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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:00:27 UTC

Update Date

2019-07-23 07:15:07 UTC

HMDB ID

HMDB0060802

Secondary Accession Numbers

HMDB60802

Metabolite Identification

Common Name

8-Hydroxyclomipramine

Description

114457-94-2 belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. 114457-94-2 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0060802
     RDKit          3D
8-Hydroxyclomipramine
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.2974    0.9267   -1.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2056    0.1106    0.0035 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3546   -1.3016   -0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0983    0.4014    0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7665    0.0556    0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6172    0.4016    1.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6496    0.0613    0.6664 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6014    1.1541    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    2.0462    1.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2903    3.1383    1.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2376    3.2929    0.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0863    4.4137    0.6479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3533    2.3829   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5172    1.2622   -0.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7626    0.4068   -1.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8052   -1.0471   -1.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203   -1.7164   -0.6360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8792   -3.0998   -0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0583   -3.9777   -0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1364   -3.5167    0.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9136   -4.6109    1.6139 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0527   -2.1365    0.9826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882   -1.2978    0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7011    0.5613   -2.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3651    0.9017   -1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9919    1.9632   -0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4572   -1.7512   -0.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2252   -1.5068   -0.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5109   -1.8479    0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2047   -0.2552    1.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1524    1.4271    1.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7014    0.7477   -0.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6786   -0.9188   -0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7378    1.5308    1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8287    0.1580    2.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7067    1.8306    2.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2033    3.8635    2.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7871    5.2684    0.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1077    2.5356   -1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7539    0.7219   -2.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0334    0.6369   -2.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8177   -1.3934   -1.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7236   -1.5042   -2.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5784   -3.5153   -1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1335   -5.0599   -0.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361   -1.7438    1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23  7  1  0
 14  8  1  0
 23 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  9 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 18 44  1  0
 19 45  1  0
 22 46  1  0
M  END


  Mrv0541 07041312002D          

 23 25  0  0  0  0            999 V2000
   -0.5463   -2.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -3.0967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1681   -3.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -2.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5971   -3.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3116   -2.6842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0260   -3.0967    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7077   -2.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5241   -1.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1289   -1.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9172   -1.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5220   -0.9485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1008   -2.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4960   -2.8751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7974   -3.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3849   -4.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5691   -4.4805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3856   -5.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972   -5.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9925   -4.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2041   -5.2100    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1760   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9644   -3.9193    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
  7 23  1  0  0  0  0
 17 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060802

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H23ClN2O/c1-21(2)10-3-11-22-18-9-8-17(23)12-15(18)5-4-14-6-7-16(20)13-19(14)22/h6-9,12-13,23H,3-5,10-11H2,1-2H3

> <INCHI_KEY>
PVKACZKLKCTAHR-UHFFFAOYSA-N

> <FORMULA>
C19H23ClN2O

> <MOLECULAR_WEIGHT>
330.852

> <EXACT_MASS>
330.149891075

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.03443780975242

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-chloro-2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol

> <ALOGPS_LOGP>
4.51

> <JCHEM_LOGP>
4.398936360253524

> <ALOGPS_LOGS>
-3.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.526590699039536

> <JCHEM_PKA_STRONGEST_BASIC>
9.176120082017048

> <JCHEM_POLAR_SURFACE_AREA>
26.71

> <JCHEM_REFRACTIVITY>
97.3913

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-chloro-2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060802
     RDKit          3D
8-Hydroxyclomipramine
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.2974    0.9267   -1.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2056    0.1106    0.0035 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3546   -1.3016   -0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0983    0.4014    0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7665    0.0556    0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6172    0.4016    1.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6496    0.0613    0.6664 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6014    1.1541    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    2.0462    1.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2903    3.1383    1.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2376    3.2929    0.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0863    4.4137    0.6479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3533    2.3829   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5172    1.2622   -0.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7626    0.4068   -1.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8052   -1.0471   -1.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203   -1.7164   -0.6360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8792   -3.0998   -0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0583   -3.9777   -0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1364   -3.5167    0.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9136   -4.6109    1.6139 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0527   -2.1365    0.9826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882   -1.2978    0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7011    0.5613   -2.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3651    0.9017   -1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9919    1.9632   -0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4572   -1.7512   -0.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2252   -1.5068   -0.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5109   -1.8479    0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2047   -0.2552    1.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1524    1.4271    1.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7014    0.7477   -0.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6786   -0.9188   -0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7378    1.5308    1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8287    0.1580    2.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7067    1.8306    2.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2033    3.8635    2.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7871    5.2684    0.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1077    2.5356   -1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7539    0.7219   -2.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0334    0.6369   -2.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8177   -1.3934   -1.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7236   -1.5042   -2.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5784   -3.5153   -1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1335   -5.0599   -0.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361   -1.7438    1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23  7  1  0
 14  8  1  0
 23 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  9 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 18 44  1  0
 19 45  1  0
 22 46  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0      -1.020  -5.011   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.314  -5.781   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.314  -7.321   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.648  -5.011   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.981  -5.781   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.315  -5.011   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       5.649  -5.781   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       6.921  -4.913   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.578  -3.412   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.707  -2.364   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.179  -2.818   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.308  -1.771   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.521  -4.319   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.393  -5.367   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.955  -6.800   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.185  -8.134   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.662  -8.364   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.320  -9.865   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.848 -10.319   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.719  -9.271   0.000  0.00  0.00           C+0
HETATM   21 Cl   UNK     0       2.248  -9.725   0.000  0.00  0.00          Cl+0
HETATM   22  C   UNK     0       4.062  -7.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.534  -7.316   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   23                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22    7   17                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0060802
HETATM    1  C1  UNL     1       4.297   0.927  -1.166  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.206   0.111   0.003  1.00  0.00           N  
HETATM    3  C2  UNL     1       4.355  -1.302  -0.272  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.098   0.401   0.848  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.766   0.056   0.245  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.617   0.402   1.221  1.00  0.00           C  
HETATM    7  N2  UNL     1      -0.650   0.061   0.666  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.601   1.154   0.539  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.460   2.046   1.578  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.290   3.138   1.618  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.238   3.293   0.603  1.00  0.00           C  
HETATM   12  O1  UNL     1      -4.086   4.414   0.648  1.00  0.00           O  
HETATM   13  C10 UNL     1      -3.353   2.383  -0.422  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.517   1.262  -0.482  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.763   0.407  -1.630  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.805  -1.047  -1.467  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.820  -1.716  -0.636  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.879  -3.100  -0.848  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.058  -3.978  -0.174  1.00  0.00           C  
HETATM   20  C17 UNL     1      -0.136  -3.517   0.747  1.00  0.00           C  
HETATM   21 CL1  UNL     1       0.914  -4.611   1.614  1.00  0.00          CL  
HETATM   22  C18 UNL     1      -0.053  -2.137   0.983  1.00  0.00           C  
HETATM   23  C19 UNL     1      -0.888  -1.298   0.289  1.00  0.00           C  
HETATM   24  H1  UNL     1       3.701   0.561  -2.024  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.365   0.902  -1.516  1.00  0.00           H  
HETATM   26  H3  UNL     1       3.992   1.963  -0.870  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.457  -1.751  -0.748  1.00  0.00           H  
HETATM   28  H5  UNL     1       5.225  -1.507  -0.910  1.00  0.00           H  
HETATM   29  H6  UNL     1       4.511  -1.848   0.685  1.00  0.00           H  
HETATM   30  H7  UNL     1       3.205  -0.255   1.762  1.00  0.00           H  
HETATM   31  H8  UNL     1       3.152   1.427   1.222  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.701   0.748  -0.658  1.00  0.00           H  
HETATM   33  H10 UNL     1       1.679  -0.919  -0.209  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.738   1.531   1.185  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.829   0.158   2.248  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.707   1.831   2.313  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.203   3.863   2.428  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.787   5.268   0.181  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.108   2.536  -1.200  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.754   0.722  -2.077  1.00  0.00           H  
HETATM   41  H18 UNL     1      -2.033   0.637  -2.467  1.00  0.00           H  
HETATM   42  H19 UNL     1      -3.818  -1.393  -1.122  1.00  0.00           H  
HETATM   43  H20 UNL     1      -2.724  -1.504  -2.499  1.00  0.00           H  
HETATM   44  H21 UNL     1      -2.578  -3.515  -1.554  1.00  0.00           H  
HETATM   45  H22 UNL     1      -1.133  -5.060  -0.368  1.00  0.00           H  
HETATM   46  H23 UNL     1       0.636  -1.744   1.689  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4
CONECT    3   27   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7   34   35
CONECT    7    8   23
CONECT    8    9    9   14
CONECT    9   10   36
CONECT   10   11   11   37
CONECT   11   12   13
CONECT   12   38
CONECT   13   14   14   39
CONECT   14   15
CONECT   15   16   40   41
CONECT   16   17   42   43
CONECT   17   18   18   23
CONECT   18   19   44
CONECT   19   20   20   45
CONECT   20   21   22
CONECT   22   23   23   46
END

HMDB0060802
     RDKit          3D
8-Hydroxyclomipramine
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.2974    0.9267   -1.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2056    0.1106    0.0035 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3546   -1.3016   -0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0983    0.4014    0.8484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7665    0.0556    0.2448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6172    0.4016    1.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6496    0.0613    0.6664 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6014    1.1541    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    2.0462    1.5784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2903    3.1383    1.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2376    3.2929    0.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0863    4.4137    0.6479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3533    2.3829   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5172    1.2622   -0.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7626    0.4068   -1.6296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8052   -1.0471   -1.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8203   -1.7164   -0.6360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8792   -3.0998   -0.8483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0583   -3.9777   -0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1364   -3.5167    0.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9136   -4.6109    1.6139 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0527   -2.1365    0.9826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882   -1.2978    0.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7011    0.5613   -2.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3651    0.9017   -1.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9919    1.9632   -0.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4572   -1.7512   -0.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2252   -1.5068   -0.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5109   -1.8479    0.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2047   -0.2552    1.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1524    1.4271    1.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7014    0.7477   -0.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6786   -0.9188   -0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7378    1.5308    1.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8287    0.1580    2.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7067    1.8306    2.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2033    3.8635    2.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7871    5.2684    0.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1077    2.5356   -1.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7539    0.7219   -2.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0334    0.6369   -2.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8177   -1.3934   -1.1216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7236   -1.5042   -2.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5784   -3.5153   -1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1335   -5.0599   -0.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361   -1.7438    1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23  7  1  0
 14  8  1  0
 23 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  9 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 18 44  1  0
 19 45  1  0
 22 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-Hydroxyclomipramine	MeSH

Chemical Formula

C₁₉H₂₃ClN₂O

Average Molecular Weight

330.852

Monoisotopic Molecular Weight

330.149891075

IUPAC Name

14-chloro-2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol

Traditional Name

14-chloro-2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol

CAS Registry Number

Not Available

SMILES

CN(C)CCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C12

InChI Identifier

InChI=1S/C19H23ClN2O/c1-21(2)10-3-11-22-18-9-8-17(23)12-15(18)5-4-14-6-7-16(20)13-19(14)22/h6-9,12-13,23H,3-5,10-11H2,1-2H3

InChI Key

PVKACZKLKCTAHR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
Pyrazine carboxylic acid or derivatives
Pyrazinecarboxamide
2-heteroaryl carboxamide
Monocyclic benzene moiety
Pyrazine
Benzenoid
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060802)
Liver (HMDB: HMDB0060802)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060802)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060802)

Cellular substructure

Cytoplasm (HMDB: HMDB0060802)
Membrane (HMDB: HMDB0060802)

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	0.098 g/L	ALOGPS
logP	4.51	ALOGPS
logP	4.4	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	10.53	ChemAxon
pKa (Strongest Basic)	9.18	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.71 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.39 m³·mol⁻¹	ChemAxon
Polarizability	37.03 Å³	ChemAxon
Number of Rings	3	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
DeepCCS	[M-2H]-	206.263	30932474
DeepCCS	[M+Na]+	181.828	30932474
AllCCS	[M+H]+	177.6	32859911
AllCCS	[M+H-H2O]+	174.4	32859911
AllCCS	[M+NH4]+	180.5	32859911
AllCCS	[M+Na]+	181.4	32859911
AllCCS	[M-H]-	183.5	32859911
AllCCS	[M+Na-2H]-	183.3	32859911
AllCCS	[M+HCOO]-	183.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxyclomipramine	CN(C)CCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C12	3888.4	Standard polar	33892256
8-Hydroxyclomipramine	CN(C)CCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C12	2721.1	Standard non polar	33892256
8-Hydroxyclomipramine	CN(C)CCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C12	2739.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxyclomipramine,1TMS,isomer #1	CN(C)CCCN1C2=CC=C(O[Si](C)(C)C)C=C2CCC2=CC=C(Cl)C=C21	2715.9	Semi standard non polar	33892256
8-Hydroxyclomipramine,1TBDMS,isomer #1	CN(C)CCCN1C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2CCC2=CC=C(Cl)C=C21	2929.2	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 - 8-Hydroxyclomipramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9041000000-49160155152b299105ad	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyclomipramine GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9006000000-1aa8eb768f813f19bba0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyclomipramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxyclomipramine 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 - 8-Hydroxyclomipramine 10V, Positive-QTOF	splash10-001i-1019000000-5e40277560ca9d0406fb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyclomipramine 20V, Positive-QTOF	splash10-0019-9085000000-5b771466f2aec7077f81	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyclomipramine 40V, Positive-QTOF	splash10-000l-9140000000-341b5511d1ffd0b3b3ef	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyclomipramine 10V, Negative-QTOF	splash10-004i-0009000000-405a6440ca2b2e8a967c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyclomipramine 20V, Negative-QTOF	splash10-004l-0069000000-13c26ecb317454bc76a4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyclomipramine 40V, Negative-QTOF	splash10-05mo-1090000000-a01f25df943f932960f1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyclomipramine 10V, Positive-QTOF	splash10-001r-5009000000-e30b3484272c79d2c100	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyclomipramine 20V, Positive-QTOF	splash10-000i-9000000000-c512524ce5037389dc8e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyclomipramine 40V, Positive-QTOF	splash10-0a4i-9000000000-031688c564e0596bfefd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyclomipramine 10V, Negative-QTOF	splash10-004i-0009000000-a3d27897664f6e55b7f5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyclomipramine 20V, Negative-QTOF	splash10-0006-2093000000-3bfe45eb7d6c71674398	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxyclomipramine 40V, Negative-QTOF	splash10-001i-9050000000-938c43e26e4699dc5d2c	2021-10-12	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15042559

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 8-Hydroxyclomipramine (HMDB0060802)

MOL for HMDB0060802 (8-Hydroxyclomipramine)

3D MOL for HMDB0060802 (8-Hydroxyclomipramine)

3D SDF for HMDB0060802 (8-Hydroxyclomipramine)

3D-SDF for HMDB0060802 (8-Hydroxyclomipramine)

PDB for HMDB0060802 (8-Hydroxyclomipramine)

3D PDB for HMDB0060802 (8-Hydroxyclomipramine)

SMILES for HMDB0060802 (8-Hydroxyclomipramine)

INCHI for HMDB0060802 (8-Hydroxyclomipramine)

Structure for HMDB0060802 (8-Hydroxyclomipramine)

3D Structure for HMDB0060802 (8-Hydroxyclomipramine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra