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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:11:24 UTC

Update Date

2019-07-23 07:15:32 UTC

HMDB ID

HMDB0060992

Secondary Accession Numbers

HMDB60992

Metabolite Identification

Common Name

2-hydroxydesipramine

Description

2-hydroxydesipramine is a metabolite of desipramine. Desipramine (also known as desmethylimipramine) is a tricyclic antidepressant (TCA). It inhibits the reuptake of norepinephrine and to a lesser extent serotonin. It is used to treat depression, but not considered a first line treatment since the introduction of SSRI antidepressants. Desipramine is an active metabolite of imipramine. It is sold under the brand names Norpramin and Pertofane. Along with other tricyclics, desipramine has found use in treating neuropathic pain. (Wikipedia)

Structure

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

HMDB0060992
     RDKit          3D
2-hydroxydesipramine
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.1584   -1.3171   -0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7313   -1.2950    0.0115 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0996   -0.8466   -1.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.8326   -1.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2048    0.1404    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1918    0.2048    0.2450 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8622   -1.0690    0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0825   -1.9541    1.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -3.2097    1.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -3.5421    0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6178   -2.6024    0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1174   -1.3270   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0421   -0.4714   -0.8665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3207    0.8742   -0.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1697    1.7344    0.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5531    3.0850    0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6598    4.0689    0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0950    5.3893    0.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3426    3.7700    0.7312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0774    2.4618    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333    1.5016    0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6253   -0.3332    0.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4191   -1.6152   -1.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6199   -2.0535    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039   -2.2673    0.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096    0.1637   -1.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3747   -1.4759   -2.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1533   -1.8118   -0.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2041   -0.4470   -2.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8706    0.0869    0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5032    1.0934   -0.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8964   -1.6078    1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0133   -3.9212    1.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2627   -4.5485    1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5915   -2.8717   -0.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7457   -0.4345   -1.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0303   -1.0154   -0.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9785    0.7471    0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9235    1.4168   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5850    3.3262   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4679    6.1357    0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3895    4.5024    1.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1011    2.1670    0.8792 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
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21  6  1  0
 12  7  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
M  END


  Mrv0541 07091309112D          

 21 23  0  0  0  0            999 V2000
    0.7477    3.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8913    0.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2865    0.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8911    2.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6796    0.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4701    1.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6790    1.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0915    2.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4229    4.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8182    4.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1767    3.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6056    3.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3949    3.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8632    1.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7901    3.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2113    4.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2584    1.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0017    3.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4622    2.8013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3201    2.8013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8160    4.9495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  4  1  0  0  0  0
 12  4  1  0  0  0  0
 14  5  2  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  2  0  0  0  0
 16  9  2  0  0  0  0
 16 13  1  0  0  0  0
 17  6  2  0  0  0  0
 17 14  1  0  0  0  0
 18 10  2  0  0  0  0
 18 15  1  0  0  0  0
 19  1  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 20 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060992

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H22N2O/c1-19-11-4-12-20-17-6-3-2-5-14(17)7-8-15-13-16(21)9-10-18(15)20/h2-3,5-6,9-10,13,19,21H,4,7-8,11-12H2,1H3

> <INCHI_KEY>
NVJBOLMRGMDGLD-UHFFFAOYSA-N

> <FORMULA>
C18H22N2O

> <MOLECULAR_WEIGHT>
282.3801

> <EXACT_MASS>
282.173213336

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.13430171088614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.34

> <JCHEM_LOGP>
3.1727825021278004

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.63023927374527

> <JCHEM_PKA_STRONGEST_BASIC>
9.89665840826838

> <JCHEM_POLAR_SURFACE_AREA>
35.5

> <JCHEM_REFRACTIVITY>
87.2918

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
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

$$$$

HMDB0060992
     RDKit          3D
2-hydroxydesipramine
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.1584   -1.3171   -0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7313   -1.2950    0.0115 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0996   -0.8466   -1.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.8326   -1.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2048    0.1404    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1918    0.2048    0.2450 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8622   -1.0690    0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0825   -1.9541    1.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -3.2097    1.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -3.5421    0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6178   -2.6024    0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1174   -1.3270   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0421   -0.4714   -0.8665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3207    0.8742   -0.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1697    1.7344    0.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5531    3.0850    0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6598    4.0689    0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0950    5.3893    0.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3426    3.7700    0.7312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0774    2.4618    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333    1.5016    0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6253   -0.3332    0.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4191   -1.6152   -1.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6199   -2.0535    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039   -2.2673    0.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096    0.1637   -1.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3747   -1.4759   -2.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1533   -1.8118   -0.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2041   -0.4470   -2.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8706    0.0869    0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5032    1.0934   -0.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8964   -1.6078    1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0133   -3.9212    1.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2627   -4.5485    1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5915   -2.8717   -0.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7457   -0.4345   -1.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0303   -1.0154   -0.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9785    0.7471    0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9235    1.4168   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5850    3.3262   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4679    6.1357    0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3895    4.5024    1.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1011    2.1670    0.8792 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
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21  6  1  0
 12  7  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0       1.396   5.999   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.264   0.691   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.135   1.738   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.397   5.229   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.735   1.144   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.478   3.239   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.601   2.875   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.371   4.209   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.123   8.645   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.994   7.598   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.063   5.999   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.730   5.999   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.937   6.690   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.078   2.646   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.808   5.643   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.594   8.191   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.949   3.693   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.337   6.097   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.729   5.229   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0       8.064   5.229   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      12.723   9.239   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    3    5                                                       
CONECT    3    2    6                                                       
CONECT    4   11   12                                                       
CONECT    5    2   14                                                       
CONECT    6    3   17                                                       
CONECT    7    8   14                                                       
CONECT    8    7   15                                                       
CONECT    9   10   16                                                       
CONECT   10    9   18                                                       
CONECT   11    4   19                                                       
CONECT   12    4   20                                                       
CONECT   13   15   16                                                       
CONECT   14    5    7   17                                                  
CONECT   15    8   13   18                                                  
CONECT   16    9   13   21                                                  
CONECT   17    6   14   20                                                  
CONECT   18   10   15   20                                                  
CONECT   19    1   11                                                       
CONECT   20   12   17   18                                                  
CONECT   21   16                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0060992
HETATM    1  C1  UNL     1       5.158  -1.317  -0.091  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.731  -1.295   0.011  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.100  -0.847  -1.229  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.591  -0.833  -1.094  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.205   0.140   0.058  1.00  0.00           C  
HETATM    6  N2  UNL     1      -0.192   0.205   0.245  1.00  0.00           N  
HETATM    7  C5  UNL     1      -0.862  -1.069   0.386  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.083  -1.954   1.067  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.597  -3.210   1.292  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.876  -3.542   0.828  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.618  -2.602   0.144  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.117  -1.327  -0.096  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.042  -0.471  -0.867  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.321   0.874  -0.344  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.170   1.734   0.007  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.553   3.085   0.107  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.660   4.069   0.459  1.00  0.00           C  
HETATM   18  O1  UNL     1      -2.095   5.389   0.541  1.00  0.00           O  
HETATM   19  C16 UNL     1      -0.343   3.770   0.731  1.00  0.00           C  
HETATM   20  C17 UNL     1       0.077   2.462   0.646  1.00  0.00           C  
HETATM   21  C18 UNL     1      -0.833   1.502   0.291  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.625  -0.333   0.132  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.419  -1.615  -1.126  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.620  -2.054   0.597  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.404  -2.267   0.268  1.00  0.00           H  
HETATM   26  H5  UNL     1       3.510   0.164  -1.427  1.00  0.00           H  
HETATM   27  H6  UNL     1       3.375  -1.476  -2.092  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.153  -1.812  -0.987  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.204  -0.447  -2.073  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.871   0.087   0.898  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.503   1.093  -0.494  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.896  -1.608   1.377  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.013  -3.921   1.833  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.263  -4.549   1.021  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.591  -2.872  -0.204  1.00  0.00           H  
HETATM   36  H15 UNL     1      -2.746  -0.434  -1.953  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.030  -1.015  -0.902  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.978   0.747   0.570  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.924   1.417  -1.115  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.585   3.326  -0.105  1.00  0.00           H  
HETATM   41  H20 UNL     1      -1.468   6.136   0.796  1.00  0.00           H  
HETATM   42  H21 UNL     1       0.389   4.502   1.010  1.00  0.00           H  
HETATM   43  H22 UNL     1       1.101   2.167   0.879  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   21
CONECT    7    8    8   12
CONECT    8    9   32
CONECT    9   10   10   33
CONECT   10   11   34
CONECT   11   12   12   35
CONECT   12   13
CONECT   13   14   36   37
CONECT   14   15   38   39
CONECT   15   16   16   21
CONECT   16   17   40
CONECT   17   18   19   19
CONECT   18   41
CONECT   19   20   42
CONECT   20   21   21   43
END

HMDB0060992
     RDKit          3D
2-hydroxydesipramine
 43 45  0  0  0  0  0  0  0  0999 V2000
    5.1584   -1.3171   -0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7313   -1.2950    0.0115 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0996   -0.8466   -1.2290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.8326   -1.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2048    0.1404    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1918    0.2048    0.2450 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8622   -1.0690    0.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0825   -1.9541    1.0671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -3.2097    1.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -3.5421    0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6178   -2.6024    0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1174   -1.3270   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0421   -0.4714   -0.8665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3207    0.8742   -0.3435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1697    1.7344    0.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5531    3.0850    0.1069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6598    4.0689    0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0950    5.3893    0.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3426    3.7700    0.7312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0774    2.4618    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333    1.5016    0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6253   -0.3332    0.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4191   -1.6152   -1.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6199   -2.0535    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039   -2.2673    0.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096    0.1637   -1.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3747   -1.4759   -2.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1533   -1.8118   -0.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2041   -0.4470   -2.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8706    0.0869    0.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5032    1.0934   -0.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8964   -1.6078    1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0133   -3.9212    1.8329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2627   -4.5485    1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5915   -2.8717   -0.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7457   -0.4345   -1.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0303   -1.0154   -0.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9785    0.7471    0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9235    1.4168   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5850    3.3262   -0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4679    6.1357    0.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3895    4.5024    1.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1011    2.1670    0.8792 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
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21  6  1  0
 12  7  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Hydroxydesipramine monohydrochloride	HMDB
2-Hydroxydesipramine fumarate	HMDB
2-Hydroxydesipramine monofumarate	HMDB
2-OH-DMI	HMDB
2-Hydroxydesmethylimipramine	HMDB
2-Hydroxy-desipramine	HMDB

Chemical Formula

C₁₈H₂₂N₂O

Average Molecular Weight

282.3801

Monoisotopic Molecular Weight

282.173213336

IUPAC Name

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

Traditional Name

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=CC=C2CCC2=CC(O)=CC=C12

InChI Identifier

InChI=1S/C18H22N2O/c1-19-11-4-12-20-17-6-3-2-5-14(17)7-8-15-13-16(21)9-10-18(15)20/h2-3,5-6,9-10,13,19,21H,4,7-8,11-12H2,1H3

InChI Key

NVJBOLMRGMDGLD-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
Azepine
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Tertiary amine
Secondary amine
Secondary aliphatic amine
Azacycle
Hydrocarbon derivative
Amine
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen 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: HMDB0060992)

Organ

Kidney (HMDB: HMDB0060992)
Liver (HMDB: HMDB0060992)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060992)

Cellular substructure

Cytoplasm (HMDB: HMDB0060992)
Membrane (HMDB: HMDB0060992)

Source

Endogenous

Endogenous (HMDB: HMDB0060992)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Desipramine Action Pathway (PathBank: SMP0000423)

Metabolic pathway

Desipramine Metabolism Pathway (PathBank: SMP0000626)

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	0.17 g/L	ALOGPS
logP	3.34	ALOGPS
logP	3.17	ChemAxon
logS	-3.2	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	87.29 m³·mol⁻¹	ChemAxon
Polarizability	33.13 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
DarkChem	[M+H]+	166.14	31661259
DarkChem	[M-H]-	166.163	31661259
DeepCCS	[M-2H]-	193.077	30932474
DeepCCS	[M+Na]+	168.643	30932474
AllCCS	[M+H]+	168.7	32859911
AllCCS	[M+H-H2O]+	165.1	32859911
AllCCS	[M+NH4]+	172.0	32859911
AllCCS	[M+Na]+	172.9	32859911
AllCCS	[M-H]-	175.5	32859911
AllCCS	[M+Na-2H]-	175.2	32859911
AllCCS	[M+HCOO]-	175.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.92 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9244 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.2 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1187.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	224.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	160.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	91.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	355.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	326.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	489.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	913.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	388.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1098.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	247.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	301.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	373.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	337.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	11.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-hydroxydesipramine	CNCCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C12	3761.7	Standard polar	33892256
2-hydroxydesipramine	CNCCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C12	2533.9	Standard non polar	33892256
2-hydroxydesipramine	CNCCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C12	2555.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-hydroxydesipramine,1TMS,isomer #1	CNCCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C)=CC=C21	2533.8	Semi standard non polar	33892256
2-hydroxydesipramine,1TMS,isomer #2	CN(CCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C21)[Si](C)(C)C	2785.4	Semi standard non polar	33892256
2-hydroxydesipramine,2TMS,isomer #1	CN(CCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C)=CC=C21)[Si](C)(C)C	2691.3	Semi standard non polar	33892256
2-hydroxydesipramine,2TMS,isomer #1	CN(CCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C)=CC=C21)[Si](C)(C)C	2795.7	Standard non polar	33892256
2-hydroxydesipramine,2TMS,isomer #1	CN(CCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C)=CC=C21)[Si](C)(C)C	3108.5	Standard polar	33892256
2-hydroxydesipramine,1TBDMS,isomer #1	CNCCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	2743.7	Semi standard non polar	33892256
2-hydroxydesipramine,1TBDMS,isomer #2	CN(CCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C21)[Si](C)(C)C(C)(C)C	3011.4	Semi standard non polar	33892256
2-hydroxydesipramine,2TBDMS,isomer #1	CN(CCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21)[Si](C)(C)C(C)(C)C	3120.3	Semi standard non polar	33892256
2-hydroxydesipramine,2TBDMS,isomer #1	CN(CCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21)[Si](C)(C)C(C)(C)C	3316.8	Standard non polar	33892256
2-hydroxydesipramine,2TBDMS,isomer #1	CN(CCCN1C2=CC=CC=C2CCC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21)[Si](C)(C)C(C)(C)C	3301.6	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Desipramine Action Pathway		Not Available
Desipramine Metabolism Pathway		Not Available

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

108234

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

121249

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 2-hydroxydesipramine (HMDB0060992)

MOL for HMDB0060992 (2-hydroxydesipramine)

3D MOL for HMDB0060992 (2-hydroxydesipramine)

3D SDF for HMDB0060992 (2-hydroxydesipramine)

3D-SDF for HMDB0060992 (2-hydroxydesipramine)

PDB for HMDB0060992 (2-hydroxydesipramine)

3D PDB for HMDB0060992 (2-hydroxydesipramine)

SMILES for HMDB0060992 (2-hydroxydesipramine)

INCHI for HMDB0060992 (2-hydroxydesipramine)

Structure for HMDB0060992 (2-hydroxydesipramine)

3D Structure for HMDB0060992 (2-hydroxydesipramine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized