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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:50 UTC

Update Date

2023-05-30 20:55:49 UTC

HMDB ID

HMDB0002366

Secondary Accession Numbers

HMDB02366

Metabolite Identification

Common Name

Tiglylcarnitine

Description

Tiglylcarnitine is an acylcarnitine. More specifically, it is an tiglic 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. Tiglylcarnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine Tiglylcarnitine 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. In particular Tiglylcarnitine is elevated in the blood or plasma of individuals with beta ketothiolase deficiency/acat1 gene mutation (PMID: 27264805 , PMID: 14518824 , PMID: 3435793 ), and ECHS1 deficiency (PMID: 31908952 ). It is also decreased in the blood or plasma of individuals with familial mediterranean fever (PMID: 29900937 ), carcinoma, lewis lung (PMID: 30839735 ), metabolic syndrome, type 2 diabetes mellitus, and cardiovascular diseases (PMID: 24710945 ). Tiglylcarnitine is also detected in the urinary organic acid and blood spot acylcarnitine profiles in patients with mitochondrial acetoacetyl-CoA thiolase (T2) deficiency, an inborn error of metabolism affecting isoleucine and ketone bodies in the catabolic process (PMID: 14518824 ). Tiglylcarnitine is found to be associated with celiac disease, which is also an inborn error of metabolism. Tiglylcarnitine has been identified in the human placenta (PMID: 32033212 ). 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

HMDB0002366
     RDKit          3D
Tiglylcarnitine
 38 37  0  0  0  0  0  0  0  0999 V2000
    4.8488    1.8092    0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4676    1.2926    0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2289   -0.0044    0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3763   -0.9061    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8890   -0.5550    0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7364   -1.8029    0.0407 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7918    0.2169   -0.2515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5241   -0.2886   -0.4915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0503    0.2130   -1.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1886   -0.1983   -2.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439   -0.8850   -2.7617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5070    0.1680   -4.2474 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4050    0.2326    0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7656   -0.1975    0.5785 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.2604    0.0020    1.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9340   -1.6279    0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6428    0.5390   -0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5153    0.9663    0.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2652    2.3098   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8727    2.4978    1.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643    1.9806    0.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7779   -0.7878    1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0266   -1.9777    0.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1538   -0.8071   -0.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5822   -1.3846   -0.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0768    1.3310   -1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0662   -0.1338   -2.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9612    0.0412    1.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4302    1.3644    0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1052   -0.6977    2.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4403   -0.1529    2.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6514    1.0285    2.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4863   -2.1948    1.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5292   -1.9247   -0.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0225   -1.8237    0.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1879   -0.0606   -1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1651    1.4589   -0.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4763    0.9593    0.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  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
  2 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  6
  9 26  1  0
  9 27  1  0
 13 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
M  CHG  2  12  -1  14   1
M  END

  Mrv1652311201723532D          

 17 16  0  0  0  0            999 V2000
 2500.4521 2498.9260    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 2500.4521 2499.7510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.7377 2500.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.7377 2500.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.4521 2501.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.4521 2502.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.0232 2501.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.0232 2499.7510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.7377 2498.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.7377 2497.6885    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 2499.7377 2496.8635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9127 2497.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.5627 2497.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.1666 2498.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.8811 2498.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.8811 2499.7510    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
 2502.5955 2498.5135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  1  9  1  0  0  0  0
  1 14  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  CHG  2  10   1  16  -1
M  END
> <DATABASE_ID>
HMDB0002366

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H21NO4/c1-6-9(2)12(16)17-10(7-11(14)15)8-13(3,4)5/h6,10H,7-8H2,1-5H3/b9-6+/t10-/m1/s1

> <INCHI_KEY>
WURBQCVBQNMUQT-OLKPEBQYSA-N

> <FORMULA>
C12H21NO4

> <MOLECULAR_WEIGHT>
243.303

> <EXACT_MASS>
243.14705816

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.092495819490598

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.89

> <JCHEM_LOGP>
-2.674568813471746

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.295140408588241

> <JCHEM_PKA_STRONGEST_BASIC>
-6.863909891770237

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
87.31509999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002366
     RDKit          3D
Tiglylcarnitine
 38 37  0  0  0  0  0  0  0  0999 V2000
    4.8488    1.8092    0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4676    1.2926    0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2289   -0.0044    0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3763   -0.9061    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8890   -0.5550    0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7364   -1.8029    0.0407 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7918    0.2169   -0.2515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5241   -0.2886   -0.4915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0503    0.2130   -1.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1886   -0.1983   -2.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439   -0.8850   -2.7617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5070    0.1680   -4.2474 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4050    0.2326    0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7656   -0.1975    0.5785 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.2604    0.0020    1.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9340   -1.6279    0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6428    0.5390   -0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5153    0.9663    0.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2652    2.3098   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8727    2.4978    1.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643    1.9806    0.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7779   -0.7878    1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0266   -1.9777    0.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1538   -0.8071   -0.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5822   -1.3846   -0.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0768    1.3310   -1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0662   -0.1338   -2.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9612    0.0412    1.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4302    1.3644    0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1052   -0.6977    2.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4403   -0.1529    2.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6514    1.0285    2.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4863   -2.1948    1.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5292   -1.9247   -0.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0225   -1.8237    0.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1879   -0.0606   -1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1651    1.4589   -0.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4763    0.9593    0.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  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
  2 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  6
  9 26  1  0
  9 27  1  0
 13 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
M  CHG  2  12  -1  14   1
M  END

HEADER    PROTEIN                                 20-NOV-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-NOV-17         0                                  
HETATM    1  C   UNK     0    4667.5114664.662   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    4667.5114666.202   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    4666.1774666.972   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    4666.1774668.512   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    4667.5114669.282   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    4667.5114670.822   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    4664.8434669.282   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    4664.8434666.202   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    4666.1774663.892   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0    4666.1774662.352   0.000  0.00  0.00           N+1
HETATM   11  C   UNK     0    4666.1774660.812   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4664.6374662.352   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4667.7174662.352   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    4668.8444663.892   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    4670.1784664.662   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    4670.1784666.202   0.000  0.00  0.00           O-1
HETATM   17  O   UNK     0    4671.5124663.892   0.000  0.00  0.00           O+0
CONECT    1    2    9   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4                                                            
CONECT    8    3                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    1   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0002366
HETATM    1  C1  UNL     1       4.849   1.809   0.480  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.468   1.293   0.230  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.229  -0.004   0.248  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.376  -0.906   0.524  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.889  -0.555   0.008  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.736  -1.803   0.041  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.792   0.217  -0.251  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.524  -0.289  -0.492  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.050   0.213  -1.804  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.189  -0.198  -2.948  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.844  -0.885  -2.762  1.00  0.00           O  
HETATM   12  O4  UNL     1      -0.507   0.168  -4.247  1.00  0.00           O1-
HETATM   13  C9  UNL     1      -1.405   0.233   0.616  1.00  0.00           C  
HETATM   14  N1  UNL     1      -2.766  -0.198   0.579  1.00  0.00           N1+
HETATM   15  C10 UNL     1      -3.260   0.002   1.976  1.00  0.00           C  
HETATM   16  C11 UNL     1      -2.934  -1.628   0.366  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.643   0.539  -0.268  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.515   0.966   0.726  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.265   2.310  -0.417  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.873   2.498   1.347  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.664   1.981   0.034  1.00  0.00           H  
HETATM   22  H5  UNL     1       4.778  -0.788   1.542  1.00  0.00           H  
HETATM   23  H6  UNL     1       4.027  -1.978   0.456  1.00  0.00           H  
HETATM   24  H7  UNL     1       5.154  -0.807  -0.263  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.582  -1.385  -0.467  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.077   1.331  -1.848  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.066  -0.134  -2.051  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.961   0.041   1.623  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.430   1.364   0.564  1.00  0.00           H  
HETATM   30  H13 UNL     1      -4.105  -0.698   2.160  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.440  -0.153   2.686  1.00  0.00           H  
HETATM   32  H15 UNL     1      -3.651   1.028   2.024  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.486  -2.195   1.211  1.00  0.00           H  
HETATM   34  H17 UNL     1      -2.529  -1.925  -0.613  1.00  0.00           H  
HETATM   35  H18 UNL     1      -4.022  -1.824   0.335  1.00  0.00           H  
HETATM   36  H19 UNL     1      -4.188  -0.061  -1.029  1.00  0.00           H  
HETATM   37  H20 UNL     1      -3.165   1.459  -0.686  1.00  0.00           H  
HETATM   38  H21 UNL     1      -4.476   0.959   0.371  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   21
CONECT    3    4    5
CONECT    4   22   23   24
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   13   25
CONECT    9   10   26   27
CONECT   10   11   11   12
CONECT   13   14   28   29
CONECT   14   15   16   17
CONECT   15   30   31   32
CONECT   16   33   34   35
CONECT   17   36   37   38
END

HMDB0002366
     RDKit          3D
Tiglylcarnitine
 38 37  0  0  0  0  0  0  0  0999 V2000
    4.8488    1.8092    0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4676    1.2926    0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2289   -0.0044    0.2482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3763   -0.9061    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8890   -0.5550    0.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7364   -1.8029    0.0407 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7918    0.2169   -0.2515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5241   -0.2886   -0.4915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0503    0.2130   -1.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1886   -0.1983   -2.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439   -0.8850   -2.7617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5070    0.1680   -4.2474 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.4050    0.2326    0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7656   -0.1975    0.5785 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.2604    0.0020    1.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9340   -1.6279    0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6428    0.5390   -0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5153    0.9663    0.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2652    2.3098   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8727    2.4978    1.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643    1.9806    0.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7779   -0.7878    1.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0266   -1.9777    0.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1538   -0.8071   -0.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5822   -1.3846   -0.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0768    1.3310   -1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0662   -0.1338   -2.0505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9612    0.0412    1.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4302    1.3644    0.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1052   -0.6977    2.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4403   -0.1529    2.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6514    1.0285    2.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4863   -2.1948    1.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5292   -1.9247   -0.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0225   -1.8237    0.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1879   -0.0606   -1.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1651    1.4589   -0.6859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4763    0.9593    0.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  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
  2 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  6
  9 26  1  0
  9 27  1  0
 13 28  1  0
 13 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
M  CHG  2  12  -1  14   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(R)-Tiglyl-carnitine	ChEBI
O-Tiglylcarnitine	HMDB
O-Tiglyl-L-carnitine	HMDB
Tiglyl carnitine	HMDB
Tiglylcarnitine	HMDB

Chemical Formula

C₁₂H₂₁NO₄

Average Molecular Weight

243.303

Monoisotopic Molecular Weight

243.14705816

IUPAC Name

(3R)-3-{[(2E)-2-methylbut-2-enoyl]oxy}-4-(trimethylazaniumyl)butanoate

Traditional Name

(3R)-3-{[(2E)-2-methylbut-2-enoyl]oxy}-4-(trimethylammonio)butanoate

CAS Registry Number

64681-36-3

SMILES

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

InChI Identifier

InChI=1S/C12H21NO4/c1-6-9(2)12(16)17-10(7-11(14)15)8-13(3,4)5/h6,10H,7-8H2,1-5H3/b9-6+/t10-/m1/s1

InChI Key

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-acyl-L-carnitine (CHEBI:85520 )
O-tiglylcarnitine (CHEBI:85520 )

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16425363)

Organ

Placenta (HMDB: HMDB0002366)

Excreta

Biofluid or Excreta

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

Cellular substructure

Organelle

Peroxisome (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Source

Exogenous

Exogenous (HMDB: HMDB0002366)

Food

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

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

Endogenous

Endogenous (HMDB: HMDB0002366)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

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	0.023 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-2.7	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-6.9	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	87.32 m³·mol⁻¹	ChemAxon
Polarizability	26.09 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]+	164.233	30932474
DeepCCS	[M-H]-	160.406	30932474
DeepCCS	[M-2H]-	196.67	30932474
DeepCCS	[M+Na]+	172.8	30932474
AllCCS	[M+H]+	158.2	32859911
AllCCS	[M+H-H2O]+	155.2	32859911
AllCCS	[M+NH4]+	161.1	32859911
AllCCS	[M+Na]+	161.9	32859911
AllCCS	[M-H]-	163.6	32859911
AllCCS	[M+Na-2H]-	164.7	32859911
AllCCS	[M+HCOO]-	165.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tiglylcarnitine	C\C=C(/C)C(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	2076.8	Standard polar	33892256
Tiglylcarnitine	C\C=C(/C)C(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	1410.1	Standard non polar	33892256
Tiglylcarnitine	C\C=C(/C)C(=O)O[C@H](CC([O-])=O)C[N+](C)(C)C	1551.7	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 - Tiglylcarnitine 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 - Tiglylcarnitine 10V, Positive-QTOF	splash10-0006-0090000000-e78bd389593472138484	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiglylcarnitine 20V, Positive-QTOF	splash10-000l-9050000000-1bb9d023b199264c5fe7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiglylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.05 +/- 0.01 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.040-0.080 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected and Quantified	0.033 +/- 0.003 uM	Adult (>18 years old)	Both	Normal	16425363	details
Blood	Detected and Quantified	0.040-0.080 uM	Adult (>18 years old)	Both	Normal	Molecular You	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	<0.0400 uM	Not Specified	Not Specified	Normal	16148061	details
Feces	Detected and Quantified	0.24 +/- 0.12 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.15 +/- 0.08 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Urine	Detected and Quantified	0.10 (0.05-0.20) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.07 (0.05-0.10) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected and Quantified	0.03-0.16 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.08 +/- 0.03 umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.07 +/- 0.022 umol/mmol creatinine	Newborn (0-30 days old)	Male	Normal	32340350	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.034 +/- 0.002 uM	Adult (>18 years old)	Both	Celiac disease	16425363	details

Associated Disorders and Diseases

Disease References

Celiac disease
Bene J, Komlosi K, Gasztonyi B, Juhasz M, Tulassay Z, Melegh B: Plasma carnitine ester profile in adult celiac disease patients maintained on long-term gluten free diet. World J Gastroenterol. 2005 Nov 14;11(42):6671-5. [PubMed:16425363 ]

Associated OMIM IDs

212750 (Celiac disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022980

KNApSAcK ID

Not Available

Chemspider ID

34999729

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91825636

PDB ID

Not Available

ChEBI ID

85520

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

Fontaine M, Briand G, Ser N, Armelin I, Rolland MO, Degand P, Vamecq J: Metabolic studies in twin brothers with 2-methylacetoacetyl-CoA thiolase deficiency. Clin Chim Acta. 1996 Nov 15;255(1):67-83. [PubMed:8930414 ]
Fukao T, Zhang GX, Sakura N, Kubo T, Yamaga H, Hazama A, Kohno Y, Matsuo N, Kondo M, Yamaguchi S, Shigematsu Y, Kondo N: The mitochondrial acetoacetyl-CoA thiolase (T2) deficiency in Japanese patients: urinary organic acid and blood acylcarnitine profiles under stable conditions have subtle abnormalities in T2-deficient patients with some residual T2 activity. J Inherit Metab Dis. 2003;26(5):423-31. [PubMed:14518824 ]
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Showing metabocard for Tiglylcarnitine (HMDB0002366)

MOL for HMDB0002366 (Tiglylcarnitine)

3D MOL for HMDB0002366 (Tiglylcarnitine)

3D SDF for HMDB0002366 (Tiglylcarnitine)

3D-SDF for HMDB0002366 (Tiglylcarnitine)

PDB for HMDB0002366 (Tiglylcarnitine)

3D PDB for HMDB0002366 (Tiglylcarnitine)

SMILES for HMDB0002366 (Tiglylcarnitine)

INCHI for HMDB0002366 (Tiglylcarnitine)

Structure for HMDB0002366 (Tiglylcarnitine)

3D Structure for HMDB0002366 (Tiglylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra