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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (9)transporters (2) Show 11 proteins XML

enzymes (9)transporters (2) Show 11 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:51 UTC

HMDB ID

HMDB0015069

Secondary Accession Numbers

HMDB15069

Metabolite Identification

Common Name

Maprotiline

Description

Maprotiline is a tetracyclic antidepressant with similar pharmacological properties to tricyclic antidepressants (TCAs). Similar to TCAs, maprotiline inhibits neuronal norepinephrine reuptake, possesses some anticholinergic activity, and does not affect monoamine oxidase activity. It differs from TCAs in that it does not appear to block serotonin reuptake. Maprotiline may be used to treat depressive affective disorders, including dysthymic disorder (depressive neurosis) and major depressive disorder. Maprotiline is effective at reducing symptoms of anxiety associated with depression.

Structure

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

HMDB0015069
     RDKit          3D
Maprotiline
 44 47  0  0  0  0  0  0  0  0999 V2000
    4.2922    0.4638    0.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9237   -0.8536    0.3068 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4781   -0.8631   -1.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1336   -0.1202   -1.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0877   -0.7622   -0.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2541   -0.1827   -0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8419   -0.1255   -1.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317    0.3728   -1.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8002    0.5386   -0.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8604    1.5035    0.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2653    2.6829    0.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3296    3.4854    1.4571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0098    3.1002    1.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3809    1.8837    0.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5234    1.0788    0.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5377   -0.7565    0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4898   -1.5648    0.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1084   -2.7659    1.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7758   -3.1265    1.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8126   -2.3060    0.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2213   -1.1554    0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120    0.7501    1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1730    1.2432   -0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3943    0.4409    0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6823   -1.5350    0.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2779   -1.9277   -1.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -0.3909   -1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3487    0.9106   -0.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8621   -0.0717   -2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4419   -0.9098    0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9846   -1.8139   -0.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2111    0.5484   -2.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7601   -1.1354   -2.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9409   -0.3100   -2.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3589    1.3732   -2.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8285    0.8589   -0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3032    2.9718    0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5904    4.4209    1.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508    3.6983    2.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3888    1.5737    0.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5217   -1.2508    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8543   -3.3965    1.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291   -4.0390    1.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2265   -2.5363    0.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15  6  1  0
 21 16  1  0
 21  6  1  0
 15 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
M  END

934
  Mrv0541 02231215072D          

 21 24  0  0  0  0            999 V2000
    5.3052   -1.8593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5950    0.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8000    1.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205    2.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5065    2.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0461    0.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2232   -0.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3900    0.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2511    0.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8271    0.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9501   -0.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6204   -0.4023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8217   -0.7218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0446    1.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0022    0.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7451   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4190   -0.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9966   -0.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6324    0.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5841   -0.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1002   -2.6244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  1 21  1  0  0  0  0
  2  4  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  2  8  1  0  0  0  0
  3  5  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  6  9  1  0  0  0  0
  6 12  2  0  0  0  0
  7 10  1  0  0  0  0
  7 13  2  0  0  0  0
  8 11  1  0  0  0  0
  9 14  2  0  0  0  0
 10 15  2  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015069

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCCCC12CCC(C3=CC=CC=C13)C1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C20H23N/c1-21-14-6-12-20-13-11-15(16-7-2-4-9-18(16)20)17-8-3-5-10-19(17)20/h2-5,7-10,15,21H,6,11-14H2,1H3

> <INCHI_KEY>
QSLMDECMDJKHMQ-UHFFFAOYSA-N

> <FORMULA>
C20H23N

> <MOLECULAR_WEIGHT>
277.4033

> <EXACT_MASS>
277.183049741

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
33.57280054214088

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl(3-{tetracyclo[6.6.2.0²,⁷.0⁹,¹⁴]hexadeca-2,4,6,9,11,13-hexaen-1-yl}propyl)amine

> <ALOGPS_LOGP>
4.89

> <JCHEM_LOGP>
4.372104774333334

> <ALOGPS_LOGS>
-6.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.542802753774973

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
99.30170000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
maprotiline

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015069
     RDKit          3D
Maprotiline
 44 47  0  0  0  0  0  0  0  0999 V2000
    4.2922    0.4638    0.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9237   -0.8536    0.3068 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4781   -0.8631   -1.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1336   -0.1202   -1.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0877   -0.7622   -0.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2541   -0.1827   -0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8419   -0.1255   -1.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317    0.3728   -1.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8002    0.5386   -0.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8604    1.5035    0.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2653    2.6829    0.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3296    3.4854    1.4571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0098    3.1002    1.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3809    1.8837    0.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5234    1.0788    0.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5377   -0.7565    0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4898   -1.5648    0.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1084   -2.7659    1.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7758   -3.1265    1.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8126   -2.3060    0.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2213   -1.1554    0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120    0.7501    1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1730    1.2432   -0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3943    0.4409    0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6823   -1.5350    0.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2779   -1.9277   -1.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -0.3909   -1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3487    0.9106   -0.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8621   -0.0717   -2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4419   -0.9098    0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9846   -1.8139   -0.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2111    0.5484   -2.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7601   -1.1354   -2.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9409   -0.3100   -2.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3589    1.3732   -2.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8285    0.8589   -0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3032    2.9718    0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5904    4.4209    1.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508    3.6983    2.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3888    1.5737    0.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5217   -1.2508    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8543   -3.3965    1.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291   -4.0390    1.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2265   -2.5363    0.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15  6  1  0
 21 16  1  0
 21  6  1  0
 15 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 934                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       9.903  -3.471   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       8.577   1.477   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.960   2.905   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.132   4.159   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.412   4.899   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.286   0.355   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.017  -0.002   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.195   0.049   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.669   1.783   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.277   1.278   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.240  -0.997   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.358  -0.751   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.267  -1.347   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.150   2.204   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.737   1.302   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.858  -2.425   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.849  -0.364   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.727  -1.359   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.247   1.124   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.957  -0.025   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.520  -4.899   0.000  0.00  0.00           C+0
CONECT    1   16   21                                                       
CONECT    2    4    6    7    8                                             
CONECT    3    5    9   10                                                  
CONECT    4    2    5                                                       
CONECT    5    3    4                                                       
CONECT    6    2    9   12                                                  
CONECT    7    2   10   13                                                  
CONECT    8    2   11                                                       
CONECT    9    3    6   14                                                  
CONECT   10    3    7   15                                                  
CONECT   11    8   16                                                       
CONECT   12    6   17                                                       
CONECT   13    7   18                                                       
CONECT   14    9   19                                                       
CONECT   15   10   20                                                       
CONECT   16    1   11                                                       
CONECT   17   12   19                                                       
CONECT   18   13   20                                                       
CONECT   19   14   17                                                       
CONECT   20   15   18                                                       
CONECT   21    1                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0015069
HETATM    1  C1  UNL     1       4.292   0.464   0.756  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.924  -0.854   0.307  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.478  -0.863  -1.073  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.134  -0.120  -1.198  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.088  -0.762  -0.366  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.254  -0.183  -0.358  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.842  -0.126  -1.787  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.232   0.373  -1.825  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.800   0.539  -0.423  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.860   1.504   0.253  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.265   2.683   0.821  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.330   3.485   1.457  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.010   3.100   1.517  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.381   1.884   0.925  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.523   1.079   0.292  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.538  -0.756   0.252  1.00  0.00           C  
HETATM   17  C16 UNL     1      -3.490  -1.565   0.820  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.108  -2.766   1.444  1.00  0.00           C  
HETATM   19  C18 UNL     1      -1.776  -3.127   1.482  1.00  0.00           C  
HETATM   20  C19 UNL     1      -0.813  -2.306   0.906  1.00  0.00           C  
HETATM   21  C20 UNL     1      -1.221  -1.155   0.313  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.812   0.750   1.715  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.173   1.243  -0.021  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.394   0.441   0.994  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.682  -1.535   0.420  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.278  -1.928  -1.335  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.221  -0.391  -1.737  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.349   0.911  -0.915  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.862  -0.072  -2.283  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.442  -0.910   0.670  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.985  -1.814  -0.787  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.211   0.548  -2.422  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.760  -1.135  -2.255  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.941  -0.310  -2.368  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.359   1.373  -2.314  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.828   0.859  -0.399  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.303   2.972   0.767  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.590   4.421   1.920  1.00  0.00           H  
HETATM   39  H18 UNL     1       0.751   3.698   2.005  1.00  0.00           H  
HETATM   40  H19 UNL     1       1.389   1.574   0.988  1.00  0.00           H  
HETATM   41  H20 UNL     1      -4.522  -1.251   0.771  1.00  0.00           H  
HETATM   42  H21 UNL     1      -3.854  -3.396   1.887  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.429  -4.039   1.950  1.00  0.00           H  
HETATM   44  H23 UNL     1       0.227  -2.536   0.913  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   15   21
CONECT    7    8   32   33
CONECT    8    9   34   35
CONECT    9   10   16   36
CONECT   10   11   11   15
CONECT   11   12   37
CONECT   12   13   13   38
CONECT   13   14   39
CONECT   14   15   15   40
CONECT   16   17   17   21
CONECT   17   18   41
CONECT   18   19   19   42
CONECT   19   20   43
CONECT   20   21   21   44
END

HMDB0015069
     RDKit          3D
Maprotiline
 44 47  0  0  0  0  0  0  0  0999 V2000
    4.2922    0.4638    0.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9237   -0.8536    0.3068 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4781   -0.8631   -1.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1336   -0.1202   -1.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0877   -0.7622   -0.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2541   -0.1827   -0.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8419   -0.1255   -1.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2317    0.3728   -1.8252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8002    0.5386   -0.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8604    1.5035    0.2525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2653    2.6829    0.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3296    3.4854    1.4571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0098    3.1002    1.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3809    1.8837    0.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5234    1.0788    0.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5377   -0.7565    0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4898   -1.5648    0.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1084   -2.7659    1.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7758   -3.1265    1.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8126   -2.3060    0.9059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2213   -1.1554    0.3131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8120    0.7501    1.7145 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1730    1.2432   -0.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3943    0.4409    0.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6823   -1.5350    0.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2779   -1.9277   -1.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -0.3909   -1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3487    0.9106   -0.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8621   -0.0717   -2.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4419   -0.9098    0.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9846   -1.8139   -0.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2111    0.5484   -2.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7601   -1.1354   -2.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9409   -0.3100   -2.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3589    1.3732   -2.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8285    0.8589   -0.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3032    2.9718    0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5904    4.4209    1.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7508    3.6983    2.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3888    1.5737    0.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5217   -1.2508    0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8543   -3.3965    1.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4291   -4.0390    1.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2265   -2.5363    0.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15  6  1  0
 21 16  1  0
 21  6  1  0
 15 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
BA-34276	HMDB
Declimed brand OF maprotiline hydrochloride	HMDB
Deprilept	HMDB
Dibencycladine	HMDB
Holsten brand OF maprotiline hydrochloride	HMDB
Maprotilin-teva	HMDB
Maprotilin-neuraxpharm	HMDB
Mesylate, maprotiline	HMDB
Novopharm brand OF maprotiline hydrochloride	HMDB
Psymion	HMDB
Neuraxpharm brand OF maprotiline hydrochloride	HMDB
Ratiopharm brand OF maprotiline hydrochloride	HMDB
Maprotilin neuraxpharm	HMDB
Maprotilin-ratiopharm	HMDB
Maprotiline mesylate	HMDB
Novo-maprotiline	HMDB
Teva brand OF maprotiline hydrochloride	HMDB
Maprotilin von CT	HMDB
Dolorgiet brand OF maprotiline hydrochloride	HMDB
Hexal brand OF maprotiline mesylate	HMDB
Hydrochloride, maprotiline	HMDB
Ludiomil	HMDB
Lundbeck brand OF maprotiline hydrochloride	HMDB
Maprotilin	HMDB
Maprotilin holsten	HMDB
Maprotiline hydrochloride	HMDB
Mirpan	HMDB
N-Methyl-9,10-ethanoanthracene-9(10H)-propylamine	HMDB
CT-Arzneimittel brand OF maprotiline hydrochloride	HMDB
Maprolu	HMDB
Maprotilin teva	HMDB
Maprotilin ratiopharm	HMDB
Novartis brand OF maprotiline hydrochloride	HMDB
Novo maprotiline	HMDB

Chemical Formula

C₂₀H₂₃N

Average Molecular Weight

277.4033

Monoisotopic Molecular Weight

277.183049741

IUPAC Name

methyl(3-{tetracyclo[6.6.2.0²,⁷.0⁹,¹⁴]hexadeca-2,4,6,9,11,13-hexaen-1-yl}propyl)amine

Traditional Name

maprotiline

CAS Registry Number

10262-69-8

SMILES

CNCCCC12CCC(C3=CC=CC=C13)C1=CC=CC=C21

InChI Identifier

InChI=1S/C20H23N/c1-21-14-6-12-20-13-11-15(16-7-2-4-9-18(16)20)17-8-3-5-10-19(17)20/h2-5,7-10,15,21H,6,11-14H2,1H3

InChI Key

QSLMDECMDJKHMQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Anthracenes

Sub Class

Not Available

Direct Parent

Anthracenes

Alternative Parents

Substituents

Anthracene
Tetralin
Aralkylamine
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

anthracenes (CHEBI:6690 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015069)
Membrane (HMDB: HMDB0015069)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	93 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.00015 g/L	Not Available
LogP	5.1	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	164.2	30932474
[M+H]+	Not Available	163.489	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000716

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00015 g/L	ALOGPS
logP	4.89	ALOGPS
logP	4.37	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Basic)	10.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.3 m³·mol⁻¹	ChemAxon
Polarizability	33.57 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]+	167.206	31661259
DarkChem	[M-H]-	163.929	31661259
DeepCCS	[M-2H]-	200.687	30932474
DeepCCS	[M+Na]+	176.252	30932474
AllCCS	[M+H]+	168.6	32859911
AllCCS	[M+H-H2O]+	165.2	32859911
AllCCS	[M+NH4]+	171.7	32859911
AllCCS	[M+Na]+	172.6	32859911
AllCCS	[M-H]-	176.4	32859911
AllCCS	[M+Na-2H]-	176.0	32859911
AllCCS	[M+HCOO]-	175.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Maprotiline	CNCCCC12CCC(C3=CC=CC=C13)C1=CC=CC=C21	3024.4	Standard polar	33892256
Maprotiline	CNCCCC12CCC(C3=CC=CC=C13)C1=CC=CC=C21	2359.4	Standard non polar	33892256
Maprotiline	CNCCCC12CCC(C3=CC=CC=C13)C1=CC=CC=C21	2311.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Maprotiline,1TMS,isomer #1	CN(CCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)[Si](C)(C)C	2672.5	Semi standard non polar	33892256
Maprotiline,1TMS,isomer #1	CN(CCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)[Si](C)(C)C	2772.9	Standard non polar	33892256
Maprotiline,1TMS,isomer #1	CN(CCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)[Si](C)(C)C	2762.8	Standard polar	33892256
Maprotiline,1TBDMS,isomer #1	CN(CCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)[Si](C)(C)C(C)(C)C	2913.8	Semi standard non polar	33892256
Maprotiline,1TBDMS,isomer #1	CN(CCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)[Si](C)(C)C(C)(C)C	3064.7	Standard non polar	33892256
Maprotiline,1TBDMS,isomer #1	CN(CCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)[Si](C)(C)C(C)(C)C	2878.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Maprotiline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-6090000000-8e89e932860e4ee6b072	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Maprotiline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0f6x-9560000000-f263c228ecd4df5d7e73	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline LC-ESI-QTOF , positive-QTOF	splash10-004i-0090000000-7a66545f7844123eba51	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline LC-ESI-QTOF , positive-QTOF	splash10-0fb9-0090000000-c3b045151955339e59cc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline LC-ESI-QTOF , positive-QTOF	splash10-0gb9-0590000000-bfeab480527e9e5cb70a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline LC-ESI-QTOF , positive-QTOF	splash10-0006-0930000000-406a233a8ad8a3b5d463	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline LC-ESI-QTOF , positive-QTOF	splash10-002f-0920000000-d86cbfa85ef229dfed53	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline LC-ESI-QFT , positive-QTOF	splash10-004i-0090000000-1a2bf3822fc21e2f8460	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline LC-ESI-QFT , positive-QTOF	splash10-0fb9-0190000000-cf4d09e63ae607c3f690	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline LC-ESI-QFT , positive-QTOF	splash10-0gb9-1690000000-32657b0912154e5e6eb5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline LC-ESI-QFT , positive-QTOF	splash10-00kf-1940000000-176ec01fb7ad9b4a11ca	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline LC-ESI-QFT , positive-QTOF	splash10-0006-1920000000-a721293bed4aff937490	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline LC-ESI-QFT , positive-QTOF	splash10-0006-1910000000-f2d680cb6b1ab57df4bd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline , positive-QTOF	splash10-004i-0390000000-ae291d01fb28cc38d1de	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline 40V, Positive-QTOF	splash10-002f-0930000000-1eb22c7693a749dd6c69	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline 20V, Positive-QTOF	splash10-0fb9-0090000000-23fddbd27ba3e5e42a21	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline 10V, Positive-QTOF	splash10-004i-0090000000-130477a21813cdfe3871	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline 50V, Positive-QTOF	splash10-002f-0920000000-dfc6b18aea4d0a6e7eb5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline 35V, Positive-QTOF	splash10-0gdl-0790000000-1b7b6a0fb83ed782ad78	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline 20V, Positive-QTOF	splash10-0fb9-0090000000-c978fa61248cd5a77295	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Maprotiline 15V, Positive-QTOF	splash10-004i-0090000000-d428ee7275d47b035da3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maprotiline 10V, Positive-QTOF	splash10-004j-0090000000-7ae10ab99fb7f49ffa27	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maprotiline 20V, Positive-QTOF	splash10-002b-1090000000-2d55de2a427af756ca33	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maprotiline 40V, Positive-QTOF	splash10-0a4i-3090000000-5aed5f1d5ab04a0db509	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maprotiline 10V, Negative-QTOF	splash10-004i-0090000000-067ee24bd068071dfb49	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maprotiline 20V, Negative-QTOF	splash10-004i-1090000000-75ab50229f1a5d9f943a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maprotiline 40V, Negative-QTOF	splash10-0a5a-4090000000-5c180e3dc53a4a98eb97	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00934	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00934	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00934

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3871

KEGG Compound ID

C07107

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Maprotiline

METLIN ID

Not Available

PubChem Compound

4011

PDB ID

Not Available

ChEBI ID

127713

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

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 ]
Brachtendorf L, Jetter A, Beckurts KT, Holscher AH, Fuhr U: Cytochrome P450 enzymes contributing to demethylation of maprotiline in man. Pharmacol Toxicol. 2002 Mar;90(3):144-9. [PubMed:12071336 ]

Enzyme Details

2. Cytochrome P450 1A2

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

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

3. 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

Noguchi S, Inukai T, Kuno T, Tanaka C: The suppression of olfactory bulbectomy-induced muricide by antidepressants and antihistamines via histamine H1 receptor blocking. Physiol Behav. 1992 Jun;51(6):1123-7. [PubMed:1353628 ]
Cavero I, Lefevre-Borg F, Roach AG: Effects of mianserin, desipramine and maprotiline on blood pressure responses evoked by acetylcholine, histamine and 5-hydroxytryptamine in rats. Br J Pharmacol. 1981 Sep;74(1):143-8. [PubMed:6115693 ]
Kanba S, Richelson E: Histamine H1 receptors in human brain labelled with [3H]doxepin. Brain Res. 1984 Jun 18;304(1):1-7. [PubMed:6146381 ]

Enzyme Details

4. Alpha-1A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular weight:: 51486.0

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

5. Muscarinic acetylcholine receptor M3

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM3
Uniprot ID:: P20309
Molecular weight:: 66127.4

References

El-Fakahany E, Richelson E: Antagonism by antidepressants of muscarinic acetylcholine receptors of human brain. Br J Pharmacol. 1983 Jan;78(1):97-102. [PubMed:6297650 ]
Golds PR, Przyslo FR, Strange PG: The binding of some antidepressant drugs to brain muscarinic acetylcholine receptors. Br J Pharmacol. 1980 Mar;68(3):541-9. [PubMed:7052344 ]
Doggrell SA, Vincent L: The postsynaptic effects of antidepressant drugs in the rat anococcygeus muscle. J Pharm Pharmacol. 1981 Nov;33(11):720-4. [PubMed:6118411 ]

Enzyme Details

6. Muscarinic acetylcholine receptor M1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM1
Uniprot ID:: P11229
Molecular weight:: 51420.4

References

El-Fakahany E, Richelson E: Antagonism by antidepressants of muscarinic acetylcholine receptors of human brain. Br J Pharmacol. 1983 Jan;78(1):97-102. [PubMed:6297650 ]
Golds PR, Przyslo FR, Strange PG: The binding of some antidepressant drugs to brain muscarinic acetylcholine receptors. Br J Pharmacol. 1980 Mar;68(3):541-9. [PubMed:7052344 ]
Doggrell SA, Vincent L: The postsynaptic effects of antidepressant drugs in the rat anococcygeus muscle. J Pharm Pharmacol. 1981 Nov;33(11):720-4. [PubMed:6118411 ]

Enzyme Details

7. Muscarinic acetylcholine receptor M2

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
Gene Name:: CHRM2
Uniprot ID:: P08172
Molecular weight:: 51714.6

References

El-Fakahany E, Richelson E: Antagonism by antidepressants of muscarinic acetylcholine receptors of human brain. Br J Pharmacol. 1983 Jan;78(1):97-102. [PubMed:6297650 ]
Golds PR, Przyslo FR, Strange PG: The binding of some antidepressant drugs to brain muscarinic acetylcholine receptors. Br J Pharmacol. 1980 Mar;68(3):541-9. [PubMed:7052344 ]
Doggrell SA, Vincent L: The postsynaptic effects of antidepressant drugs in the rat anococcygeus muscle. J Pharm Pharmacol. 1981 Nov;33(11):720-4. [PubMed:6118411 ]

Enzyme Details

8. Muscarinic acetylcholine receptor M4

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase
Gene Name:: CHRM4
Uniprot ID:: P08173
Molecular weight:: 53048.7

References

El-Fakahany E, Richelson E: Antagonism by antidepressants of muscarinic acetylcholine receptors of human brain. Br J Pharmacol. 1983 Jan;78(1):97-102. [PubMed:6297650 ]
Golds PR, Przyslo FR, Strange PG: The binding of some antidepressant drugs to brain muscarinic acetylcholine receptors. Br J Pharmacol. 1980 Mar;68(3):541-9. [PubMed:7052344 ]
Doggrell SA, Vincent L: The postsynaptic effects of antidepressant drugs in the rat anococcygeus muscle. J Pharm Pharmacol. 1981 Nov;33(11):720-4. [PubMed:6118411 ]

Enzyme Details

9. Muscarinic acetylcholine receptor M5

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM5
Uniprot ID:: P08912
Molecular weight:: 60073.2

References

El-Fakahany E, Richelson E: Antagonism by antidepressants of muscarinic acetylcholine receptors of human brain. Br J Pharmacol. 1983 Jan;78(1):97-102. [PubMed:6297650 ]
Golds PR, Przyslo FR, Strange PG: The binding of some antidepressant drugs to brain muscarinic acetylcholine receptors. Br J Pharmacol. 1980 Mar;68(3):541-9. [PubMed:7052344 ]
Doggrell SA, Vincent L: The postsynaptic effects of antidepressant drugs in the rat anococcygeus muscle. J Pharm Pharmacol. 1981 Nov;33(11):720-4. [PubMed:6118411 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524 ]
Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]

Enzyme Details

2. Sodium-dependent noradrenaline transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular weight:: 69331.42

References

Saba W, Valette H, Schollhorn-Peyronneau MA, Coulon C, Ottaviani M, Chalon S, Dolle F, Emond P, Halldin C, Helfenbein J, Madelmont JC, Deloye JB, Guilloteau D, Bottlaender M: [11C]LBT-999: a suitable radioligand for investigation of extra-striatal dopamine transporter with PET. Synapse. 2007 Jan;61(1):17-23. [PubMed:17068778 ]
Arai S, Morita K, Kitayama S, Kumagai K, Kumagai M, Kihira K, Dohi T: Chronic inhibition of the norepinephrine transporter in the brain participates in seizure sensitization to cocaine and local anesthetics. Brain Res. 2003 Feb 21;964(1):83-90. [PubMed:12573515 ]
Cloonan SM, Drozgowska A, Fayne D, Williams DC: The antidepressants maprotiline and fluoxetine have potent selective antiproliferative effects against Burkitt lymphoma independently of the norepinephrine and serotonin transporters. Leuk Lymphoma. 2010 Mar;51(3):523-39. doi: 10.3109/10428190903552112. [PubMed:20141432 ]
Dronjak S, Spasojevic N, Gavrilovic L, Varagic V: Effects of noradrenaline and serotonin reuptake inhibitors on pituitary-adrenocortical and sympatho-adrenomedullar system of adult rats. Neuro Endocrinol Lett. 2007 Oct;28(5):614-20. [PubMed:17984940 ]
Mochizucki D: Serotonin and noradrenaline reuptake inhibitors in animal models of pain. Hum Psychopharmacol. 2004 Oct;19 Suppl 1:S15-9. [PubMed:15378668 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Showing metabocard for Maprotiline (HMDB0015069)

MOL for HMDB0015069 (Maprotiline)

3D MOL for HMDB0015069 (Maprotiline)

3D SDF for HMDB0015069 (Maprotiline)

3D-SDF for HMDB0015069 (Maprotiline)

PDB for HMDB0015069 (Maprotiline)

3D PDB for HMDB0015069 (Maprotiline)

SMILES for HMDB0015069 (Maprotiline)

INCHI for HMDB0015069 (Maprotiline)

Structure for HMDB0015069 (Maprotiline)

3D Structure for HMDB0015069 (Maprotiline)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References

References

Transporters

References

References