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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:03 UTC

HMDB ID

HMDB0015602

Secondary Accession Numbers

HMDB15602

Metabolite Identification

Common Name

Milnacipran

Description

Milnacipran, also known as F2207 or midalcipran, belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids. Milnacipran is a very strong basic compound (based on its pKa). During its development for fibromyalgia, milnacipran was evaluated utilizing a composite responder approach. As with other antidepressants, 1 to 3 weeks may elapse before significant antidepressant action becomes clinically evident. Administration of milnacipran should be done with caution in individuals with the following:Concomitant treatment with parenteral epinephrine, norepinephrine, with clonidine, reversible MAO-A Inhibitors (such as moclobemide, toloxatone) or 5-HT1D-agonists (e.g. triptan migraine drugs)Advanced renal disease (decreased dosage required)Hypertrophy of the prostate gland (possibly urination hesitancy induced), with hypertension and heart disease (tachycardia may be a problem) as well as with open angle glaucoma.Milnacipran should not be used during pregnancy because it may cross the placenta barrier and no clinical data exists on harmful effects in humans and animal studies. Recently, levomilnacipran, the levorotatory enantiomer of milnacipran, has been found to act as an inhibitor of beta-site amyloid precursor protein cleaving enzyme-1 (BACE-1), which is responsible for β-amyloid plaque formation, and hence may be a potentially useful drug in the treatment of Alzheimer's disease.

Structure

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

HMDB0015602
     RDKit          3D
Milnacipran
 40 41  0  0  0  0  0  0  0  0999 V2000
    2.5629    1.1435    1.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052   -0.1265    0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421   -0.2215   -0.3972 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7320   -0.0291   -1.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8531    1.4352   -1.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4384   -0.4489   -0.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2383   -0.5880   -2.0900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8232   -0.5854   -0.0518 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4619    0.6587    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    1.8734    0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4979    3.0156    1.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8325    2.9704    1.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4874    1.7783    1.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8211    0.6715    0.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156   -1.7329    0.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6123   -1.8377   -0.2183 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2319   -2.7822   -1.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1331   -3.9164   -1.2921 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5757    1.5862    1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8225    1.9211    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7300    0.8779    2.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3189   -0.6678    0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6613   -0.7356    1.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3465   -0.5273   -2.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7018   -0.4562   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0032    1.8264   -2.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7683    1.4871   -2.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0571    2.0461   -0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1751    1.9782    0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9641    3.9294    1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3670    3.8447    1.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5537    1.7229    1.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3846   -0.2264    0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0542   -1.4561    1.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1471   -2.4124    0.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6665   -1.8838    0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4758   -2.2238   -2.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1732   -3.0251   -1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6612   -4.7637   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4260   -4.1196   -0.2922 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
  3  6  1  0
  6  7  2  0
  8  6  1  6
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16  8  1  0
 14  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  1
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
M  END

  Mrv0541 02231218002D          

 18 19  0  0  1  0            999 V2000
    3.7935    1.2433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.0058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6350    1.9578    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.0058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9205    0.7202    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3330    0.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205    1.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2  9  1  0  0  0  0
  2 12  1  0  0  0  0
  2 13  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  1  0  0  0
  5  6  1  0  0  0  0
  5  7  1  1  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  2  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015602

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)C(=O)[C@@]1(C[C@@H]1CN)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22N2O/c1-3-17(4-2)14(18)15(10-13(15)11-16)12-8-6-5-7-9-12/h5-9,13H,3-4,10-11,16H2,1-2H3/t13-,15+/m1/s1

> <INCHI_KEY>
GJJFMKBJSRMPLA-HIFRSBDPSA-N

> <FORMULA>
C15H22N2O

> <MOLECULAR_WEIGHT>
246.348

> <EXACT_MASS>
246.173213336

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.027975637873595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S)-2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
1.421706622999999

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.827548067218556

> <JCHEM_POLAR_SURFACE_AREA>
46.33

> <JCHEM_REFRACTIVITY>
73.80950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
milnacipran

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015602
     RDKit          3D
Milnacipran
 40 41  0  0  0  0  0  0  0  0999 V2000
    2.5629    1.1435    1.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052   -0.1265    0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421   -0.2215   -0.3972 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7320   -0.0291   -1.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8531    1.4352   -1.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4384   -0.4489   -0.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2383   -0.5880   -2.0900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8232   -0.5854   -0.0518 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4619    0.6587    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    1.8734    0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4979    3.0156    1.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8325    2.9704    1.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4874    1.7783    1.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8211    0.6715    0.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156   -1.7329    0.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6123   -1.8377   -0.2183 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2319   -2.7822   -1.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1331   -3.9164   -1.2921 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5757    1.5862    1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8225    1.9211    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7300    0.8779    2.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3189   -0.6678    0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6613   -0.7356    1.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3465   -0.5273   -2.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7018   -0.4562   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0032    1.8264   -2.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7683    1.4871   -2.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0571    2.0461   -0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1751    1.9782    0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9641    3.9294    1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3670    3.8447    1.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5537    1.7229    1.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3846   -0.2264    0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0542   -1.4561    1.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1471   -2.4124    0.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6665   -1.8838    0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4758   -2.2238   -2.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1732   -3.0251   -1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6612   -4.7637   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4260   -4.1196   -0.2922 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
  3  6  1  0
  6  7  2  0
  8  6  1  6
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16  8  1  0
 14  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  1
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.081   2.321   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       5.748   0.011   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      10.519   3.655   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.415   0.011   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.185   1.344   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.955   0.011   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.185   2.885   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415  -1.529   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   0.781   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748  -2.299   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -2.299   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -1.529   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   0.781   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.748  -3.839   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -3.839   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415  -4.609   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414  -2.299   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080   0.011   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    9   12   13                                                  
CONECT    3    7                                                            
CONECT    4    5    6    8    9                                             
CONECT    5    4    6    7                                                  
CONECT    6    4    5                                                       
CONECT    7    3    5                                                       
CONECT    8    4   10   11                                                  
CONECT    9    1    2    4                                                  
CONECT   10    8   14                                                       
CONECT   11    8   15                                                       
CONECT   12    2   17                                                       
CONECT   13    2   18                                                       
CONECT   14   10   16                                                       
CONECT   15   11   16                                                       
CONECT   16   14   15                                                       
CONECT   17   12                                                            
CONECT   18   13                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0015602
HETATM    1  C1  UNL     1       2.563   1.144   1.576  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.305  -0.126   0.902  1.00  0.00           C  
HETATM    3  N1  UNL     1       1.742  -0.222  -0.397  1.00  0.00           N  
HETATM    4  C3  UNL     1       2.732  -0.029  -1.496  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.853   1.435  -1.859  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.438  -0.449  -0.820  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.238  -0.588  -2.090  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.823  -0.585  -0.052  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.462   0.659   0.399  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.836   1.873   0.559  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.498   3.016   1.020  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.832   2.970   1.336  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.487   1.778   1.187  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.821   0.671   0.736  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.716  -1.733   0.951  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.612  -1.838  -0.218  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.232  -2.782  -1.363  1.00  0.00           C  
HETATM   18  N2  UNL     1      -2.133  -3.916  -1.292  1.00  0.00           N  
HETATM   19  H1  UNL     1       3.576   1.586   1.325  1.00  0.00           H  
HETATM   20  H2  UNL     1       1.823   1.921   1.618  1.00  0.00           H  
HETATM   21  H3  UNL     1       2.730   0.878   2.687  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.319  -0.668   0.852  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.661  -0.736   1.633  1.00  0.00           H  
HETATM   24  H6  UNL     1       2.346  -0.527  -2.415  1.00  0.00           H  
HETATM   25  H7  UNL     1       3.702  -0.456  -1.253  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.003   1.826  -2.426  1.00  0.00           H  
HETATM   27  H9  UNL     1       3.768   1.487  -2.519  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.057   2.046  -0.954  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.175   1.978   0.284  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.964   3.929   1.132  1.00  0.00           H  
HETATM   31  H13 UNL     1      -3.367   3.845   1.695  1.00  0.00           H  
HETATM   32  H14 UNL     1      -4.554   1.723   1.429  1.00  0.00           H  
HETATM   33  H15 UNL     1      -3.385  -0.226   0.643  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.054  -1.456   1.952  1.00  0.00           H  
HETATM   35  H17 UNL     1       0.147  -2.412   0.926  1.00  0.00           H  
HETATM   36  H18 UNL     1      -2.666  -1.884   0.010  1.00  0.00           H  
HETATM   37  H19 UNL     1      -1.476  -2.224  -2.323  1.00  0.00           H  
HETATM   38  H20 UNL     1      -0.173  -3.025  -1.396  1.00  0.00           H  
HETATM   39  H21 UNL     1      -1.661  -4.764  -1.682  1.00  0.00           H  
HETATM   40  H22 UNL     1      -2.426  -4.120  -0.292  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4    6
CONECT    4    5   24   25
CONECT    5   26   27   28
CONECT    6    7    7    8
CONECT    8    9   15   16
CONECT    9   10   10   14
CONECT   10   11   29
CONECT   11   12   12   30
CONECT   12   13   31
CONECT   13   14   14   32
CONECT   14   33
CONECT   15   16   34   35
CONECT   16   17   36
CONECT   17   18   37   38
CONECT   18   39   40
END

HMDB0015602
     RDKit          3D
Milnacipran
 40 41  0  0  0  0  0  0  0  0999 V2000
    2.5629    1.1435    1.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052   -0.1265    0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421   -0.2215   -0.3972 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7320   -0.0291   -1.4955 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8531    1.4352   -1.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4384   -0.4489   -0.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2383   -0.5880   -2.0900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8232   -0.5854   -0.0518 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4619    0.6587    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    1.8734    0.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4979    3.0156    1.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8325    2.9704    1.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4874    1.7783    1.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8211    0.6715    0.7359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156   -1.7329    0.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6123   -1.8377   -0.2183 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2319   -2.7822   -1.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1331   -3.9164   -1.2921 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5757    1.5862    1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8225    1.9211    1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7300    0.8779    2.6871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3189   -0.6678    0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6613   -0.7356    1.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3465   -0.5273   -2.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7018   -0.4562   -1.2531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0032    1.8264   -2.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7683    1.4871   -2.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0571    2.0461   -0.9543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1751    1.9782    0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9641    3.9294    1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3670    3.8447    1.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5537    1.7229    1.4295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3846   -0.2264    0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0542   -1.4561    1.9515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1471   -2.4124    0.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6665   -1.8838    0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4758   -2.2238   -2.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1732   -3.0251   -1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6612   -4.7637   -1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4260   -4.1196   -0.2922 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
  3  6  1  0
  6  7  2  0
  8  6  1  6
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16  8  1  0
 14  9  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  1
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Milnacipran	HMDB
F2207	HMDB
Midalcipran	HMDB
Ixel	HMDB
Savella	HMDB
Levomilnacipran	HMDB
Milnacipran hydrochloride	HMDB
1-Phenyl-1-diethylaminocarbonyl-2-aminomethylcyclopropane HCL	HMDB
Fetzima	HMDB
1 Phenyl 1 diethylaminocarbonyl 2 aminomethylcyclopropane HCL	HMDB

Chemical Formula

C₁₅H₂₂N₂O

Average Molecular Weight

246.348

Monoisotopic Molecular Weight

246.173213336

IUPAC Name

(1R,2S)-2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide

Traditional Name

milnacipran

CAS Registry Number

92623-85-3

SMILES

CCN(CC)C(=O)[C@@]1(C[C@@H]1CN)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H22N2O/c1-3-17(4-2)14(18)15(10-13(15)11-16)12-8-6-5-7-9-12/h5-9,13H,3-4,10-11,16H2,1-2H3/t13-,15+/m1/s1

InChI Key

GJJFMKBJSRMPLA-HIFRSBDPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylacetamides

Direct Parent

Phenylacetamides

Alternative Parents

Substituents

Phenylacetamide
Aralkylamine
Cyclopropanecarboxylic acid or derivatives
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Carboxylic acid derivative
Organopnictogen compound
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Amine
Carbonyl group
Organic oxide
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: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015602)

Source

Exogenous

Exogenous (HMDB: HMDB0015602)

Process

Not Available

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	1.23 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.23 g/L	ALOGPS
logP	1.72	ALOGPS
logP	1.42	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	9.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.33 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.81 m³·mol⁻¹	ChemAxon
Polarizability	28.03 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]+	158.733	31661259
DarkChem	[M-H]-	155.225	31661259
DeepCCS	[M+H]+	160.089	30932474
DeepCCS	[M-H]-	157.731	30932474
DeepCCS	[M-2H]-	190.616	30932474
DeepCCS	[M+Na]+	166.182	30932474
AllCCS	[M+H]+	157.5	32859911
AllCCS	[M+H-H2O]+	153.8	32859911
AllCCS	[M+NH4]+	160.9	32859911
AllCCS	[M+Na]+	161.8	32859911
AllCCS	[M-H]-	163.6	32859911
AllCCS	[M+Na-2H]-	163.9	32859911
AllCCS	[M+HCOO]-	164.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Milnacipran	CCN(CC)C(=O)[C@@]1(C[C@@H]1CN)C1=CC=CC=C1	2979.1	Standard polar	33892256
Milnacipran	CCN(CC)C(=O)[C@@]1(C[C@@H]1CN)C1=CC=CC=C1	1991.8	Standard non polar	33892256
Milnacipran	CCN(CC)C(=O)[C@@]1(C[C@@H]1CN)C1=CC=CC=C1	1915.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Milnacipran,1TMS,isomer #1	CCN(CC)C(=O)[C@]1(C2=CC=CC=C2)C[C@@H]1CN[Si](C)(C)C	2034.7	Semi standard non polar	33892256
Milnacipran,1TMS,isomer #1	CCN(CC)C(=O)[C@]1(C2=CC=CC=C2)C[C@@H]1CN[Si](C)(C)C	2139.5	Standard non polar	33892256
Milnacipran,1TMS,isomer #1	CCN(CC)C(=O)[C@]1(C2=CC=CC=C2)C[C@@H]1CN[Si](C)(C)C	2504.4	Standard polar	33892256
Milnacipran,2TMS,isomer #1	CCN(CC)C(=O)[C@]1(C2=CC=CC=C2)C[C@@H]1CN([Si](C)(C)C)[Si](C)(C)C	2134.3	Semi standard non polar	33892256
Milnacipran,2TMS,isomer #1	CCN(CC)C(=O)[C@]1(C2=CC=CC=C2)C[C@@H]1CN([Si](C)(C)C)[Si](C)(C)C	2369.7	Standard non polar	33892256
Milnacipran,2TMS,isomer #1	CCN(CC)C(=O)[C@]1(C2=CC=CC=C2)C[C@@H]1CN([Si](C)(C)C)[Si](C)(C)C	2408.2	Standard polar	33892256
Milnacipran,1TBDMS,isomer #1	CCN(CC)C(=O)[C@]1(C2=CC=CC=C2)C[C@@H]1CN[Si](C)(C)C(C)(C)C	2241.8	Semi standard non polar	33892256
Milnacipran,1TBDMS,isomer #1	CCN(CC)C(=O)[C@]1(C2=CC=CC=C2)C[C@@H]1CN[Si](C)(C)C(C)(C)C	2385.5	Standard non polar	33892256
Milnacipran,1TBDMS,isomer #1	CCN(CC)C(=O)[C@]1(C2=CC=CC=C2)C[C@@H]1CN[Si](C)(C)C(C)(C)C	2610.1	Standard polar	33892256
Milnacipran,2TBDMS,isomer #1	CCN(CC)C(=O)[C@]1(C2=CC=CC=C2)C[C@@H]1CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2554.1	Semi standard non polar	33892256
Milnacipran,2TBDMS,isomer #1	CCN(CC)C(=O)[C@]1(C2=CC=CC=C2)C[C@@H]1CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2765.7	Standard non polar	33892256
Milnacipran,2TBDMS,isomer #1	CCN(CC)C(=O)[C@]1(C2=CC=CC=C2)C[C@@H]1CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2606.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Milnacipran GC-MS (Non-derivatized) - 70eV, Positive	splash10-003s-9720000000-ca5db3dd96b3bf602e80	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Milnacipran 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 - Milnacipran , positive-QTOF	splash10-001i-1590000000-14ea613049f0be797cc6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Milnacipran 35V, Positive-QTOF	splash10-0fai-2950000000-0d6b47bfb625a8443c78	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Milnacipran 10V, Positive-QTOF	splash10-000t-0190000000-ac9945cd8c8043e9e92f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Milnacipran 20V, Positive-QTOF	splash10-008a-1980000000-989c19c8db76f07da08b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Milnacipran 40V, Positive-QTOF	splash10-004i-5900000000-10e08ed18b692dc26d79	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Milnacipran 10V, Negative-QTOF	splash10-0002-0090000000-a43b5ce382df221bf86d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Milnacipran 20V, Negative-QTOF	splash10-0002-4490000000-60028333af69e8af02bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Milnacipran 40V, Negative-QTOF	splash10-00dl-9400000000-4f89e1fb8d13d48f3511	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Milnacipran 10V, Positive-QTOF	splash10-0002-0590000000-1f4d137f80628e35c827	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Milnacipran 20V, Positive-QTOF	splash10-0002-2960000000-8f12df3429c555732cd0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Milnacipran 40V, Positive-QTOF	splash10-00ba-6900000000-efba65f220764b405ef1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Milnacipran 10V, Negative-QTOF	splash10-0002-0290000000-722c0acf3966aec48c62	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Milnacipran 20V, Negative-QTOF	splash10-0002-5290000000-6c41adc4efeb91c44163	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Milnacipran 40V, Negative-QTOF	splash10-0006-4900000000-3e4a9ec417730d813614	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB04896	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04896	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04896

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

59245

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Milnacipran

METLIN ID

Not Available

PubChem Compound

65833

PDB ID

Not Available

ChEBI ID

521102

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

Leo RJ, Brooks VL: Clinical potential of milnacipran, a serotonin and norepinephrine reuptake inhibitor, in pain. Curr Opin Investig Drugs. 2006 Jul;7(7):637-42. [PubMed:16869117 ]
Moret C, Charveron M, Finberg JP, Couzinier JP, Briley M: Biochemical profile of midalcipran (F 2207), 1-phenyl-1-diethyl-aminocarbonyl-2-aminomethyl-cyclopropane (Z) hydrochloride, a potential fourth generation antidepressant drug. Neuropharmacology. 1985 Dec;24(12):1211-9. [PubMed:3005901 ]
Briley M, Prost JF, Moret C: Preclinical pharmacology of milnacipran. Int Clin Psychopharmacol. 1996 Sep;11 Suppl 4:9-14. [PubMed:8923122 ]
Leinonen E, Lepola U, Koponen H, Mehtonen OP, Rimon R: Long-term efficacy and safety of milnacipran compared to clomipramine in patients with major depression. Acta Psychiatr Scand. 1997 Dec;96(6):497-504. [PubMed:9421348 ]
Puozzo C, Panconi E, Deprez D: Pharmacology and pharmacokinetics of milnacipran. Int Clin Psychopharmacol. 2002 Jun;17 Suppl 1:S25-35. [PubMed:12369608 ]
Moojen VK, Martins MR, Reinke A, Feier G, Agostinho FR, Cechin EM, Quevedo J: Effects of milnacipran in animal models of anxiety and memory. Neurochem Res. 2006 Apr;31(4):571-7. Epub 2006 May 9. [PubMed:16758367 ]
Papakostas GI, Fava M: A meta-analysis of clinical trials comparing milnacipran, a serotonin--norepinephrine reuptake inhibitor, with a selective serotonin reuptake inhibitor for the treatment of major depressive disorder. Eur Neuropsychopharmacol. 2007 Jan;17(1):32-6. Epub 2006 Jun 8. [PubMed:16762534 ]
King T, Rao S, Vanderah T, Chen Q, Vardanyan A, Porreca F: Differential blockade of nerve injury-induced shift in weight bearing and thermal and tactile hypersensitivity by milnacipran. J Pain. 2006 Jul;7(7):513-20. [PubMed:16814690 ]
Soya A, Terao T, Nakajima M, Kojima H, Okamoto T, Inoue Y, Iwakawa M, Shinkai K, Yoshimura R, Ueta Y, Nakamura J: Effects of repeated milnacipran administration on brain serotonergic and noradrenergic functions in healthy volunteers. Psychopharmacology (Berl). 2006 Sep;187(4):526-7. Epub 2006 Jul 8. [PubMed:16830129 ]
Simon LS: Is milnacipran effective in treating pain in patients with fibromyalgia? Nat Clin Pract Rheumatol. 2006 Mar;2(3):126-7. [PubMed:16932669 ]
Sato S, Yamakawa Y, Terashima Y, Ohta H, Asada T: Efficacy of milnacipran on cognitive dysfunction with post-stroke depression: preliminary open-label study. Psychiatry Clin Neurosci. 2006 Oct;60(5):584-9. [PubMed:16958942 ]
Kako Y, Niwa Y, Toyomaki A, Yamanaka H, Kitagawa N, Denda K, Koyama T: A case of adult attention-deficit/hyperactivity disorder alleviated by milnacipran. Prog Neuropsychopharmacol Biol Psychiatry. 2007 Apr 13;31(3):772-5. Epub 2007 Jan 12. [PubMed:17300859 ]
Bernstein CD, Albrecht KL, Marcus DA: Milnacipran for fibromyalgia: a useful addition to the treatment armamentarium. Expert Opin Pharmacother. 2013 May;14(7):905-16. doi: 10.1517/14656566.2013.779670. Epub 2013 Mar 19. [PubMed:23506481 ]

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

Leo RJ, Brooks VL: Clinical potential of milnacipran, a serotonin and norepinephrine reuptake inhibitor, in pain. Curr Opin Investig Drugs. 2006 Jul;7(7):637-42. [PubMed:16869117 ]
Moret C, Charveron M, Finberg JP, Couzinier JP, Briley M: Biochemical profile of midalcipran (F 2207), 1-phenyl-1-diethyl-aminocarbonyl-2-aminomethyl-cyclopropane (Z) hydrochloride, a potential fourth generation antidepressant drug. Neuropharmacology. 1985 Dec;24(12):1211-9. [PubMed:3005901 ]

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

Leo RJ, Brooks VL: Clinical potential of milnacipran, a serotonin and norepinephrine reuptake inhibitor, in pain. Curr Opin Investig Drugs. 2006 Jul;7(7):637-42. [PubMed:16869117 ]
Moret C, Charveron M, Finberg JP, Couzinier JP, Briley M: Biochemical profile of midalcipran (F 2207), 1-phenyl-1-diethyl-aminocarbonyl-2-aminomethyl-cyclopropane (Z) hydrochloride, a potential fourth generation antidepressant drug. Neuropharmacology. 1985 Dec;24(12):1211-9. [PubMed:3005901 ]

Showing metabocard for Milnacipran (HMDB0015602)

MOL for HMDB0015602 (Milnacipran)

3D MOL for HMDB0015602 (Milnacipran)

3D SDF for HMDB0015602 (Milnacipran)

3D-SDF for HMDB0015602 (Milnacipran)

PDB for HMDB0015602 (Milnacipran)

3D PDB for HMDB0015602 (Milnacipran)

SMILES for HMDB0015602 (Milnacipran)

INCHI for HMDB0015602 (Milnacipran)

Structure for HMDB0015602 (Milnacipran)

3D Structure for HMDB0015602 (Milnacipran)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Transporters

References

References