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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:50:46 UTC

Update Date

2021-09-26 23:07:32 UTC

HMDB ID

HMDB0253940

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Lacosamide

Description

N-benzyl-2-[(1-hydroxyethylidene)amino]-3-methoxypropanimidic acid belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. Based on a literature review very few articles have been published on N-benzyl-2-[(1-hydroxyethylidene)amino]-3-methoxypropanimidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Lacosamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lacosamide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0253940
     RDKit          3D
Lacosamide
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.1103   -2.3571    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -1.5056    0.6056 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6953   -0.9336   -0.6397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5153    0.0110   -0.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8086    1.0719    0.4498 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    2.2264    0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4620    2.5197   -1.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000    3.1986    1.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3615   -0.8113   -0.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4172   -1.5490    1.1221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6943   -0.8492   -0.7683 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723   -1.6012   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9468   -0.6533   -0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277    0.7148   -0.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7058    1.6081    0.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9624    1.1700    0.6652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1986   -0.2034    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2216   -1.1070    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7351   -3.1143   -0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4620   -2.8452    1.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8932   -1.7459   -0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5920   -0.4398   -1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4380   -1.7808   -1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3308    0.4535   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741    2.4464   -1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8860    3.5393   -1.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2055    1.8044   -1.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0759    3.9955    0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3706   -1.6356    1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1942   -2.1508   -1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7394   -2.3401    0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7215    1.0554   -0.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4900    2.6606    0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7674    1.8401    0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1966   -0.5229    0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4173   -2.1698    0.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
  9 11  2  3
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END


  Mrv1652306031608282D          

 18 18  0  0  0  0            999 V2000
   -0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 10  1  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  4  0  0  0
 14 13  2  0  0  0  0
 15 10  2  0  0  0  0
 15 12  1  4  0  0  0
 16 10  1  0  0  0  0
 17 13  1  0  0  0  0
 18  2  1  0  0  0  0
 18  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253940

> <DATABASE_NAME>
hmdb

> <SMILES>
COCC(N=C(C)O)C(O)=NCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H18N2O3/c1-10(16)15-12(9-18-2)13(17)14-8-11-6-4-3-5-7-11/h3-7,12H,8-9H2,1-2H3,(H,14,17)(H,15,16)

> <INCHI_KEY>
VPPJLAIAVCUEMN-UHFFFAOYSA-N

> <FORMULA>
C13H18N2O3

> <MOLECULAR_WEIGHT>
250.298

> <EXACT_MASS>
250.131742448

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.998931382299094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-benzyl-2-[(1-hydroxyethylidene)amino]-3-methoxypropanimidic acid

> <ALOGPS_LOGP>
1.40

> <JCHEM_LOGP>
0.48440529061713106

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
6.194037546019828

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.229088566103046

> <JCHEM_PKA_STRONGEST_BASIC>
4.750009432989703

> <JCHEM_POLAR_SURFACE_AREA>
74.41000000000001

> <JCHEM_REFRACTIVITY>
68.61090000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-benzyl-2-[(1-hydroxyethylidene)amino]-3-methoxypropanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253940
     RDKit          3D
Lacosamide
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.1103   -2.3571    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -1.5056    0.6056 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6953   -0.9336   -0.6397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5153    0.0110   -0.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8086    1.0719    0.4498 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    2.2264    0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4620    2.5197   -1.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000    3.1986    1.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3615   -0.8113   -0.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4172   -1.5490    1.1221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6943   -0.8492   -0.7683 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723   -1.6012   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9468   -0.6533   -0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277    0.7148   -0.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7058    1.6081    0.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9624    1.1700    0.6652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1986   -0.2034    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2216   -1.1070    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7351   -3.1143   -0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4620   -2.8452    1.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8932   -1.7459   -0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5920   -0.4398   -1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4380   -1.7808   -1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3308    0.4535   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741    2.4464   -1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8860    3.5393   -1.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2055    1.8044   -1.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0759    3.9955    0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3706   -1.6356    1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1942   -2.1508   -1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7394   -2.3401    0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7215    1.0554   -0.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4900    2.6606    0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7674    1.8401    0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1966   -0.5229    0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4173   -2.1698    0.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
  9 11  2  3
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      -0.000  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.000   4.620   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      -1.334   8.470   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       1.334   8.470   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   18                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8   11   14                                                       
CONECT    9   12   18                                                       
CONECT   10    1   15   16                                                  
CONECT   11    6    7    8                                                  
CONECT   12    9   13   15                                                  
CONECT   13   12   14   17                                                  
CONECT   14    8   13                                                       
CONECT   15   10   12                                                       
CONECT   16   10                                                            
CONECT   17   13                                                            
CONECT   18    2    9                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0253940
HETATM    1  C1  UNL     1       4.110  -2.357   0.367  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.023  -1.506   0.606  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.695  -0.934  -0.640  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.515   0.011  -0.469  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.809   1.072   0.450  1.00  0.00           N  
HETATM    6  C4  UNL     1       2.241   2.226   0.070  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.462   2.520  -1.376  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.500   3.199   1.032  1.00  0.00           O  
HETATM    9  C6  UNL     1       0.362  -0.811  -0.052  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.417  -1.549   1.122  1.00  0.00           O  
HETATM   11  N2  UNL     1      -0.694  -0.849  -0.768  1.00  0.00           N  
HETATM   12  C7  UNL     1      -1.872  -1.601  -0.477  1.00  0.00           C  
HETATM   13  C8  UNL     1      -2.947  -0.653  -0.081  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.728   0.715  -0.037  1.00  0.00           C  
HETATM   15  C10 UNL     1      -3.706   1.608   0.326  1.00  0.00           C  
HETATM   16  C11 UNL     1      -4.962   1.170   0.665  1.00  0.00           C  
HETATM   17  C12 UNL     1      -5.199  -0.203   0.625  1.00  0.00           C  
HETATM   18  C13 UNL     1      -4.222  -1.107   0.262  1.00  0.00           C  
HETATM   19  H1  UNL     1       3.735  -3.114  -0.381  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.462  -2.845   1.293  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.893  -1.746  -0.127  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.592  -0.440  -1.022  1.00  0.00           H  
HETATM   23  H5  UNL     1       2.438  -1.781  -1.298  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.331   0.454  -1.469  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.474   2.446  -1.886  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.886   3.539  -1.471  1.00  0.00           H  
HETATM   27  H9  UNL     1       3.205   1.804  -1.779  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.076   3.996   0.863  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.371  -1.636   1.764  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.194  -2.151  -1.397  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.739  -2.340   0.337  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.721   1.055  -0.309  1.00  0.00           H  
HETATM   33  H15 UNL     1      -3.490   2.661   0.347  1.00  0.00           H  
HETATM   34  H16 UNL     1      -5.767   1.840   0.959  1.00  0.00           H  
HETATM   35  H17 UNL     1      -6.197  -0.523   0.897  1.00  0.00           H  
HETATM   36  H18 UNL     1      -4.417  -2.170   0.235  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3
CONECT    3    4   22   23
CONECT    4    5    9   24
CONECT    5    6    6
CONECT    6    7    8
CONECT    7   25   26   27
CONECT    8   28
CONECT    9   10   11   11
CONECT   10   29
CONECT   11   12
CONECT   12   13   30   31
CONECT   13   14   14   18
CONECT   14   15   32
CONECT   15   16   16   33
CONECT   16   17   34
CONECT   17   18   18   35
CONECT   18   36
END

HMDB0253940
     RDKit          3D
Lacosamide
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.1103   -2.3571    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -1.5056    0.6056 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6953   -0.9336   -0.6397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5153    0.0110   -0.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8086    1.0719    0.4498 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    2.2264    0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4620    2.5197   -1.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000    3.1986    1.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3615   -0.8113   -0.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4172   -1.5490    1.1221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6943   -0.8492   -0.7683 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8723   -1.6012   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9468   -0.6533   -0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277    0.7148   -0.0365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7058    1.6081    0.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9624    1.1700    0.6652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1986   -0.2034    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2216   -1.1070    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7351   -3.1143   -0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4620   -2.8452    1.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8932   -1.7459   -0.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5920   -0.4398   -1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4380   -1.7808   -1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3308    0.4535   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741    2.4464   -1.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8860    3.5393   -1.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2055    1.8044   -1.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0759    3.9955    0.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3706   -1.6356    1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1942   -2.1508   -1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7394   -2.3401    0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7215    1.0554   -0.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4900    2.6606    0.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7674    1.8401    0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1966   -0.5229    0.8966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4173   -2.1698    0.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
  9 11  2  3
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Benzyl-2-[(1-hydroxyethylidene)amino]-3-methoxypropanimidate	Generator
N-Benzyl-2-acetamido-3-methoxypropionamide	MeSH
N-Benzyl-acmeoprnh2	MeSH
Lacosamide	MeSH
Vimpat	MeSH

Chemical Formula

C₁₃H₁₈N₂O₃

Average Molecular Weight

250.298

Monoisotopic Molecular Weight

250.131742448

IUPAC Name

N-benzyl-2-[(1-hydroxyethylidene)amino]-3-methoxypropanimidic acid

Traditional Name

N-benzyl-2-[(1-hydroxyethylidene)amino]-3-methoxypropanimidic acid

CAS Registry Number

Not Available

SMILES

COCC(N=C(C)O)C(O)=NCC1=CC=CC=C1

InChI Identifier

InChI=1S/C13H18N2O3/c1-10(16)15-12(9-18-2)13(17)14-8-11-6-4-3-5-7-11/h3-7,12H,8-9H2,1-2H3,(H,14,17)(H,15,16)

InChI Key

VPPJLAIAVCUEMN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids and derivatives

Alternative Parents

Substituents

N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Monocyclic benzene moiety
Benzenoid
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Dialkyl ether
Ether
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
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: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.4	ALOGPS
logP	0.48	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	2.23	ChemAxon
pKa (Strongest Basic)	4.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.41 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	68.61 m³·mol⁻¹	ChemAxon
Polarizability	27 Å³	ChemAxon
Number of Rings	1	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
DeepCCS	[M+H]+	158.832	30932474
DeepCCS	[M-H]-	156.474	30932474
DeepCCS	[M-2H]-	189.36	30932474
DeepCCS	[M+Na]+	164.925	30932474
AllCCS	[M+H]+	158.3	32859911
AllCCS	[M+H-H2O]+	154.8	32859911
AllCCS	[M+NH4]+	161.6	32859911
AllCCS	[M+Na]+	162.5	32859911
AllCCS	[M-H]-	159.9	32859911
AllCCS	[M+Na-2H]-	160.4	32859911
AllCCS	[M+HCOO]-	161.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lacosamide	COCC(N=C(C)O)C(O)=NCC1=CC=CC=C1	2956.0	Standard polar	33892256
Lacosamide	COCC(N=C(C)O)C(O)=NCC1=CC=CC=C1	2011.7	Standard non polar	33892256
Lacosamide	COCC(N=C(C)O)C(O)=NCC1=CC=CC=C1	2013.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lacosamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9520000000-0236025c878fe2ca63f3	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lacosamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lacosamide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lacosamide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lacosamide GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lacosamide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lacosamide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lacosamide GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lacosamide 45V, Positive-QTOF	splash10-006x-9300000000-3a7f5509748932b09d59	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lacosamide 30V, Positive-QTOF	splash10-05mo-5900000000-d9631217d69a31dc2ca4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lacosamide 75V, Positive-QTOF	splash10-006x-9000000000-336d9db90e7b34220364	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lacosamide 15V, Positive-QTOF	splash10-0a4l-1900000000-2a5b86e39b573b906771	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lacosamide 90V, Positive-QTOF	splash10-006x-9000000000-bece44af5a7f0b79630b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lacosamide 60V, Positive-QTOF	splash10-006x-9000000000-cec510edb99168e1f1d8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lacosamide 15V, Negative-QTOF	splash10-014j-0290000000-f6882a16427d262d6710	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lacosamide 30V, Negative-QTOF	splash10-0ar1-0890000000-8ce3da6a6c7e215c14d8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lacosamide 60V, Negative-QTOF	splash10-055b-3920000000-b0e6ff27c0b23df550d7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lacosamide 45V, Negative-QTOF	splash10-0a6s-1950000000-3c5539c8a49724c8b66d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lacosamide 75V, Negative-QTOF	splash10-0a59-8900000000-5d1504898e5e6309e7e3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lacosamide 90V, Negative-QTOF	splash10-0a4i-9400000000-4f522b43843f4111ff8f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lacosamide 10V, Positive-QTOF	splash10-0a4i-3890000000-2796291872ed60187c8c	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lacosamide 20V, Positive-QTOF	splash10-0a4i-4900000000-c862c76bdc3034cde756	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lacosamide 40V, Positive-QTOF	splash10-052f-9300000000-37a082134aeebd986448	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lacosamide 10V, Negative-QTOF	splash10-052b-0290000000-c9ab70dde08cfa189165	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lacosamide 20V, Negative-QTOF	splash10-0a4i-5890000000-5bbe89a5712cf2074fdb	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lacosamide 40V, Negative-QTOF	splash10-0a6r-9500000000-e43bfaa7863c9d74dfb3	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lacosamide 10V, Positive-QTOF	splash10-0k96-6980000000-177ae04d49e82099173d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lacosamide 20V, Positive-QTOF	splash10-0006-9400000000-5b1e1d385ffacec69588	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lacosamide 40V, Positive-QTOF	splash10-0006-9300000000-1a50a6634806c82ca7af	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lacosamide 10V, Negative-QTOF	splash10-0002-7690000000-0a1fba58deffb0dcfab7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lacosamide 20V, Negative-QTOF	splash10-0pbl-8900000000-a94d1c8411186a50f4ce	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lacosamide 40V, Negative-QTOF	splash10-0f6x-9600000000-315a1503dc048e9c84e3	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10266281

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21634109

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Lacosamide (HMDB0253940)

MOL for HMDB0253940 (Lacosamide)

3D MOL for HMDB0253940 (Lacosamide)

3D SDF for HMDB0253940 (Lacosamide)

3D-SDF for HMDB0253940 (Lacosamide)

PDB for HMDB0253940 (Lacosamide)

3D PDB for HMDB0253940 (Lacosamide)

SMILES for HMDB0253940 (Lacosamide)

INCHI for HMDB0253940 (Lacosamide)

Structure for HMDB0253940 (Lacosamide)

3D Structure for HMDB0253940 (Lacosamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra