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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-12 17:33:37 UTC

Update Date

2021-09-14 15:45:14 UTC

HMDB ID

HMDB0060551

Secondary Accession Numbers

HMDB60551

Metabolite Identification

Common Name

Norfluoxetine

Description

Norfluoxetine is a metabolite of fluoxetine. (S)-Norfluoxetine, also known as seproxetine, is a selective serotonin reuptake inhibitor (SSRI). It is the most important active metabolite of the widely used antidepressant fluoxetine but little is known about its pharmacological actions. Seproxetine was being investigated by Eli Lilly and Company as an antidepressant, however, a cardiac side effect was noted and development was discontinued (Wikipedia ).

Structure

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

HMDB0060551
     RDKit          3D
Norfluoxetine
 37 38  0  0  0  0  0  0  0  0999 V2000
   -2.7443    3.4184    1.0138 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1614    2.0791    1.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5182    1.8463   -0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8623    0.4763   -0.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410    0.2485    0.5222 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4730    0.0373    0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1251   -0.0152   -0.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4823   -0.2494   -0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2419   -0.4393    0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7164   -0.6907    0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2657    0.5467   -0.1930 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.9412   -1.5178   -0.9460 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.2141   -1.1862    1.2912 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5845   -0.3835    1.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2308   -0.1500    1.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8868   -0.6088   -0.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3463   -1.0438   -1.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2759   -2.0178   -1.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7994   -2.6099   -0.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3807   -2.2159    0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4384   -1.2300    0.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681    3.9640    0.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4029    3.9827    1.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0299    1.4110    1.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4160    2.0484    1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2122    1.9234   -1.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7107    2.5909   -0.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3826    0.4984   -1.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5490    0.1336   -1.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9941   -0.2898   -1.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892   -0.5408    2.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7886   -0.1316    2.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8962   -0.5431   -2.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6077   -2.3136   -2.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5601   -3.3819   -0.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8313   -2.7190    1.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1053   -0.9269    1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
  9 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15  6  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  7 29  1  0
  8 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

4541
  Mrv0541 02241213002D          

 21 22  0  0  1  0            999 V2000
    4.9509    3.5063    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.7760    2.6813    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.1259    2.6813    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.6188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  2 21  1  0  0  0  0
  3 21  1  0  0  0  0
  4  6  1  0  0  0  0
  4 10  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 11  2  0  0  0  0
  8 12  1  0  0  0  0
 10 13  2  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  2  0  0  0  0
 13 18  1  0  0  0  0
 14 19  2  0  0  0  0
 15 20  2  0  0  0  0
 16 20  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 17 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060551

> <DATABASE_NAME>
hmdb

> <SMILES>
NCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16F3NO/c17-16(18,19)13-6-8-14(9-7-13)21-15(10-11-20)12-4-2-1-3-5-12/h1-9,15H,10-11,20H2

> <INCHI_KEY>
WIQRCHMSJFFONW-UHFFFAOYSA-N

> <FORMULA>
C16H16F3NO

> <MOLECULAR_WEIGHT>
295.2995

> <EXACT_MASS>
295.118398754

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.12837068078571

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine

> <ALOGPS_LOGP>
3.80

> <JCHEM_LOGP>
3.740639149666666

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.767873558652434

> <JCHEM_POLAR_SURFACE_AREA>
35.25

> <JCHEM_REFRACTIVITY>
75.59290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.15e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0060551
     RDKit          3D
Norfluoxetine
 37 38  0  0  0  0  0  0  0  0999 V2000
   -2.7443    3.4184    1.0138 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1614    2.0791    1.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5182    1.8463   -0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8623    0.4763   -0.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410    0.2485    0.5222 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4730    0.0373    0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1251   -0.0152   -0.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4823   -0.2494   -0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2419   -0.4393    0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7164   -0.6907    0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2657    0.5467   -0.1930 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.9412   -1.5178   -0.9460 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.2141   -1.1862    1.2912 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5845   -0.3835    1.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2308   -0.1500    1.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8868   -0.6088   -0.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3463   -1.0438   -1.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2759   -2.0178   -1.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7994   -2.6099   -0.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3807   -2.2159    0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4384   -1.2300    0.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681    3.9640    0.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4029    3.9827    1.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0299    1.4110    1.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4160    2.0484    1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2122    1.9234   -1.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7107    2.5909   -0.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3826    0.4984   -1.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5490    0.1336   -1.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9941   -0.2898   -1.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892   -0.5408    2.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7886   -0.1316    2.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8962   -0.5431   -2.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6077   -2.3136   -2.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5601   -3.3819   -0.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8313   -2.7190    1.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1053   -0.9269    1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
  9 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15  6  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  7 29  1  0
  8 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 4541                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  F   UNK     0       9.242   6.545   0.000  0.00  0.00           F+0
HETATM    2  F   UNK     0      10.782   5.005   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       7.702   5.005   0.000  0.00  0.00           F+0
HETATM    4  O   UNK     0       9.242  -1.155   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       3.907  -1.155   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.908  -1.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.574  -1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.908  -3.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.241  -1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.242   0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.242  -4.235   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574  -4.235   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.576   1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.908   1.155   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.242  -5.775   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.574  -5.775   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.242   3.465   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.576   2.695   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.908   2.695   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.908  -6.545   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.242   5.005   0.000  0.00  0.00           C+0
CONECT    1   21                                                            
CONECT    2   21                                                            
CONECT    3   21                                                            
CONECT    4    6   10                                                       
CONECT    5    9                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6    9                                                       
CONECT    8    6   11   12                                                  
CONECT    9    5    7                                                       
CONECT   10    4   13   14                                                  
CONECT   11    8   15                                                       
CONECT   12    8   16                                                       
CONECT   13   10   18                                                       
CONECT   14   10   19                                                       
CONECT   15   11   20                                                       
CONECT   16   12   20                                                       
CONECT   17   18   19   21                                                  
CONECT   18   13   17                                                       
CONECT   19   14   17                                                       
CONECT   20   15   16                                                       
CONECT   21    1    2    3   17                                             
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0243740
HETATM    1  N1  UNL     1      -2.639   3.478  -0.554  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.598   2.551  -0.101  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.256   1.211  -0.003  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.232   0.194   0.475  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.196   0.194  -0.469  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.139   0.302  -0.242  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.991   0.287  -1.335  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.346   0.395  -1.119  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.904   0.515   0.134  1.00  0.00           C  
HETATM   10  C8  UNL     1       5.393   0.631   0.351  1.00  0.00           C  
HETATM   11  F1  UNL     1       5.568   1.284   1.554  1.00  0.00           F  
HETATM   12  F2  UNL     1       5.897   1.362  -0.699  1.00  0.00           F  
HETATM   13  F3  UNL     1       5.916  -0.648   0.420  1.00  0.00           F  
HETATM   14  C9  UNL     1       3.042   0.527   1.209  1.00  0.00           C  
HETATM   15  C10 UNL     1       1.657   0.422   1.030  1.00  0.00           C  
HETATM   16  C11 UNL     1      -1.806  -1.197   0.412  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.134  -1.484   0.426  1.00  0.00           C  
HETATM   18  C13 UNL     1      -3.591  -2.787   0.359  1.00  0.00           C  
HETATM   19  C14 UNL     1      -2.664  -3.832   0.275  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.313  -3.550   0.261  1.00  0.00           C  
HETATM   21  C16 UNL     1      -0.898  -2.232   0.330  1.00  0.00           C  
HETATM   22  H1  UNL     1      -3.598   3.107  -0.433  1.00  0.00           H  
HETATM   23  H2  UNL     1      -2.487   4.449  -0.245  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.123   2.887   0.823  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.814   2.589  -0.895  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.650   0.948  -1.007  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.143   1.249   0.659  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.922   0.365   1.518  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.575   0.190  -2.352  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.028   0.383  -1.956  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.473   0.625   2.200  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.047   0.449   1.921  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.844  -0.691   0.495  1.00  0.00           H  
HETATM   34  H13 UNL     1      -4.649  -2.992   0.373  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.030  -4.848   0.223  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.555  -4.318   0.194  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.165  -2.018   0.320  1.00  0.00           H  
CONECT    1    2   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   16   28
CONECT    5    6
CONECT    6    7    7   15
CONECT    7    8   29
CONECT    8    9    9   30
CONECT    9   10   14
CONECT   10   11   12   13
CONECT   14   15   15   31
CONECT   15   32
CONECT   16   17   17   21
CONECT   17   18   33
CONECT   18   19   19   34
CONECT   19   20   35
CONECT   20   21   21   36
CONECT   21   37
END

HMDB0060551
     RDKit          3D
Norfluoxetine
 37 38  0  0  0  0  0  0  0  0999 V2000
   -2.7443    3.4184    1.0138 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1614    2.0791    1.0664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5182    1.8463   -0.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8623    0.4763   -0.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410    0.2485    0.5222 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4730    0.0373    0.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1251   -0.0152   -0.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4823   -0.2494   -0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2419   -0.4393    0.2322 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7164   -0.6907    0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2657    0.5467   -0.1930 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.9412   -1.5178   -0.9460 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.2141   -1.1862    1.2912 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5845   -0.3835    1.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2308   -0.1500    1.4956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8868   -0.6088   -0.5045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3463   -1.0438   -1.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2759   -2.0178   -1.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7994   -2.6099   -0.7690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3807   -2.2159    0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4384   -1.2300    0.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681    3.9640    0.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4029    3.9827    1.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0299    1.4110    1.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4160    2.0484    1.8575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2122    1.9234   -1.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7107    2.5909   -0.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3826    0.4984   -1.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5490    0.1336   -1.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9941   -0.2898   -1.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892   -0.5408    2.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7886   -0.1316    2.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8962   -0.5431   -2.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6077   -2.3136   -2.9036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5601   -3.3819   -0.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8313   -2.7190    1.3510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1053   -0.9269    1.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
  9 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 15  6  1  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  7 29  1  0
  8 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Desmethylfluoxetine	HMDB
Norfluoxetine hydrochloride	HMDB
Norfluoxetine, (+-)-isomer	HMDB
Norfluoxetin	HMDB

Chemical Formula

C₁₆H₁₆F₃NO

Average Molecular Weight

295.2995

Monoisotopic Molecular Weight

295.118398754

IUPAC Name

3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine

Traditional Name

3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine

CAS Registry Number

83891-03-6

SMILES

NCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H16F3NO/c17-16(18,19)13-6-8-14(9-7-13)21-15(10-11-20)12-4-2-1-3-5-12/h1-9,15H,10-11,20H2

InChI Key

WIQRCHMSJFFONW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Trifluoromethylbenzenes

Direct Parent

Trifluoromethylbenzenes

Alternative Parents

Substituents

Trifluoromethylbenzene
Phenoxy compound
Phenol ether
Alkyl aryl ether
Aralkylamine
Ether
Organopnictogen compound
Primary amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Primary aliphatic amine
Organic nitrogen compound
Amine
Alkyl halide
Alkyl fluoride
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

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	0.0092 g/L	ALOGPS
logP	3.8	ALOGPS
logP	3.74	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	9.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	35.25 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	75.59 m³·mol⁻¹	ChemAxon
Polarizability	28.13 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	169.527	30932474
DeepCCS	[M-H]-	167.169	30932474
DeepCCS	[M-2H]-	200.055	30932474
DeepCCS	[M+Na]+	175.62	30932474
AllCCS	[M+H]+	167.0	32859911
AllCCS	[M+H-H2O]+	163.5	32859911
AllCCS	[M+NH4]+	170.2	32859911
AllCCS	[M+Na]+	171.1	32859911
AllCCS	[M-H]-	167.7	32859911
AllCCS	[M+Na-2H]-	167.3	32859911
AllCCS	[M+HCOO]-	166.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norfluoxetine	NCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1	2532.4	Standard polar	33892256
Norfluoxetine	NCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1	1844.2	Standard non polar	33892256
Norfluoxetine	NCCC(OC1=CC=C(C=C1)C(F)(F)F)C1=CC=CC=C1	1855.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norfluoxetine,1TMS,isomer #1	C[Si](C)(C)NCCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1	1989.8	Semi standard non polar	33892256
Norfluoxetine,1TMS,isomer #1	C[Si](C)(C)NCCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1	2015.9	Standard non polar	33892256
Norfluoxetine,1TMS,isomer #1	C[Si](C)(C)NCCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1	2378.0	Standard polar	33892256
Norfluoxetine,2TMS,isomer #1	C[Si](C)(C)N(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C	2220.3	Semi standard non polar	33892256
Norfluoxetine,2TMS,isomer #1	C[Si](C)(C)N(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C	2177.0	Standard non polar	33892256
Norfluoxetine,2TMS,isomer #1	C[Si](C)(C)N(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C	2343.1	Standard polar	33892256
Norfluoxetine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1	2195.9	Semi standard non polar	33892256
Norfluoxetine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1	2215.9	Standard non polar	33892256
Norfluoxetine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1	2489.1	Standard polar	33892256
Norfluoxetine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2619.0	Semi standard non polar	33892256
Norfluoxetine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2507.5	Standard non polar	33892256
Norfluoxetine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC(OC1=CC=C(C(F)(F)F)C=C1)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2512.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norfluoxetine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9530000000-1d1921b3e558002b4265	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfluoxetine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfluoxetine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfluoxetine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine LC-ESI-QTOF , positive-QTOF	splash10-001i-0930000000-12529dbdb377b88c4733	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine LC-ESI-QTOF , positive-QTOF	splash10-08fr-0900000000-05fc106f911df500cfaa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine LC-ESI-QFT , positive-QTOF	splash10-001i-0900000000-855cefc7af9cdec22287	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine LC-ESI-QFT , positive-QTOF	splash10-053r-0900000000-8a2cb526ea6f38118096	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine LC-ESI-QFT , positive-QTOF	splash10-0a4i-0900000000-5f755900e576941440f9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine LC-ESI-QFT , positive-QTOF	splash10-0a4i-0900000000-04475c118e62898d8dd3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine LC-ESI-QFT , positive-QTOF	splash10-0a4i-2900000000-e430a1b96151050f596e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine LC-ESI-QFT , positive-QTOF	splash10-0a4l-6900000000-ee6c1f78837485d4929d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine LC-ESI-QFT , positive-QTOF	splash10-004l-9300000000-eedceb33116e0494f251	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine LC-ESI-QFT , positive-QTOF	splash10-014l-9200000000-2a90c866a2a01ea5fabe	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine LC-ESI-QFT , positive-QTOF	splash10-0gdl-9100000000-c962014ce63f6ae6d46a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine 45V, Positive-QTOF	splash10-0a4i-0900000000-5f755900e576941440f9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine 15V, Positive-QTOF	splash10-001i-0900000000-855cefc7af9cdec22287	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine 30V, Positive-QTOF	splash10-053r-0900000000-8a2cb526ea6f38118096	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine 60V, Positive-QTOF	splash10-0a4i-0900000000-04475c118e62898d8dd3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine 75V, Positive-QTOF	splash10-0a4i-2900000000-e430a1b96151050f596e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine 10V, Positive-QTOF	splash10-001i-0930000000-12529dbdb377b88c4733	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine 20V, Positive-QTOF	splash10-08fr-0900000000-05fc106f911df500cfaa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Norfluoxetine 90V, Positive-QTOF	splash10-0a4l-6900000000-ee6c1f78837485d4929d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfluoxetine 10V, Positive-QTOF	splash10-002b-0090000000-301e5b7c9a951e84c3f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfluoxetine 20V, Positive-QTOF	splash10-004i-1290000000-385d029287df6a34168c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfluoxetine 40V, Positive-QTOF	splash10-0v04-4930000000-244849306e7ac93b33c1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfluoxetine 10V, Negative-QTOF	splash10-0006-0090000000-afb53435e02ef79c4a2b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfluoxetine 20V, Negative-QTOF	splash10-0006-1290000000-f20ccd8f9244ed4bf54c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfluoxetine 40V, Negative-QTOF	splash10-03di-2900000000-6e6b251cd653a2b6fd8a	2016-08-03	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
Fluoxetine Action Pathway		Not Available
Fluoxetine 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

4382

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Seproxetine

METLIN ID

Not Available

PubChem Compound

4541

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 Norfluoxetine (HMDB0060551)

MOL for HMDB0060551 (Norfluoxetine)

3D MOL for HMDB0060551 (Norfluoxetine)

3D SDF for HMDB0060551 (Norfluoxetine)

3D-SDF for HMDB0060551 (Norfluoxetine)

PDB for HMDB0060551 (Norfluoxetine)

3D PDB for HMDB0060551 (Norfluoxetine)

SMILES for HMDB0060551 (Norfluoxetine)

INCHI for HMDB0060551 (Norfluoxetine)

Structure for HMDB0060551 (Norfluoxetine)

3D Structure for HMDB0060551 (Norfluoxetine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra