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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:00:30 UTC

Update Date

2019-07-23 07:15:07 UTC

HMDB ID

HMDB0060803

Secondary Accession Numbers

HMDB60803

Metabolite Identification

Common Name

8-Hydroxydesmethylclomipramine

Description

8-Hydroxydesmethylclomipramine belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom. Based on a literature review a small amount of articles have been published on 8-Hydroxydesmethylclomipramine.

Structure

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

HMDB0060803
     RDKit          3D
8-Hydroxydesmethylclomipramine
 43 45  0  0  0  0  0  0  0  0999 V2000
    4.3450    0.2272    1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796   -0.2732   -0.1885 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3245   -1.4673   -0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8710   -1.3461    0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1451   -0.3182   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241   -0.1260   -0.4581 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7400    1.2378   -0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0689    2.0336   -1.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2705    3.3530   -1.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3999    3.8509   -0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7221    5.2122   -0.9978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1838    3.0177   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8947    1.6606    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9183    0.9995    0.9539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5359   -0.2535    1.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0260   -1.3373    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6876   -2.5346    0.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3004   -3.6271    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2685   -3.5302   -0.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7730   -4.8789   -1.7701 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6009   -2.3370   -0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0136   -1.2941   -0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7812   -0.2359    1.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2937    1.3379    1.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4326    0.0066    1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234    0.4023   -0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135   -1.7672   -1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7717   -2.3194    0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691   -0.9469    1.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3778   -2.2912    0.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784    0.6140   -0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4368   -0.3847   -1.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9309    1.5794   -1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3793    3.9755   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3061    5.8288   -0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0802    3.4050    0.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2346    1.7237    1.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8440    0.8110    0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911   -0.0309    2.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4082   -0.6374    2.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5024   -2.6204    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8092   -4.5670    0.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2128   -2.1521   -1.6383 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22  6  1  0
 13  7  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 21 43  1  0
M  END

  Mrv0541 07041312002D          

 22 24  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
    0.8826   -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
  3  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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
  6 22  1  0  0  0  0
 16 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060803

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C18H21ClN2O/c1-20-9-2-10-21-17-8-7-16(22)11-14(17)4-3-13-5-6-15(19)12-18(13)21/h5-8,11-12,20,22H,2-4,9-10H2,1H3

> <INCHI_KEY>
MRLCQGACIDFFSH-UHFFFAOYSA-N

> <FORMULA>
C18H21ClN2O

> <MOLECULAR_WEIGHT>
316.825

> <EXACT_MASS>
316.134241011

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.15958438897379

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.88

> <JCHEM_LOGP>
3.776296017950861

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.62838954651343

> <JCHEM_PKA_STRONGEST_BASIC>
9.896056403548158

> <JCHEM_POLAR_SURFACE_AREA>
35.5

> <JCHEM_REFRACTIVITY>
92.0966

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.08e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060803
     RDKit          3D
8-Hydroxydesmethylclomipramine
 43 45  0  0  0  0  0  0  0  0999 V2000
    4.3450    0.2272    1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796   -0.2732   -0.1885 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3245   -1.4673   -0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8710   -1.3461    0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1451   -0.3182   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241   -0.1260   -0.4581 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7400    1.2378   -0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0689    2.0336   -1.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2705    3.3530   -1.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3999    3.8509   -0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7221    5.2122   -0.9978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1838    3.0177   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8947    1.6606    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9183    0.9995    0.9539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5359   -0.2535    1.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0260   -1.3373    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6876   -2.5346    0.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3004   -3.6271    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2685   -3.5302   -0.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7730   -4.8789   -1.7701 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6009   -2.3370   -0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0136   -1.2941   -0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7812   -0.2359    1.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2937    1.3379    1.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4326    0.0066    1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234    0.4023   -0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135   -1.7672   -1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7717   -2.3194    0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691   -0.9469    1.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3778   -2.2912    0.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784    0.6140   -0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4368   -0.3847   -1.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9309    1.5794   -1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3793    3.9755   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3061    5.8288   -0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0802    3.4050    0.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2346    1.7237    1.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8440    0.8110    0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911   -0.0309    2.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4082   -0.6374    2.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5024   -2.6204    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8092   -4.5670    0.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2128   -2.1521   -1.6383 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22  6  1  0
 13  7  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 21 43  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       1.648  -5.011   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.981  -5.781   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.315  -5.011   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       5.649  -5.781   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       6.921  -4.913   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.578  -3.412   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.707  -2.364   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.179  -2.818   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.308  -1.771   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.521  -4.319   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.393  -5.367   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.955  -6.800   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.185  -8.134   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.662  -8.364   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.320  -9.865   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.848 -10.319   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.719  -9.271   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0       2.248  -9.725   0.000  0.00  0.00          Cl+0
HETATM   21  C   UNK     0       4.062  -7.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.534  -7.316   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21    6   16                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0060803
HETATM    1  C1  UNL     1       4.345   0.227   1.113  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.080  -0.273  -0.188  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.324  -1.467  -0.292  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.871  -1.346   0.128  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.145  -0.318  -0.730  1.00  0.00           C  
HETATM    6  N2  UNL     1      -0.224  -0.126  -0.458  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.740   1.238  -0.528  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.069   2.034  -1.293  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.271   3.353  -1.441  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.400   3.851  -0.829  1.00  0.00           C  
HETATM   11  O1  UNL     1      -1.722   5.212  -0.998  1.00  0.00           O  
HETATM   12  C9  UNL     1      -2.184   3.018  -0.071  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.895   1.661   0.120  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.918   0.999   0.954  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.536  -0.253   1.641  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.026  -1.337   0.755  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.688  -2.535   0.904  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.300  -3.627   0.125  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.269  -3.530  -0.791  1.00  0.00           C  
HETATM   20 CL1  UNL     1      -0.773  -4.879  -1.770  1.00  0.00          CL  
HETATM   21  C17 UNL     1      -0.601  -2.337  -0.948  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.014  -1.294  -0.164  1.00  0.00           C  
HETATM   23  H1  UNL     1       3.781  -0.236   1.925  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.294   1.338   1.090  1.00  0.00           H  
HETATM   25  H3  UNL     1       5.433   0.007   1.332  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.023   0.402  -0.948  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.313  -1.767  -1.365  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.772  -2.319   0.252  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.969  -0.947   1.201  1.00  0.00           H  
HETATM   30  H8  UNL     1       1.378  -2.291   0.297  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.678   0.614  -0.360  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.437  -0.385  -1.789  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.931   1.579  -1.763  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.379   3.975  -2.052  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.306   5.829  -0.280  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.080   3.405   0.416  1.00  0.00           H  
HETATM   37  H15 UNL     1      -3.235   1.724   1.748  1.00  0.00           H  
HETATM   38  H16 UNL     1      -3.844   0.811   0.326  1.00  0.00           H  
HETATM   39  H17 UNL     1      -1.691  -0.031   2.338  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.408  -0.637   2.176  1.00  0.00           H  
HETATM   41  H19 UNL     1      -3.502  -2.620   1.623  1.00  0.00           H  
HETATM   42  H20 UNL     1      -2.809  -4.567   0.232  1.00  0.00           H  
HETATM   43  H21 UNL     1       0.213  -2.152  -1.638  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7   22
CONECT    7    8    8   13
CONECT    8    9   33
CONECT    9   10   10   34
CONECT   10   11   12
CONECT   11   35
CONECT   12   13   13   36
CONECT   13   14
CONECT   14   15   37   38
CONECT   15   16   39   40
CONECT   16   17   17   22
CONECT   17   18   41
CONECT   18   19   19   42
CONECT   19   20   21
CONECT   21   22   22   43
END

HMDB0060803
     RDKit          3D
8-Hydroxydesmethylclomipramine
 43 45  0  0  0  0  0  0  0  0999 V2000
    4.3450    0.2272    1.1130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796   -0.2732   -0.1885 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3245   -1.4673   -0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8710   -1.3461    0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1451   -0.3182   -0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241   -0.1260   -0.4581 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7400    1.2378   -0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0689    2.0336   -1.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2705    3.3530   -1.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3999    3.8509   -0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7221    5.2122   -0.9978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1838    3.0177   -0.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8947    1.6606    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9183    0.9995    0.9539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5359   -0.2535    1.6413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0260   -1.3373    0.7552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6876   -2.5346    0.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3004   -3.6271    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2685   -3.5302   -0.7914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7730   -4.8789   -1.7701 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6009   -2.3370   -0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0136   -1.2941   -0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7812   -0.2359    1.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2937    1.3379    1.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4326    0.0066    1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0234    0.4023   -0.9481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135   -1.7672   -1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7717   -2.3194    0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691   -0.9469    1.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3778   -2.2912    0.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784    0.6140   -0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4368   -0.3847   -1.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9309    1.5794   -1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3793    3.9755   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3061    5.8288   -0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0802    3.4050    0.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2346    1.7237    1.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8440    0.8110    0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911   -0.0309    2.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4082   -0.6374    2.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5024   -2.6204    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8092   -4.5670    0.2316 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2128   -2.1521   -1.6383 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  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22  6  1  0
 13  7  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  8 33  1  0
  9 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 18 42  1  0
 21 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S,3S,4S,5R,6S)-6-({14-chloro-2-[3-(dimethylamino)propyl]-6-hydroxy-2-azatricyclo[9.4.0.0,]pentadeca-1(11),3(8),4,6,12,14-hexaen-7-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylate	HMDB

Chemical Formula

C₁₈H₂₁ClN₂O

Average Molecular Weight

316.825

Monoisotopic Molecular Weight

316.134241011

IUPAC Name

14-chloro-2-[3-(methylamino)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-(methylamino)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

CNCCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C12

InChI Identifier

InChI=1S/C18H21ClN2O/c1-20-9-2-10-21-17-8-7-16(22)11-14(17)4-3-13-5-6-15(19)12-18(13)21/h5-8,11-12,20,22H,2-4,9-10H2,1H3

InChI Key

MRLCQGACIDFFSH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzazepines

Sub Class

Dibenzazepines

Direct Parent

Dibenzazepines

Alternative Parents

Substituents

Dibenzazepine
Alkyldiarylamine
Tertiary aliphatic/aromatic amine
1-hydroxy-2-unsubstituted benzenoid
Azepine
Aryl chloride
Aryl halide
Benzenoid
Tertiary amine
Secondary aliphatic amine
Secondary amine
Azacycle
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Amine
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060803)

Organ

Kidney (HMDB: HMDB0060803)
Liver (HMDB: HMDB0060803)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060803)

Cellular substructure

Cytoplasm (HMDB: HMDB0060803)
Membrane (HMDB: HMDB0060803)

Source

Endogenous

Endogenous (HMDB: HMDB0060803)

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	0.041 g/L	ALOGPS
logP	3.88	ALOGPS
logP	3.78	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	10.63	ChemAxon
pKa (Strongest Basic)	9.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	35.5 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.1 m³·mol⁻¹	ChemAxon
Polarizability	35.16 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]-	203.883	30932474
DeepCCS	[M+Na]+	179.448	30932474
AllCCS	[M+H]+	174.1	32859911
AllCCS	[M+H-H2O]+	170.8	32859911
AllCCS	[M+NH4]+	177.2	32859911
AllCCS	[M+Na]+	178.1	32859911
AllCCS	[M-H]-	179.0	32859911
AllCCS	[M+Na-2H]-	178.8	32859911
AllCCS	[M+HCOO]-	178.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxydesmethylclomipramine	CNCCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C12	3980.1	Standard polar	33892256
8-Hydroxydesmethylclomipramine	CNCCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C12	2786.0	Standard non polar	33892256
8-Hydroxydesmethylclomipramine	CNCCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C12	2788.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Hydroxydesmethylclomipramine,1TMS,isomer #1	CNCCCN1C2=CC=C(O[Si](C)(C)C)C=C2CCC2=CC=C(Cl)C=C21	2701.9	Semi standard non polar	33892256
8-Hydroxydesmethylclomipramine,1TMS,isomer #2	CN(CCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C21)[Si](C)(C)C	2948.4	Semi standard non polar	33892256
8-Hydroxydesmethylclomipramine,2TMS,isomer #1	CN(CCCN1C2=CC=C(O[Si](C)(C)C)C=C2CCC2=CC=C(Cl)C=C21)[Si](C)(C)C	2852.7	Semi standard non polar	33892256
8-Hydroxydesmethylclomipramine,2TMS,isomer #1	CN(CCCN1C2=CC=C(O[Si](C)(C)C)C=C2CCC2=CC=C(Cl)C=C21)[Si](C)(C)C	2979.8	Standard non polar	33892256
8-Hydroxydesmethylclomipramine,2TMS,isomer #1	CN(CCCN1C2=CC=C(O[Si](C)(C)C)C=C2CCC2=CC=C(Cl)C=C21)[Si](C)(C)C	3316.7	Standard polar	33892256
8-Hydroxydesmethylclomipramine,1TBDMS,isomer #1	CNCCCN1C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2CCC2=CC=C(Cl)C=C21	2905.6	Semi standard non polar	33892256
8-Hydroxydesmethylclomipramine,1TBDMS,isomer #2	CN(CCCN1C2=CC=C(O)C=C2CCC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C	3154.4	Semi standard non polar	33892256
8-Hydroxydesmethylclomipramine,2TBDMS,isomer #1	CN(CCCN1C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2CCC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C	3279.9	Semi standard non polar	33892256
8-Hydroxydesmethylclomipramine,2TBDMS,isomer #1	CN(CCCN1C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2CCC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C	3491.0	Standard non polar	33892256
8-Hydroxydesmethylclomipramine,2TBDMS,isomer #1	CN(CCCN1C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2CCC2=CC=C(Cl)C=C21)[Si](C)(C)C(C)(C)C	3488.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxydesmethylclomipramine GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-7090000000-4b1a3d56016fa5618f9b	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxydesmethylclomipramine GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9006000000-173771675d64f59fa4a7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxydesmethylclomipramine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Hydroxydesmethylclomipramine 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-Hydroxydesmethylclomipramine 10V, Positive-QTOF	splash10-014r-1049000000-f70a869828ef28c08a15	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 20V, Positive-QTOF	splash10-00rl-6093000000-41eb3f645b893ebed626	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 40V, Positive-QTOF	splash10-0006-9150000000-7e44a16a91368607b848	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 10V, Negative-QTOF	splash10-014i-0009000000-1f984de31886b39a29fd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 20V, Negative-QTOF	splash10-014l-1079000000-f55bbf2457fa321e4281	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 40V, Negative-QTOF	splash10-05mo-2090000000-e8a8147accd3df890ae5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 10V, Positive-QTOF	splash10-00di-9003000000-34df45c4708af600dea7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 20V, Positive-QTOF	splash10-00dl-9010000000-2d144cfd68b2b1271fd7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 40V, Positive-QTOF	splash10-0596-9010000000-05b3a9ffb8e7186c3580	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 10V, Negative-QTOF	splash10-014i-0049000000-ba57917986af04137004	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 20V, Negative-QTOF	splash10-014l-1097000000-c33567b6ece7e293b353	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Hydroxydesmethylclomipramine 40V, Negative-QTOF	splash10-000x-6090000000-d25fa0f33efdafe1023c	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

8194268

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10018695

PDB ID

Not Available

ChEBI ID

169626

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-Hydroxydesmethylclomipramine (HMDB0060803)

MOL for HMDB0060803 (8-Hydroxydesmethylclomipramine)

3D MOL for HMDB0060803 (8-Hydroxydesmethylclomipramine)

3D SDF for HMDB0060803 (8-Hydroxydesmethylclomipramine)

3D-SDF for HMDB0060803 (8-Hydroxydesmethylclomipramine)

PDB for HMDB0060803 (8-Hydroxydesmethylclomipramine)

3D PDB for HMDB0060803 (8-Hydroxydesmethylclomipramine)

SMILES for HMDB0060803 (8-Hydroxydesmethylclomipramine)

INCHI for HMDB0060803 (8-Hydroxydesmethylclomipramine)

Structure for HMDB0060803 (8-Hydroxydesmethylclomipramine)

3D Structure for HMDB0060803 (8-Hydroxydesmethylclomipramine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra