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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:32 UTC

Update Date

2023-05-30 20:55:51 UTC

HMDB ID

HMDB0002013

Secondary Accession Numbers

HMDB0062510
HMDB02013
HMDB62510

Metabolite Identification

Common Name

Butyrylcarnitine

Description

Butyrylcarnitine, also known as (3R)-3-(butyryloxy)-4-(trimethylammonio)butanoate or L-carnitine butyryl ester, is classified as a member of the acylcarnitines. Acylcarnitines are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond. Butyrylcarnitine is considered to be practically insoluble (in water) and acidic. Butyrylcarnitine is elevated in patients with short-chain acyl-CoA dehydrogenase (SCAD) deficiency, in infants with acute acidosis and generalized muscle weakness, and in middle-aged patients with chronic myopathy localized in muscle (OMIM: 201470 ).

Structure

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

HMDB0002013
     RDKit          3D
Butyrylcarnitine
 37 36  0  0  0  0  0  0  0  0999 V2000
    4.2210    0.1292    0.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3646    0.5243   -0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2345   -0.0200   -1.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9135    0.4606   -1.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5599    1.6609   -1.4101 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0110   -0.2916   -0.4272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2599    0.1219    0.0159 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2762    0.2353    1.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7199    1.2240    1.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    0.9084    2.5951 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4867    2.5946    1.7366 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2815   -0.6947   -0.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6494   -0.4961   -0.3715 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0933    0.8596   -0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1495   -1.3571    0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3603   -1.0207   -1.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0907   -0.5111    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2346    0.9823    1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2837   -0.4756    0.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3227    0.1396   -1.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4229    1.6242   -0.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2400   -1.1201   -1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285    0.3246   -2.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492    1.1868   -0.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2199    0.5288    1.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007   -0.7371    1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0811   -1.7852   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1507   -0.6118   -1.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0009    1.0945   -0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4901    1.0521    0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3600    1.6341   -0.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3020   -2.4082    0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1667   -0.9917    0.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4685   -1.4469    1.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4204   -1.1823   -1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2663   -0.2254   -2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8435   -1.9102   -1.9458 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
M  CHG  2  11  -1  13   1
M  END

      
  Mrv1652304251823492D          

 16 15  0  0  0  0            999 V2000
10018.531810018.7422    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10018.531810019.7487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10019.246410020.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.959910019.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10020.673410020.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10021.391110019.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.246410020.9840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10019.254710018.3432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.254710017.5185    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
10018.153110016.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.965910017.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10019.110310016.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.817710018.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10017.103510018.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10016.389410018.3290    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
10017.103510019.5673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  8  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  CHG  2   9   1  15  -1
M  END
> <DATABASE_ID>
HMDB0002013

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H21NO4/c1-5-6-11(15)16-9(7-10(13)14)8-12(2,3)4/h9H,5-8H2,1-4H3/t9-/m1/s1

> <INCHI_KEY>
QWYFHHGCZUCMBN-SECBINFHSA-N

> <FORMULA>
C11H21NO4

> <MOLECULAR_WEIGHT>
231.292

> <EXACT_MASS>
231.14705816

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
24.796522551548037

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-(butanoyloxy)-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-2.10

> <JCHEM_LOGP>
-3.3012761258050785

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.26892391250365

> <JCHEM_PKA_STRONGEST_BASIC>
-7.057078620656008

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
81.8647

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-butanoylcarnitine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002013
     RDKit          3D
Butyrylcarnitine
 37 36  0  0  0  0  0  0  0  0999 V2000
    4.2210    0.1292    0.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3646    0.5243   -0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2345   -0.0200   -1.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9135    0.4606   -1.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5599    1.6609   -1.4101 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0110   -0.2916   -0.4272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2599    0.1219    0.0159 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2762    0.2353    1.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7199    1.2240    1.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    0.9084    2.5951 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4867    2.5946    1.7366 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2815   -0.6947   -0.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6494   -0.4961   -0.3715 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0933    0.8596   -0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1495   -1.3571    0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3603   -1.0207   -1.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0907   -0.5111    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2346    0.9823    1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2837   -0.4756    0.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3227    0.1396   -1.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4229    1.6242   -0.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2400   -1.1201   -1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285    0.3246   -2.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492    1.1868   -0.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2199    0.5288    1.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007   -0.7371    1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0811   -1.7852   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1507   -0.6118   -1.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0009    1.0945   -0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4901    1.0521    0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3600    1.6341   -0.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3020   -2.4082    0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1667   -0.9917    0.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4685   -1.4469    1.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4204   -1.1823   -1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2663   -0.2254   -2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8435   -1.9102   -1.9458 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
M  CHG  2  11  -1  13   1
M  END

HEADER    PROTEIN                                 25-APR-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-18         0                                  
HETATM    1  C   UNK     0    8701.2598701.652   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8701.2598703.531   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8702.5938704.301   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8703.9258703.531   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8705.2578704.301   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8706.5978703.531   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8702.5938705.837   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8702.6098700.907   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0    8702.6098699.368   0.000  0.00  0.00           N+1
HETATM   10  C   UNK     0    8700.5528698.135   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8703.9368698.597   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8702.3398697.852   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8699.9268700.881   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8698.5938701.652   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8697.2608700.881   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0    8698.5938703.192   0.000  0.00  0.00           O+0
CONECT    1    2    8   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    3                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0002013
HETATM    1  C1  UNL     1       4.221   0.129   0.676  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.365   0.524  -0.760  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.234  -0.020  -1.587  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.914   0.461  -1.135  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.560   1.661  -1.410  1.00  0.00           O  
HETATM    6  O2  UNL     1       1.011  -0.292  -0.427  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.260   0.122   0.016  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.276   0.235   1.474  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.720   1.224   1.975  1.00  0.00           C  
HETATM   10  O3  UNL     1       1.755   0.908   2.595  1.00  0.00           O  
HETATM   11  O4  UNL     1       0.487   2.595   1.737  1.00  0.00           O1-
HETATM   12  C8  UNL     1      -1.282  -0.695  -0.660  1.00  0.00           C  
HETATM   13  N1  UNL     1      -2.649  -0.496  -0.371  1.00  0.00           N1+
HETATM   14  C9  UNL     1      -3.093   0.860  -0.223  1.00  0.00           C  
HETATM   15  C10 UNL     1      -3.150  -1.357   0.700  1.00  0.00           C  
HETATM   16  C11 UNL     1      -3.360  -1.021  -1.553  1.00  0.00           C  
HETATM   17  H1  UNL     1       5.091  -0.511   0.961  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.235   0.982   1.371  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.284  -0.476   0.804  1.00  0.00           H  
HETATM   20  H4  UNL     1       5.323   0.140  -1.201  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.423   1.624  -0.833  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.240  -1.120  -1.642  1.00  0.00           H  
HETATM   23  H7  UNL     1       3.328   0.325  -2.655  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.349   1.187  -0.379  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.220   0.529   1.958  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.001  -0.737   1.968  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.081  -1.785  -0.456  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.151  -0.612  -1.762  1.00  0.00           H  
HETATM   29  H13 UNL     1      -4.001   1.095  -0.858  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.490   1.052   0.821  1.00  0.00           H  
HETATM   31  H15 UNL     1      -2.360   1.634  -0.520  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.302  -2.408   0.319  1.00  0.00           H  
HETATM   33  H17 UNL     1      -4.167  -0.992   0.944  1.00  0.00           H  
HETATM   34  H18 UNL     1      -2.468  -1.447   1.542  1.00  0.00           H  
HETATM   35  H19 UNL     1      -4.420  -1.182  -1.294  1.00  0.00           H  
HETATM   36  H20 UNL     1      -3.266  -0.225  -2.322  1.00  0.00           H  
HETATM   37  H21 UNL     1      -2.844  -1.910  -1.946  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8   12   24
CONECT    8    9   25   26
CONECT    9   10   10   11
CONECT   12   13   27   28
CONECT   13   14   15   16
CONECT   14   29   30   31
CONECT   15   32   33   34
CONECT   16   35   36   37
END

HMDB0002013
     RDKit          3D
Butyrylcarnitine
 37 36  0  0  0  0  0  0  0  0999 V2000
    4.2210    0.1292    0.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3646    0.5243   -0.7601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2345   -0.0200   -1.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9135    0.4606   -1.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5599    1.6609   -1.4101 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0110   -0.2916   -0.4272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2599    0.1219    0.0159 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2762    0.2353    1.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7199    1.2240    1.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    0.9084    2.5951 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4867    2.5946    1.7366 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2815   -0.6947   -0.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6494   -0.4961   -0.3715 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.0933    0.8596   -0.2228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1495   -1.3571    0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3603   -1.0207   -1.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0907   -0.5111    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2346    0.9823    1.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2837   -0.4756    0.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3227    0.1396   -1.2011 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4229    1.6242   -0.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2400   -1.1201   -1.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3285    0.3246   -2.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3492    1.1868   -0.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2199    0.5288    1.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007   -0.7371    1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0811   -1.7852   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1507   -0.6118   -1.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0009    1.0945   -0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4901    1.0521    0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3600    1.6341   -0.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3020   -2.4082    0.3187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1667   -0.9917    0.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4685   -1.4469    1.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4204   -1.1823   -1.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2663   -0.2254   -2.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8435   -1.9102   -1.9458 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  6
  8 25  1  0
  8 26  1  0
 12 27  1  0
 12 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
M  CHG  2  11  -1  13   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3R)-3-(Butyryloxy)-4-(trimethylammonio)butanoate	ChEBI
Butyryl-L-carnitine	ChEBI
L-Carnitine butyryl ester	ChEBI
N-Butyryl-L-(-)-carnitin	ChEBI
O-Butanoyl-(R)-carnitine	ChEBI
(3R)-3-(Butyryloxy)-4-(trimethylammonio)butanoic acid	Generator
Butylcarnitine	HMDB
O-Butanoyl-carnitine	HMDB
O-Butanoylcarnitine	HMDB
Butyrylcarnitine	ChEBI

Chemical Formula

C₁₁H₂₁NO₄

Average Molecular Weight

231.292

Monoisotopic Molecular Weight

231.14705816

IUPAC Name

(3R)-3-(butanoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

O-butanoylcarnitine

CAS Registry Number

25576-40-3

SMILES

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

InChI Identifier

InChI=1S/C11H21NO4/c1-5-6-11(15)16-9(7-10(13)14)8-12(2,3)4/h9H,5-8H2,1-4H3/t9-/m1/s1

InChI Key

QWYFHHGCZUCMBN-SECBINFHSA-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
Dicarboxylic acid or derivatives
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-butanoylcarnitine (CHEBI:21949 )
Fatty acyl carnitines (LMFA07070003 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16425363)
Cerebrospinal Fluid (CSF) (PMID: 22546835)
Saliva (PMID: 22308371)

Cell

Fibroblasts (HMDB: HMDB0002013)

Organ

Placenta (HMDB: HMDB0002013)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)
Feces (PMID: 27624970)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002013)

Source

Endogenous

Endogenous (HMDB: HMDB0002013)

Animal

Animal (HMDB: HMDB0002013)

Exogenous

Food

Food (HMDB: HMDB0002013)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)
Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Exogenous (HMDB: HMDB0002013)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Short-Chain Acyl-CoA Dehydrogenase Deficiency (SCAD Deficiency) (HMDB: HMDB0002013)

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0002013)

Lipid metabolism pathway (HMDB: HMDB0002013)

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002013)

Biochemical process

Lipid transport (HMDB: HMDB0002013)

Role

Biological role

Energy source (HMDB: HMDB0002013)

Industrial application

Pharmaceutical industry

Biomarker

Obesity (MarkerDB: MDB00000365)
Eosinophilic esophagitis (MarkerDB: MDB00000365)
Glutaric Acidemia Type 2 (MarkerDB: MDB00000365)

Physical Properties

State

Solid

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	0.052 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3.3	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.27	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	66.43 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	81.86 m³·mol⁻¹	ChemAxon
Polarizability	24.8 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]+	150.991	30932474
DeepCCS	[M-H]-	148.633	30932474
DeepCCS	[M-2H]-	181.517	30932474
DeepCCS	[M+Na]+	157.085	30932474
AllCCS	[M+H]+	156.0	32859911
AllCCS	[M+H-H2O]+	152.8	32859911
AllCCS	[M+NH4]+	158.9	32859911
AllCCS	[M+Na]+	159.8	32859911
AllCCS	[M-H]-	160.9	32859911
AllCCS	[M+Na-2H]-	162.0	32859911
AllCCS	[M+HCOO]-	163.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Butyrylcarnitine	CCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	1992.9	Standard polar	33892256
Butyrylcarnitine	CCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	1271.3	Standard non polar	33892256
Butyrylcarnitine	CCCC(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	1507.0	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 - Butyrylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Butyrylcarnitine 30V, Positive-QTOF	splash10-000i-9000000000-a5dda83cb139267daf89	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Butyrylcarnitine 10V, Positive-QTOF	splash10-001r-8390000000-ceb4241ebded9660319e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Butyrylcarnitine 0V, Positive-QTOF	splash10-001i-0090000000-5c14cfc2ec68c45a3c6d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Butyrylcarnitine 0V, Positive-QTOF	splash10-001i-0090000000-ffb54886a9c9e0dd59c0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Butyrylcarnitine 30V, Positive-QTOF	splash10-000i-9000000000-45000c412d54fe872024	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Butyrylcarnitine 10V, Positive-QTOF	splash10-001r-6290000000-a53c2ce500986fed88fd	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyrylcarnitine 10V, Positive-QTOF	splash10-001i-0090000000-cf95ec9e05e8b6c1a98f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyrylcarnitine 20V, Positive-QTOF	splash10-0019-9050000000-ebf3a8e1eb1d0ceaaeba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyrylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Fibroblasts
Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.26 +/- 0.16 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.10-0.45 uM	Adult (>18 years old)	Both	Normal	The Metabolo...	details
Blood	Detected and Quantified	0.267 +/- 0.013 uM	Adult (>18 years old)	Both	Normal	16425363	details
Blood	Detected and Quantified	0.10-0.45 uM	Adult (>18 years old)	Both	Normal	The Metabolo...	details
Blood	Detected and Quantified	0.13 (0.11-0.16) uM	Newborn (0-30 days old)	Not Available	Normal	25754623	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.39 (0.31-0.55) uM	Infant (0-1 year old)	Not Available	Normal	25754623	details
Blood	Detected and Quantified	<0.12 uM	Adolescent (13-18 years old)	Male	Normal	24453145	details
Blood	Detected and Quantified	0.26(0.1) uM	Adult (>18 years old)	Both	Normal	26010610	details
Blood	Detected and Quantified	0.21 +/- 0.09 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	0.079 (0.023-0.174) uM	Children (1-13 years old)	Both	Normal	9034211	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.024 +/- 0.007 uM	Adult (>18 years old)	Not Specified	Normal	22546835	details
Feces	Detected and Quantified	0.21 +/- 0.1 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.15 +/- 0.06 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Saliva	Detected and Quantified	0.073 +/- 0.044 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected and Quantified	702.56 +/- 39.76 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	26910390	details
Urine	Detected and Quantified	0.76 (0.12-1.81) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	7776094	details
Urine	Detected and Quantified	0.21 (0.10-0.37) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	0.05-0.33 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.11 +/- 0.06 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.13 +/- 0.07 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected and Quantified	2.3594 +/- 1.3471 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.152 +/- 0.011 uM	Adult (>18 years old)	Both	Celiac disease	16425363	details
Blood	Detected and Quantified	0.38 uM	Adolescent (13-18 years old)	Male	Glutaric aciduria II	24453145	details
Blood	Detected and Quantified	0.33(0.18) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	0.33(0.14) uM	Adult (>18 years old)	Both	Heart failure with reduced ejection fraction	26010610	details
Blood	Detected and Quantified	0.1378 (0.119) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	0.2169 (0.0736) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Blood	Detected and Quantified	0.005 (0.0-0.009) uM	Adult (>18 years old)	Both	Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD)	9034211	details
Blood	Detected and Quantified	0.069 +/- 0.047 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.078 +/- 0.035 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Missing teeth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Urine	Detected and Quantified	565.44 +/- 32.46 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Obese	26910390	details
Urine	Detected and Quantified	0-8.966 umol/mmol creatinine	Infant (0-1 year old)	Both	Short chain acyl-CoA dehydrogenase deficiency (SCAD)	7776094	details
Urine	Detected and Quantified	1.368 +/- 1.1114 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	1.2564 +/- 1.26 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Celiac disease
Bene J, Komlosi K, Gasztonyi B, Juhasz M, Tulassay Z, Melegh B: Plasma carnitine ester profile in adult celiac disease patients maintained on long-term gluten free diet. World J Gastroenterol. 2005 Nov 14;11(42):6671-5. [PubMed:16425363 ]
Very Long Chain Acyl-CoA Dehydrogenase Deficiency
Costa CG, Struys EA, Bootsma A, ten Brink HJ, Dorland L, Tavares de Almeida I, Duran M, Jakobs C: Quantitative analysis of plasma acylcarnitines using gas chromatography chemical ionization mass fragmentography. J Lipid Res. 1997 Jan;38(1):173-82. [PubMed:9034211 ]
Pregnancy
Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Glutaric aciduria II
Prasad M, Hussain S: Glutaric aciduria type II presenting as myopathy and rhabdomyolysis in a teenager. J Child Neurol. 2015 Jan;30(1):96-9. doi: 10.1177/0883073813516676. Epub 2014 Jan 21. [PubMed:24453145 ]
Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Short Chain Acyl-Coa Dehydrogenase Deficiency
Bhala A, Willi SM, Rinaldo P, Bennett MJ, Schmidt-Sommerfeld E, Hale DE: Clinical and biochemical characterization of short-chain acyl-coenzyme A dehydrogenase deficiency. J Pediatr. 1995 Jun;126(6):910-5. [PubMed:7776094 ]
Obesity
Cho K, Moon JS, Kang JH, Jang HB, Lee HJ, Park SI, Yu KS, Cho JY: Combined untargeted and targeted metabolomic profiling reveals urinary biomarkers for discriminating obese from normal-weight adolescents. Pediatr Obes. 2017 Apr;12(2):93-101. doi: 10.1111/ijpo.12114. Epub 2016 Feb 22. [PubMed:26910390 ] Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.

Associated OMIM IDs

212750 (Celiac disease)
201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)
231680 (Glutaric aciduria II)
610247 (Eosinophilic esophagitis)
601665 (Obesity)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6436

PubChem Compound

213144

PDB ID

Not Available

ChEBI ID

21949

Food Biomarker Ontology

Not Available

VMH ID

C4CRN

MarkerDB ID

MDB00000365

Good Scents ID

Not Available

References

Synthesis Reference

Lozano Pedro; Daz Mirta; de Diego Teresa; Iborra Jose L Ester synthesis from trimethylammonium alcohols in dry organic media catalyzed by immobilized Candida antarctica lipase B. Biotechnology and bioengineering (2003), 82(3), 352-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Young SP, Matern D, Gregersen N, Stevens RD, Bali D, Liu HM, Koeberl DD, Millington DS: A comparison of in vitro acylcarnitine profiling methods for the diagnosis of classical and variant short chain acyl-CoA dehydrogenase deficiency. Clin Chim Acta. 2003 Nov;337(1-2):103-13. [PubMed:14568186 ]
Golan R, Soffer Y, Katz S, Weissenberg R, Wasserzug O, Lewin LM: Carnitine and short-chain acylcarnitines in the lumen of the human male reproductive tract. Int J Androl. 1983 Aug;6(4):349-57. [PubMed:6618689 ]
Bhala A, Willi SM, Rinaldo P, Bennett MJ, Schmidt-Sommerfeld E, Hale DE: Clinical and biochemical characterization of short-chain acyl-coenzyme A dehydrogenase deficiency. J Pediatr. 1995 Jun;126(6):910-5. [PubMed:7776094 ]
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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
OMMBID - The Metabolic and Molecular Bases of Inherited Disease [Link]

Showing metabocard for Butyrylcarnitine (HMDB0002013)

MOL for HMDB0002013 (Butyrylcarnitine)

3D MOL for HMDB0002013 (Butyrylcarnitine)

3D SDF for HMDB0002013 (Butyrylcarnitine)

3D-SDF for HMDB0002013 (Butyrylcarnitine)

PDB for HMDB0002013 (Butyrylcarnitine)

3D PDB for HMDB0002013 (Butyrylcarnitine)

SMILES for HMDB0002013 (Butyrylcarnitine)

INCHI for HMDB0002013 (Butyrylcarnitine)

Structure for HMDB0002013 (Butyrylcarnitine)

3D Structure for HMDB0002013 (Butyrylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra