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Showing metabocard for Acamprosate (HMDB0014797)

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enzymes (3) Show 3 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2023-02-21 17:18:17 UTC
HMDB IDHMDB0014797
Secondary Accession Numbers
  • HMDB14797
Metabolite Identification
Common NameAcamprosate
DescriptionAcamprosate, also known by the brand name Campral™, is a drug used for treating alcohol dependence. Acamprosate is thought to stabilize the chemical balance in the brain that would otherwise be disrupted by alcoholism, possibly by blocking glutaminergic N-methyl-D-aspartate receptors, while gamma-aminobutyric acid type A receptors are activated. Reports indicate that acamprosate only works with a combination of attending support groups and abstinence from alcohol. Certain serious side effects include allergic reactions, irregular heartbeats, and low or high blood pressure, while less serious side effects include headaches, insomnia, and impotence. Acamprosate should not be taken by people with kidney problems or allergies to the drug.
Structure
Data?1676999897
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014797 (Acamprosate)

659
  Mrv0541 02231214522D          

 11 10  0  0  0  0            999 V2000
    2.8075   -0.2615    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3950    0.4529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200   -0.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    0.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.2615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  8  1  0  0  0  0
  5 10  2  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
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3D MOL for HMDB0014797 (Acamprosate)

HMDB0014797
     RDKit          3D
Acamprosate
 22 21  0  0  0  0  0  0  0  0999 V2000
   -3.4410    0.0675    0.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6964    0.6204   -1.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6807    0.7044   -1.4575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3700    0.5073   -0.5479 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7996    0.1064    0.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6949    0.2063    0.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4029   -0.6108   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1415   -0.3024   -0.1256 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.4779   -0.8023    1.2394 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3406    1.1902   -0.2380 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -1.1236   -1.2056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4412    0.1169    0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9489   -0.8579    0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0843    0.8818    1.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302    0.8461   -1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1069   -0.9033    1.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1318    0.8027    1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0812   -0.2201    1.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0192    1.2651    0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1013   -0.3304   -1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2137   -1.6889   -0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7410   -0.5334   -1.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
 11 22  1  0
M  END
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3D SDF for HMDB0014797 (Acamprosate)

659
  Mrv0541 02231214522D          

 11 10  0  0  0  0            999 V2000
    2.8075   -0.2615    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3950    0.4529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2200   -0.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    0.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655   -0.2615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3799    0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0944   -0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  8  1  0  0  0  0
  5 10  2  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014797

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NCCCS(O)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H11NO4S/c1-5(7)6-3-2-4-11(8,9)10/h2-4H2,1H3,(H,6,7)(H,8,9,10)

> <INCHI_KEY>
AFCGFAGUEYAMAO-UHFFFAOYSA-N

> <FORMULA>
C5H11NO4S

> <MOLECULAR_WEIGHT>
181.21

> <EXACT_MASS>
181.040878535

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
17.165782807209713

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-acetamidopropane-1-sulfonic acid

> <ALOGPS_LOGP>
-1.79

> <JCHEM_LOGP>
-2.829227371083991

> <ALOGPS_LOGS>
-0.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.12379824950273

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.1448904008673297

> <JCHEM_PKA_STRONGEST_BASIC>
-0.46995019711612296

> <JCHEM_POLAR_SURFACE_AREA>
83.47

> <JCHEM_REFRACTIVITY>
38.9143

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acamprosate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0014797 (Acamprosate)

HMDB0014797
     RDKit          3D
Acamprosate
 22 21  0  0  0  0  0  0  0  0999 V2000
   -3.4410    0.0675    0.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6964    0.6204   -1.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6807    0.7044   -1.4575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3700    0.5073   -0.5479 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7996    0.1064    0.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6949    0.2063    0.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4029   -0.6108   -0.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1415   -0.3024   -0.1256 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.4779   -0.8023    1.2394 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3406    1.1902   -0.2380 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -1.1236   -1.2056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4412    0.1169    0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9489   -0.8579    0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0843    0.8818    1.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302    0.8461   -1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1069   -0.9033    1.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1318    0.8027    1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0812   -0.2201    1.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0192    1.2651    0.6750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1013   -0.3304   -1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2137   -1.6889   -0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7410   -0.5334   -1.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
 11 22  1  0
M  END
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PDB for HMDB0014797 (Acamprosate)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 659                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       5.241  -0.488   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       3.907  -1.258   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.471   0.845   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.011  -1.822   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.909   1.822   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      10.576  -0.488   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.908  -0.488   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.574   0.282   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.242   0.282   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.909   0.282   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.243  -0.488   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    8                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5   10                                                            
CONECT    6    9   10                                                       
CONECT    7    8    9                                                       
CONECT    8    1    7                                                       
CONECT    9    6    7                                                       
CONECT   10    5    6   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for HMDB0014797 (Acamprosate)

COMPND    HMDB0014797
HETATM    1  C1  UNL     1      -3.441   0.067   0.524  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.696   0.620  -1.070  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.681   0.704  -1.458  1.00  0.00           O  
HETATM    4  N1  UNL     1      -1.370   0.507  -0.548  1.00  0.00           N  
HETATM    5  C3  UNL     1      -0.800   0.106   0.651  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.695   0.206   0.687  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.403  -0.611  -0.372  1.00  0.00           C  
HETATM    8  S1  UNL     1       3.141  -0.302  -0.126  1.00  0.00           S  
HETATM    9  O2  UNL     1       3.478  -0.802   1.239  1.00  0.00           O  
HETATM   10  O3  UNL     1       3.341   1.190  -0.238  1.00  0.00           O  
HETATM   11  O4  UNL     1       4.117  -1.124  -1.206  1.00  0.00           O  
HETATM   12  H1  UNL     1      -4.441   0.117   0.164  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.949  -0.858   0.463  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.084   0.882   1.071  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.630   0.846  -1.295  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.107  -0.903   1.022  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.132   0.803   1.481  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.081  -0.220   1.654  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.019   1.265   0.675  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.101  -0.330  -1.396  1.00  0.00           H  
HETATM   21  H10 UNL     1       1.214  -1.689  -0.283  1.00  0.00           H  
HETATM   22  H11 UNL     1       4.741  -0.533  -1.641  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3    4
CONECT    4    5   15
CONECT    5    6   16   17
CONECT    6    7   18   19
CONECT    7    8   20   21
CONECT    8    9    9   10   10
CONECT    8   11
CONECT   11   22
END
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SMILES for HMDB0014797 (Acamprosate)

CC(=O)NCCCS(O)(=O)=O
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INCHI for HMDB0014797 (Acamprosate)

InChI=1S/C5H11NO4S/c1-5(7)6-3-2-4-11(8,9)10/h2-4H2,1H3,(H,6,7)(H,8,9,10)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-Acetamido-1-propanesulfonic acidChEBI
AcamprosatoChEBI
AcamprosatumChEBI
N-AcetylhomotaurineChEBI
AotalKegg
3-Acetamido-1-propanesulfonateGenerator
3-Acetamido-1-propanesulphonateGenerator
3-Acetamido-1-propanesulphonic acidGenerator
Acamprosic acidGenerator
3-(Acetylamino)propanesulphonic acidHMDB
CampralHMDB
Campral ecHMDB
N-Acetylhomotaurine, monopotassium saltHMDB
N-Acetylhomotaurine, zinc (2:1) saltHMDB
RegtectHMDB
Acamprosate calciumHMDB
N-Acetylhomotaurine, calcium (2:1) saltHMDB
N-Acetylhomotaurine, magnesium (2:1) saltHMDB
N-Acetylhomotaurine, monolithium saltHMDB
N-Acetylhomotaurine, monosodium saltHMDB
ZulexHMDB
Calcium acetyl homotaurinateHMDB
Calcium acetylhomotaurineHMDB
Sodium acetylhomotaurineHMDB
AOTAHMDB
AcamprostateHMDB
Calcium acetylhomotaurinateHMDB
Acetyl homotaurinate, calciumHMDB
Acetylhomotaurinate, calciumHMDB
N Acetylhomotaurine, monolithium saltHMDB
Acetylhomotaurine, calciumHMDB
Acetylhomotaurine, sodiumHMDB
N Acetylhomotaurine, monosodium saltHMDB
N AcetylhomotaurineHMDB
N Acetylhomotaurine, monopotassium saltHMDB
Chemical FormulaC5H11NO4S
Average Molecular Weight181.21
Monoisotopic Molecular Weight181.040878535
IUPAC Name3-acetamidopropane-1-sulfonic acid
Traditional Nameacamprosate
CAS Registry Number77337-76-9
SMILES
CC(=O)NCCCS(O)(=O)=O
InChI Identifier
InChI=1S/C5H11NO4S/c1-5(7)6-3-2-4-11(8,9)10/h2-4H2,1H3,(H,6,7)(H,8,9,10)
InChI KeyAFCGFAGUEYAMAO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organosulfonic acids. Organosulfonic acids are compounds containing the sulfonic acid group, which has the general structure RS(=O)2OH (R is not a hydrogen atom).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfonic acids and derivatives
Sub ClassOrganosulfonic acids and derivatives
Direct ParentOrganosulfonic acids
Alternative Parents
Substituents
  • Organosulfonic acid
  • Sulfonyl
  • Alkanesulfonic acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility18.8 g/LNot Available
LogP-1.1Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility18.8 g/LALOGPS
logP-1.8ALOGPS
logP-2.8ChemAxon
logS-0.98ALOGPS
pKa (Strongest Acidic)-1.1ChemAxon
pKa (Strongest Basic)-0.47ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.47 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity38.91 m³·mol⁻¹ChemAxon
Polarizability17.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.67631661259
DarkChem[M-H]-134.16531661259
DeepCCS[M+H]+134.74230932474
DeepCCS[M-H]-130.91330932474
DeepCCS[M-2H]-168.12930932474
DeepCCS[M+Na]+143.57430932474
AllCCS[M+H]+139.132859911
AllCCS[M+H-H2O]+135.432859911
AllCCS[M+NH4]+142.632859911
AllCCS[M+Na]+143.632859911
AllCCS[M-H]-135.132859911
AllCCS[M+Na-2H]-137.132859911
AllCCS[M+HCOO]-139.332859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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, 2022.3.32 minutes32390414
Predicted by Siyang on May 30, 20228.772 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.91 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid152.0 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid989.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid279.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid73.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid170.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid56.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid238.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid254.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)630.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid594.6 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid67.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid779.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid178.9 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid169.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate524.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA246.8 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water201.1 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AcamprosateCC(=O)NCCCS(O)(=O)=O3050.5Standard polar33892256
AcamprosateCC(=O)NCCCS(O)(=O)=O1483.6Standard non polar33892256
AcamprosateCC(=O)NCCCS(O)(=O)=O1816.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Acamprosate,1TMS,isomer #1CC(=O)NCCCS(=O)(=O)O[Si](C)(C)C1793.7Semi standard non polar33892256
Acamprosate,1TMS,isomer #1CC(=O)NCCCS(=O)(=O)O[Si](C)(C)C1637.0Standard non polar33892256
Acamprosate,1TMS,isomer #1CC(=O)NCCCS(=O)(=O)O[Si](C)(C)C2570.9Standard polar33892256
Acamprosate,1TMS,isomer #2CC(=O)N(CCCS(=O)(=O)O)[Si](C)(C)C1774.5Semi standard non polar33892256
Acamprosate,1TMS,isomer #2CC(=O)N(CCCS(=O)(=O)O)[Si](C)(C)C1697.9Standard non polar33892256
Acamprosate,1TMS,isomer #2CC(=O)N(CCCS(=O)(=O)O)[Si](C)(C)C2887.8Standard polar33892256
Acamprosate,2TMS,isomer #1CC(=O)N(CCCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C1788.4Semi standard non polar33892256
Acamprosate,2TMS,isomer #1CC(=O)N(CCCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C1843.5Standard non polar33892256
Acamprosate,2TMS,isomer #1CC(=O)N(CCCS(=O)(=O)O[Si](C)(C)C)[Si](C)(C)C2291.0Standard polar33892256
Acamprosate,1TBDMS,isomer #1CC(=O)NCCCS(=O)(=O)O[Si](C)(C)C(C)(C)C2061.8Semi standard non polar33892256
Acamprosate,1TBDMS,isomer #1CC(=O)NCCCS(=O)(=O)O[Si](C)(C)C(C)(C)C1919.7Standard non polar33892256
Acamprosate,1TBDMS,isomer #1CC(=O)NCCCS(=O)(=O)O[Si](C)(C)C(C)(C)C2630.2Standard polar33892256
Acamprosate,1TBDMS,isomer #2CC(=O)N(CCCS(=O)(=O)O)[Si](C)(C)C(C)(C)C1994.0Semi standard non polar33892256
Acamprosate,1TBDMS,isomer #2CC(=O)N(CCCS(=O)(=O)O)[Si](C)(C)C(C)(C)C1973.6Standard non polar33892256
Acamprosate,1TBDMS,isomer #2CC(=O)N(CCCS(=O)(=O)O)[Si](C)(C)C(C)(C)C2914.1Standard polar33892256
Acamprosate,2TBDMS,isomer #1CC(=O)N(CCCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2269.0Semi standard non polar33892256
Acamprosate,2TBDMS,isomer #1CC(=O)N(CCCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2386.5Standard non polar33892256
Acamprosate,2TBDMS,isomer #1CC(=O)N(CCCS(=O)(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2408.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Acamprosate GC-MS (Non-derivatized) - 70eV, Positivesplash10-007o-9100000000-8420bb56903c56b30a732017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acamprosate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acamprosate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-ITFT , negative-QTOFsplash10-001i-1900000000-095fc64fb4490a8d6b4d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-c177d5ee7162b0b8756d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-40eaa1bb480a683309402017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-ITFT , negative-QTOFsplash10-001i-1900000000-35bfe6cae36755d1cf1c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-ITFT , negative-QTOFsplash10-0059-9500000000-d366cda3213379d7501b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-ITFT , negative-QTOFsplash10-004i-9000000000-4374601f59e1dc8df0eb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-ITFT , negative-QTOFsplash10-004i-9000000000-011f30e0257faffd45532017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-c179316d784a91f87c592017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-8cf123c7cf7dddcf68382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-ITFT , negative-QTOFsplash10-001i-1900000000-84a7d1cc6ca5022d4da72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-ITFT , negative-QTOFsplash10-0059-9500000000-4503d9afc6bab741521b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-ITFT , negative-QTOFsplash10-004i-9000000000-8c2ba21c044eeada78392017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-ITFT , negative-QTOFsplash10-004i-9000000000-dd14c920c5211780d1722017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-ITFT , negative-QTOFsplash10-001i-1900000000-dac38f625c8648b643c42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-QTOF , positive-QTOFsplash10-0006-0900000000-3684e08456a971400c3d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-QTOF , positive-QTOFsplash10-0006-0900000000-6137fe4463b3675f55eb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-QTOF , positive-QTOFsplash10-00di-0900000000-58f776a52000101b8fb72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-ITFT , positive-QTOFsplash10-0006-0900000000-d8de420d40b45a34ea952017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acamprosate LC-ESI-ITFT , positive-QTOFsplash10-001l-0900000000-1bb28abe8034966ad8292017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acamprosate 10V, Positive-QTOFsplash10-0019-0900000000-343cd651472c88796a612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acamprosate 20V, Positive-QTOFsplash10-05g0-5900000000-0c71e48c69c18769563d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acamprosate 40V, Positive-QTOFsplash10-0006-9300000000-181e815cd85a7505ce4a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acamprosate 10V, Negative-QTOFsplash10-001i-4900000000-1f6b18b2f30371ea12ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acamprosate 20V, Negative-QTOFsplash10-001i-9500000000-50bd4d569514037edb1b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acamprosate 40V, Negative-QTOFsplash10-001i-9000000000-ec0629ff72c5e58a04132016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00659 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00659 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00659
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID64300
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcamprosate
METLIN IDNot Available
PubChem Compound71158
PDB IDNot Available
ChEBI ID51041
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tsai G, Coyle JT: The role of glutamatergic neurotransmission in the pathophysiology of alcoholism. Annu Rev Med. 1998;49:173-84. [PubMed:9509257 ]
  2. Mason BJ: Treatment of alcohol-dependent outpatients with acamprosate: a clinical review. J Clin Psychiatry. 2001;62 Suppl 20:42-8. [PubMed:11584875 ]
  3. Williams SH: Medications for treating alcohol dependence. Am Fam Physician. 2005 Nov 1;72(9):1775-80. [PubMed:16300039 ]
  4. Feeney GF, Connor JP, Young RM, Tucker J, McPherson A: Combined acamprosate and naltrexone, with cognitive behavioural therapy is superior to either medication alone for alcohol abstinence: a single centres' experience with pharmacotherapy. Alcohol Alcohol. 2006 May-Jun;41(3):321-7. Epub 2006 Feb 8. [PubMed:16467406 ]
  5. Mason BJ, Goodman AM, Chabac S, Lehert P: Effect of oral acamprosate on abstinence in patients with alcohol dependence in a double-blind, placebo-controlled trial: the role of patient motivation. J Psychiatr Res. 2006 Aug;40(5):383-93. Epub 2006 Mar 20. [PubMed:16546214 ]

Enzymes

Enzyme Details
1. Metabotropic glutamate receptor 5
General function:
Involved in G-protein coupled receptor activity
Specific function:
Receptor for glutamate. The activity of this receptor is mediated by a G-protein that activates a phosphatidylinositol- calcium second messenger system and generates a calcium-activated chloride current
Gene Name:
GRM5
Uniprot ID:
P41594
Molecular weight:
132467.6
References
  1. De Witte P, Littleton J, Parot P, Koob G: Neuroprotective and abstinence-promoting effects of acamprosate: elucidating the mechanism of action. CNS Drugs. 2005;19(6):517-37. [PubMed:15963001 ]
Enzyme Details
2. Metabotropic glutamate receptor 1
General function:
Involved in G-protein coupled receptor activity
Specific function:
Receptor for glutamate. The activity of this receptor is mediated by a G-protein that activates a phosphatidylinositol- calcium second messenger system. May participate in the central action of glutamate in the CNS, such as long-term potentiation in the hippocampus and long-term depression in the cerebellum
Gene Name:
GRM1
Uniprot ID:
Q13255
Molecular weight:
132365.9
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Enzyme Details
3. Glutamate [NMDA] receptor subunit 3A
General function:
Involved in ionotropic glutamate receptor activity
Specific function:
NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May play a role in the development of dendritic spines. May play a role in PPP2CB-NMDAR mediated signaling mechanism
Gene Name:
GRIN3A
Uniprot ID:
Q8TCU5
Molecular weight:
125464.1
References
  1. Smothers CT, Woodward JJ: Pharmacological characterization of glycine-activated currents in HEK 293 cells expressing N-methyl-D-aspartate NR1 and NR3 subunits. J Pharmacol Exp Ther. 2007 Aug;322(2):739-48. Epub 2007 May 14. [PubMed:17502428 ]