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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1)transporters (2) Show 3 proteins XML

enzymes (1)transporters (2) Show 3 proteins

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:03 UTC

HMDB ID

HMDB0015646

Secondary Accession Numbers

HMDB0060532
HMDB15646
HMDB60532

Metabolite Identification

Common Name

Desvenlafaxine

Description

Desvenlafaxine, also known as khedezla or pristiq, belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring. In humans, desvenlafaxine is involved in the venlafaxine metabolism pathway. Desvenlafaxine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Desvenlafaxine.

Structure

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

HMDB0015646
     RDKit          3D
Desvenlafaxine
 44 45  0  0  0  0  0  0  0  0999 V2000
   -2.6652   -3.0002   -0.6304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1465   -1.6505   -0.9561 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1476   -0.7462   -0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8424   -1.4924   -0.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1490   -0.2216   -0.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7705    1.0245   -0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2180    1.3268    1.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7917    2.5154    1.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9309    3.4784    0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4937    4.7247    0.6526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980    3.2385   -0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9319    2.0247   -1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2805   -0.1987   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8548    1.0467   -0.4245 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4004   -0.3915    1.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7716   -0.9984    1.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -0.4907    0.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5621   -0.7738   -0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1288   -1.2363   -0.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3390   -3.7284   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3223   -3.2904    0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7682   -3.0113   -0.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1856   -0.7414    0.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519    0.2383   -0.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1388   -1.2067   -0.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8560   -1.7819    0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155   -2.3051   -0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0097   -0.1928   -1.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1090    0.5753    1.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345    2.7307    2.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9623    5.5327    0.9398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6030    3.9907   -1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6059    1.8789   -2.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8441    1.6658    0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3727    0.5873    1.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6588   -1.0326    1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7151   -2.0940    1.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0560   -0.6641    2.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0714    0.5702    0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7699   -1.0530    1.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6236    0.1935   -1.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2754   -1.5103   -1.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9744   -2.2239   -0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8002   -1.3068   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  5 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  6  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  8 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

285
  Mrv1652305211922462D          

 19 20  0  0  1  0            999 V2000
    2.1624    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2877    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875    1.5395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8604   -1.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2894   -1.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8604   -1.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2894   -1.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750   -2.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750    2.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0501    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0501   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4626    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  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
  3 16  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 17  1  0  0  0  0
 14 18  2  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015646

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C)CC(C1=CC=C(O)C=C1)C1(O)CCCCC1

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

> <INCHI_KEY>
KYYIDSXMWOZKMP-UHFFFAOYSA-N

> <FORMULA>
C16H25NO2

> <MOLECULAR_WEIGHT>
263.3752

> <EXACT_MASS>
263.188529049

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
30.321550562188158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
2.293426606330164

> <ALOGPS_LOGS>
-2.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.456634663426502

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.111714219159039

> <JCHEM_PKA_STRONGEST_BASIC>
8.871147401604278

> <JCHEM_POLAR_SURFACE_AREA>
43.7

> <JCHEM_REFRACTIVITY>
78.5419

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
desvenlafaxine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015646
     RDKit          3D
Desvenlafaxine
 44 45  0  0  0  0  0  0  0  0999 V2000
   -2.6652   -3.0002   -0.6304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1465   -1.6505   -0.9561 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1476   -0.7462   -0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8424   -1.4924   -0.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1490   -0.2216   -0.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7705    1.0245   -0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2180    1.3268    1.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7917    2.5154    1.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9309    3.4784    0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4937    4.7247    0.6526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980    3.2385   -0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9319    2.0247   -1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2805   -0.1987   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8548    1.0467   -0.4245 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4004   -0.3915    1.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7716   -0.9984    1.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -0.4907    0.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5621   -0.7738   -0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1288   -1.2363   -0.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3390   -3.7284   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3223   -3.2904    0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7682   -3.0113   -0.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1856   -0.7414    0.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519    0.2383   -0.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1388   -1.2067   -0.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8560   -1.7819    0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155   -2.3051   -0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0097   -0.1928   -1.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1090    0.5753    1.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345    2.7307    2.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9623    5.5327    0.9398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6030    3.9907   -1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6059    1.8789   -2.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8441    1.6658    0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3727    0.5873    1.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6588   -1.0326    1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7151   -2.0940    1.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0560   -0.6641    2.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0714    0.5702    0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7699   -1.0530    1.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6236    0.1935   -1.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2754   -1.5103   -1.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9744   -2.2239   -0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8002   -1.3068   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  5 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  6  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  8 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                                 21-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 285                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-MAY-19         0                                  
HETATM    1  O   UNK     0       4.037   0.206   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.737   0.206   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.577   2.874   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.807  -1.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.577   0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.473  -1.898   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.140  -1.898   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.473  -3.438   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.140  -3.438   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.807  -4.208   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.807   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.117   0.206   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.887   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.887  -1.127   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.807   4.208   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.117   2.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.427   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.427  -1.127   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.197   0.206   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2   19                                                            
CONECT    3   11   15   16                                                  
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   17                                                       
CONECT   14   12   18                                                       
CONECT   15    3                                                            
CONECT   16    3                                                            
CONECT   17   13   19                                                       
CONECT   18   14   19                                                       
CONECT   19    2   17   18                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0015646
HETATM    1  C1  UNL     1      -2.665  -3.000  -0.630  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.147  -1.651  -0.956  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.148  -0.746  -0.416  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.842  -1.492  -0.346  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.149  -0.222  -0.631  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.771   1.024  -0.233  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.218   1.327   1.035  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.792   2.515   1.398  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.931   3.478   0.423  1.00  0.00           C  
HETATM   10  O1  UNL     1      -2.494   4.725   0.653  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.498   3.238  -0.886  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.932   2.025  -1.180  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.281  -0.199  -0.106  1.00  0.00           C  
HETATM   14  O2  UNL     1       1.855   1.047  -0.424  1.00  0.00           O  
HETATM   15  C12 UNL     1       1.400  -0.391   1.363  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.772  -0.998   1.696  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.827  -0.491   0.757  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.562  -0.774  -0.692  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.129  -1.236  -0.834  1.00  0.00           C  
HETATM   20  H1  UNL     1      -2.339  -3.728  -1.402  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.322  -3.290   0.393  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.768  -3.011  -0.620  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.186  -0.741   0.678  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.152   0.238  -0.905  1.00  0.00           H  
HETATM   25  H6  UNL     1      -4.139  -1.207  -0.725  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.856  -1.782   0.729  1.00  0.00           H  
HETATM   27  H8  UNL     1      -0.216  -2.305  -0.826  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.010  -0.193  -1.759  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.109   0.575   1.790  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.135   2.731   2.394  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.962   5.533   0.940  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.603   3.991  -1.662  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.606   1.879  -2.221  1.00  0.00           H  
HETATM   34  H15 UNL     1       1.844   1.666   0.362  1.00  0.00           H  
HETATM   35  H16 UNL     1       1.373   0.587   1.927  1.00  0.00           H  
HETATM   36  H17 UNL     1       0.659  -1.033   1.839  1.00  0.00           H  
HETATM   37  H18 UNL     1       2.715  -2.094   1.739  1.00  0.00           H  
HETATM   38  H19 UNL     1       3.056  -0.664   2.714  1.00  0.00           H  
HETATM   39  H20 UNL     1       4.071   0.570   0.964  1.00  0.00           H  
HETATM   40  H21 UNL     1       4.770  -1.053   1.027  1.00  0.00           H  
HETATM   41  H22 UNL     1       3.624   0.193  -1.274  1.00  0.00           H  
HETATM   42  H23 UNL     1       4.275  -1.510  -1.134  1.00  0.00           H  
HETATM   43  H24 UNL     1       1.974  -2.224  -0.351  1.00  0.00           H  
HETATM   44  H25 UNL     1       1.800  -1.307  -1.885  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4
CONECT    3   23   24   25
CONECT    4    5   26   27
CONECT    5    6   13   28
CONECT    6    7    7   12
CONECT    7    8   29
CONECT    8    9    9   30
CONECT    9   10   11
CONECT   10   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

HMDB0015646
     RDKit          3D
Desvenlafaxine
 44 45  0  0  0  0  0  0  0  0999 V2000
   -2.6652   -3.0002   -0.6304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1465   -1.6505   -0.9561 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1476   -0.7462   -0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8424   -1.4924   -0.3461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1490   -0.2216   -0.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7705    1.0245   -0.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2180    1.3268    1.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7917    2.5154    1.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9309    3.4784    0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4937    4.7247    0.6526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980    3.2385   -0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9319    2.0247   -1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2805   -0.1987   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8548    1.0467   -0.4245 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4004   -0.3915    1.3635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7716   -0.9984    1.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8273   -0.4907    0.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5621   -0.7738   -0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1288   -1.2363   -0.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3390   -3.7284   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3223   -3.2904    0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7682   -3.0113   -0.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1856   -0.7414    0.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1519    0.2383   -0.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1388   -1.2067   -0.7247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8560   -1.7819    0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155   -2.3051   -0.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0097   -0.1928   -1.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1090    0.5753    1.7905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345    2.7307    2.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9623    5.5327    0.9398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6030    3.9907   -1.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6059    1.8789   -2.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8441    1.6658    0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3727    0.5873    1.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6588   -1.0326    1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7151   -2.0940    1.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0560   -0.6641    2.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0714    0.5702    0.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7699   -1.0530    1.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6236    0.1935   -1.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2754   -1.5103   -1.1335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9744   -2.2239   -0.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8002   -1.3068   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
  5 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  6  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  7 29  1  0
  8 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
1-[2-(Dimethylamino)-1-(4-hydroxyphenyl)ethyl]cyclohexanol	ChEBI
4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol	ChEBI
Khedezla	Kegg
O-Desmethylvenlafaxine succinate	HMDB
4-(2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenol	HMDB
Succinate, desvenlafaxine	HMDB
2-(1-Hydroxycyclohexyl)-2-((4-hydroxyphenyl)ethyl)dimethylammonium 3-carboxypropanoate monohydrate	HMDB
O Desmethylvenlafaxine	HMDB
O Desmethylvenlafaxine succinate	HMDB
O-Desmethylvenlafaxine succinate monohydrate	HMDB
Succinate, O-desmethylvenlafaxine	HMDB
Desvenlafaxine succinate	HMDB
Monohydrate, O-desmethylvenlafaxine succinate	HMDB
O Desmethylvenlafaxine succinate monohydrate	HMDB
O-Desmethylvenlafaxine	HMDB
Pristiq	HMDB
Succinate monohydrate, O-desmethylvenlafaxine	HMDB
O-Desvenlafaxine	HMDB
Desvenlafaxine	ChEBI

Chemical Formula

C₁₆H₂₅NO₂

Average Molecular Weight

263.3752

Monoisotopic Molecular Weight

263.188529049

IUPAC Name

4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol

Traditional Name

desvenlafaxine

CAS Registry Number

93413-62-8

SMILES

CN(C)CC(C1=CC=C(O)C=C1)C1(O)CCCCC1

InChI Identifier

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

InChI Key

KYYIDSXMWOZKMP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclohexanols

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
1,3-aminoalcohol
Cyclic alcohol
Tertiary alcohol
Tertiary amine
Tertiary aliphatic amine
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Amine
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:83527 )
phenols (CHEBI:83527 )
cyclohexanols (CHEBI:83527 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060532)

Organ

Kidney (HMDB: HMDB0060532)
Liver (HMDB: HMDB0060532)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060532)

Cellular substructure

Cytoplasm (HMDB: HMDB0060532)
Membrane (HMDB: HMDB0060532)

Source

Endogenous

Endogenous (HMDB: HMDB0060532)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Venlafaxine Metabolism Pathway (PathBank: SMP0000636)

Role

Not Available

Physical Properties

State

Solid

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	166.7	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.4 g/L	ALOGPS
logP	2.6	ALOGPS
logP	2.29	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	10.11	ChemAxon
pKa (Strongest Basic)	8.87	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.54 m³·mol⁻¹	ChemAxon
Polarizability	30.32 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]+	163.444	31661259
DarkChem	[M-H]-	164.015	31661259
DeepCCS	[M+H]+	165.467	30932474
DeepCCS	[M-H]-	163.109	30932474
DeepCCS	[M-2H]-	196.091	30932474
DeepCCS	[M+Na]+	171.561	30932474
AllCCS	[M+H]+	163.6	32859911
AllCCS	[M+H-H2O]+	159.9	32859911
AllCCS	[M+NH4]+	166.9	32859911
AllCCS	[M+Na]+	167.9	32859911
AllCCS	[M-H]-	169.2	32859911
AllCCS	[M+Na-2H]-	169.7	32859911
AllCCS	[M+HCOO]-	170.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.37 minutes	32390414
Predicted by Siyang on May 30, 2022	9.6812 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.98 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	167.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Desvenlafaxine	CN(C)CC(C1=CC=C(O)C=C1)C1(O)CCCCC1	2813.7	Standard polar	33892256
Desvenlafaxine	CN(C)CC(C1=CC=C(O)C=C1)C1(O)CCCCC1	2133.7	Standard non polar	33892256
Desvenlafaxine	CN(C)CC(C1=CC=C(O)C=C1)C1(O)CCCCC1	2154.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Desvenlafaxine,1TMS,isomer #1	CN(C)CC(C1=CC=C(O[Si](C)(C)C)C=C1)C1(O)CCCCC1	2139.4	Semi standard non polar	33892256
Desvenlafaxine,1TMS,isomer #2	CN(C)CC(C1=CC=C(O)C=C1)C1(O[Si](C)(C)C)CCCCC1	2207.6	Semi standard non polar	33892256
Desvenlafaxine,2TMS,isomer #1	CN(C)CC(C1=CC=C(O[Si](C)(C)C)C=C1)C1(O[Si](C)(C)C)CCCCC1	2145.0	Semi standard non polar	33892256
Desvenlafaxine,1TBDMS,isomer #1	CN(C)CC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1(O)CCCCC1	2386.2	Semi standard non polar	33892256
Desvenlafaxine,1TBDMS,isomer #2	CN(C)CC(C1=CC=C(O)C=C1)C1(O[Si](C)(C)C(C)(C)C)CCCCC1	2462.5	Semi standard non polar	33892256
Desvenlafaxine,2TBDMS,isomer #1	CN(C)CC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1(O[Si](C)(C)C(C)(C)C)CCCCC1	2624.5	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 - Desvenlafaxine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9110000000-bddb56f900488038ac8f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desvenlafaxine GC-MS (2 TMS) - 70eV, Positive	splash10-0ab9-9426000000-d585011517fe757dd5ff	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desvenlafaxine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desvenlafaxine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desvenlafaxine 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 - Desvenlafaxine LC-ESI-QTOF , negative-QTOF	splash10-03di-0090000000-90abc876cc91a398d25d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-QTOF , negative-QTOF	splash10-03y0-0960000000-0219d7d7ea1a46c8cfdf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-QTOF , negative-QTOF	splash10-014i-0900000000-529d7fb237a99866f0b4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-QTOF , positive-QTOF	splash10-03di-0090000000-ccb6c8906a1ac7d27cd6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-QTOF , positive-QTOF	splash10-0002-0290000000-422a5daa0d4bf51308ef	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-QTOF , positive-QTOF	splash10-001i-0910000000-03ecfc411d730c35b892	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-QTOF , positive-QTOF	splash10-001i-0900000000-d0fa1892dfaae0510ee8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-QTOF , positive-QTOF	splash10-001m-0900000000-7515704132219cf15c78	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0002-0090000000-1a8bdddd358a8706e896	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-03di-0090000000-c218ef4ab652831ee930	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-06r2-4090000000-b1767a9c9c01cb43bca9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9320000000-e38b2ae07ab3cc9b7693	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9600000000-edbb26312a47b22bffb7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9800000000-b41801091e3c7132fec9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9800000000-4b30d7e9d71dab81d9d7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-03di-0090000000-5e859f484b6e3a5560c4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-06r2-4090000000-ef1215dc6fc4eb904b90	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9310000000-dac7bd983af34469bc5f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Desvenlafaxine LC-ESI-ITFT , positive-QTOF	splash10-0a4i-9600000000-8ea073e198c8a9a9a528	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desvenlafaxine 10V, Positive-QTOF	splash10-01ot-0090000000-8bdd9e87d70ac30b0f4b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desvenlafaxine 20V, Positive-QTOF	splash10-0i01-3190000000-e9a4354f756616119ea4	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desvenlafaxine 40V, Positive-QTOF	splash10-1003-9030000000-d873fc36430c62fd51b9	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desvenlafaxine 10V, Negative-QTOF	splash10-03di-0090000000-3151e03b6d1268750f4e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desvenlafaxine 20V, Negative-QTOF	splash10-03di-1390000000-6f6b5ce6a7122f629702	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desvenlafaxine 40V, Negative-QTOF	splash10-052f-9810000000-cf06f7edcabc2b491fb3	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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 DB06700	21059682	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06700	21059682	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06700

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

111300

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Desvenlafaxine

METLIN ID

Not Available

PubChem Compound

125017

PDB ID

Not Available

ChEBI ID

83527

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

Mason JN, Deecher DC, Richmond RL, Stack G, Mahaney PE, Trybulski E, Winneker RC, Blakely RD: Desvenlafaxine succinate identifies novel antagonist binding determinants in the human norepinephrine transporter. J Pharmacol Exp Ther. 2007 Nov;323(2):720-9. Epub 2007 Aug 2. [PubMed:17673606 ]
Kamath J, Handratta V: Desvenlafaxine succinate for major depressive disorder: a critical review of the evidence. Expert Rev Neurother. 2008 Dec;8(12):1787-97. doi: 10.1586/14737175.8.12.1787. [PubMed:19086875 ]
Liebowitz MR, Tourian KA: Efficacy, safety, and tolerability of Desvenlafaxine 50 mg/d for the treatment of major depressive disorder:a systematic review of clinical trials. Prim Care Companion J Clin Psychiatry. 2010;12(3). pii: PCC.09r00845. doi: 10.4088/PCC.09r00845blu. [PubMed:20944767 ]
Reddy S, Kane C, Pitrosky B, Musgnung J, Ninan PT, Guico-Pabia CJ: Clinical utility of desvenlafaxine 50 mg/d for treating MDD: a review of two randomized placebo-controlled trials for the practicing physician. Curr Med Res Opin. 2010 Jan;26(1):139-50. doi: 10.1185/03007990903408678. [PubMed:19919295 ]
Pae CU, Park MH, Marks DM, Han C, Patkar AA, Masand PS: Desvenlafaxine, a serotonin-norepinephrine uptake inhibitor for major depressive disorder, neuropathic pain and the vasomotor symptoms associated with menopause. Curr Opin Investig Drugs. 2009 Jan;10(1):75-90. [PubMed:19127490 ]
Preskorn S, Patroneva A, Silman H, Jiang Q, Isler JA, Burczynski ME, Ahmed S, Paul J, Nichols AI: Comparison of the pharmacokinetics of venlafaxine extended release and desvenlafaxine in extensive and poor cytochrome P450 2D6 metabolizers. J Clin Psychopharmacol. 2009 Feb;29(1):39-43. doi: 10.1097/JCP.0b013e318192e4c1. [PubMed:19142106 ]
Oganesian A, Shilling AD, Young-Sciame R, Tran J, Watanyar A, Azam F, Kao J, Leung L: Desvenlafaxine and venlafaxine exert minimal in vitro inhibition of human cytochrome P450 and P-glycoprotein activities. Psychopharmacol Bull. 2009;42(2):47-63. [PubMed:19629022 ]
Montgomery SA, Fava M, Padmanabhan SK, Guico-Pabia CJ, Tourian KA: Discontinuation symptoms and taper/poststudy-emergent adverse events with desvenlafaxine treatment for major depressive disorder. Int Clin Psychopharmacol. 2009 Nov;24(6):296-305. doi: 10.1097/YIC.0b013e32832fbb5a. [PubMed:19779354 ]
Kornstein SG, Jiang Q, Reddy S, Musgnung JJ, Guico-Pabia CJ: Short-term efficacy and safety of desvenlafaxine in a randomized, placebo-controlled study of perimenopausal and postmenopausal women with major depressive disorder. J Clin Psychiatry. 2010 Aug;71(8):1088-96. doi: 10.4088/JCP.10m06018blu. [PubMed:20797382 ]
Ilett KF, Watt F, Hackett LP, Kohan R, Teoh S: Assessment of infant dose through milk in a lactating woman taking amisulpride and desvenlafaxine for treatment-resistant depression. Ther Drug Monit. 2010 Dec;32(6):704-7. doi: 10.1097/FTD.0b013e3181f88f70. [PubMed:20926994 ]
Pae CU: Desvenlafaxine in the treatment of major depressive disorder. Expert Opin Pharmacother. 2011 Dec;12(18):2923-8. doi: 10.1517/14656566.2011.636033. [PubMed:22098230 ]
Berm EJ, Brummel-Mulder E, Paardekooper J, Hak E, Wilffert B, Maring JG: Determination of venlafaxine and O-desmethylvenlafaxine in dried blood spots for TDM purposes, using LC-MS/MS. Anal Bioanal Chem. 2014 Apr;406(9-10):2349-53. doi: 10.1007/s00216-014-7619-9. Epub 2014 Feb 4. [PubMed:24493333 ]
Murrell MD, Cruz DA, Javors MA, Thompson PM: Distribution of venlafaxine, O-desmethylvenlafaxine, and O-desmethylvenlafaxine to venlafaxine ratio in postmortem human brain tissue. J Forensic Sci. 2014 May;59(3):683-9. doi: 10.1111/1556-4029.12393. Epub 2014 Feb 6. [PubMed:24502274 ]
ter Horst PG, Larmene-Beld KH, Bosman J, van der Veen EL, Wieringa A, Smit JP: Concentrations of venlafaxine and its main metabolite O-desmethylvenlafaxine during pregnancy. J Clin Pharm Ther. 2014 Oct;39(5):541-4. doi: 10.1111/jcpt.12188. Epub 2014 Jul 3. [PubMed:24989434 ]
Vignali C, Morini L, Chen Y, Stramesi C, Groppi A: Distribution of venlafaxine and O-desmethylvenlafaxine in a fatal case. Forensic Sci Int. 2014 Sep;242:e48-e51. doi: 10.1016/j.forsciint.2014.07.011. Epub 2014 Jul 21. [PubMed:25086830 ]
Paulzen M, Groppe S, Tauber SC, Veselinovic T, Hiemke C, Grunder G: Venlafaxine and O-desmethylvenlafaxine concentrations in plasma and cerebrospinal fluid. J Clin Psychiatry. 2015 Jan;76(1):25-31. doi: 10.4088/JCP.13m08921. [PubMed:25188033 ]
(). FDA label . .
(). Wyeth Laboratories Inc. PristiqÃ‚Â® (desvenlafaxine succinate) extended-release tablets prescribing information. Philadelphia, PA; 2010 Sept.. .
PharmGKB [Link]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Transporters

Enzyme Details

1. Sodium-dependent noradrenaline transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A2
Uniprot ID:: P23975
Molecular weight:: 69331.42

References

Deecher DC, Beyer CE, Johnston G, Bray J, Shah S, Abou-Gharbia M, Andree TH: Desvenlafaxine succinate: A new serotonin and norepinephrine reuptake inhibitor. J Pharmacol Exp Ther. 2006 Aug;318(2):657-65. Epub 2006 May 4. [PubMed:16675639 ]
Mason JN, Deecher DC, Richmond RL, Stack G, Mahaney PE, Trybulski E, Winneker RC, Blakely RD: Desvenlafaxine succinate identifies novel antagonist binding determinants in the human norepinephrine transporter. J Pharmacol Exp Ther. 2007 Nov;323(2):720-9. Epub 2007 Aug 2. [PubMed:17673606 ]
Perry R, Cassagnol M: Desvenlafaxine: a new serotonin-norepinephrine reuptake inhibitor for the treatment of adults with major depressive disorder. Clin Ther. 2009 Jun;31 Pt 1:1374-404. doi: 10.1016/j.clinthera.2009.07.012. [PubMed:19698900 ]
Kamath J, Handratta V: Desvenlafaxine succinate for major depressive disorder: a critical review of the evidence. Expert Rev Neurother. 2008 Dec;8(12):1787-97. doi: 10.1586/14737175.8.12.1787. [PubMed:19086875 ]
Liebowitz MR, Tourian KA: Efficacy, safety, and tolerability of Desvenlafaxine 50 mg/d for the treatment of major depressive disorder:a systematic review of clinical trials. Prim Care Companion J Clin Psychiatry. 2010;12(3). pii: PCC.09r00845. doi: 10.4088/PCC.09r00845blu. [PubMed:20944767 ]
Reddy S, Kane C, Pitrosky B, Musgnung J, Ninan PT, Guico-Pabia CJ: Clinical utility of desvenlafaxine 50 mg/d for treating MDD: a review of two randomized placebo-controlled trials for the practicing physician. Curr Med Res Opin. 2010 Jan;26(1):139-50. doi: 10.1185/03007990903408678. [PubMed:19919295 ]

Enzyme Details

2. Sodium-dependent serotonin transporter

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:: SLC6A4
Uniprot ID:: P31645
Molecular weight:: 70324.165

References

Deecher DC, Beyer CE, Johnston G, Bray J, Shah S, Abou-Gharbia M, Andree TH: Desvenlafaxine succinate: A new serotonin and norepinephrine reuptake inhibitor. J Pharmacol Exp Ther. 2006 Aug;318(2):657-65. Epub 2006 May 4. [PubMed:16675639 ]
Mason JN, Deecher DC, Richmond RL, Stack G, Mahaney PE, Trybulski E, Winneker RC, Blakely RD: Desvenlafaxine succinate identifies novel antagonist binding determinants in the human norepinephrine transporter. J Pharmacol Exp Ther. 2007 Nov;323(2):720-9. Epub 2007 Aug 2. [PubMed:17673606 ]
Perry R, Cassagnol M: Desvenlafaxine: a new serotonin-norepinephrine reuptake inhibitor for the treatment of adults with major depressive disorder. Clin Ther. 2009 Jun;31 Pt 1:1374-404. doi: 10.1016/j.clinthera.2009.07.012. [PubMed:19698900 ]
Kamath J, Handratta V: Desvenlafaxine succinate for major depressive disorder: a critical review of the evidence. Expert Rev Neurother. 2008 Dec;8(12):1787-97. doi: 10.1586/14737175.8.12.1787. [PubMed:19086875 ]
Liebowitz MR, Tourian KA: Efficacy, safety, and tolerability of Desvenlafaxine 50 mg/d for the treatment of major depressive disorder:a systematic review of clinical trials. Prim Care Companion J Clin Psychiatry. 2010;12(3). pii: PCC.09r00845. doi: 10.4088/PCC.09r00845blu. [PubMed:20944767 ]
Reddy S, Kane C, Pitrosky B, Musgnung J, Ninan PT, Guico-Pabia CJ: Clinical utility of desvenlafaxine 50 mg/d for treating MDD: a review of two randomized placebo-controlled trials for the practicing physician. Curr Med Res Opin. 2010 Jan;26(1):139-50. doi: 10.1185/03007990903408678. [PubMed:19919295 ]

Showing metabocard for Desvenlafaxine (HMDB0015646)

MOL for HMDB0015646 (Desvenlafaxine)

3D MOL for HMDB0015646 (Desvenlafaxine)

3D SDF for HMDB0015646 (Desvenlafaxine)

3D-SDF for HMDB0015646 (Desvenlafaxine)

PDB for HMDB0015646 (Desvenlafaxine)

3D PDB for HMDB0015646 (Desvenlafaxine)

SMILES for HMDB0015646 (Desvenlafaxine)

INCHI for HMDB0015646 (Desvenlafaxine)

Structure for HMDB0015646 (Desvenlafaxine)

3D Structure for HMDB0015646 (Desvenlafaxine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Transporters

References

References