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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:04 UTC

HMDB ID

HMDB0015670

Secondary Accession Numbers

HMDB15670

Metabolite Identification

Common Name

Alcaftadine

Description

Alcaftadine is only found in individuals that have used or taken this drug. It is a H1 histamine receptor antagonist indicated for the prevention of itching associated with allergic conjunctivitis. This drug was approved in July 2010.Alcaftadine is a H1 histamine receptor antagonist and inhibitor of the release of histamine from mast cells. Decreased chemotaxis and inhibition of eosinophil activation has also been demonstrated.

Structure

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

HMDB0015670
     RDKit          3D
Alcaftadine
 44 47  0  0  0  0  0  0  0  0999 V2000
    4.5867    0.0679    1.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3315    0.0981    0.6737 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0191    1.4402    0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6615    1.5647   -0.3888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9993    0.2079   -0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1687    0.0534    0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883   -1.2857    0.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1566   -2.1760    0.8388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1947   -3.4852    1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5130   -3.8717    0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4711   -2.9929    0.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -1.6502    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2598   -0.8113   -0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0407    0.5705   -0.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2590    1.4524    0.1788 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6479    2.6632    0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9500    3.2728    0.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2219    4.4048    0.9667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5771    3.1557    1.3723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5482    2.2639    1.3133 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9770    1.2584    0.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8063   -0.8400   -0.9016 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334   -0.8720   -0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4334   -0.4509    2.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809   -0.4624    0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9809    1.0860    1.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9601    2.0473    1.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300    1.9088   -0.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9271    1.6142   -1.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    2.3766   -0.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1398   -1.7892    1.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5317   -4.1896    1.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7989   -4.9228    0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4976   -3.2326    0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9095   -0.7415    0.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9101   -1.3825   -0.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5256    0.5330   -1.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0246    1.0630   -0.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7109    2.7803   -0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5424    4.0913    1.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9204   -0.4145   -1.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3363   -1.7918   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3794   -1.8720    0.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9613   -0.7396   -1.1984 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  1  0
 16 17  1  0
 17 18  2  0
 16 19  2  0
 19 20  1  0
 20 21  2  0
  5 22  1  0
 22 23  1  0
 23  2  1  0
 21  6  1  0
 12  7  1  0
 21 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 19 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
M  END


  Mrv0541 02241214192D          

 23 26  0  0  0  0            999 V2000
    3.5539   -3.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5539   -2.2172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684   -1.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684   -0.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5539   -0.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5539    0.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2972    0.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9020    0.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6903    0.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8739    1.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2691    1.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4808    1.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9664    2.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1414    2.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6270    1.4200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8106    0.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1024    0.1926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811    0.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8054    1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3822    2.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7840    2.9228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8394   -0.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8394   -1.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015670

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC(CC1)=C1C2=NC=C(C=O)N2CCC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H21N3O/c1-21-9-6-15(7-10-21)18-17-5-3-2-4-14(17)8-11-22-16(13-23)12-20-19(18)22/h2-5,12-13H,6-11H2,1H3

> <INCHI_KEY>
MWTBKTRZPHJQLH-UHFFFAOYSA-N

> <FORMULA>
C19H21N3O

> <MOLECULAR_WEIGHT>
307.3895

> <EXACT_MASS>
307.168462309

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.68058927944821

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(1-methylpiperidin-4-ylidene)-4,7-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),3,5,10,12-pentaene-6-carbaldehyde

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
2.1713893323333333

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.162953769226122

> <JCHEM_POLAR_SURFACE_AREA>
38.13

> <JCHEM_REFRACTIVITY>
102.87719999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
alcaftadine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015670
     RDKit          3D
Alcaftadine
 44 47  0  0  0  0  0  0  0  0999 V2000
    4.5867    0.0679    1.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3315    0.0981    0.6737 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0191    1.4402    0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6615    1.5647   -0.3888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9993    0.2079   -0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1687    0.0534    0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883   -1.2857    0.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1566   -2.1760    0.8388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1947   -3.4852    1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5130   -3.8717    0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4711   -2.9929    0.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -1.6502    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2598   -0.8113   -0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0407    0.5705   -0.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2590    1.4524    0.1788 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6479    2.6632    0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9500    3.2728    0.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2219    4.4048    0.9667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5771    3.1557    1.3723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5482    2.2639    1.3133 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9770    1.2584    0.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8063   -0.8400   -0.9016 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334   -0.8720   -0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4334   -0.4509    2.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809   -0.4624    0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9809    1.0860    1.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9601    2.0473    1.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300    1.9088   -0.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9271    1.6142   -1.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    2.3766   -0.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1398   -1.7892    1.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5317   -4.1896    1.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7989   -4.9228    0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4976   -3.2326    0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9095   -0.7415    0.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9101   -1.3825   -0.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5256    0.5330   -1.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0246    1.0630   -0.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7109    2.7803   -0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5424    4.0913    1.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9204   -0.4145   -1.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3363   -1.7918   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3794   -1.8720    0.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9613   -0.7396   -1.1984 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  1  0
 16 17  1  0
 17 18  2  0
 16 19  2  0
 19 20  1  0
 20 21  2  0
  5 22  1  0
 22 23  1  0
 23  2  1  0
 21  6  1  0
 12  7  1  0
 21 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 19 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       6.634  -5.679   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.634  -4.139   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.968  -3.369   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.968  -1.829   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.634  -1.059   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.634   0.481   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.021   1.149   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.150   0.102   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.622   0.556   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.965   2.057   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.836   3.105   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.364   2.651   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.404   3.855   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.864   3.855   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.904   2.651   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       5.246   1.149   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       3.924   0.360   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.765   1.373   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.370   2.789   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.580   4.111   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.330   5.456   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.300  -1.829   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.300  -3.369   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15    6   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22    5   23                                                       
CONECT   23   22    2                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0015670
HETATM    1  C1  UNL     1       4.587   0.068   1.358  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.332   0.098   0.674  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.019   1.440   0.285  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.661   1.565  -0.389  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.999   0.208  -0.242  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.169   0.053   0.268  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.788  -1.286   0.418  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.157  -2.176   0.839  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.195  -3.485   1.003  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.513  -3.872   0.738  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.471  -2.993   0.322  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.094  -1.650   0.157  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.260  -0.811  -0.204  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.041   0.570  -0.658  1.00  0.00           C  
HETATM   15  N2  UNL     1      -2.259   1.452   0.179  1.00  0.00           N  
HETATM   16  C14 UNL     1      -2.648   2.663   0.671  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.950   3.273   0.470  1.00  0.00           C  
HETATM   18  O1  UNL     1      -4.222   4.405   0.967  1.00  0.00           O  
HETATM   19  C16 UNL     1      -1.577   3.156   1.372  1.00  0.00           C  
HETATM   20  N3  UNL     1      -0.548   2.264   1.313  1.00  0.00           N  
HETATM   21  C17 UNL     1      -0.977   1.258   0.598  1.00  0.00           C  
HETATM   22  C18 UNL     1       1.806  -0.840  -0.902  1.00  0.00           C  
HETATM   23  C19 UNL     1       3.233  -0.872  -0.401  1.00  0.00           C  
HETATM   24  H1  UNL     1       4.433  -0.451   2.339  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.381  -0.462   0.823  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.981   1.086   1.588  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.960   2.047   1.208  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.830   1.909  -0.329  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.927   1.614  -1.499  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.055   2.377  -0.081  1.00  0.00           H  
HETATM   31  H8  UNL     1       1.140  -1.789   1.084  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.532  -4.190   1.328  1.00  0.00           H  
HETATM   33  H10 UNL     1      -1.799  -4.923   0.868  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.498  -3.233   0.105  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.910  -0.741   0.735  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.910  -1.383  -0.920  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.526   0.533  -1.673  1.00  0.00           H  
HETATM   38  H15 UNL     1      -4.025   1.063  -0.873  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.711   2.780  -0.103  1.00  0.00           H  
HETATM   40  H17 UNL     1      -1.542   4.091   1.885  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.920  -0.414  -1.994  1.00  0.00           H  
HETATM   42  H19 UNL     1       1.336  -1.792  -1.113  1.00  0.00           H  
HETATM   43  H20 UNL     1       3.379  -1.872   0.074  1.00  0.00           H  
HETATM   44  H21 UNL     1       3.961  -0.740  -1.198  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   23
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6    6   22
CONECT    6    7   21
CONECT    7    8    8   12
CONECT    8    9   31
CONECT    9   10   10   32
CONECT   10   11   33
CONECT   11   12   12   34
CONECT   12   13
CONECT   13   14   35   36
CONECT   14   15   37   38
CONECT   15   16   21
CONECT   16   17   19   19
CONECT   17   18   18   39
CONECT   19   20   40
CONECT   20   21   21
CONECT   22   23   41   42
CONECT   23   43   44
END

HMDB0015670
     RDKit          3D
Alcaftadine
 44 47  0  0  0  0  0  0  0  0999 V2000
    4.5867    0.0679    1.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3315    0.0981    0.6737 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0191    1.4402    0.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6615    1.5647   -0.3888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9993    0.2079   -0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1687    0.0534    0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883   -1.2857    0.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1566   -2.1760    0.8388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1947   -3.4852    1.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5130   -3.8717    0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4711   -2.9929    0.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -1.6502    0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2598   -0.8113   -0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0407    0.5705   -0.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2590    1.4524    0.1788 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6479    2.6632    0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9500    3.2728    0.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2219    4.4048    0.9667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5771    3.1557    1.3723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5482    2.2639    1.3133 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9770    1.2584    0.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8063   -0.8400   -0.9016 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2334   -0.8720   -0.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4334   -0.4509    2.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809   -0.4624    0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9809    1.0860    1.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9601    2.0473    1.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300    1.9088   -0.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9271    1.6142   -1.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    2.3766   -0.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1398   -1.7892    1.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5317   -4.1896    1.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7989   -4.9228    0.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4976   -3.2326    0.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9095   -0.7415    0.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9101   -1.3825   -0.9198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5256    0.5330   -1.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0246    1.0630   -0.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7109    2.7803   -0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5424    4.0913    1.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9204   -0.4145   -1.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3363   -1.7918   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3794   -1.8720    0.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9613   -0.7396   -1.1984 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  1  0
 16 17  1  0
 17 18  2  0
 16 19  2  0
 19 20  1  0
 20 21  2  0
  5 22  1  0
 22 23  1  0
 23  2  1  0
 21  6  1  0
 12  7  1  0
 21 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
 19 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Alcaftadina	ChEBI
Alcaftadinum	ChEBI
Lastacaft	ChEBI

Chemical Formula

C₁₉H₂₁N₃O

Average Molecular Weight

307.3895

Monoisotopic Molecular Weight

307.168462309

IUPAC Name

2-(1-methylpiperidin-4-ylidene)-4,7-diazatricyclo[8.4.0.0³,⁷]tetradeca-1(14),3,5,10,12-pentaene-6-carbaldehyde

Traditional Name

alcaftadine

CAS Registry Number

147084-10-4

SMILES

CN1CCC(CC1)=C1C2=NC=C(C=O)N2CCC2=CC=CC=C12

InChI Identifier

InChI=1S/C19H21N3O/c1-21-9-6-15(7-10-21)18-17-5-3-2-4-14(17)8-11-22-16(13-23)12-20-19(18)22/h2-5,12-13H,6-11H2,1H3

InChI Key

MWTBKTRZPHJQLH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzazepines

Sub Class

Not Available

Direct Parent

Benzazepines

Alternative Parents

Substituents

Benzazepine
Azepine
Imidazole-4-carbonyl group
Aryl-aldehyde
N-substituted imidazole
Piperidine
Benzenoid
Imidazole
Azole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organic oxide
Amine
Organooxygen compound
Organonitrogen compound
Aldehyde
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

piperidines (CHEBI:71023 )
tertiary amino compound (CHEBI:71023 )
aldehyde (CHEBI:71023 )
imidazobenzazepine (CHEBI:71023 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015670)

Source

Exogenous

Exogenous (HMDB: HMDB0015670)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Alcaftadine H1-Antihistamine Action (PathBank: SMP0062881)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.33 g/L	ALOGPS
logP	2.09	ALOGPS
logP	2.17	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	7.16	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	102.88 m³·mol⁻¹	ChemAxon
Polarizability	34.68 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]+	168.406	31661259
DarkChem	[M-H]-	171.422	31661259
DeepCCS	[M-2H]-	203.173	30932474
DeepCCS	[M+Na]+	178.738	30932474
AllCCS	[M+H]+	174.2	32859911
AllCCS	[M+H-H2O]+	170.9	32859911
AllCCS	[M+NH4]+	177.3	32859911
AllCCS	[M+Na]+	178.2	32859911
AllCCS	[M-H]-	180.8	32859911
AllCCS	[M+Na-2H]-	180.2	32859911
AllCCS	[M+HCOO]-	179.8	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.	4.16 minutes	32390414
Predicted by Siyang on May 30, 2022	10.4048 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.42 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	74.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	847.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	203.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	148.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	67.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	298.4 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	376.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	608.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	756.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	221.6 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	1138.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	191.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	292.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	397.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	430.8 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	50.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alcaftadine	CN1CCC(CC1)=C1C2=NC=C(C=O)N2CCC2=CC=CC=C12	3848.7	Standard polar	33892256
Alcaftadine	CN1CCC(CC1)=C1C2=NC=C(C=O)N2CCC2=CC=CC=C12	2592.0	Standard non polar	33892256
Alcaftadine	CN1CCC(CC1)=C1C2=NC=C(C=O)N2CCC2=CC=CC=C12	2694.4	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 - Alcaftadine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-0290000000-89e154e3d89dbad02320	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alcaftadine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alcaftadine 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 - Alcaftadine 10V, Positive-QTOF	splash10-0a4i-0039000000-edbab9f942994bcdc834	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcaftadine 20V, Positive-QTOF	splash10-0a6r-2095000000-99aa3370392cde3889c1	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcaftadine 40V, Positive-QTOF	splash10-0909-4290000000-9455884b1ad78d19deb8	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcaftadine 10V, Negative-QTOF	splash10-0a4i-0019000000-f9c0d18e0b95b14486cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcaftadine 20V, Negative-QTOF	splash10-0a4i-0096000000-07fa6dab65a51dd3e0ae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcaftadine 40V, Negative-QTOF	splash10-0w5d-9030000000-4a0dbea890140ccf214e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcaftadine 10V, Positive-QTOF	splash10-0a4i-0009000000-9cadee9fb7834616dbdb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcaftadine 20V, Positive-QTOF	splash10-0a4i-0019000000-ba6c1afcd8f5ef945287	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcaftadine 40V, Positive-QTOF	splash10-03fr-1390000000-b81ba0d09cb861c5aa36	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcaftadine 10V, Negative-QTOF	splash10-0a4i-0009000000-de69c65803e567e26cea	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcaftadine 20V, Negative-QTOF	splash10-0a6r-0089000000-5b1ba00893773270529d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alcaftadine 40V, Negative-QTOF	splash10-001u-0190000000-b417833e34387c256453	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
Alcaftadine 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 DB06766	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06766	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06766

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14201635

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alcaftadine

METLIN ID

Not Available

PubChem Compound

19371515

PDB ID

Not Available

ChEBI ID

71023

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

Simons FE, Simons KJ: Histamine and H1-antihistamines: celebrating a century of progress. J Allergy Clin Immunol. 2011 Dec;128(6):1139-1150.e4. doi: 10.1016/j.jaci.2011.09.005. Epub 2011 Oct 27. [PubMed:22035879 ]
Hussar DA, Samuel J: Vilazodone hydrochloride, linagliptin, and alcaftadine. J Am Pharm Assoc (2003). 2011 Jul-Aug;51(4):557-9. doi: 10.1331/JAPhA.2011.11534. [PubMed:21752782 ]
Mahvan TD, Buckley WA, Hornecker JR: Alcaftadine for the prevention of itching associated with allergic conjunctivitis. Ann Pharmacother. 2012 Jul-Aug;46(7-8):1025-32. doi: 10.1345/aph.1Q755. Epub 2012 Jul 17. [PubMed:22811343 ]

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

Showing metabocard for Alcaftadine (HMDB0015670)

MOL for HMDB0015670 (Alcaftadine)

3D MOL for HMDB0015670 (Alcaftadine)

3D SDF for HMDB0015670 (Alcaftadine)

3D-SDF for HMDB0015670 (Alcaftadine)

PDB for HMDB0015670 (Alcaftadine)

3D PDB for HMDB0015670 (Alcaftadine)

SMILES for HMDB0015670 (Alcaftadine)

INCHI for HMDB0015670 (Alcaftadine)

Structure for HMDB0015670 (Alcaftadine)

3D Structure for HMDB0015670 (Alcaftadine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes