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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-11-02 23:54:56 UTC

Update Date

2023-05-30 20:55:49 UTC

HMDB ID

HMDB0013129

Secondary Accession Numbers

HMDB13129

Metabolite Identification

Common Name

Glutaconylcarnitine

Description

Glutaconylcarnitine is an acylcarnitine. More specifically, it is an glutaconic 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. Glutaconylcarnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine glutaconylcarnitine 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

HMDB0013129
     RDKit          3D
Glutaconylcarnitine
 38 37  0  0  0  0  0  0  0  0999 V2000
   -2.9531    1.5166   -1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4597    0.6619   -0.2412 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.6247    0.3639    0.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5563    1.4575    0.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8908   -0.4990   -0.8489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9010   -1.2416   -0.0261 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4646   -1.9826    1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4409   -3.0046    0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0540   -3.6509    1.6794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7777   -3.3543   -0.5341 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.2229   -0.4680    0.3366 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4953   -0.7641   -0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6067   -1.7721   -0.8863 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6731    0.0447    0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8487   -0.2646   -0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1387    0.3953    0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1438    1.5565    0.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1747    2.0778    1.4753 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3887    2.1753    1.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5409    0.8514   -2.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5649    2.3582   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0775    1.8796   -1.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0520   -0.6287    0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4596    1.0949    0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867    0.4874    1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1203    2.3928    0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022    0.9914    1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708    1.8076   -0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6743   -1.1613   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3435   -0.1589   -1.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5040   -2.0559   -0.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5944   -2.5344    1.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8241   -1.3097    1.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4841    0.8674    0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8504   -1.1693   -0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8422   -0.4034    0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6011    0.6158   -0.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7674    2.8273    0.5005 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  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  6
  7 32  1  0
  7 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 19 38  1  0
M  CHG  2   2   1  10  -1
M  END


  Mrv0541 02251208172D          

 19 18  0  0  1  0            999 V2000
   12.3407   -4.3230    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0533   -3.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7658   -4.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7658   -5.1457    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   12.3407   -5.1457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4784   -3.9116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6282   -3.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6282   -3.0888    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   12.4509   -3.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8054   -3.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6282   -2.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4826   -5.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1972   -6.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9117   -5.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6262   -6.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3407   -5.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7681   -6.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0553   -6.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4826   -5.1457    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  6  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  1  0  0  0  0
 15 14  2  0  0  0  0
 16 15  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  2  0  0  0  0
 16  5  1  0  0  0  0
 12 19  2  0  0  0  0
M  CHG  2   4  -1   8   1
M  END
> <DATABASE_ID>
HMDB0013129

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H19NO6/c1-13(2,3)8-9(7-11(16)17)19-12(18)6-4-5-10(14)15/h4,6,9H,5,7-8H2,1-3H3,(H-,14,15,16,17)/b6-4+/t9-/m0/s1

> <INCHI_KEY>
JXVUHLILXGZLFR-DNQSNQRASA-N

> <FORMULA>
C12H19NO6

> <MOLECULAR_WEIGHT>
273.2824

> <EXACT_MASS>
273.121237345

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.05432860275114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.71

> <JCHEM_LOGP>
-3.9457924028050786

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.150325171419424

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2412157203860907

> <JCHEM_PKA_STRONGEST_BASIC>
-6.815825826284404

> <JCHEM_POLAR_SURFACE_AREA>
103.72999999999999

> <JCHEM_REFRACTIVITY>
89.22439999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013129
     RDKit          3D
Glutaconylcarnitine
 38 37  0  0  0  0  0  0  0  0999 V2000
   -2.9531    1.5166   -1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4597    0.6619   -0.2412 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.6247    0.3639    0.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5563    1.4575    0.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8908   -0.4990   -0.8489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9010   -1.2416   -0.0261 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4646   -1.9826    1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4409   -3.0046    0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0540   -3.6509    1.6794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7777   -3.3543   -0.5341 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.2229   -0.4680    0.3366 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4953   -0.7641   -0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6067   -1.7721   -0.8863 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6731    0.0447    0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8487   -0.2646   -0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1387    0.3953    0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1438    1.5565    0.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1747    2.0778    1.4753 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3887    2.1753    1.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5409    0.8514   -2.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5649    2.3582   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0775    1.8796   -1.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0520   -0.6287    0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4596    1.0949    0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867    0.4874    1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1203    2.3928    0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022    0.9914    1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708    1.8076   -0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6743   -1.1613   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3435   -0.1589   -1.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5040   -2.0559   -0.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5944   -2.5344    1.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8241   -1.3097    1.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4841    0.8674    0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8504   -1.1693   -0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8422   -0.4034    0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6011    0.6158   -0.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7674    2.8273    0.5005 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  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  6
  7 32  1  0
  7 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 19 38  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      23.036  -8.070   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.366  -7.302   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.696  -8.070   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      25.696  -9.605   0.000  0.00  0.00           O-1
HETATM    5  O   UNK     0      23.036  -9.605   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      27.026  -7.302   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      21.706  -7.302   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      21.706  -5.766   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0      23.242  -5.766   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.170  -5.766   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.706  -4.230   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.701 -11.145   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.035 -11.915   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.369 -11.145   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.702 -11.915   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.036 -11.145   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.367 -11.915   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      24.370 -11.915   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      17.701  -9.605   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   16                                                       
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   17   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   18    5                                                  
CONECT   17   12                                                            
CONECT   18   16                                                            
CONECT   19   12                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0013129
HETATM    1  C1  UNL     1      -2.953   1.517  -1.335  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.460   0.662  -0.241  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -3.625   0.364   0.573  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.556   1.457   0.526  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.891  -0.499  -0.849  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.901  -1.242  -0.026  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.465  -1.983   1.150  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.441  -3.005   0.765  1.00  0.00           C  
HETATM    9  O1  UNL     1      -3.054  -3.651   1.679  1.00  0.00           O  
HETATM   10  O2  UNL     1      -2.778  -3.354  -0.534  1.00  0.00           O1-
HETATM   11  O3  UNL     1       0.223  -0.468   0.337  1.00  0.00           O  
HETATM   12  C8  UNL     1       1.495  -0.764  -0.119  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.607  -1.772  -0.886  1.00  0.00           O  
HETATM   14  C9  UNL     1       2.673   0.045   0.260  1.00  0.00           C  
HETATM   15  C10 UNL     1       3.849  -0.265  -0.185  1.00  0.00           C  
HETATM   16  C11 UNL     1       5.139   0.395   0.064  1.00  0.00           C  
HETATM   17  C12 UNL     1       5.144   1.557   0.920  1.00  0.00           C  
HETATM   18  O5  UNL     1       4.175   2.078   1.475  1.00  0.00           O  
HETATM   19  O6  UNL     1       6.389   2.175   1.158  1.00  0.00           O  
HETATM   20  H1  UNL     1      -3.541   0.851  -2.012  1.00  0.00           H  
HETATM   21  H2  UNL     1      -3.565   2.358  -0.937  1.00  0.00           H  
HETATM   22  H3  UNL     1      -2.078   1.880  -1.892  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.052  -0.629   0.362  1.00  0.00           H  
HETATM   24  H5  UNL     1      -4.460   1.095   0.387  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.387   0.487   1.663  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.120   2.393   0.812  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.302   0.991   1.519  1.00  0.00           H  
HETATM   28  H9  UNL     1      -0.671   1.808  -0.019  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.674  -1.161  -1.198  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.343  -0.159  -1.773  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.504  -2.056  -0.708  1.00  0.00           H  
HETATM   32  H13 UNL     1      -0.594  -2.534   1.613  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.824  -1.310   1.954  1.00  0.00           H  
HETATM   34  H15 UNL     1       2.484   0.867   0.903  1.00  0.00           H  
HETATM   35  H16 UNL     1       3.850  -1.169  -0.854  1.00  0.00           H  
HETATM   36  H17 UNL     1       5.842  -0.403   0.450  1.00  0.00           H  
HETATM   37  H18 UNL     1       5.601   0.616  -0.960  1.00  0.00           H  
HETATM   38  H19 UNL     1       6.767   2.827   0.501  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    4    5
CONECT    3   23   24   25
CONECT    4   26   27   28
CONECT    5    6   29   30
CONECT    6    7   11   31
CONECT    7    8   32   33
CONECT    8    9    9   10
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   34
CONECT   15   16   35
CONECT   16   17   36   37
CONECT   17   18   18   19
CONECT   19   38
END

HMDB0013129
     RDKit          3D
Glutaconylcarnitine
 38 37  0  0  0  0  0  0  0  0999 V2000
   -2.9531    1.5166   -1.3351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4597    0.6619   -0.2412 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.6247    0.3639    0.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5563    1.4575    0.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8908   -0.4990   -0.8489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9010   -1.2416   -0.0261 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4646   -1.9826    1.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4409   -3.0046    0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0540   -3.6509    1.6794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7777   -3.3543   -0.5341 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.2229   -0.4680    0.3366 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4953   -0.7641   -0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6067   -1.7721   -0.8863 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6731    0.0447    0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8487   -0.2646   -0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1387    0.3953    0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1438    1.5565    0.9201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1747    2.0778    1.4753 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3887    2.1753    1.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5409    0.8514   -2.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5649    2.3582   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0775    1.8796   -1.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0520   -0.6287    0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4596    1.0949    0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867    0.4874    1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1203    2.3928    0.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022    0.9914    1.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708    1.8076   -0.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6743   -1.1613   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3435   -0.1589   -1.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5040   -2.0559   -0.7079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5944   -2.5344    1.6132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8241   -1.3097    1.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4841    0.8674    0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8504   -1.1693   -0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8422   -0.4034    0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6011    0.6158   -0.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7674    2.8273    0.5005 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  1  0
 17 18  2  0
 17 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  6
  7 32  1  0
  7 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 19 38  1  0
M  CHG  2   2   1  10  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Glutaconyl-L-carnitine	HMDB

Chemical Formula

C₁₂H₁₉NO₆

Average Molecular Weight

273.2824

Monoisotopic Molecular Weight

273.121237345

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H19NO6/c1-13(2,3)8-9(7-11(16)17)19-12(18)6-4-5-10(14)15/h4,6,9H,5,7-8H2,1-3H3,(H-,14,15,16,17)/b6-4+/t9-/m0/s1

InChI Key

JXVUHLILXGZLFR-DNQSNQRASA-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

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)

Cellular substructure

Organelle

Peroxisome (PMID: 35710135)

Excreta

Biofluid or Excreta

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

Cell

All cells and tissues (PMID: 35710135)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013129)

Source

Exogenous

Food

Food (HMDB: HMDB0013129)

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)

Exogenous (HMDB: HMDB0013129)

Endogenous

Animal

Animal (HMDB: HMDB0013129)

Endogenous (HMDB: HMDB0013129)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0013129)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0013129)

Lipid metabolism pathway (HMDB: HMDB0013129)

Cellular process

Cell signaling (HMDB: HMDB0013129)

Biochemical process

Lipid transport (HMDB: HMDB0013129)

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	0.13 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-3.9	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.24	ChemAxon
pKa (Strongest Basic)	-6.8	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	9	ChemAxon
Refractivity	89.22 m³·mol⁻¹	ChemAxon
Polarizability	27.05 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]+	166.241	30932474
DeepCCS	[M-H]-	162.412	30932474
DeepCCS	[M-2H]-	198.776	30932474
DeepCCS	[M+Na]+	174.929	30932474
AllCCS	[M+H]+	163.8	32859911
AllCCS	[M+H-H2O]+	160.9	32859911
AllCCS	[M+NH4]+	166.6	32859911
AllCCS	[M+Na]+	167.3	32859911
AllCCS	[M-H]-	168.3	32859911
AllCCS	[M+Na-2H]-	169.1	32859911
AllCCS	[M+HCOO]-	170.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Glutaconylcarnitine	OC(=O)C\C=C\C(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C	3242.4	Standard polar	33892256
Glutaconylcarnitine	OC(=O)C\C=C\C(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C	1689.3	Standard non polar	33892256
Glutaconylcarnitine	OC(=O)C\C=C\C(=O)O[C@@H](CC([O-])=O)C[N+](C)(C)C	1937.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Glutaconylcarnitine,1TMS,isomer #1	C[N+](C)(C)C[C@H](CC(=O)[O-])OC(=O)/C=C/CC(=O)O[Si](C)(C)C	1920.3	Semi standard non polar	33892256
Glutaconylcarnitine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C/C=C/C(=O)O[C@@H](CC(=O)[O-])C[N+](C)(C)C	2167.0	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 - Glutaconylcarnitine GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9200000000-2add729af098ddd82694	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Glutaconylcarnitine 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 - Glutaconylcarnitine 10V, Positive-QTOF	splash10-00di-0090000000-d796ba44a440c7170659	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutaconylcarnitine 20V, Positive-QTOF	splash10-0079-9050000000-f8db13805439a7cd8cc3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Glutaconylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.02 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.005-0.030 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Feces	Detected and Quantified	0.17 +/- 0.07 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.2 +/- 0.09 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Urine	Detected and Quantified	0.04 (0.01-0.06) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.04 (0.02-0.05) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	0.0-0.03 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.01 +/- 0.01 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.02 +/- 0.01 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0725 (0.1405) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	0.0262 (0.005) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details

Associated Disorders and Diseases

Disease References

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 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029302

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481620

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 ]
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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 ]
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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 ]
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Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Glutaconylcarnitine (HMDB0013129)

MOL for HMDB0013129 (Glutaconylcarnitine)

3D MOL for HMDB0013129 (Glutaconylcarnitine)

3D SDF for HMDB0013129 (Glutaconylcarnitine)

3D-SDF for HMDB0013129 (Glutaconylcarnitine)

PDB for HMDB0013129 (Glutaconylcarnitine)

3D PDB for HMDB0013129 (Glutaconylcarnitine)

SMILES for HMDB0013129 (Glutaconylcarnitine)

INCHI for HMDB0013129 (Glutaconylcarnitine)

Structure for HMDB0013129 (Glutaconylcarnitine)

3D Structure for HMDB0013129 (Glutaconylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra