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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

HMDB0015633

Secondary Accession Numbers

HMDB15633

Metabolite Identification

Common Name

Amisulpride

Description

Amisulpride, also known as deniban or solian, belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring. Amisulpride is a very strong basic compound (based on its pKa). Another recent study concluded that amisulpride is an appropriate first-line treatment for the management of acute psychosis. The British National Formulary recommends a gradual withdrawal when discontinuing antipsychotics to avoid acute withdrawal syndrome or rapid relapse. The clinical implications of this, if any, are unclear.

Structure

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

HMDB0015633
     RDKit          3D
Amisulpride
 52 53  0  0  0  0  0  0  0  0999 V2000
    4.5714    2.5607   -0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1767    1.2806   -0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042    0.1309    0.0553 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3244   -1.0376   -0.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5286   -1.3201   -1.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2477   -0.5560   -1.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2791   -0.0611   -0.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7788   -1.1094    0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3603   -1.3867    0.6596 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3928   -0.3875    0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8024    0.7994    1.1983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396   -0.5548    0.7736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8638    0.5544    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2367    0.4851    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2547    1.8610    1.2612 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.1665    1.6484    2.4153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3888    3.0527    1.5004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2165    2.1980   -0.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1223    3.3870   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8358   -0.7121    0.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2446   -0.7697    0.5437 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0822   -1.8355    0.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6811   -1.7186    0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9433   -2.8497    0.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5364   -4.0769   -0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2491    3.3880   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5396    2.7102   -0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6398    2.5101    0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0039    1.1784   -1.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2748    1.3547   -0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3662   -0.7243   -0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3666   -1.9028    0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3582   -2.4143   -1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0358   -0.9657   -2.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1785    0.3032   -2.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3662   -1.2017   -1.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7200    0.8899   -0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3962   -2.0257    0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9238   -0.7777    1.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1087   -2.3440    0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113    1.4972    1.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8701    1.3238   -0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5596    2.3331   -1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6324    3.3146    0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5234    4.3103   -0.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8636    3.3681   -0.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8267   -0.4319    1.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7727   -1.1361   -0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5478   -2.7696    0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747   -4.4910    0.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2495   -3.9750   -1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499   -4.7888   -0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  2  0
 15 18  1  0
 18 19  1  0
 14 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
  7  3  1  0
 23 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 13 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
M  END


  Mrv0541 02231218162D          

 25 26  0  0  1  0            999 V2000
    3.5220    1.2375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3470    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6970    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1806   -0.0045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8482   -1.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4002   -0.5475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9877    0.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5676    0.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7391    1.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  1  5  2  0  0  0  0
  1 18  1  0  0  0  0
  1 23  1  0  0  0  0
  2 16  2  0  0  0  0
  3 20  1  0  0  0  0
  3 25  1  0  0  0  0
  6  9  1  0  0  0  0
  6 12  1  0  0  0  0
  6 14  1  0  0  0  0
  7 13  1  0  0  0  0
  7 16  1  0  0  0  0
  8 21  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  2  0  0  0  0
 17 20  1  0  0  0  0
 18 19  1  0  0  0  0
 18 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015633

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN1CCCC1CNC(=O)C1=CC(=C(N)C=C1OC)S(=O)(=O)CC

> <INCHI_IDENTIFIER>
InChI=1S/C17H27N3O4S/c1-4-20-8-6-7-12(20)11-19-17(21)13-9-16(25(22,23)5-2)14(18)10-15(13)24-3/h9-10,12H,4-8,11,18H2,1-3H3,(H,19,21)

> <INCHI_KEY>
NTJOBXMMWNYJFB-UHFFFAOYSA-N

> <FORMULA>
C17H27N3O4S

> <MOLECULAR_WEIGHT>
369.479

> <EXACT_MASS>
369.172227057

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
39.82259907992241

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-amino-5-(ethanesulfonyl)-N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide

> <ALOGPS_LOGP>
1.50

> <JCHEM_LOGP>
0.2512876846666668

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.611193365980647

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.032645979721941

> <JCHEM_PKA_STRONGEST_BASIC>
7.0515122111657424

> <JCHEM_POLAR_SURFACE_AREA>
101.73

> <JCHEM_REFRACTIVITY>
99.84480000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
amisulpride

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015633
     RDKit          3D
Amisulpride
 52 53  0  0  0  0  0  0  0  0999 V2000
    4.5714    2.5607   -0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1767    1.2806   -0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042    0.1309    0.0553 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3244   -1.0376   -0.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5286   -1.3201   -1.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2477   -0.5560   -1.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2791   -0.0611   -0.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7788   -1.1094    0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3603   -1.3867    0.6596 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3928   -0.3875    0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8024    0.7994    1.1983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396   -0.5548    0.7736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8638    0.5544    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2367    0.4851    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2547    1.8610    1.2612 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.1665    1.6484    2.4153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3888    3.0527    1.5004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2165    2.1980   -0.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1223    3.3870   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8358   -0.7121    0.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2446   -0.7697    0.5437 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0822   -1.8355    0.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6811   -1.7186    0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9433   -2.8497    0.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5364   -4.0769   -0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2491    3.3880   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5396    2.7102   -0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6398    2.5101    0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0039    1.1784   -1.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2748    1.3547   -0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3662   -0.7243   -0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3666   -1.9028    0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3582   -2.4143   -1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0358   -0.9657   -2.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1785    0.3032   -2.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3662   -1.2017   -1.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7200    0.8899   -0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3962   -2.0257    0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9238   -0.7777    1.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1087   -2.3440    0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113    1.4972    1.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8701    1.3238   -0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5596    2.3331   -1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6324    3.3146    0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5234    4.3103   -0.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8636    3.3681   -0.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8267   -0.4319    1.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7727   -1.1361   -0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5478   -2.7696    0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747   -4.4910    0.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2495   -3.9750   -1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499   -4.7888   -0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  2  0
 15 18  1  0
 18 19  1  0
 14 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
  7  3  1  0
 23 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 13 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  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  S   UNK     0       6.574   2.310   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       9.242  -3.850   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.574  -3.850   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.114   2.310   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.034   2.310   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      13.404  -0.008   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      10.576  -1.540   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       3.907   0.770   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      13.243  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.650  -2.166   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.680  -1.022   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.910   0.312   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.909  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.260   1.022   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.580   2.528   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.242  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.908  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.574   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.908   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.574  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.241   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.241  -1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.574   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.908   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.241  -4.620   0.000  0.00  0.00           C+0
CONECT    1    4    5   18   23                                             
CONECT    2   16                                                            
CONECT    3   20   25                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    9   12   14                                                  
CONECT    7   13   16                                                       
CONECT    8   21                                                            
CONECT    9    6   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    6   11                                                       
CONECT   13    7    9                                                       
CONECT   14    6   15                                                       
CONECT   15   14                                                            
CONECT   16    2    7   17                                                  
CONECT   17   16   19   20                                                  
CONECT   18    1   19   21                                                  
CONECT   19   17   18                                                       
CONECT   20    3   17   22                                                  
CONECT   21    8   18   22                                                  
CONECT   22   20   21                                                       
CONECT   23    1   24                                                       
CONECT   24   23                                                            
CONECT   25    3                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0015633
HETATM    1  C1  UNL     1       4.571   2.561  -0.170  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.177   1.281  -0.689  1.00  0.00           C  
HETATM    3  N1  UNL     1       4.704   0.131   0.055  1.00  0.00           N  
HETATM    4  C3  UNL     1       5.324  -1.038  -0.500  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.529  -1.320  -1.742  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.248  -0.556  -1.603  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.279  -0.061  -0.162  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.779  -1.109   0.787  1.00  0.00           C  
HETATM    9  N2  UNL     1       1.360  -1.387   0.660  1.00  0.00           N  
HETATM   10  C8  UNL     1       0.393  -0.388   0.876  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.802   0.799   1.198  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.040  -0.555   0.774  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.864   0.554   1.025  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.237   0.485   0.950  1.00  0.00           C  
HETATM   15  S1  UNL     1      -4.255   1.861   1.261  1.00  0.00           S  
HETATM   16  O2  UNL     1      -5.166   1.648   2.415  1.00  0.00           O  
HETATM   17  O3  UNL     1      -3.389   3.053   1.500  1.00  0.00           O  
HETATM   18  C12 UNL     1      -5.216   2.198  -0.220  1.00  0.00           C  
HETATM   19  C13 UNL     1      -6.122   3.387  -0.008  1.00  0.00           C  
HETATM   20  C14 UNL     1      -3.836  -0.712   0.617  1.00  0.00           C  
HETATM   21  N3  UNL     1      -5.245  -0.770   0.544  1.00  0.00           N  
HETATM   22  C15 UNL     1      -3.082  -1.835   0.359  1.00  0.00           C  
HETATM   23  C16 UNL     1      -1.681  -1.719   0.448  1.00  0.00           C  
HETATM   24  O4  UNL     1      -0.943  -2.850   0.188  1.00  0.00           O  
HETATM   25  C17 UNL     1      -1.536  -4.077  -0.153  1.00  0.00           C  
HETATM   26  H1  UNL     1       5.249   3.388  -0.475  1.00  0.00           H  
HETATM   27  H2  UNL     1       3.540   2.710  -0.508  1.00  0.00           H  
HETATM   28  H3  UNL     1       4.640   2.510   0.955  1.00  0.00           H  
HETATM   29  H4  UNL     1       5.004   1.178  -1.771  1.00  0.00           H  
HETATM   30  H5  UNL     1       6.275   1.355  -0.534  1.00  0.00           H  
HETATM   31  H6  UNL     1       6.366  -0.724  -0.797  1.00  0.00           H  
HETATM   32  H7  UNL     1       5.367  -1.903   0.204  1.00  0.00           H  
HETATM   33  H8  UNL     1       4.358  -2.414  -1.837  1.00  0.00           H  
HETATM   34  H9  UNL     1       5.036  -0.966  -2.663  1.00  0.00           H  
HETATM   35  H10 UNL     1       3.179   0.303  -2.290  1.00  0.00           H  
HETATM   36  H11 UNL     1       2.366  -1.202  -1.798  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.720   0.890  -0.073  1.00  0.00           H  
HETATM   38  H13 UNL     1       3.396  -2.026   0.692  1.00  0.00           H  
HETATM   39  H14 UNL     1       2.924  -0.778   1.846  1.00  0.00           H  
HETATM   40  H15 UNL     1       1.109  -2.344   0.405  1.00  0.00           H  
HETATM   41  H16 UNL     1      -1.411   1.497   1.286  1.00  0.00           H  
HETATM   42  H17 UNL     1      -5.870   1.324  -0.400  1.00  0.00           H  
HETATM   43  H18 UNL     1      -4.560   2.333  -1.090  1.00  0.00           H  
HETATM   44  H19 UNL     1      -6.632   3.315   0.959  1.00  0.00           H  
HETATM   45  H20 UNL     1      -5.523   4.310  -0.088  1.00  0.00           H  
HETATM   46  H21 UNL     1      -6.864   3.368  -0.847  1.00  0.00           H  
HETATM   47  H22 UNL     1      -5.827  -0.432   1.345  1.00  0.00           H  
HETATM   48  H23 UNL     1      -5.773  -1.136  -0.277  1.00  0.00           H  
HETATM   49  H24 UNL     1      -3.548  -2.770   0.100  1.00  0.00           H  
HETATM   50  H25 UNL     1      -2.075  -4.491   0.739  1.00  0.00           H  
HETATM   51  H26 UNL     1      -2.249  -3.975  -1.002  1.00  0.00           H  
HETATM   52  H27 UNL     1      -0.750  -4.789  -0.491  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4    7
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7   35   36
CONECT    7    8   37
CONECT    8    9   38   39
CONECT    9   10   40
CONECT   10   11   11   12
CONECT   12   13   13   23
CONECT   13   14   41
CONECT   14   15   20   20
CONECT   15   16   16   17   17
CONECT   15   18
CONECT   18   19   42   43
CONECT   19   44   45   46
CONECT   20   21   22
CONECT   21   47   48
CONECT   22   23   23   49
CONECT   23   24
CONECT   24   25
CONECT   25   50   51   52
END

HMDB0015633
     RDKit          3D
Amisulpride
 52 53  0  0  0  0  0  0  0  0999 V2000
    4.5714    2.5607   -0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1767    1.2806   -0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7042    0.1309    0.0553 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3244   -1.0376   -0.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5286   -1.3201   -1.7418 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2477   -0.5560   -1.6030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2791   -0.0611   -0.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7788   -1.1094    0.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3603   -1.3867    0.6596 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3928   -0.3875    0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8024    0.7994    1.1983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396   -0.5548    0.7736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8638    0.5544    1.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2367    0.4851    0.9497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2547    1.8610    1.2612 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.1665    1.6484    2.4153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3888    3.0527    1.5004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2165    2.1980   -0.2203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1223    3.3870   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8358   -0.7121    0.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2446   -0.7697    0.5437 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0822   -1.8355    0.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6811   -1.7186    0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9433   -2.8497    0.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5364   -4.0769   -0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2491    3.3880   -0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5396    2.7102   -0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6398    2.5101    0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0039    1.1784   -1.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2748    1.3547   -0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3662   -0.7243   -0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3666   -1.9028    0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3582   -2.4143   -1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0358   -0.9657   -2.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1785    0.3032   -2.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3662   -1.2017   -1.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7200    0.8899   -0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3962   -2.0257    0.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9238   -0.7777    1.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1087   -2.3440    0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113    1.4972    1.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8701    1.3238   -0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5596    2.3331   -1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6324    3.3146    0.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5234    4.3103   -0.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8636    3.3681   -0.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8267   -0.4319    1.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7727   -1.1361   -0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5478   -2.7696    0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747   -4.4910    0.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2495   -3.9750   -1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499   -4.7888   -0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  2  0
 15 18  1  0
 18 19  1  0
 14 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
  7  3  1  0
 23 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 13 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 21 47  1  0
 21 48  1  0
 22 49  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide	ChEBI
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-O-anisamide	ChEBI
Aminosultopride	ChEBI
Amisulprida	ChEBI
Amisulpridum	ChEBI
Deniban	Kegg
Solian	Kegg
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulphonyl)-2-methoxybenzamide	Generator
4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulphonyl)-O-anisamide	Generator
Barnetil	HMDB
Sultopride hydrochloride	HMDB
N-(Ethyl-1-pyrrolidinyl- 2-methyl)methoxy-2-ethylsulfonyl-5-benzamide	HMDB
Sultopride	HMDB

Chemical Formula

C₁₇H₂₇N₃O₄S

Average Molecular Weight

369.479

Monoisotopic Molecular Weight

369.172227057

IUPAC Name

4-amino-5-(ethanesulfonyl)-N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide

Traditional Name

amisulpride

CAS Registry Number

53583-79-2

SMILES

CCN1CCCC1CNC(=O)C1=CC(=C(N)C=C1OC)S(=O)(=O)CC

InChI Identifier

InChI=1S/C17H27N3O4S/c1-4-20-8-6-7-12(20)11-19-17(21)13-9-16(25(22,23)5-2)14(18)10-15(13)24-3/h9-10,12H,4-8,11,18H2,1-3H3,(H,19,21)

InChI Key

NTJOBXMMWNYJFB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Aminobenzamides

Alternative Parents

Substituents

Aminobenzamide
Methoxyaniline
Benzamide
Aminophenyl ether
Benzenesulfonyl group
Phenol ether
Aniline or substituted anilines
Methoxybenzene
Benzoyl
Phenoxy compound
Anisole
Alkyl aryl ether
N-alkylpyrrolidine
Pyrrolidine
Sulfone
Sulfonyl
Carboxamide group
Tertiary aliphatic amine
Secondary carboxylic acid amide
Amino acid or derivatives
Tertiary amine
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Primary amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfone (CHEBI:64045 )
benzamides (CHEBI:64045 )
pyrrolidines (CHEBI:64045 )
aromatic amine (CHEBI:64045 )
aromatic amide (CHEBI:64045 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	126 - 127 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.29 g/L	Not Available
LogP	1.10	MANNHOLD,R ET AL. (1990)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	193.1	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.29 g/L	ALOGPS
logP	1.5	ALOGPS
logP	0.25	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	14.03	ChemAxon
pKa (Strongest Basic)	7.05	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	101.73 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	99.84 m³·mol⁻¹	ChemAxon
Polarizability	39.82 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]+	190.116	31661259
DarkChem	[M-H]-	185.818	31661259
DeepCCS	[M+H]+	184.42	30932474
DeepCCS	[M-H]-	181.995	30932474
DeepCCS	[M-2H]-	215.912	30932474
DeepCCS	[M+Na]+	191.949	30932474
AllCCS	[M+H]+	187.0	32859911
AllCCS	[M+H-H2O]+	184.3	32859911
AllCCS	[M+NH4]+	189.4	32859911
AllCCS	[M+Na]+	190.1	32859911
AllCCS	[M-H]-	183.0	32859911
AllCCS	[M+Na-2H]-	183.6	32859911
AllCCS	[M+HCOO]-	184.5	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.	4.26 minutes	32390414
Predicted by Siyang on May 30, 2022	9.6616 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.05 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	186.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	705.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	180.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	112.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	155.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	53.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	244.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	306.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	512.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	619.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	98.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	709.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	183.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	213.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	538.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	462.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	185.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Amisulpride	CCN1CCCC1CNC(=O)C1=CC(=C(N)C=C1OC)S(=O)(=O)CC	4160.4	Standard polar	33892256
Amisulpride	CCN1CCCC1CNC(=O)C1=CC(=C(N)C=C1OC)S(=O)(=O)CC	3182.2	Standard non polar	33892256
Amisulpride	CCN1CCCC1CNC(=O)C1=CC(=C(N)C=C1OC)S(=O)(=O)CC	3352.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Amisulpride,1TMS,isomer #1	CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C)C=C1OC	3250.4	Semi standard non polar	33892256
Amisulpride,1TMS,isomer #1	CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C)C=C1OC	3126.0	Standard non polar	33892256
Amisulpride,1TMS,isomer #1	CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C)C=C1OC	4391.1	Standard polar	33892256
Amisulpride,1TMS,isomer #2	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC)[Si](C)(C)C	3143.1	Semi standard non polar	33892256
Amisulpride,1TMS,isomer #2	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC)[Si](C)(C)C	3066.0	Standard non polar	33892256
Amisulpride,1TMS,isomer #2	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC)[Si](C)(C)C	4598.9	Standard polar	33892256
Amisulpride,2TMS,isomer #1	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C)C=C1OC)[Si](C)(C)C	3198.6	Semi standard non polar	33892256
Amisulpride,2TMS,isomer #1	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C)C=C1OC)[Si](C)(C)C	3235.4	Standard non polar	33892256
Amisulpride,2TMS,isomer #1	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C)C=C1OC)[Si](C)(C)C	4066.4	Standard polar	33892256
Amisulpride,2TMS,isomer #2	CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC	3165.9	Semi standard non polar	33892256
Amisulpride,2TMS,isomer #2	CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC	3318.9	Standard non polar	33892256
Amisulpride,2TMS,isomer #2	CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC	4008.3	Standard polar	33892256
Amisulpride,3TMS,isomer #1	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC)[Si](C)(C)C	3141.7	Semi standard non polar	33892256
Amisulpride,3TMS,isomer #1	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC)[Si](C)(C)C	3436.2	Standard non polar	33892256
Amisulpride,3TMS,isomer #1	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C)[Si](C)(C)C)C=C1OC)[Si](C)(C)C	3683.6	Standard polar	33892256
Amisulpride,1TBDMS,isomer #1	CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C(C)(C)C)C=C1OC	3461.9	Semi standard non polar	33892256
Amisulpride,1TBDMS,isomer #1	CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C(C)(C)C)C=C1OC	3383.0	Standard non polar	33892256
Amisulpride,1TBDMS,isomer #1	CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C(C)(C)C)C=C1OC	4403.7	Standard polar	33892256
Amisulpride,1TBDMS,isomer #2	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC)[Si](C)(C)C(C)(C)C	3385.6	Semi standard non polar	33892256
Amisulpride,1TBDMS,isomer #2	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC)[Si](C)(C)C(C)(C)C	3300.3	Standard non polar	33892256
Amisulpride,1TBDMS,isomer #2	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC)[Si](C)(C)C(C)(C)C	4619.2	Standard polar	33892256
Amisulpride,2TBDMS,isomer #1	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C	3623.1	Semi standard non polar	33892256
Amisulpride,2TBDMS,isomer #1	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C	3725.6	Standard non polar	33892256
Amisulpride,2TBDMS,isomer #1	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C	4125.8	Standard polar	33892256
Amisulpride,2TBDMS,isomer #2	CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC	3611.3	Semi standard non polar	33892256
Amisulpride,2TBDMS,isomer #2	CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC	3794.3	Standard non polar	33892256
Amisulpride,2TBDMS,isomer #2	CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC	4032.1	Standard polar	33892256
Amisulpride,3TBDMS,isomer #1	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C	3772.5	Semi standard non polar	33892256
Amisulpride,3TBDMS,isomer #1	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C	4133.4	Standard non polar	33892256
Amisulpride,3TBDMS,isomer #1	CCN1CCCC1CN(C(=O)C1=CC(S(=O)(=O)CC)=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC)[Si](C)(C)C(C)(C)C	3840.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Amisulpride GC-MS (Non-derivatized) - 70eV, Positive	splash10-002g-9054000000-b1dc7fa1718d7f3a0b9c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amisulpride 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 - Amisulpride LC-ESI-ITFT , negative-QTOF	splash10-0006-0609000000-2b372299b7870a4920eb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-ITFT , negative-QTOF	splash10-014i-0009000000-99c1cc37ab9cf4683323	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-ITFT , negative-QTOF	splash10-014i-0409000000-4e053b8ec1d55ced8499	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-ITFT , negative-QTOF	splash10-004l-0974000000-de9354d79437a4df60bc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-ITFT , negative-QTOF	splash10-01q9-0900000000-f91d53fb9c883bae9ca3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-ITFT , negative-QTOF	splash10-001i-0900000000-324b93e2df83509f8048	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-ITFT , negative-QTOF	splash10-014i-0009000000-99ab45809f8e56fbb616	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-ITFT , negative-QTOF	splash10-014l-0109000000-93205a0e84bbb061506a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-ITFT , negative-QTOF	splash10-057i-0960000000-23d53c22f66a40ded55b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-ITFT , negative-QTOF	splash10-0006-0509000000-de0803e7c69539424a4e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-QTOF , positive-QTOF	splash10-00di-0019000000-7dec57b5001ab24504cc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-QTOF , positive-QTOF	splash10-00di-0019000000-c532dacf370f0075220b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-QTOF , positive-QTOF	splash10-0006-0092000000-6deb7fed54b4631e9813	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-QTOF , positive-QTOF	splash10-0005-0980000000-c78d2a361bbc674b41ce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-QTOF , positive-QTOF	splash10-0005-0960000000-6a4706ff5588c4035137	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-ITFT , positive-QTOF	splash10-0006-0190000000-e410c0158058e8740df0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-ITFT , positive-QTOF	splash10-00di-0009000000-2237ffbc12b8e6459da5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-ITFT , positive-QTOF	splash10-00di-0029000000-2143af7abc829fd8cacd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amisulpride LC-ESI-ITFT , positive-QTOF	splash10-0006-0290000000-bb210e691e1906ae74a7	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amisulpride 10V, Positive-QTOF	splash10-0h90-0519000000-5ab63698962ae89e61c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amisulpride 20V, Positive-QTOF	splash10-03fr-2931000000-0389f02977c474a38ddb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amisulpride 40V, Positive-QTOF	splash10-0inc-9410000000-85d4a156f97187c4fdbe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amisulpride 10V, Negative-QTOF	splash10-014i-0009000000-5027ef7cd64034ec73ed	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amisulpride 20V, Negative-QTOF	splash10-006x-1239000000-9ed19ba6319c5152a548	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amisulpride 40V, Negative-QTOF	splash10-00r6-8961000000-6b1c70a700a07ca0e565	2016-08-04	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 DB06288	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB06288	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06288

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2074

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Amisulpride

METLIN ID

Not Available

PubChem Compound

2159

PDB ID

Not Available

ChEBI ID

64045

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

Weizman T, Pick CG, Backer MM, Rigai T, Bloch M, Schreiber S: The antinociceptive effect of amisulpride in mice is mediated through opioid mechanisms. Eur J Pharmacol. 2003 Oct 8;478(2-3):155-9. [PubMed:14575800 ]
Rosenzweig P, Canal M, Patat A, Bergougnan L, Zieleniuk I, Bianchetti G: A review of the pharmacokinetics, tolerability and pharmacodynamics of amisulpride in healthy volunteers. Hum Psychopharmacol. 2002 Jan;17(1):1-13. [PubMed:12404702 ]
Leucht S, Pitschel-Walz G, Engel RR, Kissling W: Amisulpride, an unusual "atypical" antipsychotic: a meta-analysis of randomized controlled trials. Am J Psychiatry. 2002 Feb;159(2):180-90. [PubMed:11823257 ]
Moller HJ: Amisulpride: limbic specificity and the mechanism of antipsychotic atypicality. Prog Neuropsychopharmacol Biol Psychiatry. 2003 Oct;27(7):1101-11. [PubMed:14642970 ]

Enzymes

Enzyme Details

1. D(2) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD2
Uniprot ID:: P14416
Molecular weight:: 50618.9

References

Rosenzweig P, Canal M, Patat A, Bergougnan L, Zieleniuk I, Bianchetti G: A review of the pharmacokinetics, tolerability and pharmacodynamics of amisulpride in healthy volunteers. Hum Psychopharmacol. 2002 Jan;17(1):1-13. [PubMed:12404702 ]
Horacek J, Bubenikova-Valesova V, Kopecek M, Palenicek T, Dockery C, Mohr P, Hoschl C: Mechanism of action of atypical antipsychotic drugs and the neurobiology of schizophrenia. CNS Drugs. 2006;20(5):389-409. [PubMed:16696579 ]
Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]

Enzyme Details

2. 5-hydroxytryptamine receptor 7

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase
Gene Name:: HTR7
Uniprot ID:: P34969
Molecular weight:: 53554.4

References

Abbas AI, Hedlund PB, Huang XP, Tran TB, Meltzer HY, Roth BL: Amisulpride is a potent 5-HT7 antagonist: relevance for antidepressant actions in vivo. Psychopharmacology (Berl). 2009 Jul;205(1):119-28. doi: 10.1007/s00213-009-1521-8. Epub 2009 Apr 1. [PubMed:19337725 ]

Enzyme Details

3. 5-hydroxytryptamine receptor 2A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

References

Tyson PJ, Roberts KH, Mortimer AM: Are the cognitive effects of atypical antipsychotics influenced by their affinity to 5HT-2A receptors? Int J Neurosci. 2004 Jun;114(6):593-611. [PubMed:15204055 ]

Enzyme Details

4. D(3) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation
Gene Name:: DRD3
Uniprot ID:: P35462
Molecular weight:: 44224.3

References

Rosenzweig P, Canal M, Patat A, Bergougnan L, Zieleniuk I, Bianchetti G: A review of the pharmacokinetics, tolerability and pharmacodynamics of amisulpride in healthy volunteers. Hum Psychopharmacol. 2002 Jan;17(1):1-13. [PubMed:12404702 ]
Horacek J, Bubenikova-Valesova V, Kopecek M, Palenicek T, Dockery C, Mohr P, Hoschl C: Mechanism of action of atypical antipsychotic drugs and the neurobiology of schizophrenia. CNS Drugs. 2006;20(5):389-409. [PubMed:16696579 ]
Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]

Showing metabocard for Amisulpride (HMDB0015633)

MOL for HMDB0015633 (Amisulpride)

3D MOL for HMDB0015633 (Amisulpride)

3D SDF for HMDB0015633 (Amisulpride)

3D-SDF for HMDB0015633 (Amisulpride)

PDB for HMDB0015633 (Amisulpride)

3D PDB for HMDB0015633 (Amisulpride)

SMILES for HMDB0015633 (Amisulpride)

INCHI for HMDB0015633 (Amisulpride)

Structure for HMDB0015633 (Amisulpride)

3D Structure for HMDB0015633 (Amisulpride)

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

References

References

References

References