Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:11:27 UTC

Update Date

2019-07-23 07:15:32 UTC

HMDB ID

HMDB0060993

Secondary Accession Numbers

HMDB60993

Metabolite Identification

Common Name

demethylmaprotiline

Description

demethylmaprotiline is a metabolite of maprotiline. Maprotiline (sold as Deprilept, Ludiomil, Psymion) is a tetracyclic antidepressant (TeCA). However, Maprotiline's fourth ring is spurious, as formed by a bridge across the central tricyclic ring. It is a strong norepinephrine reuptake inhibitor with only weak effects on serotonin and dopamine reuptake. (Wikipedia)

Structure

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

HMDB0060993
     RDKit          3D
demethylmaprotiline
 41 44  0  0  0  0  0  0  0  0999 V2000
    4.2247    0.4155   -0.6109 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9997    0.1626    0.7963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5344    0.5336    1.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5996   -0.2855    0.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1662   -0.0789    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -0.2799    1.8298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8207   -0.2618    1.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4685   -0.1250    0.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8720    1.1166   -0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6560    2.1374   -0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397    3.2480   -1.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6723    3.2902   -1.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1043    2.2131   -0.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4805    1.1159   -0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8829   -1.2415   -0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6219   -2.2072   -0.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9459   -3.1774   -1.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5720   -3.1587   -1.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1822   -2.1625   -1.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5089   -1.2330   -0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4957   -0.4386   -1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4806    0.9692   -1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6033    0.9068    1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2101   -0.8813    1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4561    1.5947    0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4148    0.3677    2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8068   -1.3573    0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8719   -0.2640   -0.8166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0561    0.5587    2.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0820   -1.2108    2.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2061    0.5778    2.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2443   -1.1838    2.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5442   -0.1225    0.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7385    2.1275   -0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6946    4.0573   -1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1952    4.1469   -1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1611    2.3340   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6900   -2.1771   -0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5090   -3.9628   -2.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001   -3.9020   -2.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2539   -2.1620   -1.1330 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  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14  5  1  0
 20 15  1  0
 20  5  1  0
 14  9  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END

934
  Mrv0541 02271201052D          

 20 23  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
  1 16  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>
HMDB0060993

> <DATABASE_NAME>
hmdb

> <SMILES>
NCCCC12CCC(C3=CC=CC=C13)C1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C19H21N/c20-13-5-11-19-12-10-14(15-6-1-3-8-17(15)19)16-7-2-4-9-18(16)19/h1-4,6-9,14H,5,10-13,20H2

> <INCHI_KEY>
IFHUOEQJTQWFGJ-UHFFFAOYSA-N

> <FORMULA>
C19H21N

> <MOLECULAR_WEIGHT>
263.3767

> <EXACT_MASS>
263.167399677

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
31.391538290228233

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.87

> <JCHEM_LOGP>
3.9395243806666667

> <ALOGPS_LOGS>
-6.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.20419349522038

> <JCHEM_POLAR_SURFACE_AREA>
26.02

> <JCHEM_REFRACTIVITY>
94.52710000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.76e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{tetracyclo[6.6.2.0²,⁷.0⁹,¹⁴]hexadeca-2,4,6,9,11,13-hexaen-1-yl}propan-1-amine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060993
     RDKit          3D
demethylmaprotiline
 41 44  0  0  0  0  0  0  0  0999 V2000
    4.2247    0.4155   -0.6109 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9997    0.1626    0.7963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5344    0.5336    1.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5996   -0.2855    0.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1662   -0.0789    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -0.2799    1.8298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8207   -0.2618    1.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4685   -0.1250    0.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8720    1.1166   -0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6560    2.1374   -0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397    3.2480   -1.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6723    3.2902   -1.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1043    2.2131   -0.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4805    1.1159   -0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8829   -1.2415   -0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6219   -2.2072   -0.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9459   -3.1774   -1.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5720   -3.1587   -1.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1822   -2.1625   -1.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5089   -1.2330   -0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4957   -0.4386   -1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4806    0.9692   -1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6033    0.9068    1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2101   -0.8813    1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4561    1.5947    0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4148    0.3677    2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8068   -1.3573    0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8719   -0.2640   -0.8166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0561    0.5587    2.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0820   -1.2108    2.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2061    0.5778    2.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2443   -1.1838    2.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5442   -0.1225    0.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7385    2.1275   -0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6946    4.0573   -1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1952    4.1469   -1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1611    2.3340   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6900   -2.1771   -0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5090   -3.9628   -2.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001   -3.9020   -2.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2539   -2.1620   -1.1330 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  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14  5  1  0
 20 15  1  0
 20  5  1  0
 14  9  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 934                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-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
CONECT    1   16                                                            
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                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0060993
HETATM    1  N1  UNL     1       4.225   0.416  -0.611  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.000   0.163   0.796  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.534   0.534   1.089  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.600  -0.285   0.269  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.166  -0.079   0.398  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.341  -0.280   1.830  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.821  -0.262   1.921  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.468  -0.125   0.561  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.872   1.117  -0.029  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.656   2.137  -0.460  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.040   3.248  -1.024  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.672   3.290  -1.134  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.104   2.213  -0.676  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.480   1.116  -0.119  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.883  -1.242  -0.249  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.622  -2.207  -0.861  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.946  -3.177  -1.585  1.00  0.00           C  
HETATM   18  C17 UNL     1      -0.572  -3.159  -1.678  1.00  0.00           C  
HETATM   19  C18 UNL     1       0.182  -2.163  -1.046  1.00  0.00           C  
HETATM   20  C19 UNL     1      -0.509  -1.233  -0.349  1.00  0.00           C  
HETATM   21  H1  UNL     1       4.496  -0.439  -1.144  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.481   0.969  -1.046  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.603   0.907   1.364  1.00  0.00           H  
HETATM   24  H4  UNL     1       4.210  -0.881   1.086  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.456   1.595   0.849  1.00  0.00           H  
HETATM   26  H6  UNL     1       2.415   0.368   2.183  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.807  -1.357   0.592  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.872  -0.264  -0.817  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.056   0.559   2.443  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.082  -1.211   2.265  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.206   0.578   2.567  1.00  0.00           H  
HETATM   32  H12 UNL     1      -2.244  -1.184   2.378  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.544  -0.123   0.588  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.739   2.128  -0.384  1.00  0.00           H  
HETATM   35  H15 UNL     1      -2.695   4.057  -1.362  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.195   4.147  -1.569  1.00  0.00           H  
HETATM   37  H17 UNL     1       1.161   2.334  -0.823  1.00  0.00           H  
HETATM   38  H18 UNL     1      -3.690  -2.177  -0.758  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.509  -3.963  -2.085  1.00  0.00           H  
HETATM   40  H20 UNL     1       0.000  -3.902  -2.236  1.00  0.00           H  
HETATM   41  H21 UNL     1       1.254  -2.162  -1.133  1.00  0.00           H  
CONECT    1    2   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   14   20
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9   15   33
CONECT    9   10   10   14
CONECT   10   11   34
CONECT   11   12   12   35
CONECT   12   13   36
CONECT   13   14   14   37
CONECT   15   16   16   20
CONECT   16   17   38
CONECT   17   18   18   39
CONECT   18   19   40
CONECT   19   20   20   41
END

HMDB0060993
     RDKit          3D
demethylmaprotiline
 41 44  0  0  0  0  0  0  0  0999 V2000
    4.2247    0.4155   -0.6109 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9997    0.1626    0.7963 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5344    0.5336    1.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5996   -0.2855    0.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1662   -0.0789    0.3984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -0.2799    1.8298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8207   -0.2618    1.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4685   -0.1250    0.5610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8720    1.1166   -0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6560    2.1374   -0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0397    3.2480   -1.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6723    3.2902   -1.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1043    2.2131   -0.6763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4805    1.1159   -0.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8829   -1.2415   -0.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6219   -2.2072   -0.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9459   -3.1774   -1.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5720   -3.1587   -1.6777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1822   -2.1625   -1.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5089   -1.2330   -0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4957   -0.4386   -1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4806    0.9692   -1.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6033    0.9068    1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2101   -0.8813    1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4561    1.5947    0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4148    0.3677    2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8068   -1.3573    0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8719   -0.2640   -0.8166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0561    0.5587    2.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0820   -1.2108    2.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2061    0.5778    2.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2443   -1.1838    2.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5442   -0.1225    0.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7385    2.1275   -0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6946    4.0573   -1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1952    4.1469   -1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1611    2.3340   -0.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6900   -2.1771   -0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5090   -3.9628   -2.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001   -3.9020   -2.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2539   -2.1620   -1.1330 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  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14  5  1  0
 20 15  1  0
 20  5  1  0
 14  9  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9,10-Ethanoanthracene-9(10H)-propylamine	HMDB

Chemical Formula

C₁₉H₂₁N

Average Molecular Weight

263.3767

Monoisotopic Molecular Weight

263.167399677

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

NCCCC12CCC(C3=CC=CC=C13)C1=CC=CC=C21

InChI Identifier

InChI=1S/C19H21N/c20-13-5-11-19-12-10-14(15-6-1-3-8-17(15)19)16-7-2-4-9-18(16)19/h1-4,6-9,14H,5,10-13,20H2

InChI Key

IFHUOEQJTQWFGJ-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
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Primary aliphatic amine
Amine
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060993)
Liver (HMDB: HMDB0060993)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060993)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060993)

Cellular substructure

Cytoplasm (HMDB: HMDB0060993)
Membrane (HMDB: HMDB0060993)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.8e-05 g/L	ALOGPS
logP	4.87	ALOGPS
logP	3.94	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Basic)	10.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.53 m³·mol⁻¹	ChemAxon
Polarizability	31.39 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]+	160.476	31661259
DarkChem	[M-H]-	159.552	31661259
DeepCCS	[M-2H]-	196.635	30932474
DeepCCS	[M+Na]+	172.2	30932474
AllCCS	[M+H]+	164.2	32859911
AllCCS	[M+H-H2O]+	160.7	32859911
AllCCS	[M+NH4]+	167.5	32859911
AllCCS	[M+Na]+	168.4	32859911
AllCCS	[M-H]-	171.7	32859911
AllCCS	[M+Na-2H]-	171.2	32859911
AllCCS	[M+HCOO]-	170.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
demethylmaprotiline	NCCCC12CCC(C3=CC=CC=C13)C1=CC=CC=C21	3051.0	Standard polar	33892256
demethylmaprotiline	NCCCC12CCC(C3=CC=CC=C13)C1=CC=CC=C21	2423.3	Standard non polar	33892256
demethylmaprotiline	NCCCC12CCC(C3=CC=CC=C13)C1=CC=CC=C21	2274.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
demethylmaprotiline,1TMS,isomer #1	C[Si](C)(C)NCCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12	2573.3	Semi standard non polar	33892256
demethylmaprotiline,1TMS,isomer #1	C[Si](C)(C)NCCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12	2628.7	Standard non polar	33892256
demethylmaprotiline,1TMS,isomer #1	C[Si](C)(C)NCCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12	2794.7	Standard polar	33892256
demethylmaprotiline,2TMS,isomer #1	C[Si](C)(C)N(CCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)[Si](C)(C)C	2842.0	Semi standard non polar	33892256
demethylmaprotiline,2TMS,isomer #1	C[Si](C)(C)N(CCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)[Si](C)(C)C	2947.0	Standard non polar	33892256
demethylmaprotiline,2TMS,isomer #1	C[Si](C)(C)N(CCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)[Si](C)(C)C	2740.7	Standard polar	33892256
demethylmaprotiline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12	2836.9	Semi standard non polar	33892256
demethylmaprotiline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12	2933.4	Standard non polar	33892256
demethylmaprotiline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12	2902.7	Standard polar	33892256
demethylmaprotiline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)[Si](C)(C)C(C)(C)C	3272.1	Semi standard non polar	33892256
demethylmaprotiline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)[Si](C)(C)C(C)(C)C	3403.4	Standard non polar	33892256
demethylmaprotiline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCCC12CCC(C3=CC=CC=C31)C1=CC=CC=C12)[Si](C)(C)C(C)(C)C	2890.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - demethylmaprotiline GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-9080000000-12ddba41c4c4cee9f454	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - demethylmaprotiline 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 - demethylmaprotiline 10V, Positive-QTOF	splash10-03dj-0090000000-e3cf814b95b418ce270c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - demethylmaprotiline 20V, Positive-QTOF	splash10-01ot-0090000000-98929235ad1abaa60b3e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - demethylmaprotiline 40V, Positive-QTOF	splash10-066u-5590000000-cdd9a806a71ed0783368	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - demethylmaprotiline 10V, Negative-QTOF	splash10-03di-0090000000-2cfe1fcdcee2b938ffd1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - demethylmaprotiline 20V, Negative-QTOF	splash10-03di-0090000000-e3b2f824800d5a86f61c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - demethylmaprotiline 40V, Negative-QTOF	splash10-0apj-2090000000-988a143a12803492905e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - demethylmaprotiline 10V, Negative-QTOF	splash10-03di-0090000000-330f29be739abf456d25	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - demethylmaprotiline 20V, Negative-QTOF	splash10-03di-0090000000-d89ebdfa727b727f5887	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - demethylmaprotiline 40V, Negative-QTOF	splash10-0udi-0090000000-802b45c948e9f2a77ba7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - demethylmaprotiline 10V, Positive-QTOF	splash10-03dj-0090000000-1a23789291e198a78c4a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - demethylmaprotiline 20V, Positive-QTOF	splash10-01ot-0090000000-88c2720aa68a8b184f9c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - demethylmaprotiline 40V, Positive-QTOF	splash10-066u-0190000000-16c0738d2febf5623de6	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

106651

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2734

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for demethylmaprotiline (HMDB0060993)

MOL for HMDB0060993 (demethylmaprotiline)

3D MOL for HMDB0060993 (demethylmaprotiline)

3D SDF for HMDB0060993 (demethylmaprotiline)

3D-SDF for HMDB0060993 (demethylmaprotiline)

PDB for HMDB0060993 (demethylmaprotiline)

3D PDB for HMDB0060993 (demethylmaprotiline)

SMILES for HMDB0060993 (demethylmaprotiline)

INCHI for HMDB0060993 (demethylmaprotiline)

Structure for HMDB0060993 (demethylmaprotiline)

3D Structure for HMDB0060993 (demethylmaprotiline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra