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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 19:03:42 UTC

Update Date

2021-09-14 15:45:49 UTC

HMDB ID

HMDB0060855

Secondary Accession Numbers

HMDB60855

Metabolite Identification

Common Name

O-Desmethyl-lacosamide

Description

O-Desmethyl-lacosamide is a metabolite of lacosamide. Lacosamide (formerly known as erlosamide) is a medication developed by UCB for the adjunctive treatment of partial-onset seizures and diabetic neuropathic pain marketed under the trade name Vimpat. The U.S. Food and Drug Administration accepted UCB's New Drug Application for lacosamide as of November 29, 2007, beginning the approval process for the drug. (Wikipedia)

Structure

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

HMDB0060855
     RDKit          3D
O-Desmethyl-lacosamide
 33 33  0  0  0  0  0  0  0  0999 V2000
   -3.5650    3.1169    0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896    1.9011   -0.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9198    1.8485   -1.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5253    0.8133    0.7477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709   -0.3554    0.0618 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7866   -1.5924    0.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2418   -2.6711   -0.2231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5870   -0.5980    0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1615    0.1553    1.5372 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2589   -1.6067    0.0988 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5727   -1.7799    0.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5517   -0.7715    0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9278    0.2531    1.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8459    1.1674    0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3740    1.0742   -0.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0001    0.0443   -1.5636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784   -0.8681   -1.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707    3.4484    1.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5507    2.8242    1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6883    3.9206   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5685    0.8251    1.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9996   -0.1983   -1.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6167   -1.7269    1.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8624   -1.4377    0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9245   -3.3504   -0.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0586   -2.2176   -0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613   -1.7596    1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9291   -2.7980    0.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185    0.3318    2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1593    1.9926    1.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0780    1.7919   -1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3807   -0.0771   -2.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7513   -1.6998   -1.6918 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
  5  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  6
  6 23  1  0
  6 24  1  0
  7 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
M  END


  Mrv0541 07041312032D          

 17 17  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060855

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)N[C@H](CO)C(=O)NCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N2O3/c1-9(16)14-11(8-15)12(17)13-7-10-5-3-2-4-6-10/h2-6,11,15H,7-8H2,1H3,(H,13,17)(H,14,16)/t11-/m1/s1

> <INCHI_KEY>
XRKSCJLQKGLSKU-LLVKDONJSA-N

> <FORMULA>
C12H16N2O3

> <MOLECULAR_WEIGHT>
236.267

> <EXACT_MASS>
236.116092388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.30578417717955

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-N-benzyl-2-acetamido-3-hydroxypropanamide

> <ALOGPS_LOGP>
-0.05

> <JCHEM_LOGP>
-0.6655681090000003

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.607009984791638

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.407984797228742

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5072894951541582

> <JCHEM_POLAR_SURFACE_AREA>
78.43

> <JCHEM_REFRACTIVITY>
62.81630000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-N-benzyl-2-acetamido-3-hydroxypropanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060855
     RDKit          3D
O-Desmethyl-lacosamide
 33 33  0  0  0  0  0  0  0  0999 V2000
   -3.5650    3.1169    0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896    1.9011   -0.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9198    1.8485   -1.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5253    0.8133    0.7477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709   -0.3554    0.0618 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7866   -1.5924    0.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2418   -2.6711   -0.2231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5870   -0.5980    0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1615    0.1553    1.5372 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2589   -1.6067    0.0988 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5727   -1.7799    0.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5517   -0.7715    0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9278    0.2531    1.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8459    1.1674    0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3740    1.0742   -0.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0001    0.0443   -1.5636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784   -0.8681   -1.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707    3.4484    1.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5507    2.8242    1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6883    3.9206   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5685    0.8251    1.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9996   -0.1983   -1.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6167   -1.7269    1.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8624   -1.4377    0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9245   -3.3504   -0.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0586   -2.2176   -0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613   -1.7596    1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9291   -2.7980    0.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185    0.3318    2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1593    1.9926    1.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0780    1.7919   -1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3807   -0.0771   -2.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7513   -1.6998   -1.6918 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
  5  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  6
  6 23  1  0
  6 24  1  0
  7 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.001  -6.930   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       8.002  -7.700   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0060855
HETATM    1  C1  UNL     1      -3.565   3.117   0.625  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.990   1.901  -0.026  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.920   1.848  -1.272  1.00  0.00           O  
HETATM    4  N1  UNL     1      -2.525   0.813   0.748  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.971  -0.355   0.062  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.787  -1.592   0.452  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.242  -2.671  -0.223  1.00  0.00           O  
HETATM    8  C5  UNL     1      -0.587  -0.598   0.592  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.162   0.155   1.537  1.00  0.00           O  
HETATM   10  N2  UNL     1       0.259  -1.607   0.099  1.00  0.00           N  
HETATM   11  C6  UNL     1       1.573  -1.780   0.658  1.00  0.00           C  
HETATM   12  C7  UNL     1       2.552  -0.772   0.206  1.00  0.00           C  
HETATM   13  C8  UNL     1       2.928   0.253   1.038  1.00  0.00           C  
HETATM   14  C9  UNL     1       3.846   1.167   0.548  1.00  0.00           C  
HETATM   15  C10 UNL     1       4.374   1.074  -0.718  1.00  0.00           C  
HETATM   16  C11 UNL     1       4.000   0.044  -1.564  1.00  0.00           C  
HETATM   17  C12 UNL     1       3.078  -0.868  -1.063  1.00  0.00           C  
HETATM   18  H1  UNL     1      -2.871   3.448   1.411  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.551   2.824   1.027  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.688   3.921  -0.128  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.569   0.825   1.777  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.000  -0.198  -1.009  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.617  -1.727   1.554  1.00  0.00           H  
HETATM   24  H7  UNL     1      -3.862  -1.438   0.231  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.925  -3.350  -0.419  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.059  -2.218  -0.668  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.461  -1.760   1.765  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.929  -2.798   0.388  1.00  0.00           H  
HETATM   29  H12 UNL     1       2.519   0.332   2.037  1.00  0.00           H  
HETATM   30  H13 UNL     1       4.159   1.993   1.197  1.00  0.00           H  
HETATM   31  H14 UNL     1       5.078   1.792  -1.068  1.00  0.00           H  
HETATM   32  H15 UNL     1       4.381  -0.077  -2.560  1.00  0.00           H  
HETATM   33  H16 UNL     1       2.751  -1.700  -1.692  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3    4
CONECT    4    5   21
CONECT    5    6    8   22
CONECT    6    7   23   24
CONECT    7   25
CONECT    8    9    9   10
CONECT   10   11   26
CONECT   11   12   27   28
CONECT   12   13   13   17
CONECT   13   14   29
CONECT   14   15   15   30
CONECT   15   16   31
CONECT   16   17   17   32
CONECT   17   33
END

HMDB0060855
     RDKit          3D
O-Desmethyl-lacosamide
 33 33  0  0  0  0  0  0  0  0999 V2000
   -3.5650    3.1169    0.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9896    1.9011   -0.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9198    1.8485   -1.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5253    0.8133    0.7477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709   -0.3554    0.0618 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7866   -1.5924    0.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2418   -2.6711   -0.2231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5870   -0.5980    0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1615    0.1553    1.5372 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2589   -1.6067    0.0988 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5727   -1.7799    0.6580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5517   -0.7715    0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9278    0.2531    1.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8459    1.1674    0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3740    1.0742   -0.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0001    0.0443   -1.5636 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0784   -0.8681   -1.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8707    3.4484    1.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5507    2.8242    1.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6883    3.9206   -0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5685    0.8251    1.7770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9996   -0.1983   -1.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6167   -1.7269    1.5540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8624   -1.4377    0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9245   -3.3504   -0.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0586   -2.2176   -0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4613   -1.7596    1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9291   -2.7980    0.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185    0.3318    2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1593    1.9926    1.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0780    1.7919   -1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3807   -0.0771   -2.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7513   -1.6998   -1.6918 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
  5  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  6
  6 23  1  0
  6 24  1  0
  7 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 15 31  1  0
 16 32  1  0
 17 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₂H₁₆N₂O₃

Average Molecular Weight

236.267

Monoisotopic Molecular Weight

236.116092388

IUPAC Name

(2R)-N-benzyl-2-acetamido-3-hydroxypropanamide

Traditional Name

(2R)-N-benzyl-2-acetamido-3-hydroxypropanamide

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@H](CO)C(=O)NCC1=CC=CC=C1

InChI Identifier

InChI=1S/C12H16N2O3/c1-9(16)14-11(8-15)12(17)13-7-10-5-3-2-4-6-10/h2-6,11,15H,7-8H2,1H3,(H,13,17)(H,14,16)/t11-/m1/s1

InChI Key

XRKSCJLQKGLSKU-LLVKDONJSA-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
Serine or derivatives
Monocyclic benzene moiety
Benzenoid
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Alcohol
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060855)
Liver (HMDB: HMDB0060855)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060855)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060855)

Cellular substructure

Cytoplasm (HMDB: HMDB0060855)

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
Water Solubility	0.82 g/L	ALOGPS
logP	-0.05	ALOGPS
logP	-0.67	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	12.41	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.43 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	62.82 m³·mol⁻¹	ChemAxon
Polarizability	24.31 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	154.442	31661259
DarkChem	[M-H]-	150.857	31661259
DeepCCS	[M+H]+	153.22	30932474
DeepCCS	[M-H]-	150.824	30932474
DeepCCS	[M-2H]-	183.899	30932474
DeepCCS	[M+Na]+	159.141	30932474
AllCCS	[M+H]+	153.9	32859911
AllCCS	[M+H-H2O]+	150.3	32859911
AllCCS	[M+NH4]+	157.2	32859911
AllCCS	[M+Na]+	158.2	32859911
AllCCS	[M-H]-	155.4	32859911
AllCCS	[M+Na-2H]-	155.8	32859911
AllCCS	[M+HCOO]-	156.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-Desmethyl-lacosamide	CC(=O)N[C@H](CO)C(=O)NCC1=CC=CC=C1	3188.2	Standard polar	33892256
O-Desmethyl-lacosamide	CC(=O)N[C@H](CO)C(=O)NCC1=CC=CC=C1	1961.7	Standard non polar	33892256
O-Desmethyl-lacosamide	CC(=O)N[C@H](CO)C(=O)NCC1=CC=CC=C1	2178.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-Desmethyl-lacosamide,1TMS,isomer #1	CC(=O)N[C@H](CO[Si](C)(C)C)C(=O)NCC1=CC=CC=C1	2142.2	Semi standard non polar	33892256
O-Desmethyl-lacosamide,1TMS,isomer #2	CC(=O)N([C@H](CO)C(=O)NCC1=CC=CC=C1)[Si](C)(C)C	2065.7	Semi standard non polar	33892256
O-Desmethyl-lacosamide,1TMS,isomer #3	CC(=O)N[C@H](CO)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C	2100.6	Semi standard non polar	33892256
O-Desmethyl-lacosamide,2TMS,isomer #1	CC(=O)N([C@H](CO[Si](C)(C)C)C(=O)NCC1=CC=CC=C1)[Si](C)(C)C	2098.9	Semi standard non polar	33892256
O-Desmethyl-lacosamide,2TMS,isomer #1	CC(=O)N([C@H](CO[Si](C)(C)C)C(=O)NCC1=CC=CC=C1)[Si](C)(C)C	2188.7	Standard non polar	33892256
O-Desmethyl-lacosamide,2TMS,isomer #1	CC(=O)N([C@H](CO[Si](C)(C)C)C(=O)NCC1=CC=CC=C1)[Si](C)(C)C	2644.0	Standard polar	33892256
O-Desmethyl-lacosamide,2TMS,isomer #2	CC(=O)N[C@H](CO[Si](C)(C)C)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C	2088.0	Semi standard non polar	33892256
O-Desmethyl-lacosamide,2TMS,isomer #2	CC(=O)N[C@H](CO[Si](C)(C)C)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C	2179.0	Standard non polar	33892256
O-Desmethyl-lacosamide,2TMS,isomer #2	CC(=O)N[C@H](CO[Si](C)(C)C)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C	2678.6	Standard polar	33892256
O-Desmethyl-lacosamide,2TMS,isomer #3	CC(=O)N([C@H](CO)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C)[Si](C)(C)C	1994.4	Semi standard non polar	33892256
O-Desmethyl-lacosamide,2TMS,isomer #3	CC(=O)N([C@H](CO)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C)[Si](C)(C)C	2170.4	Standard non polar	33892256
O-Desmethyl-lacosamide,2TMS,isomer #3	CC(=O)N([C@H](CO)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C)[Si](C)(C)C	2670.9	Standard polar	33892256
O-Desmethyl-lacosamide,3TMS,isomer #1	CC(=O)N([C@H](CO[Si](C)(C)C)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C)[Si](C)(C)C	2069.7	Semi standard non polar	33892256
O-Desmethyl-lacosamide,3TMS,isomer #1	CC(=O)N([C@H](CO[Si](C)(C)C)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C)[Si](C)(C)C	2250.0	Standard non polar	33892256
O-Desmethyl-lacosamide,3TMS,isomer #1	CC(=O)N([C@H](CO[Si](C)(C)C)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C)[Si](C)(C)C	2478.0	Standard polar	33892256
O-Desmethyl-lacosamide,1TBDMS,isomer #1	CC(=O)N[C@H](CO[Si](C)(C)C(C)(C)C)C(=O)NCC1=CC=CC=C1	2380.5	Semi standard non polar	33892256
O-Desmethyl-lacosamide,1TBDMS,isomer #2	CC(=O)N([C@H](CO)C(=O)NCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2320.0	Semi standard non polar	33892256
O-Desmethyl-lacosamide,1TBDMS,isomer #3	CC(=O)N[C@H](CO)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2345.6	Semi standard non polar	33892256
O-Desmethyl-lacosamide,2TBDMS,isomer #1	CC(=O)N([C@H](CO[Si](C)(C)C(C)(C)C)C(=O)NCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2582.1	Semi standard non polar	33892256
O-Desmethyl-lacosamide,2TBDMS,isomer #1	CC(=O)N([C@H](CO[Si](C)(C)C(C)(C)C)C(=O)NCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2606.8	Standard non polar	33892256
O-Desmethyl-lacosamide,2TBDMS,isomer #1	CC(=O)N([C@H](CO[Si](C)(C)C(C)(C)C)C(=O)NCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2845.2	Standard polar	33892256
O-Desmethyl-lacosamide,2TBDMS,isomer #2	CC(=O)N[C@H](CO[Si](C)(C)C(C)(C)C)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2591.1	Semi standard non polar	33892256
O-Desmethyl-lacosamide,2TBDMS,isomer #2	CC(=O)N[C@H](CO[Si](C)(C)C(C)(C)C)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2567.3	Standard non polar	33892256
O-Desmethyl-lacosamide,2TBDMS,isomer #2	CC(=O)N[C@H](CO[Si](C)(C)C(C)(C)C)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2877.1	Standard polar	33892256
O-Desmethyl-lacosamide,2TBDMS,isomer #3	CC(=O)N([C@H](CO)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2522.1	Semi standard non polar	33892256
O-Desmethyl-lacosamide,2TBDMS,isomer #3	CC(=O)N([C@H](CO)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2574.8	Standard non polar	33892256
O-Desmethyl-lacosamide,2TBDMS,isomer #3	CC(=O)N([C@H](CO)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2860.4	Standard polar	33892256
O-Desmethyl-lacosamide,3TBDMS,isomer #1	CC(=O)N([C@H](CO[Si](C)(C)C(C)(C)C)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2779.4	Semi standard non polar	33892256
O-Desmethyl-lacosamide,3TBDMS,isomer #1	CC(=O)N([C@H](CO[Si](C)(C)C(C)(C)C)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2837.8	Standard non polar	33892256
O-Desmethyl-lacosamide,3TBDMS,isomer #1	CC(=O)N([C@H](CO[Si](C)(C)C(C)(C)C)C(=O)N(CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2798.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethyl-lacosamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9410000000-5f1e312da0573983d50f	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethyl-lacosamide GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9510000000-97909c60d7d6d561502d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-Desmethyl-lacosamide 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyl-lacosamide 10V, Positive-QTOF	splash10-00ku-5690000000-c462f5516dbe61694cf5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyl-lacosamide 20V, Positive-QTOF	splash10-01ox-9500000000-0a4cd19f9e432207835b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyl-lacosamide 40V, Positive-QTOF	splash10-0006-9000000000-2fe724f0b57e692e0e6f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyl-lacosamide 10V, Negative-QTOF	splash10-0a4r-0390000000-1fed705c8096588a4f84	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyl-lacosamide 20V, Negative-QTOF	splash10-0a4i-3950000000-f926ceba2b1574a0b7df	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyl-lacosamide 40V, Negative-QTOF	splash10-0a4i-9400000000-35da46b0bec5a179f2e0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyl-lacosamide 10V, Positive-QTOF	splash10-000g-7940000000-e349a2b6ed23aecfddb0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyl-lacosamide 20V, Positive-QTOF	splash10-0006-9500000000-8d2423474fd96bb658e1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyl-lacosamide 40V, Positive-QTOF	splash10-0006-9100000000-5bf880c2fe833c8978da	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyl-lacosamide 10V, Negative-QTOF	splash10-000i-7390000000-a9f63a1d4b04c93c72be	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyl-lacosamide 20V, Negative-QTOF	splash10-0a4i-9200000000-f48ddc322cb07e57cd6e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-Desmethyl-lacosamide 40V, Negative-QTOF	splash10-0006-9100000000-97a9ddf0c2d635d9dd85	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10889901

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

Not Available

Showing metabocard for O-Desmethyl-lacosamide (HMDB0060855)

MOL for HMDB0060855 (O-Desmethyl-lacosamide)

3D MOL for HMDB0060855 (O-Desmethyl-lacosamide)

3D SDF for HMDB0060855 (O-Desmethyl-lacosamide)

3D-SDF for HMDB0060855 (O-Desmethyl-lacosamide)

PDB for HMDB0060855 (O-Desmethyl-lacosamide)

3D PDB for HMDB0060855 (O-Desmethyl-lacosamide)

SMILES for HMDB0060855 (O-Desmethyl-lacosamide)

INCHI for HMDB0060855 (O-Desmethyl-lacosamide)

Structure for HMDB0060855 (O-Desmethyl-lacosamide)

3D Structure for HMDB0060855 (O-Desmethyl-lacosamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra