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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-11-03 15:38:56 UTC

Update Date

2022-10-24 19:44:11 UTC

HMDB ID

HMDB0013134

Secondary Accession Numbers

HMDB13134

Metabolite Identification

Common Name

Fumarycarnitine

Description

Fumarycarnitine is an acylcarnitine. More specifically, it is an fumaric 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. Fumarycarnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine fumarycarnitine 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

HMDB0013134
     RDKit          3D
Fumarycarnitine
 35 34  0  0  0  0  0  0  0  0999 V2000
   -3.4684   -0.1710   -0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3956   -0.2084    0.4877 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.5369    0.9032    1.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7826   -1.3736    1.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1121   -0.5018    0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1515    0.4864   -0.4384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3702    1.1397   -1.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5728    1.9106   -1.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4026    1.5337   -2.8738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9152    3.0559   -1.2959 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.0857   -0.2777   -0.6975 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2673    0.0610   -0.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2912    1.0423    0.6733 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4692   -0.7317   -0.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6328   -0.4256    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8091   -1.2302   -0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7633   -2.2156   -0.9233 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0138   -0.9075    0.4550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1265   -0.6692   -1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3614   -0.7765   -0.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8820    0.8460   -0.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2664    0.5829    2.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6248    1.1250    1.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0344    1.8232    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8923   -1.6491    1.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0380   -2.1850    0.6559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6631   -1.1043    1.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6013   -1.1837    0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2449   -1.2472   -0.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1664    1.2657    0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5012    1.8700   -1.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1796    0.3935   -2.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4459   -1.5708   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6881    0.4081    0.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4886   -0.0181    0.3178 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  1
  7 31  1  0
  7 32  1  0
 14 33  1  0
 15 34  1  0
 18 35  1  0
M  CHG  2   2   1  10  -1
M  END


  Mrv0541 02251208172D          

 18 17  0  0  1  0            999 V2000
   10.6306   -4.7662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0431   -4.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6306   -3.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8057   -3.3373    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.8057   -4.7662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0431   -2.6228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0431   -5.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8681   -5.4807    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   11.8681   -4.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8681   -6.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6931   -5.4807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9477   -4.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6622   -5.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3767   -4.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0912   -5.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2333   -5.1788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9477   -3.9412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0912   -6.0038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  1  5  1  1  0  0  0
  3  6  2  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  2  0  0  0  0
 14 15  1  0  0  0  0
 12 16  1  0  0  0  0
 12 17  2  0  0  0  0
 15  5  1  0  0  0  0
 15 18  2  0  0  0  0
M  CHG  2   4  -1   8   1
M  END
> <DATABASE_ID>
HMDB0013134

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H17NO6/c1-12(2,3)7-8(6-10(15)16)18-11(17)5-4-9(13)14/h4-5,8H,6-7H2,1-3H3,(H-,13,14,15,16)/b5-4+/t8-/m0/s1

> <INCHI_KEY>
QMRSJQVUNCCUCI-ZJELKQJVSA-N

> <FORMULA>
C11H17NO6

> <MOLECULAR_WEIGHT>
259.2558

> <EXACT_MASS>
259.105587281

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
24.949577698353103

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-{[(2E)-3-carboxyprop-2-enoyl]oxy}-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-1.73

> <JCHEM_LOGP>
-4.030615921471746

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.054598889998025

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.161534632026481

> <JCHEM_PKA_STRONGEST_BASIC>
-6.856750006289515

> <JCHEM_POLAR_SURFACE_AREA>
103.72999999999999

> <JCHEM_REFRACTIVITY>
84.60009999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-{[(2E)-3-carboxyprop-2-enoyl]oxy}-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013134
     RDKit          3D
Fumarycarnitine
 35 34  0  0  0  0  0  0  0  0999 V2000
   -3.4684   -0.1710   -0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3956   -0.2084    0.4877 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.5369    0.9032    1.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7826   -1.3736    1.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1121   -0.5018    0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1515    0.4864   -0.4384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3702    1.1397   -1.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5728    1.9106   -1.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4026    1.5337   -2.8738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9152    3.0559   -1.2959 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.0857   -0.2777   -0.6975 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2673    0.0610   -0.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2912    1.0423    0.6733 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4692   -0.7317   -0.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6328   -0.4256    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8091   -1.2302   -0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7633   -2.2156   -0.9233 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0138   -0.9075    0.4550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1265   -0.6692   -1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3614   -0.7765   -0.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8820    0.8460   -0.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2664    0.5829    2.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6248    1.1250    1.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0344    1.8232    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8923   -1.6491    1.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0380   -2.1850    0.6559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6631   -1.1043    1.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6013   -1.1837    0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2449   -1.2472   -0.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1664    1.2657    0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5012    1.8700   -1.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1796    0.3935   -2.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4459   -1.5708   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6881    0.4081    0.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4886   -0.0181    0.3178 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  1
  7 31  1  0
  7 32  1  0
 14 33  1  0
 15 34  1  0
 18 35  1  0
M  CHG  2   2   1  10  -1
M  END

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      19.844  -8.897   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.614  -7.563   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.844  -6.230   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      18.304  -6.230   0.000  0.00  0.00           O-1
HETATM    5  O   UNK     0      18.304  -8.897   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      20.614  -4.896   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      20.614 -10.231   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      22.154 -10.231   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0      22.154  -8.691   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.154 -11.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.694 -10.231   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.969  -8.897   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.303  -9.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.637  -8.897   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.970  -9.667   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      11.635  -9.667   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      12.969  -7.357   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      16.970 -11.207   0.000  0.00  0.00           O+0
CONECT    1    2    5    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3                                                            
CONECT    5    1   15                                                       
CONECT    6    3                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12   13   16   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    5   18                                                  
CONECT   16   12                                                            
CONECT   17   12                                                            
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0013134
HETATM    1  C1  UNL     1      -3.468  -0.171  -0.474  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.396  -0.208   0.488  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -2.537   0.903   1.398  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.783  -1.374   1.356  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.112  -0.502   0.039  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.152   0.486  -0.438  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.370   1.140  -1.772  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.573   1.911  -1.987  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.403   1.534  -2.874  1.00  0.00           O  
HETATM   10  O2  UNL     1      -1.915   3.056  -1.296  1.00  0.00           O1-
HETATM   11  O3  UNL     1       1.086  -0.278  -0.697  1.00  0.00           O  
HETATM   12  C8  UNL     1       2.267   0.061  -0.104  1.00  0.00           C  
HETATM   13  O4  UNL     1       2.291   1.042   0.673  1.00  0.00           O  
HETATM   14  C9  UNL     1       3.469  -0.732  -0.393  1.00  0.00           C  
HETATM   15  C10 UNL     1       4.633  -0.426   0.171  1.00  0.00           C  
HETATM   16  C11 UNL     1       5.809  -1.230  -0.135  1.00  0.00           C  
HETATM   17  O5  UNL     1       5.763  -2.216  -0.923  1.00  0.00           O  
HETATM   18  O6  UNL     1       7.014  -0.908   0.455  1.00  0.00           O  
HETATM   19  H1  UNL     1      -3.126  -0.669  -1.406  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.361  -0.777  -0.151  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.882   0.846  -0.638  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.266   0.583   2.452  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.625   1.125   1.458  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.034   1.823   1.117  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.892  -1.649   1.957  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.038  -2.185   0.656  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.663  -1.104   1.961  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.601  -1.184   0.802  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.245  -1.247  -0.825  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.166   1.266   0.261  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.501   1.870  -1.876  1.00  0.00           H  
HETATM   32  H14 UNL     1      -0.180   0.394  -2.592  1.00  0.00           H  
HETATM   33  H15 UNL     1       3.446  -1.571  -1.056  1.00  0.00           H  
HETATM   34  H16 UNL     1       4.688   0.408   0.843  1.00  0.00           H  
HETATM   35  H17 UNL     1       7.489  -0.018   0.318  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4    5
CONECT    3   22   23   24
CONECT    4   25   26   27
CONECT    5    6   28   29
CONECT    6    7   11   30
CONECT    7    8   31   32
CONECT    8    9    9   10
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   33
CONECT   15   16   34
CONECT   16   17   17   18
CONECT   18   35
END

HMDB0013134
     RDKit          3D
Fumarycarnitine
 35 34  0  0  0  0  0  0  0  0999 V2000
   -3.4684   -0.1710   -0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3956   -0.2084    0.4877 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.5369    0.9032    1.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7826   -1.3736    1.3564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1121   -0.5018    0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1515    0.4864   -0.4384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3702    1.1397   -1.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5728    1.9106   -1.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4026    1.5337   -2.8738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9152    3.0559   -1.2959 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.0857   -0.2777   -0.6975 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2673    0.0610   -0.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2912    1.0423    0.6733 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4692   -0.7317   -0.3927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6328   -0.4256    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8091   -1.2302   -0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7633   -2.2156   -0.9233 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0138   -0.9075    0.4550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1265   -0.6692   -1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3614   -0.7765   -0.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8820    0.8460   -0.6382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2664    0.5829    2.4524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6248    1.1250    1.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0344    1.8232    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8923   -1.6491    1.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0380   -2.1850    0.6559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6631   -1.1043    1.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6013   -1.1837    0.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2449   -1.2472   -0.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1664    1.2657    0.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5012    1.8700   -1.8760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1796    0.3935   -2.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4459   -1.5708   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6881    0.4081    0.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4886   -0.0181    0.3178 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  1
  7 31  1  0
  7 32  1  0
 14 33  1  0
 15 34  1  0
 18 35  1  0
M  CHG  2   2   1  10  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₁H₁₇NO₆

Average Molecular Weight

259.2558

Monoisotopic Molecular Weight

259.105587281

IUPAC Name

(3S)-3-{[(2E)-3-carboxyprop-2-enoyl]oxy}-4-(trimethylazaniumyl)butanoate

Traditional Name

(3S)-3-{[(2E)-3-carboxyprop-2-enoyl]oxy}-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H17NO6/c1-12(2,3)7-8(6-10(15)16)18-11(17)5-4-9(13)14/h4-5,8H,6-7H2,1-3H3,(H-,13,14,15,16)/b5-4+/t8-/m0/s1

InChI Key

QMRSJQVUNCCUCI-ZJELKQJVSA-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
Quaternary ammonium salt
Enoate ester
Tetraalkylammonium salt
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Amine
Hydrocarbon derivative
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Cancer

Breast cancer (PMID: 35710135)

Diabetes mellitus type 2 (PMID: 35710135)
Celiac disease (PMID: 35710135)
Inflammatory bowel disease (PMID: 35710135)

Circulatory system disorder

Cardiac disorder

Cardiovascular disease (PMID: 35710135)
Heart failure (PMID: 35710135)

Renal system and urinary system

Renal disorder

Renal cell carcinoma (PMID: 35710135)

Disposition

Biological location

Cytoplasm (HMDB: HMDB0013134)
Cell membrane (HMDB: HMDB0013134)

Biofluid or Excreta

Blood (HMDB: HMDB0013134)
Urine (HMDB: HMDB0013134)

Cellular substructure

Organelle

peroxisome (PMID: 35710135)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Excreta

Biofluid or Excreta

Urine (PMID: 35710135)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013134)

Source

Endogenous

Endogenous (HMDB: HMDB0013134)

Animal

Animal (HMDB: HMDB0013134)

Exogenous

Food

Food (HMDB: HMDB0013134)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0013134)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0013134)

Cellular process

Cell signaling (HMDB: HMDB0013134)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0013134)

Role

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	0.1 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-4	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	3.16	ChemAxon
pKa (Strongest Basic)	-6.9	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	84.6 m³·mol⁻¹	ChemAxon
Polarizability	24.95 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]+	161.672	30932474
DeepCCS	[M-H]-	158.244	30932474
DeepCCS	[M-2H]-	194.316	30932474
DeepCCS	[M+Na]+	170.123	30932474
AllCCS	[M+H]+	158.9	32859911
AllCCS	[M+H-H2O]+	155.9	32859911
AllCCS	[M+NH4]+	161.7	32859911
AllCCS	[M+Na]+	162.5	32859911
AllCCS	[M-H]-	164.0	32859911
AllCCS	[M+Na-2H]-	164.8	32859911
AllCCS	[M+HCOO]-	165.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fumarycarnitine	[O-]C(=O)C[C@H](OC(=O)\C=C\C(O)=O)C[N+](C)(C)C	3282.7	Standard polar	33892256
Fumarycarnitine	[O-]C(=O)C[C@H](OC(=O)\C=C\C(O)=O)C[N+](C)(C)C	1642.9	Standard non polar	33892256
Fumarycarnitine	[O-]C(=O)C[C@H](OC(=O)\C=C\C(O)=O)C[N+](C)(C)C	1858.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fumarycarnitine,1TMS,isomer #1	C[N+](C)(C)C[C@H](CC(=O)[O-])OC(=O)/C=C/C(=O)O[Si](C)(C)C	1855.3	Semi standard non polar	33892256
Fumarycarnitine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C/C(=O)O[C@@H](CC(=O)[O-])C[N+](C)(C)C	2084.8	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 - Fumarycarnitine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9200000000-968aa662ef427804c970	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fumarycarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fumarycarnitine 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 - Fumarycarnitine 10V, Positive-QTOF	splash10-03di-0090000000-388e581a6a46a4ad3b48	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumarycarnitine 20V, Positive-QTOF	splash10-01p9-9050000000-db3ee9387c9ed21983bd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fumarycarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB029307

KNApSAcK ID

Not Available

Chemspider ID

30776697

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481699

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 Fumarycarnitine (HMDB0013134)

MOL for HMDB0013134 (Fumarycarnitine)

3D MOL for HMDB0013134 (Fumarycarnitine)

3D SDF for HMDB0013134 (Fumarycarnitine)

3D-SDF for HMDB0013134 (Fumarycarnitine)

PDB for HMDB0013134 (Fumarycarnitine)

3D PDB for HMDB0013134 (Fumarycarnitine)

SMILES for HMDB0013134 (Fumarycarnitine)

INCHI for HMDB0013134 (Fumarycarnitine)

Structure for HMDB0013134 (Fumarycarnitine)

3D Structure for HMDB0013134 (Fumarycarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra