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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-13 11:52:03 UTC

Update Date

2022-10-24 19:44:13 UTC

HMDB ID

HMDB0041993

Secondary Accession Numbers

HMDB41993

Metabolite Identification

Common Name

Pivaloylcarnitine

Description

Pivaloylcarnitine is an acylcarnitine. More specifically, it is an pivalic acid ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279 ). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review (PMID: 35710135 ), acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. Pivaloylcarnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine Pivaloylcarnitine is a member of the most abundant group of carnitines in the body, comprising more than 50% of all acylcarnitines quantified in tissues and biofluids (PMID: 31920980 ). Some short-chain carnitines have been studied as supplements or treatments for a number of diseases, including neurological disorders and inborn errors of metabolism. Carnitine acetyltransferase (CrAT, EC:2.3.1.7) is responsible for the synthesis of all short-chain and short branched-chain acylcarnitines (PMID: 23485643 ). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available (PMID: 35710135 ).

Structure

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

HMDB0041993
     RDKit          3D
Pivaloylcarnitine
 40 39  0  0  0  0  0  0  0  0999 V2000
    3.5431    0.9049    1.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626    0.3157    0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4100    1.4014   -0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4420   -0.8133   -0.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3937   -0.1749    0.6481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2162   -0.0496    1.8818 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3824   -0.7638   -0.0653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7807   -1.1991    0.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9551   -2.7104    0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0107   -3.2602   -0.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9278   -2.6473   -1.9093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1784   -4.6537   -0.9301 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.0493   -0.6027    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1553    0.8113    0.1433 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.5886    1.1427    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6867    1.3940    1.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419    1.4631   -1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3371    0.4828    2.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4078    2.0102    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6320    0.7556    0.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7983    1.0598   -1.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8868    2.2479   -0.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3732    1.8279   -1.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3191   -1.7323    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5212   -0.5486   -0.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1434   -0.9863   -1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7109   -0.9785    1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9488   -2.9054    1.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2095   -3.2180    1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1574   -0.8762   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8934   -1.0920    0.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0065    1.0553    1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7395    2.1397   -0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1028    0.3424   -0.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6303    0.7545    2.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2840    2.3014    1.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6605    1.8178    1.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590    2.4573   -1.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7154    0.8746   -1.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764    1.6521   -0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 13 30  1  0
 13 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
 17 38  1  0
 17 39  1  0
 17 40  1  0
M  CHG  2  12  -1  14   1
M  END


  Mrv1652304032016532D          

 17 16  0  0  0  0            999 V2000
   -0.6039    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.3184    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12 11  1  0  0  0  0
 13  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14 10  2  0  0  0  0
 15 10  1  0  0  0  0
 16 11  2  0  0  0  0
 17  9  1  0  0  0  0
 17 11  1  0  0  0  0
M  CHG  2  13   1  15  -1
M  END
> <DATABASE_ID>
HMDB0041993

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H23NO4/c1-12(2,3)11(16)17-9(7-10(14)15)8-13(4,5)6/h9H,7-8H2,1-6H3

> <INCHI_KEY>
YICAQFPUDACYGQ-UHFFFAOYSA-N

> <FORMULA>
C12H23NO4

> <MOLECULAR_WEIGHT>
245.3153

> <EXACT_MASS>
245.162708229

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
26.527667008129658

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2,2-dimethylpropanoyl)oxy]-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-1.98

> <JCHEM_LOGP>
-2.6468442104717456

> <ALOGPS_LOGS>
-4.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.342854288792191

> <JCHEM_PKA_STRONGEST_BASIC>
-7.125804440918044

> <JCHEM_POLAR_SURFACE_AREA>
66.42999999999999

> <JCHEM_REFRACTIVITY>
86.3392

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2,2-dimethylpropanoyl)oxy]-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041993
     RDKit          3D
Pivaloylcarnitine
 40 39  0  0  0  0  0  0  0  0999 V2000
    3.5431    0.9049    1.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626    0.3157    0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4100    1.4014   -0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4420   -0.8133   -0.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3937   -0.1749    0.6481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2162   -0.0496    1.8818 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3824   -0.7638   -0.0653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7807   -1.1991    0.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9551   -2.7104    0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0107   -3.2602   -0.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9278   -2.6473   -1.9093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1784   -4.6537   -0.9301 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.0493   -0.6027    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1553    0.8113    0.1433 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.5886    1.1427    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6867    1.3940    1.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419    1.4631   -1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3371    0.4828    2.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4078    2.0102    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6320    0.7556    0.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7983    1.0598   -1.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8868    2.2479   -0.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3732    1.8279   -1.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3191   -1.7323    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5212   -0.5486   -0.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1434   -0.9863   -1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7109   -0.9785    1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9488   -2.9054    1.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2095   -3.2180    1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1574   -0.8762   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8934   -1.0920    0.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0065    1.0553    1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7395    2.1397   -0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1028    0.3424   -0.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6303    0.7545    2.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2840    2.3014    1.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6605    1.8178    1.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590    2.4573   -1.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7154    0.8746   -1.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764    1.6521   -0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 13 30  1  0
 13 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
 17 38  1  0
 17 39  1  0
 17 40  1  0
M  CHG  2  12  -1  14   1
M  END

HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0      -1.127   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.413   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.127  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.413  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.127   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.127   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.127   4.620   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.127  -1.540   0.000  0.00  0.00           N+1
HETATM   14  O   UNK     0       2.874   2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.207   0.000   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0      -2.461   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.206   2.310   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   12                                                            
CONECT    4   13                                                            
CONECT    5   13                                                            
CONECT    6   13                                                            
CONECT    7    9   10                                                       
CONECT    8    9   13                                                       
CONECT    9    7    8   17                                                  
CONECT   10    7   14   15                                                  
CONECT   11   12   16   17                                                  
CONECT   12    1    2    3   11                                             
CONECT   13    4    5    6    8                                             
CONECT   14   10                                                            
CONECT   15   10                                                            
CONECT   16   11                                                            
CONECT   17    9   11                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0041993
HETATM    1  C1  UNL     1       3.543   0.905   1.145  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.663   0.316   0.068  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.410   1.401  -0.949  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.442  -0.813  -0.574  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.394  -0.175   0.648  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.216  -0.050   1.882  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.382  -0.764  -0.065  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.781  -1.199   0.553  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.955  -2.710   0.515  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.011  -3.260  -0.831  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.928  -2.647  -1.909  1.00  0.00           O  
HETATM   12  O4  UNL     1      -1.178  -4.654  -0.930  1.00  0.00           O1-
HETATM   13  C9  UNL     1      -2.049  -0.603   0.039  1.00  0.00           C  
HETATM   14  N1  UNL     1      -2.155   0.811   0.143  1.00  0.00           N1+
HETATM   15  C10 UNL     1      -3.589   1.143   0.032  1.00  0.00           C  
HETATM   16  C11 UNL     1      -1.687   1.394   1.345  1.00  0.00           C  
HETATM   17  C12 UNL     1      -1.542   1.463  -1.024  1.00  0.00           C  
HETATM   18  H1  UNL     1       3.337   0.483   2.141  1.00  0.00           H  
HETATM   19  H2  UNL     1       3.408   2.010   1.238  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.632   0.756   0.929  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.798   1.060  -1.807  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.887   2.248  -0.417  1.00  0.00           H  
HETATM   23  H6  UNL     1       3.373   1.828  -1.285  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.319  -1.732   0.045  1.00  0.00           H  
HETATM   25  H8  UNL     1       4.521  -0.549  -0.582  1.00  0.00           H  
HETATM   26  H9  UNL     1       3.143  -0.986  -1.615  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.711  -0.979   1.663  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.949  -2.905   1.013  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.210  -3.218   1.180  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.157  -0.876  -1.030  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.893  -1.092   0.567  1.00  0.00           H  
HETATM   32  H15 UNL     1      -4.007   1.055   1.055  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.739   2.140  -0.393  1.00  0.00           H  
HETATM   34  H17 UNL     1      -4.103   0.342  -0.572  1.00  0.00           H  
HETATM   35  H18 UNL     1      -1.630   0.754   2.218  1.00  0.00           H  
HETATM   36  H19 UNL     1      -2.284   2.301   1.657  1.00  0.00           H  
HETATM   37  H20 UNL     1      -0.660   1.818   1.141  1.00  0.00           H  
HETATM   38  H21 UNL     1      -2.059   2.457  -1.129  1.00  0.00           H  
HETATM   39  H22 UNL     1      -1.715   0.875  -1.936  1.00  0.00           H  
HETATM   40  H23 UNL     1      -0.476   1.652  -0.866  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4    5
CONECT    3   21   22   23
CONECT    4   24   25   26
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   13   27
CONECT    9   10   28   29
CONECT   10   11   11   12
CONECT   13   14   30   31
CONECT   14   15   16   17
CONECT   15   32   33   34
CONECT   16   35   36   37
CONECT   17   38   39   40
END

HMDB0041993
     RDKit          3D
Pivaloylcarnitine
 40 39  0  0  0  0  0  0  0  0999 V2000
    3.5431    0.9049    1.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6626    0.3157    0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4100    1.4014   -0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4420   -0.8133   -0.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3937   -0.1749    0.6481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2162   -0.0496    1.8818 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3824   -0.7638   -0.0653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7807   -1.1991    0.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9551   -2.7104    0.5153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0107   -3.2602   -0.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9278   -2.6473   -1.9093 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1784   -4.6537   -0.9301 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.0493   -0.6027    0.0387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1553    0.8113    0.1433 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.5886    1.1427    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6867    1.3940    1.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419    1.4631   -1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3371    0.4828    2.1412 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4078    2.0102    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6320    0.7556    0.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7983    1.0598   -1.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8868    2.2479   -0.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3732    1.8279   -1.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3191   -1.7323    0.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5212   -0.5486   -0.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1434   -0.9863   -1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7109   -0.9785    1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9488   -2.9054    1.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2095   -3.2180    1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1574   -0.8762   -1.0302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8934   -1.0920    0.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0065    1.0553    1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7395    2.1397   -0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1028    0.3424   -0.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6303    0.7545    2.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2840    2.3014    1.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6605    1.8178    1.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590    2.4573   -1.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7154    0.8746   -1.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764    1.6521   -0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 13 30  1  0
 13 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
 17 38  1  0
 17 39  1  0
 17 40  1  0
M  CHG  2  12  -1  14   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Pivaloyl carnitine	HMDB

Chemical Formula

C₁₂H₂₃NO₄

Average Molecular Weight

245.3153

Monoisotopic Molecular Weight

245.162708229

IUPAC Name

3-[(2,2-dimethylpropanoyl)oxy]-4-(trimethylazaniumyl)butanoate

Traditional Name

3-[(2,2-dimethylpropanoyl)oxy]-4-(trimethylammonio)butanoate

CAS Registry Number

98299-38-8

SMILES

CC(C)(C)C(=O)OC(CC([O-])=O)C[N+](C)(C)C

InChI Identifier

InChI=1S/C12H23NO4/c1-12(2,3)11(16)17-9(7-10(14)15)8-13(4,5)6/h9H,7-8H2,1-6H3

InChI Key

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Excreta

Biofluid or Excreta

Urine (PMID: 35710135)

Cellular substructure

Cytoplasm (PMID: 35710135)
Mitochondrion matrix (PMID: 35710135)

Organelle

Peroxisome (PMID: 35710135)

Source

Endogenous

Endogenous (HMDB: HMDB0041993)

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)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

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	0.013 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2.6	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.34	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	7	ChemAxon
Refractivity	86.34 m³·mol⁻¹	ChemAxon
Polarizability	26.53 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]+	154.15	30932474
DeepCCS	[M-H]-	151.792	30932474
DeepCCS	[M-2H]-	184.675	30932474
DeepCCS	[M+Na]+	160.243	30932474
AllCCS	[M+H]+	156.2	32859911
AllCCS	[M+H-H2O]+	153.3	32859911
AllCCS	[M+NH4]+	159.0	32859911
AllCCS	[M+Na]+	159.8	32859911
AllCCS	[M-H]-	164.3	32859911
AllCCS	[M+Na-2H]-	165.4	32859911
AllCCS	[M+HCOO]-	166.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.2 minutes	32390414
Predicted by Siyang on May 30, 2022	10.7585 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.48 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	163.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1233.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	195.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	129.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	151.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	63.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	388.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	411.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	367.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	946.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	276.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1452.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	216.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	276.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	298.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	231.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	10.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pivaloylcarnitine	CC(C)(C)C(=O)OC(CC([O-])=O)C[N+](C)(C)C	1710.3	Standard polar	33892256
Pivaloylcarnitine	CC(C)(C)C(=O)OC(CC([O-])=O)C[N+](C)(C)C	1237.2	Standard non polar	33892256
Pivaloylcarnitine	CC(C)(C)C(=O)OC(CC([O-])=O)C[N+](C)(C)C	1453.9	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 - Pivaloylcarnitine 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 - Pivaloylcarnitine 10V, Positive-QTOF	splash10-0002-0090000000-a919a7a98ddb53d7bb2b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivaloylcarnitine 20V, Positive-QTOF	splash10-000j-9050000000-87beaf2642b8fc410f0c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pivaloylcarnitine 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)	2021-09-24	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

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

FDB098028

KNApSAcK ID

Not Available

Chemspider ID

112688

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

126894

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

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 ]
Violante S, Ijlst L, Ruiter J, Koster J, van Lenthe H, Duran M, de Almeida IT, Wanders RJ, Houten SM, Ventura FV: Substrate specificity of human carnitine acetyltransferase: Implications for fatty acid and branched-chain amino acid metabolism. Biochim Biophys Acta. 2013 Jun;1832(6):773-9. doi: 10.1016/j.bbadis.2013.02.012. Epub 2013 Feb 24. [PubMed:23485643 ]
FRITZ IB: Action of carnitine on long chain fatty acid oxidation by liver. Am J Physiol. 1959 Aug;197:297-304. doi: 10.1152/ajplegacy.1959.197.2.297. [PubMed:13825279 ]
Makarova E, Makrecka-Kuka M, Vilks K, Volska K, Sevostjanovs E, Grinberga S, Zarkova-Malkova O, Dambrova M, Liepinsh E: Decreases in Circulating Concentrations of Long-Chain Acylcarnitines and Free Fatty Acids During the Glucose Tolerance Test Represent Tissue-Specific Insulin Sensitivity. Front Endocrinol (Lausanne). 2019 Dec 17;10:870. doi: 10.3389/fendo.2019.00870. eCollection 2019. [PubMed:31920980 ]
Dambrova M, Makrecka-Kuka M, Kuka J, Vilskersts R, Nordberg D, Attwood MM, Smesny S, Sen ZD, Guo AC, Oler E, Tian S, Zheng J, Wishart DS, Liepinsh E, Schioth HB: Acylcarnitines: Nomenclature, Biomarkers, Therapeutic Potential, Drug Targets, and Clinical Trials. Pharmacol Rev. 2022 Jul;74(3):506-551. doi: 10.1124/pharmrev.121.000408. [PubMed:35710135 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Pivaloylcarnitine (HMDB0041993)

MOL for HMDB0041993 (Pivaloylcarnitine)

3D MOL for HMDB0041993 (Pivaloylcarnitine)

3D SDF for HMDB0041993 (Pivaloylcarnitine)

3D-SDF for HMDB0041993 (Pivaloylcarnitine)

PDB for HMDB0041993 (Pivaloylcarnitine)

3D PDB for HMDB0041993 (Pivaloylcarnitine)

SMILES for HMDB0041993 (Pivaloylcarnitine)

INCHI for HMDB0041993 (Pivaloylcarnitine)

Structure for HMDB0041993 (Pivaloylcarnitine)

3D Structure for HMDB0041993 (Pivaloylcarnitine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra