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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2017-03-23 06:18:27 UTC

Update Date

2022-03-07 03:17:59 UTC

HMDB ID

HMDB0062785

Secondary Accession Numbers

HMDB62785

Metabolite Identification

Common Name

O-methylmalonyl-L-carnitine

Description

O-methylmalonyl-L-carnitine belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. O-methylmalonyl-L-carnitine is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0062785
     RDKit          3D
O-methylmalonyl-L-carnitine
 37 36  0  0  0  0  0  0  0  0999 V2000
    3.5315   -1.6141   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6270   -1.0111    0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4050   -0.0891    0.9546 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5228    0.3131    0.5798 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8866    0.3201    2.1653 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.5029   -0.2774   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4047   -0.2231   -1.7897 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5456    0.3581    0.2202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5477    1.0753   -0.2655 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4642    2.4966    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7625    3.2085   -0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6642    2.7116   -0.8911 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174    4.5190    0.2416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7968    0.4920    0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0234   -0.8737    0.0626 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.4533   -1.1322    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6857   -1.3104   -1.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3008   -1.7086    1.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681   -0.7976   -1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091   -2.4056   -1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4335   -2.0025   -0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2101   -1.8306    0.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6095    1.1310   -1.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5963    2.5324    1.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3199    3.1002   -0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3868    4.9170    1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6436    1.1383    0.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7067    0.6205    1.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6581   -0.7418    1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0183   -0.4511   -0.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7143   -2.1819    0.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6064   -0.5290   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4867   -2.0161   -1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7587   -1.9561   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6164   -1.0728    1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9684   -2.2154    1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025   -2.4935    0.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  9 23  1  6
 10 24  1  0
 10 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
M  CHG  2   5  -1  15   1
M  END

  Mrv1652303231707182D          

 20 19  0  0  1  0            999 V2000
    0.5230   -0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.7145    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3809   -0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    0.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809   -1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -2.3645    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.6829   -3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
M  CHG  2   5  -1  17   1
M  END
> <DATABASE_ID>
HMDB0062785

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C(C)(C([O-])=O)C(=O)O[C@]([H])(CC(O)=O)C[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C11H19NO6/c1-7(10(15)16)11(17)18-8(5-9(13)14)6-12(2,3)4/h7-8H,5-6H2,1-4H3,(H-,13,14,15,16)/t7?,8-/m1/s1

> <INCHI_KEY>
XROYFEWIXXCPAW-BRFYHDHCSA-N

> <FORMULA>
C11H19NO6

> <MOLECULAR_WEIGHT>
261.274

> <EXACT_MASS>
261.121237336

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
25.705956779393247

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2R)-1-carboxy-3-(trimethylazaniumyl)propan-2-yl]oxy}-2-methyl-3-oxopropanoate

> <ALOGPS_LOGP>
-1.76

> <JCHEM_LOGP>
-4.0111659134717454

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.23841297010917

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.534250036378786

> <JCHEM_PKA_STRONGEST_BASIC>
-7.208415042403216

> <JCHEM_POLAR_SURFACE_AREA>
103.72999999999999

> <JCHEM_REFRACTIVITY>
83.55539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2R)-1-carboxy-3-(trimethylammonio)propan-2-yl]oxy}-2-methyl-3-oxopropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0062785
     RDKit          3D
O-methylmalonyl-L-carnitine
 37 36  0  0  0  0  0  0  0  0999 V2000
    3.5315   -1.6141   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6270   -1.0111    0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4050   -0.0891    0.9546 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5228    0.3131    0.5798 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8866    0.3201    2.1653 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.5029   -0.2774   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4047   -0.2231   -1.7897 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5456    0.3581    0.2202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5477    1.0753   -0.2655 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4642    2.4966    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7625    3.2085   -0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6642    2.7116   -0.8911 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174    4.5190    0.2416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7968    0.4920    0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0234   -0.8737    0.0626 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.4533   -1.1322    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6857   -1.3104   -1.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3008   -1.7086    1.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681   -0.7976   -1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091   -2.4056   -1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4335   -2.0025   -0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2101   -1.8306    0.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6095    1.1310   -1.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5963    2.5324    1.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3199    3.1002   -0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3868    4.9170    1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6436    1.1383    0.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7067    0.6205    1.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6581   -0.7418    1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0183   -0.4511   -0.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7143   -2.1819    0.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6064   -0.5290   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4867   -2.0161   -1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7587   -1.9561   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6164   -1.0728    1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9684   -2.2154    1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025   -2.4935    0.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  9 23  1  6
 10 24  1  0
 10 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
M  CHG  2   5  -1  15   1
M  END

HEADER    PROTEIN                                 23-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAR-17         0                                  
HETATM    1  H   UNK     0       0.976  -0.564   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.357  -1.334   0.000  0.00  0.00           O-1
HETATM    6  O   UNK     0       0.976  -3.644   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.644  -2.104   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.644  -3.644   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.977  -1.334   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.311  -2.104   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       6.311  -0.564   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       7.645  -1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.645   0.206   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.978   0.976   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.311   0.976   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.311  -3.644   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       7.645  -4.414   0.000  0.00  0.00           N+1
HETATM   18  C   UNK     0       6.875  -5.747   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.978  -5.184   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    7                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12   16                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0062785
HETATM    1  C1  UNL     1       3.532  -1.614  -0.936  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.627  -1.011   0.098  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.405  -0.089   0.955  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.523   0.313   0.580  1.00  0.00           O  
HETATM    5  O2  UNL     1       2.887   0.320   2.165  1.00  0.00           O1-
HETATM    6  C4  UNL     1       1.503  -0.277  -0.544  1.00  0.00           C  
HETATM    7  O3  UNL     1       1.405  -0.223  -1.790  1.00  0.00           O  
HETATM    8  O4  UNL     1       0.546   0.358   0.220  1.00  0.00           O  
HETATM    9  C5  UNL     1      -0.548   1.075  -0.266  1.00  0.00           C  
HETATM   10  C6  UNL     1      -0.464   2.497   0.241  1.00  0.00           C  
HETATM   11  C7  UNL     1       0.762   3.208  -0.182  1.00  0.00           C  
HETATM   12  O5  UNL     1       1.664   2.712  -0.891  1.00  0.00           O  
HETATM   13  O6  UNL     1       0.917   4.519   0.242  1.00  0.00           O  
HETATM   14  C8  UNL     1      -1.797   0.492   0.349  1.00  0.00           C  
HETATM   15  N1  UNL     1      -2.023  -0.874   0.063  1.00  0.00           N1+
HETATM   16  C9  UNL     1      -3.453  -1.132   0.305  1.00  0.00           C  
HETATM   17  C10 UNL     1      -1.686  -1.310  -1.247  1.00  0.00           C  
HETATM   18  C11 UNL     1      -1.301  -1.709   1.030  1.00  0.00           C  
HETATM   19  H1  UNL     1       3.868  -0.798  -1.634  1.00  0.00           H  
HETATM   20  H2  UNL     1       3.009  -2.406  -1.498  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.434  -2.003  -0.423  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.210  -1.831   0.720  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.609   1.131  -1.368  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.596   2.532   1.353  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.320   3.100  -0.187  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.387   4.917   1.019  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.644   1.138   0.035  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.707   0.621   1.449  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.658  -0.742   1.323  1.00  0.00           H  
HETATM   30  H12 UNL     1      -4.018  -0.451  -0.392  1.00  0.00           H  
HETATM   31  H13 UNL     1      -3.714  -2.182   0.159  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.606  -0.529  -2.008  1.00  0.00           H  
HETATM   33  H15 UNL     1      -2.487  -2.016  -1.618  1.00  0.00           H  
HETATM   34  H16 UNL     1      -0.759  -1.956  -1.234  1.00  0.00           H  
HETATM   35  H17 UNL     1      -0.616  -1.073   1.657  1.00  0.00           H  
HETATM   36  H18 UNL     1      -1.968  -2.215   1.732  1.00  0.00           H  
HETATM   37  H19 UNL     1      -0.703  -2.493   0.522  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    6   22
CONECT    3    4    4    5
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   14   23
CONECT   10   11   24   25
CONECT   11   12   12   13
CONECT   13   26
CONECT   14   15   27   28
CONECT   15   16   17   18
CONECT   16   29   30   31
CONECT   17   32   33   34
CONECT   18   35   36   37
END

HMDB0062785
     RDKit          3D
O-methylmalonyl-L-carnitine
 37 36  0  0  0  0  0  0  0  0999 V2000
    3.5315   -1.6141   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6270   -1.0111    0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4050   -0.0891    0.9546 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5228    0.3131    0.5798 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8866    0.3201    2.1653 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.5029   -0.2774   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4047   -0.2231   -1.7897 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5456    0.3581    0.2202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5477    1.0753   -0.2655 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4642    2.4966    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7625    3.2085   -0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6642    2.7116   -0.8911 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9174    4.5190    0.2416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7968    0.4920    0.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0234   -0.8737    0.0626 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.4533   -1.1322    0.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6857   -1.3104   -1.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3008   -1.7086    1.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681   -0.7976   -1.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091   -2.4056   -1.4981 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4335   -2.0025   -0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2101   -1.8306    0.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6095    1.1310   -1.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5963    2.5324    1.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3199    3.1002   -0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3868    4.9170    1.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6436    1.1383    0.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7067    0.6205    1.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6581   -0.7418    1.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0183   -0.4511   -0.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7143   -2.1819    0.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6064   -0.5290   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4867   -2.0161   -1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7587   -1.9561   -1.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6164   -1.0728    1.6572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9684   -2.2154    1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7025   -2.4935    0.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  9 23  1  6
 10 24  1  0
 10 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
M  CHG  2   5  -1  15   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₁H₁₉NO₆

Average Molecular Weight

261.274

Monoisotopic Molecular Weight

261.121237336

IUPAC Name

3-{[(2R)-1-carboxy-3-(trimethylazaniumyl)propan-2-yl]oxy}-2-methyl-3-oxopropanoate

Traditional Name

3-{[(2R)-1-carboxy-3-(trimethylammonio)propan-2-yl]oxy}-2-methyl-3-oxopropanoate

CAS Registry Number

Not Available

SMILES

[H]C(C)(C([O-])=O)C(=O)O[C@]([H])(CC(O)=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C11H19NO6/c1-7(10(15)16)11(17)18-8(5-9(13)14)6-12(2,3)4/h7-8H,5-6H2,1-4H3,(H-,13,14,15,16)/t7?,8-/m1/s1

InChI Key

XROYFEWIXXCPAW-BRFYHDHCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
Tricarboxylic acid or derivatives
1,3-dicarbonyl compound
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid salt
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic salt
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-acyl-L-carnitine (CHEBI:85473 )

Ontology

Not Available

Feces (PMID: 29808030)

Source

Exogenous

Exogenous (HMDB: HMDB0062785)

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	0.27 g/l	ALOGPS
LogP	-1.62	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.8	ALOGPS
logP	-4	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.73 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	83.56 m³·mol⁻¹	ChemAxon
Polarizability	25.71 Å³	ChemAxon
Number of Rings	0	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
DeepCCS	[M+H]+	163.385	30932474
DeepCCS	[M-H]-	160.988	30932474
DeepCCS	[M-2H]-	194.402	30932474
DeepCCS	[M+Na]+	169.296	30932474
AllCCS	[M+H]+	157.8	32859911
AllCCS	[M+H-H2O]+	154.8	32859911
AllCCS	[M+NH4]+	160.6	32859911
AllCCS	[M+Na]+	161.4	32859911
AllCCS	[M-H]-	164.7	32859911
AllCCS	[M+Na-2H]-	165.6	32859911
AllCCS	[M+HCOO]-	166.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
O-methylmalonyl-L-carnitine	[H]C(C)(C([O-])=O)C(=O)O[C@]([H])(CC(O)=O)C[N+](C)(C)C	2761.2	Standard polar	33892256
O-methylmalonyl-L-carnitine	[H]C(C)(C([O-])=O)C(=O)O[C@]([H])(CC(O)=O)C[N+](C)(C)C	1384.5	Standard non polar	33892256
O-methylmalonyl-L-carnitine	[H]C(C)(C([O-])=O)C(=O)O[C@]([H])(CC(O)=O)C[N+](C)(C)C	1786.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
O-methylmalonyl-L-carnitine,1TMS,isomer #1	CC(C(=O)[O-])C(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C	1704.4	Semi standard non polar	33892256
O-methylmalonyl-L-carnitine,1TBDMS,isomer #1	CC(C(=O)[O-])C(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C	1939.8	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 - O-methylmalonyl-L-carnitine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9110000000-604e3e23d9a09a76707b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-methylmalonyl-L-carnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - O-methylmalonyl-L-carnitine 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-methylmalonyl-L-carnitine 10V, Positive-QTOF	splash10-03di-0090000000-48d875468ed156af31be	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-methylmalonyl-L-carnitine 20V, Positive-QTOF	splash10-01p9-9050000000-49b1ecee6d2effc4a365	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - O-methylmalonyl-L-carnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	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

91825610

PDB ID

Not Available

ChEBI ID

85473

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for O-methylmalonyl-L-carnitine (HMDB0062785)

MOL for HMDB0062785 (O-methylmalonyl-L-carnitine)

3D MOL for HMDB0062785 (O-methylmalonyl-L-carnitine)

3D SDF for HMDB0062785 (O-methylmalonyl-L-carnitine)

3D-SDF for HMDB0062785 (O-methylmalonyl-L-carnitine)

PDB for HMDB0062785 (O-methylmalonyl-L-carnitine)

3D PDB for HMDB0062785 (O-methylmalonyl-L-carnitine)

SMILES for HMDB0062785 (O-methylmalonyl-L-carnitine)

INCHI for HMDB0062785 (O-methylmalonyl-L-carnitine)

Structure for HMDB0062785 (O-methylmalonyl-L-carnitine)

3D Structure for HMDB0062785 (O-methylmalonyl-L-carnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra