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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 17:42:26 UTC

Update Date

2021-09-14 15:47:40 UTC

HMDB ID

HMDB0060654

Secondary Accession Numbers

HMDB60654

Metabolite Identification

Common Name

Citalopram N-oxide

Description

Citalopram N-oxide 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. Citalopram is an antidepressant drug of the selective serotonin reuptake inhibitor (SSRI) class. Citalopram N-oxide is a metabolite of citalopram. Citalopram N-oxide is a strong basic compound (based on its pKa). citalopram N-oxide can be biosynthesized from citalopram; which is mediated by the enzyme cytochrome P450 2D6. In humans, citalopram N-oxide is involved in citalopram metabolism pathway. It has U.S. Food and Drug Administration (FDA) approval to treat major depression, and is prescribed off-label for a number of anxiety conditions.

Structure

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

HMDB0060654
     RDKit          3D
Citalopram N-oxide
 46 48  0  0  0  0  0  0  0  0999 V2000
    5.0274   -0.0495   -0.8351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7961    0.2002   -0.0947 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.9733    1.5097    0.5527 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337   -0.7027    0.8870 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.6709    0.1962   -0.9729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3653   -0.1194   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2159   -0.1212   -1.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1350   -0.3948   -0.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3093   -1.6992    0.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0883   -2.7137   -0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2720   -3.9414    0.1146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856   -4.2411    1.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8503   -5.4341    1.9171 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9091   -3.2657    1.9068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7358   -2.0351    1.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9234   -0.5037   -1.7588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765    0.7522   -2.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5019    1.4629   -0.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2011    2.5890   -0.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1695    3.0689    0.8445 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4003    2.7692    2.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1486    0.7613    2.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  CHG  2   2   1   4  -1
M  END

 
  Mrv0541 06181310422D          
 
 25 27  0  0  0  0            999 V2000
   14.8585  -11.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0060654

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)(=O)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H21FN2O2/c1-23(2,24)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-25-20/h4-9,12H,3,10-11,14H2,1-2H3

> <INCHI_KEY>
DIOGFDCEWUUSBQ-UHFFFAOYSA-N

> <FORMULA>
C20H21FN2O2

> <MOLECULAR_WEIGHT>
340.3913

> <EXACT_MASS>
340.158706131

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
36.0414718300288

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[5-cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]-N,N-dimethylpropanamine oxide

> <ALOGPS_LOGP>
1.20

> <JCHEM_LOGP>
2.639929023000001

> <ALOGPS_LOGS>
-5.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.16431906719335

> <JCHEM_POLAR_SURFACE_AREA>
59.9

> <JCHEM_REFRACTIVITY>
96.06509999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.97e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
citalopram N-oxide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060654
     RDKit          3D
Citalopram N-oxide
 46 48  0  0  0  0  0  0  0  0999 V2000
    5.0274   -0.0495   -0.8351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7961    0.2002   -0.0947 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.9733    1.5097    0.5527 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337   -0.7027    0.8870 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.6709    0.1962   -0.9729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3653   -0.1194   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2159   -0.1212   -1.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1350   -0.3948   -0.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3093   -1.6992    0.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0883   -2.7137   -0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2720   -3.9414    0.1146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856   -4.2411    1.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8503   -5.4341    1.9171 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9091   -3.2657    1.9068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7358   -2.0351    1.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9234   -0.5037   -1.7588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765    0.7522   -2.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5019    1.4629   -0.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2011    2.5890   -0.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1695    3.0689    0.8445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9024    4.2583    1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4884    5.2129    1.5170 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4125    2.3751    1.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6144    1.2723   -2.6644 H   0  0  0  0  0  0  0  0  0  0  0  0
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 17 43  1  0
 19 44  1  0
 23 45  1  0
 24 46  1  0
M  CHG  2   2   1   4  -1
M  END

HEADER    PROTEIN                                 18-JUN-13   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-JUN-13         0                                  
HETATM    1  C   UNK     0      27.736 -20.894   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.267 -20.412   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      28.653 -19.649   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      26.274 -18.867   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.946 -21.182   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.749 -18.392   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.946 -18.097   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      23.606 -20.406   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.606 -18.867   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.272 -18.097   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      20.938 -17.327   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      27.736 -22.434   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.404 -23.203   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.404 -24.743   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.738 -25.513   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.070 -24.744   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.070 -23.204   0.000  0.00  0.00           C+0
HETATM   18  F   UNK     0      27.737 -27.023   0.000  0.00  0.00           F+0
HETATM   19  C   UNK     0      29.276 -20.894   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.029 -22.198   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.570 -22.198   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      32.330 -23.512   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      33.573 -24.742   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      32.037 -25.049   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      33.640 -22.327   0.000  0.00  0.00           O+0
CONECT    1    2    3   12   19                                             
CONECT    2    1    4    5                                                  
CONECT    3    1    6                                                       
CONECT    4    2    7    6                                                  
CONECT    5    2    8                                                       
CONECT    6    3    4                                                       
CONECT    7    4    9                                                       
CONECT    8    5    9                                                       
CONECT    9    7   10    8                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    1   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
CONECT   19    1   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0060654
HETATM    1  C1  UNL     1       5.027  -0.049  -0.835  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.796   0.200  -0.095  1.00  0.00           N1+
HETATM    3  C2  UNL     1       3.973   1.510   0.553  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.734  -0.703   0.887  1.00  0.00           O1-
HETATM    5  C3  UNL     1       2.671   0.196  -0.973  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.365  -0.119  -0.225  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.216  -0.121  -1.133  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.135  -0.395  -0.575  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.309  -1.699   0.086  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.088  -2.714  -0.478  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.272  -3.941   0.115  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.686  -4.241   1.319  1.00  0.00           C  
HETATM   13  F1  UNL     1      -1.850  -5.434   1.917  1.00  0.00           F  
HETATM   14  C11 UNL     1      -0.909  -3.266   1.907  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.736  -2.035   1.295  1.00  0.00           C  
HETATM   16  O2  UNL     1      -1.923  -0.504  -1.759  1.00  0.00           O  
HETATM   17  C13 UNL     1      -2.377   0.752  -2.051  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.502   1.463  -0.762  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.201   2.589  -0.436  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.169   3.069   0.845  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.902   4.258   1.207  1.00  0.00           C  
HETATM   22  N2  UNL     1      -4.488   5.213   1.517  1.00  0.00           N  
HETATM   23  C18 UNL     1      -2.412   2.375   1.775  1.00  0.00           C  
HETATM   24  C19 UNL     1      -1.708   1.228   1.416  1.00  0.00           C  
HETATM   25  C20 UNL     1      -1.738   0.745   0.135  1.00  0.00           C  
HETATM   26  H1  UNL     1       4.852  -0.898  -1.529  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.827  -0.272  -0.121  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.348   0.870  -1.388  1.00  0.00           H  
HETATM   29  H4  UNL     1       3.061   1.726   1.123  1.00  0.00           H  
HETATM   30  H5  UNL     1       4.835   1.462   1.239  1.00  0.00           H  
HETATM   31  H6  UNL     1       4.172   2.241  -0.250  1.00  0.00           H  
HETATM   32  H7  UNL     1       2.805  -0.649  -1.693  1.00  0.00           H  
HETATM   33  H8  UNL     1       2.598   1.125  -1.549  1.00  0.00           H  
HETATM   34  H9  UNL     1       1.340   0.519   0.638  1.00  0.00           H  
HETATM   35  H10 UNL     1       1.536  -1.179   0.132  1.00  0.00           H  
HETATM   36  H11 UNL     1       0.163   0.871  -1.641  1.00  0.00           H  
HETATM   37  H12 UNL     1       0.375  -0.851  -1.982  1.00  0.00           H  
HETATM   38  H13 UNL     1      -2.589  -2.541  -1.445  1.00  0.00           H  
HETATM   39  H14 UNL     1      -2.881  -4.696  -0.354  1.00  0.00           H  
HETATM   40  H15 UNL     1      -0.417  -3.451   2.869  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.129  -1.332   1.801  1.00  0.00           H  
HETATM   42  H17 UNL     1      -3.323   0.768  -2.627  1.00  0.00           H  
HETATM   43  H18 UNL     1      -1.614   1.272  -2.664  1.00  0.00           H  
HETATM   44  H19 UNL     1      -3.788   3.109  -1.201  1.00  0.00           H  
HETATM   45  H20 UNL     1      -2.400   2.769   2.778  1.00  0.00           H  
HETATM   46  H21 UNL     1      -1.149   0.761   2.213  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4    5
CONECT    3   29   30   31
CONECT    5    6   32   33
CONECT    6    7   34   35
CONECT    7    8   36   37
CONECT    8    9   16   25
CONECT    9   10   10   15
CONECT   10   11   38
CONECT   11   12   12   39
CONECT   12   13   14
CONECT   14   15   15   40
CONECT   15   41
CONECT   16   17
CONECT   17   18   42   43
CONECT   18   19   19   25
CONECT   19   20   44
CONECT   20   21   23   23
CONECT   21   22   22   22
CONECT   23   24   45
CONECT   24   25   25   46
END

HMDB0060654
     RDKit          3D
Citalopram N-oxide
 46 48  0  0  0  0  0  0  0  0999 V2000
    5.0274   -0.0495   -0.8351 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7961    0.2002   -0.0947 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.9733    1.5097    0.5527 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337   -0.7027    0.8870 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.6709    0.1962   -0.9729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3653   -0.1194   -0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2159   -0.1212   -1.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1350   -0.3948   -0.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3093   -1.6992    0.0858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0883   -2.7137   -0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2720   -3.9414    0.1146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6856   -4.2411    1.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8503   -5.4341    1.9171 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9091   -3.2657    1.9068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7358   -2.0351    1.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9234   -0.5037   -1.7588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3765    0.7522   -2.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5019    1.4629   -0.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2011    2.5890   -0.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1695    3.0689    0.8445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9024    4.2583    1.2072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4884    5.2129    1.5170 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4125    2.3751    1.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7079    1.2278    1.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7377    0.7452    0.1345 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8518   -0.8980   -1.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8271   -0.2719   -0.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3485    0.8696   -1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0613    1.7258    1.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8355    1.4618    1.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1715    2.2409   -0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8053   -0.6486   -1.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5979    1.1245   -1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3399    0.5185    0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5364   -1.1794    0.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1626    0.8706   -1.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3752   -0.8512   -1.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5889   -2.5411   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8808   -4.6957   -0.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4168   -3.4506    2.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1287   -1.3319    1.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3225    0.7679   -2.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6144    1.2723   -2.6644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7881    3.1090   -1.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4003    2.7692    2.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1486    0.7613    2.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
  8 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  3  0
 20 23  2  0
 23 24  1  0
 24 25  2  0
 25  8  1  0
 15  9  1  0
 25 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
 10 38  1  0
 11 39  1  0
 14 40  1  0
 15 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 23 45  1  0
 24 46  1  0
M  CHG  2   2   1   4  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₁FN₂O₂

Average Molecular Weight

340.3913

Monoisotopic Molecular Weight

340.158706131

IUPAC Name

3-[5-cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]-N,N-dimethylpropanamine oxide

Traditional Name

citalopram N-oxide

CAS Registry Number

Not Available

SMILES

CN(C)(=O)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

InChI Identifier

InChI=1S/C20H21FN2O2/c1-23(2,24)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-25-20/h4-9,12H,3,10-11,14H2,1-2H3

InChI Key

DIOGFDCEWUUSBQ-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
Aryl fluoride
Aryl halide
Trialkyl amine oxide
N-oxide
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Trisubstituted n-oxide
Carbonitrile
Nitrile
Organic nitrogen compound
Organohalogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic amino compound (CHEBI:80602 )
benzenes (CHEBI:80602 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060654)

Organ

Liver (HMDB: HMDB0060654)
Kidney (HMDB: HMDB0060654)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060654)

Cellular substructure

Cytoplasm (HMDB: HMDB0060654)
Membrane (HMDB: HMDB0060654)

Source

Endogenous

Endogenous (HMDB: HMDB0060654)

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	0.002 g/L	ALOGPS
logP	1.2	ALOGPS
logP	2.64	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	4.16	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	59.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.07 m³·mol⁻¹	ChemAxon
Polarizability	36.04 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]+	181.316	30932474
DeepCCS	[M-H]-	178.958	30932474
DeepCCS	[M-2H]-	212.927	30932474
DeepCCS	[M+Na]+	188.376	30932474
AllCCS	[M+H]+	180.3	32859911
AllCCS	[M+H-H2O]+	177.3	32859911
AllCCS	[M+NH4]+	183.2	32859911
AllCCS	[M+Na]+	184.0	32859911
AllCCS	[M-H]-	187.9	32859911
AllCCS	[M+Na-2H]-	188.3	32859911
AllCCS	[M+HCOO]-	188.8	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.	5.41 minutes	32390414
Predicted by Siyang on May 30, 2022	12.5227 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.55 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1590.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	241.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	192.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	190.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	121.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	523.1 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	479.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	609.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1337.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	379.6 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	1494.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	251.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	358.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	369.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	361.0 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	27.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citalopram N-oxide	CN(C)(=O)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1	3679.1	Standard polar	33892256
Citalopram N-oxide	CN(C)(=O)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1	2422.7	Standard non polar	33892256
Citalopram N-oxide	CN(C)(=O)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1	2468.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Citalopram N-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1191000000-61350a6a4e7c7ec57461	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citalopram N-oxide 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 - Citalopram N-oxide 10V, Positive-QTOF	splash10-0006-0029000000-44d92e428209f50b8f52	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram N-oxide 20V, Positive-QTOF	splash10-001c-4397000000-1ca72d34b2e820c2e98a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram N-oxide 40V, Positive-QTOF	splash10-00s9-8960000000-f90431365d18605158e6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram N-oxide 10V, Negative-QTOF	splash10-000i-0009000000-4fec0d54847fd5c5d7cc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram N-oxide 20V, Negative-QTOF	splash10-000i-1019000000-19ea08ed4fbf62970754	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram N-oxide 40V, Negative-QTOF	splash10-000j-4190000000-328d5f705437721a32ee	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C16607

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10068142

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 Citalopram N-oxide (HMDB0060654)

MOL for HMDB0060654 (Citalopram N-oxide)

3D MOL for HMDB0060654 (Citalopram N-oxide)

3D SDF for HMDB0060654 (Citalopram N-oxide)

3D-SDF for HMDB0060654 (Citalopram N-oxide)

PDB for HMDB0060654 (Citalopram N-oxide)

3D PDB for HMDB0060654 (Citalopram N-oxide)

SMILES for HMDB0060654 (Citalopram N-oxide)

INCHI for HMDB0060654 (Citalopram N-oxide)

Structure for HMDB0060654 (Citalopram N-oxide)

3D Structure for HMDB0060654 (Citalopram N-oxide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra