

SMILES for HMDB0240237 (Mebhydrolin)

INCHI for HMDB0240237 (Mebhydrolin)

Structure for HMDB0240237 (Mebhydrolin)

3D Structure for HMDB0240237 (Mebhydrolin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra