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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:22 UTC

Update Date

2021-09-14 15:45:11 UTC

HMDB ID

HMDB0013892

Secondary Accession Numbers

HMDB13892

Metabolite Identification

Common Name

N-Desmethylvenlafaxine

Description

N-Desmethylvenlafaxine is a metabolite of venlafaxine (brand name: Effexor or Efexor). Venlafaxine is a bicyclic antidepressant and is usually categorized as a serotonin-norepinephrine reuptake inhibitor (SNRI), but it has been referred to as a serotonin-norepinephrine-dopamine reuptake inhibitor. It works by blocking the transporter reuptake proteins for key neurotransmitters affecting mood, thereby leaving more active neurotransmitters in the synapse.

Structure

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

HMDB0013892
     RDKit          3D
N-Desmethylvenlafaxine
 44 45  0  0  0  0  0  0  0  0999 V2000
   -1.0454   -4.1899    0.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1910   -2.9268   -0.4319 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0660   -2.1244   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0523   -0.7252   -0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1826   -0.0877   -0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4976   -0.0408    1.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6767    0.5903    1.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5414    1.1703    0.7662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7022    1.7850    1.2143 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6366    2.3978    0.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2171    1.1181   -0.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0317    0.4832   -0.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2909   -0.0026   -0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232    0.0060    1.2548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5071   -0.7074   -0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6405    0.2665   -0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7090    1.2760    0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4720    2.1453    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3539    1.4137   -0.6829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958   -3.8651    1.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7737   -4.9350    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0150   -4.4819    0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0924   -3.1688   -1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1060   -2.1148    1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8901   -2.6640   -0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012   -0.7360   -1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8482   -0.4861    2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8998    0.6103    2.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1472    3.1116   -0.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2785    1.6871   -0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3026    3.0513    1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8756    1.5658   -1.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8509    0.4851   -2.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0610    0.8789    1.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9306   -1.4549    0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300   -1.2181   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5653   -0.3108   -0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5251    0.7222   -1.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7431    0.7120    1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6440    1.8901    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2078    2.4465    1.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7408    3.0951   -0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951    1.3613   -1.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4307    1.9706   -0.5355 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 12  5  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
M  END

      
  Mrv1652305221923532D          

 19 20  0  0  0  0            999 V2000
    6.6016   -3.7128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7269   -3.7128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4267   -2.2838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0142   -4.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4267   -3.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2997   -4.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7287   -4.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2997   -5.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7287   -5.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0142   -6.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0142   -2.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2517   -3.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6643   -2.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6643   -4.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0142   -1.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4893   -2.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4893   -4.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9018   -3.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1394   -2.9983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2 18  1  0  0  0  0
  2 19  1  0  0  0  0
  3 11  1  0  0  0  0
  3 15  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  2  0  0  0  0
 16 18  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013892

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCC(C1=CC=C(OC)C=C1)C1(O)CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NO2/c1-17-12-15(16(18)10-4-3-5-11-16)13-6-8-14(19-2)9-7-13/h6-9,15,17-18H,3-5,10-12H2,1-2H3

> <INCHI_KEY>
MKAFOJAJJMUXLW-UHFFFAOYSA-N

> <FORMULA>
C16H25NO2

> <MOLECULAR_WEIGHT>
263.3752

> <EXACT_MASS>
263.188529049

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
30.530701535932327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[1-(4-methoxyphenyl)-2-(methylamino)ethyl]cyclohexan-1-ol

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
2.3554747669999987

> <ALOGPS_LOGS>
-3.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.420572718183436

> <JCHEM_PKA_STRONGEST_BASIC>
9.779041347889278

> <JCHEM_POLAR_SURFACE_AREA>
41.49

> <JCHEM_REFRACTIVITY>
77.7295

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[1-(4-methoxyphenyl)-2-(methylamino)ethyl]cyclohexan-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013892
     RDKit          3D
N-Desmethylvenlafaxine
 44 45  0  0  0  0  0  0  0  0999 V2000
   -1.0454   -4.1899    0.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1910   -2.9268   -0.4319 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0660   -2.1244   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0523   -0.7252   -0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1826   -0.0877   -0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4976   -0.0408    1.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6767    0.5903    1.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5414    1.1703    0.7662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7022    1.7850    1.2143 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6366    2.3978    0.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2171    1.1181   -0.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0317    0.4832   -0.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2909   -0.0026   -0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232    0.0060    1.2548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5071   -0.7074   -0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6405    0.2665   -0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7090    1.2760    0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4720    2.1453    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3539    1.4137   -0.6829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958   -3.8651    1.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7737   -4.9350    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0150   -4.4819    0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0924   -3.1688   -1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1060   -2.1148    1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8901   -2.6640   -0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012   -0.7360   -1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8482   -0.4861    2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8998    0.6103    2.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1472    3.1116   -0.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2785    1.6871   -0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3026    3.0513    1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8756    1.5658   -1.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8509    0.4851   -2.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0610    0.8789    1.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9306   -1.4549    0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300   -1.2181   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5653   -0.3108   -0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5251    0.7222   -1.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7431    0.7120    1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6440    1.8901    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2078    2.4465    1.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7408    3.0951   -0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951    1.3613   -1.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4307    1.9706   -0.5355 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 12  5  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
M  END

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  O   UNK     0      12.323  -6.931   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      20.024  -6.931   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      13.863  -4.263   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      13.093  -8.264   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.863  -6.931   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.759  -9.035   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.427  -9.035   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.759 -10.575   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.427 -10.575   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.093 -11.345   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.093  -5.597   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.403  -6.931   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.173  -5.597   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.173  -8.264   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.093  -2.929   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.713  -5.597   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.713  -8.264   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.483  -6.931   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.793  -5.597   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2   18   19                                                       
CONECT    3   11   15                                                       
CONECT    4    1    5    6    7                                             
CONECT    5    4   11   12                                                  
CONECT    6    4    8                                                       
CONECT    7    4    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   10                                                       
CONECT   10    8    9                                                       
CONECT   11    3    5                                                       
CONECT   12    5   13   14                                                  
CONECT   13   12   16                                                       
CONECT   14   12   17                                                       
CONECT   15    3                                                            
CONECT   16   13   18                                                       
CONECT   17   14   18                                                       
CONECT   18    2   16   17                                                  
CONECT   19    2                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0013892
HETATM    1  C1  UNL     1      -1.045  -4.190   0.333  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.191  -2.927  -0.432  1.00  0.00           N  
HETATM    3  C2  UNL     1      -0.066  -2.124  -0.010  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.052  -0.725  -0.561  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.183  -0.088  -0.046  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.498  -0.041   1.290  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.677   0.590   1.673  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.541   1.170   0.766  1.00  0.00           C  
HETATM    9  O1  UNL     1       4.702   1.785   1.214  1.00  0.00           O  
HETATM   10  C8  UNL     1       5.637   2.398   0.385  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.217   1.118  -0.573  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.032   0.483  -0.957  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.291  -0.003  -0.137  1.00  0.00           C  
HETATM   14  O2  UNL     1      -1.323   0.006   1.255  1.00  0.00           O  
HETATM   15  C12 UNL     1      -2.507  -0.707  -0.639  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.640   0.267  -0.949  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.709   1.276   0.154  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.472   2.145   0.029  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.354   1.414  -0.683  1.00  0.00           C  
HETATM   20  H1  UNL     1      -1.196  -3.865   1.390  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.774  -4.935   0.018  1.00  0.00           H  
HETATM   22  H3  UNL     1       0.015  -4.482   0.207  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.092  -3.169  -1.463  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.106  -2.115   1.121  1.00  0.00           H  
HETATM   25  H6  UNL     1       0.890  -2.664  -0.224  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.001  -0.736  -1.664  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.848  -0.486   2.043  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.900   0.610   2.737  1.00  0.00           H  
HETATM   29  H10 UNL     1       5.147   3.112  -0.334  1.00  0.00           H  
HETATM   30  H11 UNL     1       6.279   1.687  -0.162  1.00  0.00           H  
HETATM   31  H12 UNL     1       6.303   3.051   1.005  1.00  0.00           H  
HETATM   32  H13 UNL     1       3.876   1.566  -1.322  1.00  0.00           H  
HETATM   33  H14 UNL     1       1.851   0.485  -2.034  1.00  0.00           H  
HETATM   34  H15 UNL     1      -1.061   0.879   1.631  1.00  0.00           H  
HETATM   35  H16 UNL     1      -2.931  -1.455   0.038  1.00  0.00           H  
HETATM   36  H17 UNL     1      -2.330  -1.218  -1.628  1.00  0.00           H  
HETATM   37  H18 UNL     1      -4.565  -0.311  -0.968  1.00  0.00           H  
HETATM   38  H19 UNL     1      -3.525   0.722  -1.955  1.00  0.00           H  
HETATM   39  H20 UNL     1      -3.743   0.712   1.114  1.00  0.00           H  
HETATM   40  H21 UNL     1      -4.644   1.890   0.033  1.00  0.00           H  
HETATM   41  H22 UNL     1      -2.208   2.446   1.071  1.00  0.00           H  
HETATM   42  H23 UNL     1      -2.741   3.095  -0.492  1.00  0.00           H  
HETATM   43  H24 UNL     1      -1.595   1.361  -1.740  1.00  0.00           H  
HETATM   44  H25 UNL     1      -0.431   1.971  -0.535  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23
CONECT    3    4   24   25
CONECT    4    5   13   26
CONECT    5    6    6   12
CONECT    6    7   27
CONECT    7    8    8   28
CONECT    8    9   11
CONECT    9   10
CONECT   10   29   30   31
CONECT   11   12   12   32
CONECT   12   33
CONECT   13   14   15   19
CONECT   14   34
CONECT   15   16   35   36
CONECT   16   17   37   38
CONECT   17   18   39   40
CONECT   18   19   41   42
CONECT   19   43   44
END

HMDB0013892
     RDKit          3D
N-Desmethylvenlafaxine
 44 45  0  0  0  0  0  0  0  0999 V2000
   -1.0454   -4.1899    0.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1910   -2.9268   -0.4319 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0660   -2.1244   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0523   -0.7252   -0.5611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1826   -0.0877   -0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4976   -0.0408    1.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6767    0.5903    1.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5414    1.1703    0.7662 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7022    1.7850    1.2143 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6366    2.3978    0.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2171    1.1181   -0.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0317    0.4832   -0.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2909   -0.0026   -0.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232    0.0060    1.2548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5071   -0.7074   -0.6388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6405    0.2665   -0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7090    1.2760    0.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4720    2.1453    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3539    1.4137   -0.6829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958   -3.8651    1.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7737   -4.9350    0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0150   -4.4819    0.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0924   -3.1688   -1.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1060   -2.1148    1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8901   -2.6640   -0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012   -0.7360   -1.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8482   -0.4861    2.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8998    0.6103    2.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1472    3.1116   -0.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2785    1.6871   -0.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3026    3.0513    1.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8756    1.5658   -1.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8509    0.4851   -2.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0610    0.8789    1.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9306   -1.4549    0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300   -1.2181   -1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5653   -0.3108   -0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5251    0.7222   -1.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7431    0.7120    1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6440    1.8901    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2078    2.4465    1.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7408    3.0951   -0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5951    1.3613   -1.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4307    1.9706   -0.5355 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  2  0
  4 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 12  5  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Norvenlafaxine	ChEBI
N-Desmethyl venlafaxine	HMDB

Chemical Formula

C₁₆H₂₅NO₂

Average Molecular Weight

263.3752

Monoisotopic Molecular Weight

263.188529049

IUPAC Name

1-[1-(4-methoxyphenyl)-2-(methylamino)ethyl]cyclohexan-1-ol

Traditional Name

1-[1-(4-methoxyphenyl)-2-(methylamino)ethyl]cyclohexan-1-ol

CAS Registry Number

149289-30-5

SMILES

CNCC(C1=CC=C(OC)C=C1)C1(O)CCCCC1

InChI Identifier

InChI=1S/C16H25NO2/c1-17-12-15(16(18)10-4-3-5-11-16)13-6-8-14(19-2)9-7-13/h6-9,15,17-18H,3-5,10-12H2,1-2H3

InChI Key

MKAFOJAJJMUXLW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Anisole
Methoxybenzene
Alkyl aryl ether
Aralkylamine
Cyclohexanol
Monocyclic benzene moiety
1,3-aminoalcohol
Tertiary alcohol
Cyclic alcohol
Secondary amine
Ether
Secondary aliphatic amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic oxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary amino compound (CHEBI:83525 )
monomethoxybenzene (CHEBI:83525 )
cyclohexanols (CHEBI:83525 )

Ontology

Not Available

Liver (HMDB: HMDB0013892)
Kidney (HMDB: HMDB0013892)

Biofluid or Excreta

Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0013892)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Venlafaxine Metabolism Pathway (PathBank: SMP0000636)

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	0.077 g/L	ALOGPS
logP	2.9	ALOGPS
logP	2.36	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	14.42	ChemAxon
pKa (Strongest Basic)	9.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.49 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.73 m³·mol⁻¹	ChemAxon
Polarizability	30.53 Å³	ChemAxon
Number of Rings	2	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
DarkChem	[M+H]+	164.059	31661259
DarkChem	[M-H]-	162.66	31661259
DeepCCS	[M+H]+	164.3	30932474
DeepCCS	[M-H]-	161.942	30932474
DeepCCS	[M-2H]-	194.828	30932474
DeepCCS	[M+Na]+	170.393	30932474
AllCCS	[M+H]+	164.3	32859911
AllCCS	[M+H-H2O]+	160.6	32859911
AllCCS	[M+NH4]+	167.7	32859911
AllCCS	[M+Na]+	168.6	32859911
AllCCS	[M-H]-	169.4	32859911
AllCCS	[M+Na-2H]-	169.9	32859911
AllCCS	[M+HCOO]-	170.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethylvenlafaxine	CNCC(C1=CC=C(OC)C=C1)C1(O)CCCCC1	2450.6	Standard polar	33892256
N-Desmethylvenlafaxine	CNCC(C1=CC=C(OC)C=C1)C1(O)CCCCC1	2101.7	Standard non polar	33892256
N-Desmethylvenlafaxine	CNCC(C1=CC=C(OC)C=C1)C1(O)CCCCC1	2114.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Desmethylvenlafaxine,1TMS,isomer #1	CNCC(C1=CC=C(OC)C=C1)C1(O[Si](C)(C)C)CCCCC1	2072.0	Semi standard non polar	33892256
N-Desmethylvenlafaxine,1TMS,isomer #2	COC1=CC=C(C(CN(C)[Si](C)(C)C)C2(O)CCCCC2)C=C1	2277.3	Semi standard non polar	33892256
N-Desmethylvenlafaxine,2TMS,isomer #1	COC1=CC=C(C(CN(C)[Si](C)(C)C)C2(O[Si](C)(C)C)CCCCC2)C=C1	2253.5	Semi standard non polar	33892256
N-Desmethylvenlafaxine,2TMS,isomer #1	COC1=CC=C(C(CN(C)[Si](C)(C)C)C2(O[Si](C)(C)C)CCCCC2)C=C1	2284.8	Standard non polar	33892256
N-Desmethylvenlafaxine,2TMS,isomer #1	COC1=CC=C(C(CN(C)[Si](C)(C)C)C2(O[Si](C)(C)C)CCCCC2)C=C1	2650.8	Standard polar	33892256
N-Desmethylvenlafaxine,1TBDMS,isomer #1	CNCC(C1=CC=C(OC)C=C1)C1(O[Si](C)(C)C(C)(C)C)CCCCC1	2341.8	Semi standard non polar	33892256
N-Desmethylvenlafaxine,1TBDMS,isomer #2	COC1=CC=C(C(CN(C)[Si](C)(C)C(C)(C)C)C2(O)CCCCC2)C=C1	2508.4	Semi standard non polar	33892256
N-Desmethylvenlafaxine,2TBDMS,isomer #1	COC1=CC=C(C(CN(C)[Si](C)(C)C(C)(C)C)C2(O[Si](C)(C)C(C)(C)C)CCCCC2)C=C1	2760.8	Semi standard non polar	33892256
N-Desmethylvenlafaxine,2TBDMS,isomer #1	COC1=CC=C(C(CN(C)[Si](C)(C)C(C)(C)C)C2(O[Si](C)(C)C(C)(C)C)CCCCC2)C=C1	2693.5	Standard non polar	33892256
N-Desmethylvenlafaxine,2TBDMS,isomer #1	COC1=CC=C(C(CN(C)[Si](C)(C)C(C)(C)C)C2(O[Si](C)(C)C(C)(C)C)CCCCC2)C=C1	2845.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethylvenlafaxine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9210000000-aab665454291edd16052	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethylvenlafaxine GC-MS (1 TMS) - 70eV, Positive	splash10-00xr-9731000000-47520d33fdc9810a02fa	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Desmethylvenlafaxine 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 - N-Desmethylvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0002-0090000000-533ca365ea256055d3b0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-03di-0090000000-46e385f2602e684517d0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-00kb-0190000000-b7d7d25c880d08bc4aeb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-00xs-0930000000-b436eb1574ad46e65b18	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-00dj-1900000000-9a0c6f02711fca704371	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-00di-2900000000-30ee69f8c1dacca9f5f4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-00di-3900000000-5912a9b34239024f1998	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-03di-0090000000-41b1e606fdbd91c19598	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-00kb-0190000000-4163188e31f87ff68eb6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-00xs-0930000000-3697f291e768e2585c7b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-00dj-1900000000-d0de757b8106cb6a64ec	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-00di-1900000000-9233623570cde0bc6e82	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-00di-3900000000-43f974edaebb4691f471	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0002-0090000000-0765f2e7b3aab953f799	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-QFT , positive-QTOF	splash10-00dl-5900000000-8510c2654ac94f93ec56	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-QFT , positive-QTOF	splash10-01ot-0090000000-836c194578f4828ab7c0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-QFT , positive-QTOF	splash10-01ba-0590000000-314da1ba8c2f7e65bc27	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-QFT , positive-QTOF	splash10-00dj-0910000000-280a882b1a11fbce3d14	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Desmethylvenlafaxine LC-ESI-QFT , positive-QTOF	splash10-00di-1900000000-77f74756a387359f288b	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylvenlafaxine 10V, Positive-QTOF	splash10-01pk-0090000000-f934f21a5e46eec47730	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylvenlafaxine 20V, Positive-QTOF	splash10-015a-4090000000-a1c95251249ef523d3c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylvenlafaxine 40V, Positive-QTOF	splash10-0ldl-9130000000-26b439772b0aa3662aa7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylvenlafaxine 10V, Negative-QTOF	splash10-03di-1090000000-b35b15366954b6c62c43	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylvenlafaxine 20V, Negative-QTOF	splash10-03di-1390000000-b623ba38b0f2a8c81f84	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Desmethylvenlafaxine 40V, Negative-QTOF	splash10-0f7k-6940000000-14a01f354aca8f9e1211	2016-08-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Venlafaxine Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2741972

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Desvenlafaxine

METLIN ID

Not Available

PubChem Compound

3501942

PDB ID

Not Available

ChEBI ID

83525

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 N-Desmethylvenlafaxine (HMDB0013892)

MOL for HMDB0013892 (N-Desmethylvenlafaxine)

3D MOL for HMDB0013892 (N-Desmethylvenlafaxine)

3D SDF for HMDB0013892 (N-Desmethylvenlafaxine)

3D-SDF for HMDB0013892 (N-Desmethylvenlafaxine)

PDB for HMDB0013892 (N-Desmethylvenlafaxine)

3D PDB for HMDB0013892 (N-Desmethylvenlafaxine)

SMILES for HMDB0013892 (N-Desmethylvenlafaxine)

INCHI for HMDB0013892 (N-Desmethylvenlafaxine)

Structure for HMDB0013892 (N-Desmethylvenlafaxine)

3D Structure for HMDB0013892 (N-Desmethylvenlafaxine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra