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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:22:30 UTC

Update Date

2021-09-14 15:47:54 UTC

HMDB ID

HMDB0060462

Secondary Accession Numbers

HMDB60462

Metabolite Identification

Common Name

Citalopram aldehyde

Description

Citalopram aldehyde belongs to the class of organic compounds known as isocoumarans. Isocoumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 1,3-dihydrofuran ring. Citalopram is an antidepressant drug of the selective serotonin reuptake inhibitor (SSRI) class. Citalopram aldehyde is a metabolite of citalopram. Citalopram aldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Citalopram aldehyde exists in all living organisms, ranging from bacteria to humans. Within humans, citalopram aldehyde participates in a number of enzymatic reactions. In particular, citalopram aldehyde and dimethylamine can be biosynthesized from citalopram; which is catalyzed by the enzymes amine oxidase [flavin-containing] a and amine oxidase [flavin-containing] b. In addition, citalopram aldehyde and methylammonium can be biosynthesized from N-desmethylcitalopram through the action of the enzymes amine oxidase [flavin-containing] a and amine oxidase [flavin-containing] b. In humans, citalopram aldehyde 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

HMDB0060462
     RDKit          3D
Citalopram aldehyde
 36 38  0  0  0  0  0  0  0  0999 V2000
    6.1931   -0.9920   -0.8162 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0577   -0.9569   -0.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6577   -0.9231   -0.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -1.8502   -0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4316   -1.7847   -0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9647   -0.8072    0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8759    0.1244    0.9121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1937    0.0585    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0671    1.0196    1.8229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0897    0.1114    2.2265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3107   -0.3663    0.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4623   -1.2682    1.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9659   -1.6778   -0.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555   -2.5901   -0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7333   -3.0517   -1.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897    0.8867    0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7600    1.6181    0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2785    2.7807    0.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7802    3.1907   -0.8858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860    4.3373   -1.4299 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8115    2.4808   -1.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3230    1.3093   -0.9531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1105   -2.6318   -1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -2.5466   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995    0.7810    1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6136    1.8538    1.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6939    1.3544    2.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2563   -2.1929    1.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2864   -0.7178    1.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2873   -2.1984   -0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2945   -0.7589   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4722   -2.8161    0.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1586    1.3155    1.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0411    3.3657    0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295    2.8050   -2.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321    0.7380   -1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 11 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
  8  3  1  0
 22 16  1  0
 11  6  1  0
  4 23  1  0
  5 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
 18 34  1  0
 21 35  1  0
 22 36  1  0
M  END


  Mrv0541 05161318222D          

 22 24  0  0  0  0            999 V2000
    2.9359    1.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654    2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    2.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3636    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154    1.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2714    2.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3636    2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780    2.7299    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0919    2.7598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  2  2  0  0  0  0
  8  1  1  0  0  0  0
  9  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13 10  2  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 14 12  1  0  0  0  0
 15  3  2  0  0  0  0
 15  4  1  0  0  0  0
 16  5  2  0  0  0  0
 16  6  1  0  0  0  0
 17  7  1  0  0  0  0
 17 14  2  0  0  0  0
 18  8  1  0  0  0  0
 18 15  1  0  0  0  0
 18 17  1  0  0  0  0
 19 16  1  0  0  0  0
 20 11  3  0  0  0  0
 21  9  2  0  0  0  0
 22 12  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060462

> <DATABASE_NAME>
hmdb

> <SMILES>
FC1=CC=C(C=C1)C1(CCC=O)OCC2=C1C=CC(=C2)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C18H14FNO2/c19-16-5-3-15(4-6-16)18(8-1-9-21)17-7-2-13(11-20)10-14(17)12-22-18/h2-7,9-10H,1,8,12H2

> <INCHI_KEY>
BBYAFETUIKMLSF-UHFFFAOYSA-N

> <FORMULA>
C18H14FNO2

> <MOLECULAR_WEIGHT>
295.3077

> <EXACT_MASS>
295.100856902

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.74990386317021

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(4-fluorophenyl)-1-(3-oxopropyl)-1,3-dihydro-2-benzofuran-5-carbonitrile

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
3.013378271333333

> <ALOGPS_LOGS>
-4.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.934949111503933

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2609066042930985

> <JCHEM_POLAR_SURFACE_AREA>
50.09

> <JCHEM_REFRACTIVITY>
81.10470000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.44e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
citalopram aldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060462
     RDKit          3D
Citalopram aldehyde
 36 38  0  0  0  0  0  0  0  0999 V2000
    6.1931   -0.9920   -0.8162 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0577   -0.9569   -0.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6577   -0.9231   -0.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -1.8502   -0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4316   -1.7847   -0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9647   -0.8072    0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8759    0.1244    0.9121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1937    0.0585    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0671    1.0196    1.8229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0897    0.1114    2.2265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3107   -0.3663    0.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4623   -1.2682    1.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9659   -1.6778   -0.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555   -2.5901   -0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7333   -3.0517   -1.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897    0.8867    0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7600    1.6181    0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2785    2.7807    0.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7802    3.1907   -0.8858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860    4.3373   -1.4299 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8115    2.4808   -1.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3230    1.3093   -0.9531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1105   -2.6318   -1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -2.5466   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995    0.7810    1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6136    1.8538    1.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6939    1.3544    2.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2563   -2.1929    1.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2864   -0.7178    1.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2873   -2.1984   -0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2945   -0.7589   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4722   -2.8161    0.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1586    1.3155    1.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0411    3.3657    0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295    2.8050   -2.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321    0.7380   -1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 11 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
  8  3  1  0
 22 16  1  0
 11  6  1  0
  4 23  1  0
  5 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
 18 34  1  0
 21 35  1  0
 22 36  1  0
M  END

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0       5.480   3.584   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.989   4.326   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.655   5.096   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.679   2.786   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.949   3.423   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.107   4.991   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.989   2.786   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.679   4.326   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   19  F   UNK     0      -2.012   5.096   0.000  0.00  0.00           F+0
HETATM   20  N   UNK     0      10.122  -1.540   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0       7.638   5.152   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.417   0.770   0.000  0.00  0.00           O+0
CONECT    1    8    9                                                       
CONECT    2    7   13                                                       
CONECT    3    5   15                                                       
CONECT    4    6   15                                                       
CONECT    5    3   16                                                       
CONECT    6    4   16                                                       
CONECT    7    2   17                                                       
CONECT    8    1   18                                                       
CONECT    9    1   21                                                       
CONECT   10   13   14                                                       
CONECT   11   13   20                                                       
CONECT   12   14   22                                                       
CONECT   13    2   10   11                                                  
CONECT   14   10   12   17                                                  
CONECT   15    3    4   18                                                  
CONECT   16    5    6   19                                                  
CONECT   17    7   14   18                                                  
CONECT   18    8   15   17   22                                             
CONECT   19   16                                                            
CONECT   20   11                                                            
CONECT   21    9                                                            
CONECT   22   12   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0060462
HETATM    1  N1  UNL     1       6.193  -0.992  -0.816  1.00  0.00           N  
HETATM    2  C1  UNL     1       5.058  -0.957  -0.575  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.658  -0.923  -0.262  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.792  -1.850  -0.799  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.432  -1.785  -0.471  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.965  -0.807   0.378  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.876   0.124   0.912  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.194   0.059   0.591  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.067   1.020   1.823  1.00  0.00           C  
HETATM   10  O1  UNL     1       0.090   0.111   2.226  1.00  0.00           O  
HETATM   11  C9  UNL     1      -0.311  -0.366   0.955  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.462  -1.268   1.020  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.966  -1.678  -0.322  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.156  -2.590  -0.162  1.00  0.00           C  
HETATM   15  O2  UNL     1      -3.733  -3.052  -1.117  1.00  0.00           O  
HETATM   16  C13 UNL     1      -0.790   0.887   0.247  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.760   1.618   0.891  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.279   2.781   0.348  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.780   3.191  -0.886  1.00  0.00           C  
HETATM   20  F1  UNL     1      -2.286   4.337  -1.430  1.00  0.00           F  
HETATM   21  C17 UNL     1      -0.811   2.481  -1.552  1.00  0.00           C  
HETATM   22  C18 UNL     1      -0.323   1.309  -0.953  1.00  0.00           C  
HETATM   23  H1  UNL     1       3.110  -2.632  -1.467  1.00  0.00           H  
HETATM   24  H2  UNL     1       0.810  -2.547  -0.911  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.899   0.781   1.004  1.00  0.00           H  
HETATM   26  H4  UNL     1       0.614   1.854   1.294  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.694   1.354   2.680  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.256  -2.193   1.624  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.286  -0.718   1.546  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.287  -2.198  -0.980  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.294  -0.759  -0.904  1.00  0.00           H  
HETATM   32  H10 UNL     1      -3.472  -2.816   0.825  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.159   1.316   1.850  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.041   3.366   0.843  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.430   2.805  -2.510  1.00  0.00           H  
HETATM   36  H14 UNL     1       0.432   0.738  -1.452  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   23
CONECT    5    6    6   24
CONECT    6    7   11
CONECT    7    8    8    9
CONECT    8   25
CONECT    9   10   26   27
CONECT   10   11
CONECT   11   12   16
CONECT   12   13   28   29
CONECT   13   14   30   31
CONECT   14   15   15   32
CONECT   16   17   17   22
CONECT   17   18   33
CONECT   18   19   19   34
CONECT   19   20   21
CONECT   21   22   22   35
CONECT   22   36
END

HMDB0060462
     RDKit          3D
Citalopram aldehyde
 36 38  0  0  0  0  0  0  0  0999 V2000
    6.1931   -0.9920   -0.8162 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0577   -0.9569   -0.5750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6577   -0.9231   -0.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -1.8502   -0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4316   -1.7847   -0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9647   -0.8072    0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8759    0.1244    0.9121 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1937    0.0585    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0671    1.0196    1.8229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0897    0.1114    2.2265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3107   -0.3663    0.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4623   -1.2682    1.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9659   -1.6778   -0.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555   -2.5901   -0.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7333   -3.0517   -1.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897    0.8867    0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7600    1.6181    0.8915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2785    2.7807    0.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7802    3.1907   -0.8858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2860    4.3373   -1.4299 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8115    2.4808   -1.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3230    1.3093   -0.9531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1105   -2.6318   -1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101   -2.5466   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8995    0.7810    1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6136    1.8538    1.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6939    1.3544    2.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2563   -2.1929    1.6241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2864   -0.7178    1.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2873   -2.1984   -0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2945   -0.7589   -0.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4722   -2.8161    0.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1586    1.3155    1.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0411    3.3657    0.8429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4295    2.8050   -2.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4321    0.7380   -1.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 11 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
  8  3  1  0
 22 16  1  0
 11  6  1  0
  4 23  1  0
  5 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 17 33  1  0
 18 34  1  0
 21 35  1  0
 22 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₁₄FNO₂

Average Molecular Weight

295.3077

Monoisotopic Molecular Weight

295.100856902

IUPAC Name

1-(4-fluorophenyl)-1-(3-oxopropyl)-1,3-dihydro-2-benzofuran-5-carbonitrile

Traditional Name

citalopram aldehyde

CAS Registry Number

Not Available

SMILES

FC1=CC=C(C=C1)C1(CCC=O)OCC2=C1C=CC(=C2)C#N

InChI Identifier

InChI=1S/C18H14FNO2/c19-16-5-3-15(4-6-16)18(8-1-9-21)17-7-2-13(11-20)10-14(17)12-22-18/h2-7,9-10H,1,8,12H2

InChI Key

BBYAFETUIKMLSF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocoumarans. Isocoumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 1,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isocoumarans

Sub Class

Not Available

Direct Parent

Isocoumarans

Alternative Parents

Substituents

Isocoumaran
Fluorobenzene
Halobenzene
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Alpha-hydrogen aldehyde
Dialkyl ether
Ether
Oxacycle
Carbonitrile
Nitrile
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Aldehyde
Carbonyl group
Organic oxide
Organopnictogen compound
Organohalogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

nitrile (CHEBI:80607 )
benzenes (CHEBI:80607 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060462)

Organ

Liver (HMDB: HMDB0060462)
Kidney (HMDB: HMDB0060462)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060462)

Cellular substructure

Membrane (HMDB: HMDB0060462)

Source

Endogenous

Endogenous (HMDB: HMDB0060462)

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	0.0044 g/L	ALOGPS
logP	3.05	ALOGPS
logP	3.01	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	12.93	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	50.09 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	81.1 m³·mol⁻¹	ChemAxon
Polarizability	29.75 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]+	166.262	30932474
DeepCCS	[M-H]-	163.904	30932474
DeepCCS	[M-2H]-	197.547	30932474
DeepCCS	[M+Na]+	172.774	30932474
AllCCS	[M+H]+	167.9	32859911
AllCCS	[M+H-H2O]+	164.4	32859911
AllCCS	[M+NH4]+	171.1	32859911
AllCCS	[M+Na]+	172.0	32859911
AllCCS	[M-H]-	172.0	32859911
AllCCS	[M+Na-2H]-	171.3	32859911
AllCCS	[M+HCOO]-	170.8	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.	6.55 minutes	32390414
Predicted by Siyang on May 30, 2022	14.5102 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.71 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2054.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	409.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	191.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	219.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	195.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	676.3 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	747.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	83.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1306.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	464.3 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	1417.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	360.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	388.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	388.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	462.7 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	75.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citalopram aldehyde	FC1=CC=C(C=C1)C1(CCC=O)OCC2=C1C=CC(=C2)C#N	3499.8	Standard polar	33892256
Citalopram aldehyde	FC1=CC=C(C=C1)C1(CCC=O)OCC2=C1C=CC(=C2)C#N	2368.1	Standard non polar	33892256
Citalopram aldehyde	FC1=CC=C(C=C1)C1(CCC=O)OCC2=C1C=CC(=C2)C#N	2357.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Citalopram aldehyde,1TMS,isomer #1	C[Si](C)(C)OC=CCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C21	2521.5	Semi standard non polar	33892256
Citalopram aldehyde,1TMS,isomer #1	C[Si](C)(C)OC=CCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C21	2432.8	Standard non polar	33892256
Citalopram aldehyde,1TMS,isomer #1	C[Si](C)(C)OC=CCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C21	3124.3	Standard polar	33892256
Citalopram aldehyde,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C21	2770.0	Semi standard non polar	33892256
Citalopram aldehyde,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C21	2642.0	Standard non polar	33892256
Citalopram aldehyde,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC=CCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C21	3224.7	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

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

C16612

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9944000

PDB ID

Not Available

ChEBI ID

80607

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

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Aldehyde oxidase

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: AOX1
Uniprot ID:: Q06278
Molecular weight:: 147916.735

Reactions

Citalopram aldehyde + Water + Oxygen → Citalopram propionic acid + Hydrogen peroxide	details

Enzyme Details

2. 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

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

Enzyme Details

3. 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

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

Showing metabocard for Citalopram aldehyde (HMDB0060462)

MOL for HMDB0060462 (Citalopram aldehyde)

3D MOL for HMDB0060462 (Citalopram aldehyde)

3D SDF for HMDB0060462 (Citalopram aldehyde)

3D-SDF for HMDB0060462 (Citalopram aldehyde)

PDB for HMDB0060462 (Citalopram aldehyde)

3D PDB for HMDB0060462 (Citalopram aldehyde)

SMILES for HMDB0060462 (Citalopram aldehyde)

INCHI for HMDB0060462 (Citalopram aldehyde)

Structure for HMDB0060462 (Citalopram aldehyde)

3D Structure for HMDB0060462 (Citalopram aldehyde)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions

Reactions