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enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:46 UTC

HMDB ID

HMDB0014857

Secondary Accession Numbers

HMDB14857

Metabolite Identification

Common Name

Azatadine

Description

Azatadine, also known as azatadinum or azatadine maleate, belongs to the class of organic compounds known as benzocycloheptapyridines. These are aromatic compounds containing a benzene ring and a pyridine ring fused to a seven membered carbocycle. Azatadine is a drug which is used for the relief of the symptoms of upper respiratory mucosal congestion in perennial and allergic rhinitis, and for the relief of nasal congestion and eustachian t.b. congestion. Azatadine is a very strong basic compound (based on its pKa). In humans, azatadine is involved in azatadine h1-antihistamine action. A benzocycloheptapyridine having a 1-methylpiperidin-4-ylidene group at the 11-position.

Structure

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

HMDB0014857
     RDKit          3D
Azatadine
 44 47  0  0  0  0  0  0  0  0999 V2000
    4.9081    0.0958    0.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5632    0.5449    0.5140 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2051    0.9556   -0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6967    1.1931   -0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9340   -0.0247   -0.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3549   -0.0737   -0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354   -1.3264   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3722   -2.4087   -0.7695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9031   -3.6332   -0.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0289   -3.7949    0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6443   -2.6596    0.8516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535   -1.4214    0.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9772   -0.3268    1.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4412    0.6290    0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4453    1.4368   -0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9853    2.6791   -0.9644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2355    3.5641   -1.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9245    3.2149   -1.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4185    2.0387   -1.6107 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1258    1.1496   -0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8171   -1.0488    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5883   -0.2204    1.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9536   -0.6641    1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2080   -0.4375   -0.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6264    0.8954    0.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766    0.1760   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7136    1.8816   -1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4474    2.0160   -0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    1.4196   -2.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807   -2.2111   -1.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4177   -4.5077   -0.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261   -4.7649    0.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5188   -2.8171    1.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4028    0.2375    1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8741   -0.7634    1.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1418    1.3473    0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0661    0.0795   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0289    2.8561   -0.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6536    4.5287   -1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543    3.9563   -2.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2706   -1.8181    0.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5486   -1.3779   -0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8552    0.3376    1.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0930   -0.9329    1.8858 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  3
  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
  5 21  1  0
 21 22  1  0
 22  2  1  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
M  END

719
  Mrv0541 02231214572D          

 22 25  0  0  0  0            999 V2000
    4.0285   -1.7286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643    0.5102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0285   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7429   -0.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3140   -0.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7429   -1.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3139   -1.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0285    0.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7718    1.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2852    1.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9554    1.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4410    2.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6160    2.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1016    1.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0285   -2.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3926    0.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7725    2.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2844    2.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2157    0.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4070    1.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8412    0.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1 15  1  0  0  0  0
  2 10  1  0  0  0  0
  2 22  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  8  2  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 16  2  0  0  0  0
 10 14  2  0  0  0  0
 11 12  1  0  0  0  0
 11 17  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 18  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  1  0  0  0  0
 18 21  2  0  0  0  0
 19 20  2  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014857

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC(CC1)=C1C2=CC=CC=C2CCC2=C1N=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2/c1-22-13-10-16(11-14-22)19-18-7-3-2-5-15(18)8-9-17-6-4-12-21-20(17)19/h2-7,12H,8-11,13-14H2,1H3

> <INCHI_KEY>
SEBMTIQKRHYNIT-UHFFFAOYSA-N

> <FORMULA>
C20H22N2

> <MOLECULAR_WEIGHT>
290.4021

> <EXACT_MASS>
290.178298714

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.00924671743083

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(1-methylpiperidin-4-ylidene)-4-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene

> <ALOGPS_LOGP>
3.67

> <JCHEM_LOGP>
3.747541202333333

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.914622392996209

> <JCHEM_POLAR_SURFACE_AREA>
16.130000000000003

> <JCHEM_REFRACTIVITY>
101.52870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
azatadine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014857
     RDKit          3D
Azatadine
 44 47  0  0  0  0  0  0  0  0999 V2000
    4.9081    0.0958    0.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5632    0.5449    0.5140 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2051    0.9556   -0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6967    1.1931   -0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9340   -0.0247   -0.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3549   -0.0737   -0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354   -1.3264   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3722   -2.4087   -0.7695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9031   -3.6332   -0.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0289   -3.7949    0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6443   -2.6596    0.8516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535   -1.4214    0.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9772   -0.3268    1.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4412    0.6290    0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4453    1.4368   -0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9853    2.6791   -0.9644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2355    3.5641   -1.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9245    3.2149   -1.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4185    2.0387   -1.6107 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1258    1.1496   -0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8171   -1.0488    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5883   -0.2204    1.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9536   -0.6641    1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2080   -0.4375   -0.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6264    0.8954    0.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766    0.1760   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7136    1.8816   -1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4474    2.0160   -0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    1.4196   -2.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807   -2.2111   -1.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4177   -4.5077   -0.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261   -4.7649    0.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5188   -2.8171    1.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4028    0.2375    1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8741   -0.7634    1.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1418    1.3473    0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0661    0.0795   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0289    2.8561   -0.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6536    4.5287   -1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543    3.9563   -2.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2706   -1.8181    0.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5486   -1.3779   -0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8552    0.3376    1.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0930   -0.9329    1.8858 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  3
  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
  5 21  1  0
 21 22  1  0
 22  2  1  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 719                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       7.520  -3.227   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       4.973   0.952   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.520  -0.147   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.853  -0.917   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.186  -0.917   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.853  -2.457   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.186  -2.457   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.520   1.393   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.907   2.061   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.132   2.061   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.250   3.563   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.290   4.767   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.750   4.767   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.790   3.563   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.520  -4.767   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.066   0.952   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.775   4.059   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.264   4.059   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.603   1.413   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.960   2.977   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.080   2.977   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.437   1.413   0.000  0.00  0.00           C+0
CONECT    1    6    7   15                                                  
CONECT    2   10   22                                                       
CONECT    3    4    5    8                                                  
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    1    4                                                       
CONECT    7    1    5                                                       
CONECT    8    3    9   10                                                  
CONECT    9    8   11   16                                                  
CONECT   10    2    8   14                                                  
CONECT   11    9   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   10   13   18                                                  
CONECT   15    1                                                            
CONECT   16    9   19                                                       
CONECT   17   11   20                                                       
CONECT   18   14   21                                                       
CONECT   19   16   20                                                       
CONECT   20   17   19                                                       
CONECT   21   18   22                                                       
CONECT   22    2   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0014857
HETATM    1  C1  UNL     1       4.908   0.096   0.660  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.563   0.545   0.514  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.205   0.956  -0.793  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.697   1.193  -0.947  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.934  -0.025  -0.540  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.355  -0.074  -0.616  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.035  -1.326  -0.222  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.372  -2.409  -0.769  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.903  -3.633  -0.463  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.029  -3.795   0.338  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.644  -2.660   0.852  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.154  -1.421   0.575  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.977  -0.327   1.161  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.441   0.629   0.119  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.445   1.437  -0.588  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.985   2.679  -0.964  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.236   3.564  -1.649  1.00  0.00           C  
HETATM   18  C17 UNL     1      -0.924   3.215  -1.969  1.00  0.00           C  
HETATM   19  N2  UNL     1      -0.419   2.039  -1.611  1.00  0.00           N  
HETATM   20  C18 UNL     1      -1.126   1.150  -0.939  1.00  0.00           C  
HETATM   21  C19 UNL     1       1.817  -1.049   0.117  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.588  -0.220   1.198  1.00  0.00           C  
HETATM   23  H1  UNL     1       4.954  -0.664   1.466  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.208  -0.438  -0.279  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.626   0.895   0.925  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.477   0.176  -1.534  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.714   1.882  -1.134  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.447   2.016  -0.286  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.544   1.420  -2.028  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.481  -2.211  -1.403  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.418  -4.508  -0.867  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.426  -4.765   0.565  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.519  -2.817   1.471  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.403   0.237   1.922  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.874  -0.763   1.637  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.142   1.347   0.652  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.066   0.080  -0.640  1.00  0.00           H  
HETATM   38  H16 UNL     1      -4.029   2.856  -0.663  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.654   4.529  -1.942  1.00  0.00           H  
HETATM   40  H18 UNL     1      -0.354   3.956  -2.522  1.00  0.00           H  
HETATM   41  H19 UNL     1       1.271  -1.818   0.664  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.549  -1.378  -0.620  1.00  0.00           H  
HETATM   43  H21 UNL     1       1.855   0.338   1.786  1.00  0.00           H  
HETATM   44  H22 UNL     1       3.093  -0.933   1.886  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   22
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6    6   21
CONECT    6    7   20
CONECT    7    8    8   12
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11   32
CONECT   11   12   12   33
CONECT   12   13
CONECT   13   14   34   35
CONECT   14   15   36   37
CONECT   15   16   16   20
CONECT   16   17   38
CONECT   17   18   18   39
CONECT   18   19   40
CONECT   19   20   20
CONECT   21   22   41   42
CONECT   22   43   44
END

HMDB0014857
     RDKit          3D
Azatadine
 44 47  0  0  0  0  0  0  0  0999 V2000
    4.9081    0.0958    0.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5632    0.5449    0.5140 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2051    0.9556   -0.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6967    1.1931   -0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9340   -0.0247   -0.5401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3549   -0.0737   -0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354   -1.3264   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3722   -2.4087   -0.7695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9031   -3.6332   -0.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0289   -3.7949    0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6443   -2.6596    0.8516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535   -1.4214    0.5749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9772   -0.3268    1.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4412    0.6290    0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4453    1.4368   -0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9853    2.6791   -0.9644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2355    3.5641   -1.6492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9245    3.2149   -1.9694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4185    2.0387   -1.6107 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1258    1.1496   -0.9390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8171   -1.0488    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5883   -0.2204    1.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9536   -0.6641    1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2080   -0.4375   -0.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6264    0.8954    0.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4766    0.1760   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7136    1.8816   -1.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4474    2.0160   -0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    1.4196   -2.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807   -2.2111   -1.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4177   -4.5077   -0.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4261   -4.7649    0.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5188   -2.8171    1.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4028    0.2375    1.9215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8741   -0.7634    1.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1418    1.3473    0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0661    0.0795   -0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0289    2.8561   -0.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6536    4.5287   -1.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3543    3.9563   -2.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2706   -1.8181    0.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5486   -1.3779   -0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8552    0.3376    1.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0930   -0.9329    1.8858 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  3
  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
  5 21  1  0
 21 22  1  0
 22  2  1  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11-(1-Methyl-4-piperidinylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine	ChEBI
6,11-Dihydro-11-(1-methyl-4-piperidylidene)-5H-benzo(5,6)cyclohepta(1,2-b)pyridine	ChEBI
Azatadina	ChEBI
Azatadinum	ChEBI
Azatadine maleate	HMDB
Azatidine	HMDB
Idulian	HMDB
Juste brand OF azatadine maleate	HMDB
Lergocil	HMDB
Schering-plough brand OF azatadine maleate	HMDB
Optimine	HMDB
Schering brand OF azatadine maleate	HMDB
Idulamine	HMDB
Key brand OF azatadine maleate	HMDB
Zadine	HMDB

Chemical Formula

C₂₀H₂₂N₂

Average Molecular Weight

290.4021

Monoisotopic Molecular Weight

290.178298714

IUPAC Name

2-(1-methylpiperidin-4-ylidene)-4-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene

Traditional Name

azatadine

CAS Registry Number

3964-81-6

SMILES

CN1CCC(CC1)=C1C2=CC=CC=C2CCC2=C1N=CC=C2

InChI Identifier

InChI=1S/C20H22N2/c1-22-13-10-16(11-14-22)19-18-7-3-2-5-15(18)8-9-17-6-4-12-21-20(17)19/h2-7,12H,8-11,13-14H2,1H3

InChI Key

SEBMTIQKRHYNIT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzocycloheptapyridines. These are aromatic compounds containing a benzene ring and a pyridine ring fused to a seven membered carbocycle.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzocycloheptapyridines

Sub Class

Not Available

Direct Parent

Benzocycloheptapyridines

Alternative Parents

Substituents

Benzocycloheptapyridine
Benzenoid
Pyridine
Piperidine
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amine (CHEBI:2946 )
benzocycloheptapyridine (CHEBI:2946 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014857)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Azatadine H1-Antihistamine Action (PathBank: SMP0059865)

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	0.11 g/L	Not Available
LogP	2.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	3.67	ALOGPS
logP	3.75	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	7.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	16.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	101.53 m³·mol⁻¹	ChemAxon
Polarizability	34.01 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]+	171.253	31661259
DarkChem	[M-H]-	170.025	31661259
DeepCCS	[M+H]+	167.578	30932474
DeepCCS	[M-H]-	165.22	30932474
DeepCCS	[M-2H]-	198.106	30932474
DeepCCS	[M+Na]+	173.671	30932474
AllCCS	[M+H]+	171.5	32859911
AllCCS	[M+H-H2O]+	168.0	32859911
AllCCS	[M+NH4]+	174.8	32859911
AllCCS	[M+Na]+	175.7	32859911
AllCCS	[M-H]-	179.7	32859911
AllCCS	[M+Na-2H]-	179.2	32859911
AllCCS	[M+HCOO]-	178.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Azatadine	CN1CCC(CC1)=C1C2=CC=CC=C2CCC2=C1N=CC=C2	3657.4	Standard polar	33892256
Azatadine	CN1CCC(CC1)=C1C2=CC=CC=C2CCC2=C1N=CC=C2	2334.7	Standard non polar	33892256
Azatadine	CN1CCC(CC1)=C1C2=CC=CC=C2CCC2=C1N=CC=C2	2404.5	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 - Azatadine GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-1290000000-ca0638c59dea202e717c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azatadine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Azatadine 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 - Azatadine 10V, Positive-QTOF	splash10-0006-0090000000-584a39441c3649ae12e2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azatadine 20V, Positive-QTOF	splash10-01ox-1390000000-c5c0b825382fa6f3cd23	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azatadine 40V, Positive-QTOF	splash10-02u0-8290000000-f51daaefc04a58d431d2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azatadine 10V, Negative-QTOF	splash10-000i-0090000000-5ab5f6f4dcf98a4568cf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azatadine 20V, Negative-QTOF	splash10-000i-1190000000-06b890698214485f4bc3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azatadine 40V, Negative-QTOF	splash10-0229-5190000000-3d41734a0c4ce9ac0940	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azatadine 10V, Positive-QTOF	splash10-0006-0090000000-897430b0af8c07f94473	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azatadine 20V, Positive-QTOF	splash10-0006-0090000000-67eb5d7b0ea595cdb4c2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azatadine 40V, Positive-QTOF	splash10-03e9-0190000000-984c09ddd4091f9eed65	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azatadine 10V, Negative-QTOF	splash10-000i-0090000000-5f28f51a8f4e4bc977e9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azatadine 20V, Negative-QTOF	splash10-000i-0190000000-cc7ee4d2f2c29b712a28	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azatadine 40V, Negative-QTOF	splash10-015i-0090000000-9faba0c5bacb0d9e73ca	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
Azatadine 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 DB00719	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00719	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00719

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

18709

KEGG Compound ID

C07774

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Azatadine

METLIN ID

Not Available

PubChem Compound

19861

PDB ID

Not Available

ChEBI ID

2946

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

Small P, Barrett D, Biskin N: Effects of azatadine, terfenadine, and astemizole on allergen-induced nasal provocation. Ann Allergy. 1990 Feb;64(2 Pt 1):129-31. [PubMed:1968324 ]
Katelaris C: Comparative effects of loratadine and azatadine in the treatment of seasonal allergic rhinitis. Asian Pac J Allergy Immunol. 1990 Dec;8(2):103-7. [PubMed:1982614 ]
Zhang D, Hansen EB Jr, Deck J, Heinze TM, Sutherland JB, Cerniglia CE: Fungal biotransformation of the antihistamine azatadine by Cunninghamella elegans. Appl Environ Microbiol. 1996 Sep;62(9):3477-9. [PubMed:8795241 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. 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

Singh N, Puri SK: Causal prophylactic activity of antihistaminic agents against Plasmodium yoelii nigeriensis infection in Swiss mice. Acta Trop. 1998 Jun;69(3):255-60. [PubMed:9638277 ]
Mann KV, Crowe JP, Tietze KJ: Nonsedating histamine H1-receptor antagonists. Clin Pharm. 1989 May;8(5):331-44. [PubMed:2568212 ]
Clissold SP, Sorkin EM, Goa KL: Loratadine. A preliminary review of its pharmacodynamic properties and therapeutic efficacy. Drugs. 1989 Jan;37(1):42-57. [PubMed:2523301 ]
Haria M, Fitton A, Peters DH: Loratadine. A reappraisal of its pharmacological properties and therapeutic use in allergic disorders. Drugs. 1994 Oct;48(4):617-37. [PubMed:7528133 ]
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 Azatadine (HMDB0014857)

MOL for HMDB0014857 (Azatadine)

3D MOL for HMDB0014857 (Azatadine)

3D SDF for HMDB0014857 (Azatadine)

3D-SDF for HMDB0014857 (Azatadine)

PDB for HMDB0014857 (Azatadine)

3D PDB for HMDB0014857 (Azatadine)

SMILES for HMDB0014857 (Azatadine)

INCHI for HMDB0014857 (Azatadine)

Structure for HMDB0014857 (Azatadine)

3D Structure for HMDB0014857 (Azatadine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References