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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:22:34 UTC

Update Date

2021-09-14 15:46:31 UTC

HMDB ID

HMDB0060463

Secondary Accession Numbers

HMDB60463

Metabolite Identification

Common Name

Citalopram propionic acid

Description

Citalopram propionic acid 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. 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. Citalopram propionic acid is a metabolite of citalopram. Citalopram propionic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). citalopram propionic acid can be biosynthesized from citalopram aldehyde through its interaction with the enzyme aldehyde oxidase. In humans, citalopram propionic acid is involved in citalopram metabolism pathway.

Structure

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

HMDB0060463
     RDKit          3D
Citalopram propionic acid
 37 39  0  0  0  0  0  0  0  0999 V2000
    5.8407   -2.2959    0.8329 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7609   -1.9112    0.6615 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4129   -1.4165    0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4351   -1.5788    1.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1421   -1.1214    1.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8313   -0.4610    0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7970   -0.2906   -0.9272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0499   -0.7628   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1413    0.4218   -2.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2251    0.2566   -1.8381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4057    0.1515   -0.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6319   -0.6781   -0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5647   -2.0538   -0.7098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7919   -2.7953   -0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6783   -2.2453    0.3669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084   -4.1039   -0.7285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6707    1.5057    0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493    2.6284   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9954    3.8806   -0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1684    4.0420    1.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4110    5.2863    1.7329 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0933    2.9357    2.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8494    1.7097    1.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7049   -2.0920    2.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3871   -1.2615    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8072   -0.6203   -1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3887   -0.1669   -2.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4695    1.4511   -2.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7027   -0.6886    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5017   -0.1217   -0.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5156   -1.9348   -1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -2.5343   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8791   -4.2892   -1.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208    2.5266   -1.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0529    4.7565   -0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2284    3.0614    3.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7857    0.8101    2.0575 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
 14 16  1  0
 11 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
  8  3  1  0
 23 17  1  0
 11  6  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
 22 36  1  0
 23 37  1  0
M  END

  Mrv0541 05161318222D          

 23 25  0  0  0  0            999 V2000
    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
    2.9359    1.9199    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
    3.2789   -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
    3.2714    2.6735    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
    2.7865    3.3410    0.0000 O   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
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  1  2  0  0  0  0
  8  7  1  0  0  0  0
 12  1  1  0  0  0  0
 12  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14  2  2  0  0  0  0
 14  3  1  0  0  0  0
 15  4  2  0  0  0  0
 15  5  1  0  0  0  0
 16  6  1  0  0  0  0
 16 13  2  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19 15  1  0  0  0  0
 20 10  3  0  0  0  0
 21 17  2  0  0  0  0
 22 17  1  0  0  0  0
 23 11  1  0  0  0  0
 23 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060463

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H14FNO3/c19-15-4-2-14(3-5-15)18(8-7-17(21)22)16-6-1-12(10-20)9-13(16)11-23-18/h1-6,9H,7-8,11H2,(H,21,22)

> <INCHI_KEY>
JSYNRZJODZWUKX-UHFFFAOYSA-N

> <FORMULA>
C18H14FNO3

> <MOLECULAR_WEIGHT>
311.3071

> <EXACT_MASS>
311.095771524

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.707700128136658

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[5-cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]propanoic acid

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
3.1719945236666662

> <ALOGPS_LOGS>
-4.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.641666973047928

> <JCHEM_PKA_STRONGEST_BASIC>
-4.261814225889148

> <JCHEM_POLAR_SURFACE_AREA>
70.32000000000001

> <JCHEM_REFRACTIVITY>
82.03010000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
citalopram propionic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060463
     RDKit          3D
Citalopram propionic acid
 37 39  0  0  0  0  0  0  0  0999 V2000
    5.8407   -2.2959    0.8329 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7609   -1.9112    0.6615 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4129   -1.4165    0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4351   -1.5788    1.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1421   -1.1214    1.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8313   -0.4610    0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7970   -0.2906   -0.9272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0499   -0.7628   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1413    0.4218   -2.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2251    0.2566   -1.8381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4057    0.1515   -0.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6319   -0.6781   -0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5647   -2.0538   -0.7098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7919   -2.7953   -0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6783   -2.2453    0.3669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084   -4.1039   -0.7285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6707    1.5057    0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493    2.6284   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9954    3.8806   -0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1684    4.0420    1.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4110    5.2863    1.7329 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0933    2.9357    2.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8494    1.7097    1.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7049   -2.0920    2.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3871   -1.2615    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8072   -0.6203   -1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3887   -0.1669   -2.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4695    1.4511   -2.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7027   -0.6886    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5017   -0.1217   -0.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5156   -1.9348   -1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -2.5343   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8791   -4.2892   -1.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208    2.5266   -1.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0529    4.7565   -0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2284    3.0614    3.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7857    0.8101    2.0575 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
 14 16  1  0
 11 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
  8  3  1  0
 23 17  1  0
 11  6  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
 22 36  1  0
 23 37  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       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.989   4.326   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.655   5.096   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.679   2.786   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.480   3.584   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       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.989   2.786   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.679   4.326   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.107   4.991   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       5.201   6.237   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.638   5.152   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.417   0.770   0.000  0.00  0.00           O+0
CONECT    1    6   12                                                       
CONECT    2    4   14                                                       
CONECT    3    5   14                                                       
CONECT    4    2   15                                                       
CONECT    5    3   15                                                       
CONECT    6    1   16                                                       
CONECT    7    8   17                                                       
CONECT    8    7   18                                                       
CONECT    9   12   13                                                       
CONECT   10   12   20                                                       
CONECT   11   13   23                                                       
CONECT   12    1    9   10                                                  
CONECT   13    9   11   16                                                  
CONECT   14    2    3   18                                                  
CONECT   15    4    5   19                                                  
CONECT   16    6   13   18                                                  
CONECT   17    7   21   22                                                  
CONECT   18    8   14   16   23                                             
CONECT   19   15                                                            
CONECT   20   10                                                            
CONECT   21   17                                                            
CONECT   22   17                                                            
CONECT   23   11   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0060463
HETATM    1  N1  UNL     1       5.841  -2.296   0.833  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.761  -1.911   0.662  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.413  -1.417   0.452  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.435  -1.579   1.405  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.142  -1.121   1.241  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.831  -0.461   0.036  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.797  -0.291  -0.927  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.050  -0.763  -0.707  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.141   0.422  -2.052  1.00  0.00           C  
HETATM   10  O1  UNL     1      -0.225   0.257  -1.838  1.00  0.00           O  
HETATM   11  C9  UNL     1      -0.406   0.151  -0.475  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.632  -0.678  -0.134  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.565  -2.054  -0.710  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.792  -2.795  -0.332  1.00  0.00           C  
HETATM   15  O2  UNL     1      -3.678  -2.245   0.367  1.00  0.00           O  
HETATM   16  O3  UNL     1      -3.008  -4.104  -0.728  1.00  0.00           O  
HETATM   17  C13 UNL     1      -0.671   1.506   0.087  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.749   2.628  -0.711  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.995   3.881  -0.158  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.168   4.042   1.198  1.00  0.00           C  
HETATM   21  F1  UNL     1      -1.411   5.286   1.733  1.00  0.00           F  
HETATM   22  C17 UNL     1      -1.093   2.936   2.005  1.00  0.00           C  
HETATM   23  C18 UNL     1      -0.849   1.710   1.438  1.00  0.00           C  
HETATM   24  H1  UNL     1       2.705  -2.092   2.323  1.00  0.00           H  
HETATM   25  H2  UNL     1       0.387  -1.262   2.001  1.00  0.00           H  
HETATM   26  H3  UNL     1       3.807  -0.620  -1.480  1.00  0.00           H  
HETATM   27  H4  UNL     1       1.389  -0.167  -2.977  1.00  0.00           H  
HETATM   28  H5  UNL     1       1.470   1.451  -2.162  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.703  -0.689   0.978  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.502  -0.122  -0.504  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.516  -1.935  -1.830  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.638  -2.534  -0.334  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.879  -4.289  -1.236  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.621   2.527  -1.769  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.053   4.757  -0.816  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.228   3.061   3.063  1.00  0.00           H  
HETATM   37  H14 UNL     1      -0.786   0.810   2.058  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   24
CONECT    5    6    6   25
CONECT    6    7   11
CONECT    7    8    8    9
CONECT    8   26
CONECT    9   10   27   28
CONECT   10   11
CONECT   11   12   17
CONECT   12   13   29   30
CONECT   13   14   31   32
CONECT   14   15   15   16
CONECT   16   33
CONECT   17   18   18   23
CONECT   18   19   34
CONECT   19   20   20   35
CONECT   20   21   22
CONECT   22   23   23   36
CONECT   23   37
END

HMDB0060463
     RDKit          3D
Citalopram propionic acid
 37 39  0  0  0  0  0  0  0  0999 V2000
    5.8407   -2.2959    0.8329 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7609   -1.9112    0.6615 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4129   -1.4165    0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4351   -1.5788    1.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1421   -1.1214    1.2409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8313   -0.4610    0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7970   -0.2906   -0.9272 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0499   -0.7628   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1413    0.4218   -2.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2251    0.2566   -1.8381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4057    0.1515   -0.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6319   -0.6781   -0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5647   -2.0538   -0.7098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7919   -2.7953   -0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6783   -2.2453    0.3669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084   -4.1039   -0.7285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6707    1.5057    0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493    2.6284   -0.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9954    3.8806   -0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1684    4.0420    1.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4110    5.2863    1.7329 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0933    2.9357    2.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8494    1.7097    1.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7049   -2.0920    2.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3871   -1.2615    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8072   -0.6203   -1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3887   -0.1669   -2.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4695    1.4511   -2.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7027   -0.6886    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5017   -0.1217   -0.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5156   -1.9348   -1.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6382   -2.5343   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8791   -4.2892   -1.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208    2.5266   -1.7687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0529    4.7565   -0.8156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2284    3.0614    3.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7857    0.8101    2.0575 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
 14 16  1  0
 11 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
  8  3  1  0
 23 17  1  0
 11  6  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 16 33  1  0
 18 34  1  0
 19 35  1  0
 22 36  1  0
 23 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Citalopram propionate	Generator

Chemical Formula

C₁₈H₁₄FNO₃

Average Molecular Weight

311.3071

Monoisotopic Molecular Weight

311.095771524

IUPAC Name

3-[5-cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]propanoic acid

Traditional Name

citalopram propionic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

InChI Identifier

InChI=1S/C18H14FNO3/c19-15-4-2-14(3-5-15)18(8-7-17(21)22)16-6-1-12(10-20)9-13(16)11-23-18/h1-6,9H,7-8,11H2,(H,21,22)

InChI Key

JSYNRZJODZWUKX-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
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Carbonitrile
Nitrile
Oxacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organohalogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

nitrile (CHEBI:80605 )
benzenes (CHEBI:80605 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060463)

Organ

Liver (HMDB: HMDB0060463)
Kidney (HMDB: HMDB0060463)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060463)

Cellular substructure

Cytoplasm (HMDB: HMDB0060463)

Source

Endogenous

Endogenous (HMDB: HMDB0060463)

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	0.0055 g/L	ALOGPS
logP	2.88	ALOGPS
logP	3.17	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	70.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.03 m³·mol⁻¹	ChemAxon
Polarizability	30.71 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]+	174.489	30932474
DeepCCS	[M-H]-	172.132	30932474
DeepCCS	[M-2H]-	205.438	30932474
DeepCCS	[M+Na]+	180.665	30932474
AllCCS	[M+H]+	170.9	32859911
AllCCS	[M+H-H2O]+	167.6	32859911
AllCCS	[M+NH4]+	174.0	32859911
AllCCS	[M+Na]+	174.9	32859911
AllCCS	[M-H]-	174.3	32859911
AllCCS	[M+Na-2H]-	173.6	32859911
AllCCS	[M+HCOO]-	173.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citalopram propionic acid	OC(=O)CCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1	3722.2	Standard polar	33892256
Citalopram propionic acid	OC(=O)CCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1	2426.8	Standard non polar	33892256
Citalopram propionic acid	OC(=O)CCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1	2563.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Citalopram propionic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C21	2609.0	Semi standard non polar	33892256
Citalopram propionic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC1(C2=CC=C(F)C=C2)OCC2=CC(C#N)=CC=C21	2870.7	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 propionic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0190000000-3d06e9999ac297d7ff75	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citalopram propionic acid GC-MS (1 TMS) - 70eV, Positive	splash10-000i-2190000000-85bbf7d086d9c3730e81	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citalopram propionic acid 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 propionic acid 10V, Positive-QTOF	splash10-03dl-0097000000-a4cc60c1a67d15d9c509	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram propionic acid 20V, Positive-QTOF	splash10-02u3-0191000000-32bf56429ae77a046a9f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram propionic acid 40V, Positive-QTOF	splash10-000i-3690000000-f1889e924027df9a1682	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram propionic acid 10V, Negative-QTOF	splash10-03di-0039000000-205792dd03a321acfcea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram propionic acid 20V, Negative-QTOF	splash10-03di-1097000000-57e6d8b00468c04d0b19	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram propionic acid 40V, Negative-QTOF	splash10-003b-3190000000-9d9fff6b255b7514f399	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram propionic acid 10V, Positive-QTOF	splash10-03dl-0049000000-a7d194ab1cdb94ae9a7a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram propionic acid 20V, Positive-QTOF	splash10-03xu-0092000000-8cefa8ea29df30a2f797	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram propionic acid 40V, Positive-QTOF	splash10-0a4r-0960000000-6fc219207c652c40f484	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram propionic acid 10V, Negative-QTOF	splash10-03xr-0096000000-d242411d68accb5c784d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram propionic acid 20V, Negative-QTOF	splash10-000i-0090000000-1fa7dadbab9070f3b687	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citalopram propionic acid 40V, Negative-QTOF	splash10-000i-1390000000-5075c17d729f9b4abae4	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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

C16610

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10403174

PDB ID

Not Available

ChEBI ID

80605

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

Showing metabocard for Citalopram propionic acid (HMDB0060463)

MOL for HMDB0060463 (Citalopram propionic acid)

3D MOL for HMDB0060463 (Citalopram propionic acid)

3D SDF for HMDB0060463 (Citalopram propionic acid)

3D-SDF for HMDB0060463 (Citalopram propionic acid)

PDB for HMDB0060463 (Citalopram propionic acid)

3D PDB for HMDB0060463 (Citalopram propionic acid)

SMILES for HMDB0060463 (Citalopram propionic acid)

INCHI for HMDB0060463 (Citalopram propionic acid)

Structure for HMDB0060463 (Citalopram propionic acid)

3D Structure for HMDB0060463 (Citalopram propionic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions