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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8)transporters (2) Show 10 proteins XML

enzymes (8)transporters (2) Show 10 proteins

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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:51 UTC

Update Date

2021-09-14 15:46:28 UTC

HMDB ID

HMDB0014021

Secondary Accession Numbers

HMDB14021

Metabolite Identification

Common Name

N-Desmethylcitalopram

Description

N-Desmethylcitalopram belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine. N-Desmethylcitalopram exists in all living organisms, ranging from bacteria to humans. In humans, N-desmethylcitalopram is involved in the citalopram metabolism pathway. N-Desmethylcitalopram is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on N-Desmethylcitalopram.

Structure

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

HMDB0251057
     RDKit          3D
Desmethylescitalopram
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.6810    1.3043   -0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5490    0.2617    0.8516 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4295   -0.5805    0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0752    0.1197    0.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0492   -0.9062    0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3850   -0.4603    0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2599   -1.6063    0.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5196   -1.8145   -1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2855   -2.8803   -1.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7748   -3.7214   -0.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5339   -4.7842   -0.9373 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5349   -3.5401    0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7600   -2.4560    1.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6894   -0.1980    1.9940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9368    0.4331    1.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7156    1.3960    0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2745    2.6030    0.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554    3.2837   -0.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4200    4.5493   -1.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8888    5.5750   -1.3440 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546    2.6863   -1.4756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2831    1.4784   -1.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7218    0.7991   -0.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4964    1.9674    0.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710    1.8988   -0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9980    0.8171   -1.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5148    0.7107    1.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4773   -1.5400    1.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4880   -0.8905   -0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0442    0.4557    1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0324    0.9312    0.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1509   -1.8275    1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1670   -1.2688   -0.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1158   -1.1316   -1.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056   -3.0739   -2.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9593   -4.2404    1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5743   -2.3159    2.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484    0.9447    2.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7322   -0.2473    1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0470    3.0115    1.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5396    3.2409   -2.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    1.0163   -1.7504 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
  6 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  3  0
 18 21  2  0
 21 22  1  0
 22 23  2  0
 23  6  1  0
 13  7  1  0
 23 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 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
  8 34  1  0
  9 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 17 40  1  0
 21 41  1  0
 22 42  1  0
M  END

  Mrv0541 11291313402D          

 23 25  0  0  0  0            999 V2000
   11.8735   -2.2873    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.6819   -4.8864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0799   -2.3064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5617   -6.1238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2004   -4.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9469   -3.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4198   -4.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4198   -5.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1402   -3.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8687   -3.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2004   -5.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8866   -2.4793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7053   -4.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7053   -5.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7838   -2.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6218   -4.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9908   -4.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9908   -5.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4522   -2.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2899   -3.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2053   -2.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8263   -1.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2763   -5.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  2  5  1  0  0  0  0
  2 11  1  0  0  0  0
  3 12  1  0  0  0  0
  3 22  1  0  0  0  0
  4 23  3  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  2  0  0  0  0
  7 13  1  0  0  0  0
  8 11  1  0  0  0  0
  8 14  1  0  0  0  0
  9 12  1  0  0  0  0
 10 15  2  0  0  0  0
 10 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 17 18  1  0  0  0  0
 18 23  1  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014021

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H19FN2O/c1-22-10-2-9-19(16-4-6-17(20)7-5-16)18-8-3-14(12-21)11-15(18)13-23-19/h3-8,11,22H,2,9-10,13H2,1H3

> <INCHI_KEY>
PTJADDMMFYXMMG-UHFFFAOYSA-N

> <FORMULA>
C19H19FN2O

> <MOLECULAR_WEIGHT>
310.3654

> <EXACT_MASS>
310.148141445

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.486081494186266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-fluorophenyl)-1-[3-(methylamino)propyl]-1,3-dihydro-2-benzofuran-5-carbonitrile

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
3.3812562689999996

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.53921157969947

> <JCHEM_POLAR_SURFACE_AREA>
45.05

> <JCHEM_REFRACTIVITY>
88.72550000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.22e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
demethylcitalopram

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251057
     RDKit          3D
Desmethylescitalopram
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.6810    1.3043   -0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5490    0.2617    0.8516 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4295   -0.5805    0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0752    0.1197    0.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0492   -0.9062    0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3850   -0.4603    0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2599   -1.6063    0.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5196   -1.8145   -1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2855   -2.8803   -1.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7748   -3.7214   -0.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5339   -4.7842   -0.9373 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5349   -3.5401    0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7600   -2.4560    1.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6894   -0.1980    1.9940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9368    0.4331    1.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7156    1.3960    0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2745    2.6030    0.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554    3.2837   -0.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4200    4.5493   -1.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8888    5.5750   -1.3440 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546    2.6863   -1.4756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2831    1.4784   -1.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7218    0.7991   -0.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4964    1.9674    0.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710    1.8988   -0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9980    0.8171   -1.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5148    0.7107    1.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4773   -1.5400    1.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4880   -0.8905   -0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0442    0.4557    1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0324    0.9312    0.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1509   -1.8275    1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1670   -1.2688   -0.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1158   -1.1316   -1.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056   -3.0739   -2.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9593   -4.2404    1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5743   -2.3159    2.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484    0.9447    2.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7322   -0.2473    1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0470    3.0115    1.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5396    3.2409   -2.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    1.0163   -1.7504 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
  6 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  3  0
 18 21  2  0
 21 22  1  0
 22 23  2  0
 23  6  1  0
 13  7  1  0
 23 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 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
  8 34  1  0
  9 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 17 40  1  0
 21 41  1  0
 22 42  1  0
M  END

HEADER    PROTEIN                                 29-NOV-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-NOV-13         0                                  
HETATM    1  F   UNK     0      22.164  -4.270   0.000  0.00  0.00           F+0
HETATM    2  O   UNK     0      18.073  -9.121   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      13.216  -4.305   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      10.382 -11.431   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      17.174  -7.882   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.701  -6.416   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.717  -8.351   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.717  -9.891   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.195  -6.094   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.422  -6.979   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.174 -10.360   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.722  -4.628   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.383  -7.581   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.383 -10.661   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.263  -5.447   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.827  -7.608   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.049  -8.351   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.049  -9.891   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.511  -4.544   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      21.074  -6.705   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.917  -5.173   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.742  -2.840   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.716 -10.661   0.000  0.00  0.00           C+0
CONECT    1   21                                                            
CONECT    2    5   11                                                       
CONECT    3   12   22                                                       
CONECT    4   23                                                            
CONECT    5    2    6    7   10                                             
CONECT    6    5    9                                                       
CONECT    7    5    8   13                                                  
CONECT    8    7   11   14                                                  
CONECT    9    6   12                                                       
CONECT   10    5   15   16                                                  
CONECT   11    2    8                                                       
CONECT   12    3    9                                                       
CONECT   13    7   17                                                       
CONECT   14    8   18                                                       
CONECT   15   10   19                                                       
CONECT   16   10   20                                                       
CONECT   17   13   18                                                       
CONECT   18   14   17   23                                                  
CONECT   19   15   21                                                       
CONECT   20   16   21                                                       
CONECT   21    1   19   20                                                  
CONECT   22    3                                                            
CONECT   23    4   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0014021
HETATM    1  C1  UNL     1       4.467  -2.220   0.098  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.597  -1.745   1.167  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.749  -0.704   0.589  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.806  -0.144   1.620  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.930   0.939   1.118  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.000   0.635   0.006  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.761   1.906  -0.267  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.530   2.604  -1.425  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.221   3.788  -1.709  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.143   4.260  -0.816  1.00  0.00           C  
HETATM   11  F1  UNL     1      -2.823   5.421  -1.088  1.00  0.00           F  
HETATM   12  C10 UNL     1      -2.371   3.558   0.342  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.688   2.384   0.624  1.00  0.00           C  
HETATM   14  O1  UNL     1       0.721   0.333  -1.146  1.00  0.00           O  
HETATM   15  C12 UNL     1      -0.092  -0.510  -1.905  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.009  -1.163  -0.958  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.817  -2.266  -1.102  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.612  -2.705  -0.040  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.441  -3.859  -0.229  1.00  0.00           C  
HETATM   20  N2  UNL     1      -4.100  -4.813  -0.383  1.00  0.00           N  
HETATM   21  C17 UNL     1      -2.559  -2.002   1.143  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.734  -0.887   1.268  1.00  0.00           C  
HETATM   23  C19 UNL     1      -0.949  -0.451   0.224  1.00  0.00           C  
HETATM   24  H1  UNL     1       4.594  -1.408  -0.641  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.494  -2.453   0.468  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.009  -3.090  -0.432  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.961  -2.537   1.407  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.404   0.055   0.149  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.155  -1.156  -0.245  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.229  -0.957   2.130  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.483   0.234   2.449  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.585   1.793   0.749  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.422   1.395   2.005  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.185   2.296  -2.179  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.038   4.340  -2.624  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.105   3.938   1.046  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.929   1.897   1.556  1.00  0.00           H  
HETATM   38  H15 UNL     1      -0.615   0.100  -2.668  1.00  0.00           H  
HETATM   39  H16 UNL     1       0.552  -1.227  -2.469  1.00  0.00           H  
HETATM   40  H17 UNL     1      -1.874  -2.831  -2.022  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.176  -2.346   1.963  1.00  0.00           H  
HETATM   42  H19 UNL     1      -1.754  -0.397   2.231  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7   14   23
CONECT    7    8    8   13
CONECT    8    9   34
CONECT    9   10   10   35
CONECT   10   11   12
CONECT   12   13   13   36
CONECT   13   37
CONECT   14   15
CONECT   15   16   38   39
CONECT   16   17   17   23
CONECT   17   18   40
CONECT   18   19   21   21
CONECT   19   20   20   20
CONECT   21   22   41
CONECT   22   23   23   42
END

HMDB0251057
     RDKit          3D
Desmethylescitalopram
 42 44  0  0  0  0  0  0  0  0999 V2000
    4.6810    1.3043   -0.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5490    0.2617    0.8516 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4295   -0.5805    0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0752    0.1197    0.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0492   -0.9062    0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3850   -0.4603    0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2599   -1.6063    0.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5196   -1.8145   -1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2855   -2.8803   -1.5038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7748   -3.7214   -0.5095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5339   -4.7842   -0.9373 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5349   -3.5401    0.8304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7600   -2.4560    1.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6894   -0.1980    1.9940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9368    0.4331    1.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7156    1.3960    0.7378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2745    2.6030    0.4061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554    3.2837   -0.7157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4200    4.5493   -1.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8888    5.5750   -1.3440 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8546    2.6863   -1.4756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2831    1.4784   -1.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7218    0.7991   -0.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4964    1.9674    0.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710    1.8988   -0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9980    0.8171   -1.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5148    0.7107    1.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4773   -1.5400    1.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4880   -0.8905   -0.4868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0442    0.4557    1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0324    0.9312    0.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1509   -1.8275    1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1670   -1.2688   -0.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1158   -1.1316   -1.8085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056   -3.0739   -2.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9593   -4.2404    1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5743   -2.3159    2.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2484    0.9447    2.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7322   -0.2473    1.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0470    3.0115    1.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5396    3.2409   -2.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    1.0163   -1.7504 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
  6 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  3  0
 18 21  2  0
 21 22  1  0
 22 23  2  0
 23  6  1  0
 13  7  1  0
 23 16  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 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
  8 34  1  0
  9 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 17 40  1  0
 21 41  1  0
 22 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Monodesmethylcitalopram monohydrochloride	MeSH, HMDB
Monodesmethylcitalopram	MeSH, HMDB
Monodesmethylcitalopram oxalate	MeSH, HMDB

Chemical Formula

C₁₉H₁₉FN₂O

Average Molecular Weight

310.3654

Monoisotopic Molecular Weight

310.148141445

IUPAC Name

1-(4-fluorophenyl)-1-[3-(methylamino)propyl]-1,3-dihydro-2-benzofuran-5-carbonitrile

Traditional Name

demethylcitalopram

CAS Registry Number

Not Available

SMILES

CNCCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

InChI Identifier

InChI=1S/C19H19FN2O/c1-22-10-2-9-19(16-4-6-17(20)7-5-16)18-8-3-14(12-21)11-15(18)13-23-19/h3-8,11,22H,2,9-10,13H2,1H3

InChI Key

PTJADDMMFYXMMG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylbutylamines

Direct Parent

Phenylbutylamines

Alternative Parents

Substituents

Phenylbutylamine
Isocoumaran
Fluorobenzene
Halobenzene
Aralkylamine
Aryl fluoride
Aryl halide
Dialkyl ether
Secondary aliphatic amine
Ether
Carbonitrile
Nitrile
Oxacycle
Secondary amine
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Amine
Organohalogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic amino compound (CHEBI:80603 )
benzenes (CHEBI:80603 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0014021)
Kidney (HMDB: HMDB0014021)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014021)

Source

Endogenous

Endogenous (HMDB: HMDB0014021)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Citalopram Action Pathway (PathBank: SMP0000424)

Metabolic pathway

Citalopram Metabolism Pathway (PathBank: SMP0000627)

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	0.0052 g/L	ALOGPS
logP	3.24	ALOGPS
logP	3.38	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	10.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	45.05 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	88.73 m³·mol⁻¹	ChemAxon
Polarizability	33.49 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	181.354	30932474
DeepCCS	[M-H]-	178.996	30932474
DeepCCS	[M-2H]-	211.882	30932474
DeepCCS	[M+Na]+	187.447	30932474
AllCCS	[M+H]+	173.4	32859911
AllCCS	[M+H-H2O]+	170.1	32859911
AllCCS	[M+NH4]+	176.5	32859911
AllCCS	[M+Na]+	177.4	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
N-Desmethylcitalopram	CNCCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1	3614.3	Standard polar	33892256
N-Desmethylcitalopram	CNCCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1	2573.6	Standard non polar	33892256
N-Desmethylcitalopram	CNCCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1	2495.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethylcitalopram,1TMS,isomer #1	CN(CCCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C21)[Si](C)(C)C	2648.0	Semi standard non polar	33892256
N-Desmethylcitalopram,1TMS,isomer #1	CN(CCCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C21)[Si](C)(C)C	2585.7	Standard non polar	33892256
N-Desmethylcitalopram,1TMS,isomer #1	CN(CCCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C21)[Si](C)(C)C	3199.8	Standard polar	33892256
N-Desmethylcitalopram,1TBDMS,isomer #1	CN(CCCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C21)[Si](C)(C)C(C)(C)C	2907.9	Semi standard non polar	33892256
N-Desmethylcitalopram,1TBDMS,isomer #1	CN(CCCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C21)[Si](C)(C)C(C)(C)C	2801.8	Standard non polar	33892256
N-Desmethylcitalopram,1TBDMS,isomer #1	CN(CCCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C21)[Si](C)(C)C(C)(C)C	3300.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethylcitalopram GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-2190000000-0d77c4027d0a40f7e7dc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethylcitalopram GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethylcitalopram GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethylcitalopram 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 - N-Desmethylcitalopram 10V, Positive-QTOF	splash10-03e9-1098000000-21dde1b3364c57dbdd76	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylcitalopram 20V, Positive-QTOF	splash10-001l-1191000000-d1e1b3147cb08a67eaf5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylcitalopram 40V, Positive-QTOF	splash10-06dl-9540000000-33ba0b6b7cabe983d4fb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylcitalopram 10V, Negative-QTOF	splash10-0a4i-1009000000-11570b53909e284c90a5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylcitalopram 20V, Negative-QTOF	splash10-0a4i-1049000000-5002b93fb410b5342dcb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylcitalopram 40V, Negative-QTOF	splash10-0f6t-4290000000-981b4ff89efe87c1d73e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylcitalopram 10V, Negative-QTOF	splash10-0a4i-0019000000-a2921fd2ae0ab9ec199c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylcitalopram 20V, Negative-QTOF	splash10-000i-0092000000-e1374bcf1d386ad73b95	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylcitalopram 40V, Negative-QTOF	splash10-000i-1490000000-b5fe614fcfdd13a04ab8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylcitalopram 10V, Positive-QTOF	splash10-03di-0009000000-5bcca98aa4fb61ae2d26	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylcitalopram 20V, Positive-QTOF	splash10-03di-1196000000-4a5847919ee98458018d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylcitalopram 40V, Positive-QTOF	splash10-0a4j-1940000000-20062f0a4360504508b7	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Citalopram Action Pathway		Not Available
Citalopram 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	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	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

142424

KEGG Compound ID

C16608

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Desmethylcitalopram

METLIN ID

Not Available

PubChem Compound

162180

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

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Reactions

N-Desmethylcitalopram + Oxygen + Water → Citalopram aldehyde + Methylamine + Hydrogen peroxide	details

Enzyme Details

2. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Reactions

N-Desmethylcitalopram + Oxygen + Water → Citalopram aldehyde + Methylamine + Hydrogen peroxide	details

Enzyme Details

3. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Brosen K, Naranjo CA: Review of pharmacokinetic and pharmacodynamic interaction studies with citalopram. Eur Neuropsychopharmacol. 2001 Aug;11(4):275-83. [PubMed:11532381 ]
Rasmussen BB, Brosen K: Is therapeutic drug monitoring a case for optimizing clinical outcome and avoiding interactions of the selective serotonin reuptake inhibitors? Ther Drug Monit. 2000 Apr;22(2):143-54. [PubMed:10774624 ]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Pelkonen O, Maenpaa J, Taavitsainen P, Rautio A, Raunio H: Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica. 1998 Dec;28(12):1203-53. [PubMed:9890159 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Brosen K, Naranjo CA: Review of pharmacokinetic and pharmacodynamic interaction studies with citalopram. Eur Neuropsychopharmacol. 2001 Aug;11(4):275-83. [PubMed:11532381 ]
Rasmussen BB, Brosen K: Is therapeutic drug monitoring a case for optimizing clinical outcome and avoiding interactions of the selective serotonin reuptake inhibitors? Ther Drug Monit. 2000 Apr;22(2):143-54. [PubMed:10774624 ]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Pelkonen O, Maenpaa J, Taavitsainen P, Rautio A, Raunio H: Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica. 1998 Dec;28(12):1203-53. [PubMed:9890159 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 2D6

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

References

Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. [PubMed:8968657 ]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

7. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

8. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

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

References

Weiss J, Dormann SM, Martin-Facklam M, Kerpen CJ, Ketabi-Kiyanvash N, Haefeli WE: Inhibition of P-glycoprotein by newer antidepressants. J Pharmacol Exp Ther. 2003 Apr;305(1):197-204. [PubMed:12649369 ]

Enzyme Details

2. Sodium-dependent serotonin transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:: SLC6A4
Uniprot ID:: P31645
Molecular weight:: 70324.165

References

Eriksson E, Engberg G, Bing O, Nissbrandt H: Effects of mCPP on the extracellular concentrations of serotonin and dopamine in rat brain. Neuropsychopharmacology. 1999 Mar;20(3):287-96. [PubMed:10063489 ]
Maines LW, Keck BJ, Smith JE, Lakoski JM: Corticosterone regulation of serotonin transporter and 5-HT1A receptor expression in the aging brain. Synapse. 1999 Apr;32(1):58-66. [PubMed:10188639 ]
Vicentic A, Battaglia G, Carroll FI, Kuhar MJ: Serotonin transporter production and degradation rates: studies with RTI-76. Brain Res. 1999 Sep 11;841(1-2):1-10. [PubMed:10546982 ]
Dugar A, Keck BJ, Maines LW, Miller S, Njai R, Lakoski JM: Compensatory responses in the aging hippocampal serotonergic system following neurodegenerative injury with 5,7-dihydroxytryptamine. Synapse. 2001 Feb;39(2):109-21. [PubMed:11180498 ]
Dutta AK, Fei XS, Beardsley PM, Newman JL, Reith ME: Structure-activity relationship studies of 4-[2-(diphenylmethoxy)ethyl]-1-benzylpiperidine derivatives and their N-analogues: evaluation of O-and N-analogues and their binding to monoamine transporters. J Med Chem. 2001 Mar 15;44(6):937-48. [PubMed:11300876 ]
Plenge P, Wiborg O: High- and low-affinity binding of S-citalopram to the human serotonin transporter mutated at 20 putatively important amino acid positions. Neurosci Lett. 2005 Aug 5;383(3):203-8. Epub 2005 Apr 25. [PubMed:15955412 ]
Schloss P, Betz H: Heterogeneity of antidepressant binding sites on the recombinant rat serotonin transporter SERT1. Biochemistry. 1995 Oct 3;34(39):12590-5. [PubMed:7548008 ]
Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]
Zhong H, Hansen KB, Boyle NJ, Han K, Muske G, Huang X, Egebjerg J, Sanchez C: An allosteric binding site at the human serotonin transporter mediates the inhibition of escitalopram by R-citalopram: kinetic binding studies with the ALI/VFL-SI/TT mutant. Neurosci Lett. 2009 Oct 25;462(3):207-12. doi: 10.1016/j.neulet.2009.07.030. Epub 2009 Jul 16. [PubMed:19616061 ]
Rasmussen TN, Plenge P, Bay T, Egebjerg J, Gether U: A single nucleotide polymorphism in the human serotonin transporter introduces a new site for N-linked glycosylation. Neuropharmacology. 2009 Sep;57(3):287-94. doi: 10.1016/j.neuropharm.2009.05.009. Epub 2009 Jun 3. [PubMed:19500602 ]

Showing metabocard for N-Desmethylcitalopram (HMDB0014021)

MOL for HMDB0014021 (N-Desmethylcitalopram)

3D MOL for HMDB0014021 (N-Desmethylcitalopram)

3D SDF for HMDB0014021 (N-Desmethylcitalopram)

3D-SDF for HMDB0014021 (N-Desmethylcitalopram)

PDB for HMDB0014021 (N-Desmethylcitalopram)

3D PDB for HMDB0014021 (N-Desmethylcitalopram)

SMILES for HMDB0014021 (N-Desmethylcitalopram)

INCHI for HMDB0014021 (N-Desmethylcitalopram)

Structure for HMDB0014021 (N-Desmethylcitalopram)

3D Structure for HMDB0014021 (N-Desmethylcitalopram)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

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Transporters

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