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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-11-02 22:36:44 UTC

Update Date

2022-10-24 19:44:11 UTC

HMDB ID

HMDB0013124

Secondary Accession Numbers

HMDB13124

Metabolite Identification

Common Name

Propenoylcarnitine

Description

Propenoylcarnitine is an acylcarnitine. More specifically, it is an propenoic 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. Propenoylcarnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine Propenoylcarnitine 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

HMDB0013124
     RDKit          3D
Propenoylcarnitine
 32 31  0  0  0  0  0  0  0  0999 V2000
    3.7893   -2.2969    0.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0703   -1.3232   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0464   -0.6985    0.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8157   -1.0660    1.5288 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2401    0.3408   -0.1287 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2385    0.9521    0.6606 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6699    2.3756    0.9111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406    3.0692   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7041    2.4885   -1.4798 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1687    4.4320   -0.4444 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.1237    0.9505    0.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6272   -0.3870   -0.2017 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.8884   -1.0904   -1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9970   -0.2083   -0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7145   -1.1775    0.9990 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5789   -2.8007   -0.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6112   -2.6205    1.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2582   -1.0078   -1.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2090    0.4698    1.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6632    2.3946    1.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0784    2.9419    1.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8767    1.3985    0.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2418    1.5133   -0.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3516   -1.9377   -0.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2095   -0.4409   -1.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5810   -1.5631   -1.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4488    0.6103   -0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5406   -1.1623   -0.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9200    0.1070   -1.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5728   -1.9047    0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8009   -1.7973    1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9311   -0.5611    1.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  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  1  0
 12 14  1  0
 12 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  6 19  1  1
  7 20  1  0
  7 21  1  0
 11 22  1  0
 11 23  1  0
 13 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
M  CHG  2  10  -1  12   1
M  END


  Mrv0541 02251208172D          

 15 14  0  0  1  0            999 V2000
   16.0519   -8.5707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.7664   -8.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4808   -8.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4808   -9.3957    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   16.0519   -9.3957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1953   -8.1582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3375   -8.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3375   -7.3332    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   16.1625   -7.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5125   -7.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3375   -6.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3974  -10.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8110  -10.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6383  -10.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0519  -10.8286    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  2  0  0  0  0
 14 13  1  0  0  0  0
  5 14  1  0  0  0  0
 15 14  2  0  0  0  0
M  CHG  2   4  -1   8   1
M  END
> <DATABASE_ID>
HMDB0013124

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H17NO4/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4/h5,8H,1,6-7H2,2-4H3/t8-/m0/s1

> <INCHI_KEY>
YUCNWOKTRWJLGY-QMMMGPOBSA-N

> <FORMULA>
C10H17NO4

> <MOLECULAR_WEIGHT>
215.2463

> <EXACT_MASS>
215.115758037

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.912584592738924

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-(prop-2-enoyloxy)-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-2.22

> <JCHEM_LOGP>
-3.4567542974717442

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.130183878634363

> <JCHEM_PKA_STRONGEST_BASIC>
-6.801669212235793

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
77.2845

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-(prop-2-enoyloxy)-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013124
     RDKit          3D
Propenoylcarnitine
 32 31  0  0  0  0  0  0  0  0999 V2000
    3.7893   -2.2969    0.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0703   -1.3232   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0464   -0.6985    0.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8157   -1.0660    1.5288 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2401    0.3408   -0.1287 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2385    0.9521    0.6606 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6699    2.3756    0.9111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406    3.0692   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7041    2.4885   -1.4798 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1687    4.4320   -0.4444 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.1237    0.9505    0.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6272   -0.3870   -0.2017 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.8884   -1.0904   -1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9970   -0.2083   -0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7145   -1.1775    0.9990 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5789   -2.8007   -0.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6112   -2.6205    1.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2582   -1.0078   -1.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2090    0.4698    1.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6632    2.3946    1.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0784    2.9419    1.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8767    1.3985    0.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2418    1.5133   -0.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3516   -1.9377   -0.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2095   -0.4409   -1.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5810   -1.5631   -1.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4488    0.6103   -0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5406   -1.1623   -0.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9200    0.1070   -1.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5728   -1.9047    0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8009   -1.7973    1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9311   -0.5611    1.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  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  1  0
 12 14  1  0
 12 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  6 19  1  1
  7 20  1  0
  7 21  1  0
 11 22  1  0
 11 23  1  0
 13 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
M  CHG  2  10  -1  12   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      29.964 -15.999   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      31.297 -15.229   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.631 -15.999   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      32.631 -17.539   0.000  0.00  0.00           O-1
HETATM    5  O   UNK     0      29.964 -17.539   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      33.965 -15.229   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      28.630 -15.229   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      28.630 -13.689   0.000  0.00  0.00           N+1
HETATM    9  C   UNK     0      30.170 -13.689   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.090 -13.689   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.630 -12.149   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.875 -20.213   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.647 -18.876   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.191 -18.876   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      29.964 -20.213   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   14                                                       
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                                                            
CONECT   13   12   14                                                       
CONECT   14   13    5   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0013124
HETATM    1  C1  UNL     1       3.789  -2.297   0.024  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.070  -1.323  -0.477  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.046  -0.699   0.330  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.816  -1.066   1.529  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.240   0.341  -0.129  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.239   0.952   0.661  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.670   2.376   0.911  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.841   3.069  -0.385  1.00  0.00           C  
HETATM    9  O3  UNL     1       0.704   2.488  -1.480  1.00  0.00           O  
HETATM   10  O4  UNL     1       1.169   4.432  -0.444  1.00  0.00           O1-
HETATM   11  C7  UNL     1      -1.124   0.951   0.060  1.00  0.00           C  
HETATM   12  N1  UNL     1      -1.627  -0.387  -0.202  1.00  0.00           N1+
HETATM   13  C8  UNL     1      -0.888  -1.090  -1.204  1.00  0.00           C  
HETATM   14  C9  UNL     1      -2.997  -0.208  -0.694  1.00  0.00           C  
HETATM   15  C10 UNL     1      -1.714  -1.178   0.999  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.579  -2.801  -0.554  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.611  -2.621   1.028  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.258  -1.008  -1.485  1.00  0.00           H  
HETATM   19  H4  UNL     1       0.209   0.470   1.684  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.663   2.395   1.411  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.078   2.942   1.503  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.877   1.399   0.774  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.242   1.513  -0.868  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.352  -1.938  -0.723  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.210  -0.441  -1.797  1.00  0.00           H  
HETATM   26  H11 UNL     1      -1.581  -1.563  -1.934  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.449   0.610  -0.095  1.00  0.00           H  
HETATM   28  H13 UNL     1      -3.541  -1.162  -0.562  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.920   0.107  -1.757  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.573  -1.905   0.897  1.00  0.00           H  
HETATM   31  H16 UNL     1      -0.801  -1.797   1.097  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.931  -0.561   1.883  1.00  0.00           H  
CONECT    1    2    2   16   17
CONECT    2    3   18
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   11   19
CONECT    7    8   20   21
CONECT    8    9    9   10
CONECT   11   12   22   23
CONECT   12   13   14   15
CONECT   13   24   25   26
CONECT   14   27   28   29
CONECT   15   30   31   32
END

HMDB0013124
     RDKit          3D
Propenoylcarnitine
 32 31  0  0  0  0  0  0  0  0999 V2000
    3.7893   -2.2969    0.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0703   -1.3232   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0464   -0.6985    0.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8157   -1.0660    1.5288 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2401    0.3408   -0.1287 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2385    0.9521    0.6606 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6699    2.3756    0.9111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406    3.0692   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7041    2.4885   -1.4798 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1687    4.4320   -0.4444 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.1237    0.9505    0.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6272   -0.3870   -0.2017 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.8884   -1.0904   -1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9970   -0.2083   -0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7145   -1.1775    0.9990 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5789   -2.8007   -0.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6112   -2.6205    1.0277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2582   -1.0078   -1.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2090    0.4698    1.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6632    2.3946    1.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0784    2.9419    1.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8767    1.3985    0.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2418    1.5133   -0.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3516   -1.9377   -0.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2095   -0.4409   -1.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5810   -1.5631   -1.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4488    0.6103   -0.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5406   -1.1623   -0.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9200    0.1070   -1.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5728   -1.9047    0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8009   -1.7973    1.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9311   -0.5611    1.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  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  1  0
 12 14  1  0
 12 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  6 19  1  1
  7 20  1  0
  7 21  1  0
 11 22  1  0
 11 23  1  0
 13 24  1  0
 13 25  1  0
 13 26  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
 15 30  1  0
 15 31  1  0
 15 32  1  0
M  CHG  2  10  -1  12   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3S)-3-(Prop-2-enoyloxy)-4-(trimethylazaniumyl)butanoate	ChEBI
(3S)-3-(Prop-2-enoyloxy)-4-(trimethylazaniumyl)butanoic acid	Generator
Propenoyl-L-carnitine	HMDB

Chemical Formula

C₁₀H₁₇NO₄

Average Molecular Weight

215.2463

Monoisotopic Molecular Weight

215.115758037

IUPAC Name

(3S)-3-(prop-2-enoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

(3S)-3-(prop-2-enoyloxy)-4-(trimethylammonio)butanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H17NO4/c1-5-10(14)15-8(6-9(12)13)7-11(2,3)4/h5,8H,1,6-7H2,2-4H3/t8-/m0/s1

InChI Key

YUCNWOKTRWJLGY-QMMMGPOBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl carnitines. These are organic compounds containing a fatty acid with the carboxylic acid attached to carnitine through an ester bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Acyl carnitines

Alternative Parents

Substituents

Acyl-carnitine
Dicarboxylic acid or derivatives
Acrylic acid ester
Quaternary ammonium salt
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tetraalkylammonium salt
Acrylic acid or derivatives
Carboxylic acid salt
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic salt
Amine
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-acyl-L-carnitine (CHEBI:86076 )
O-propenoylcarnitine (CHEBI:86076 )

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: HMDB0013124)
Cell membrane (HMDB: HMDB0013124)

Biofluid or Excreta

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 24704061)
Saliva (HMDB: HMDB0013124)

Excreta

Biofluid or Excreta

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

Cellular substructure

Organelle

peroxisome (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013124)

Source

Endogenous

Endogenous (HMDB: HMDB0013124)

Animal

Animal (HMDB: HMDB0013124)

Exogenous

Food

Food (HMDB: HMDB0013124)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
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)

Equine

Horse (FooDB: FOOD00378)

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)

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)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0013124)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0013124)

Cellular process

Cell signaling (HMDB: HMDB0013124)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0013124)

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	0.059 g/L	ALOGPS
logP	-2.2	ALOGPS
logP	-3.5	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.13	ChemAxon
pKa (Strongest Basic)	-6.8	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	77.28 m³·mol⁻¹	ChemAxon
Polarizability	21.91 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]+	152.396	30932474
DeepCCS	[M-H]-	150.22	30932474
DeepCCS	[M-2H]-	183.485	30932474
DeepCCS	[M+Na]+	158.469	30932474
AllCCS	[M+H]+	149.9	32859911
AllCCS	[M+H-H2O]+	146.5	32859911
AllCCS	[M+NH4]+	153.0	32859911
AllCCS	[M+Na]+	153.9	32859911
AllCCS	[M-H]-	155.3	32859911
AllCCS	[M+Na-2H]-	156.4	32859911
AllCCS	[M+HCOO]-	157.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Propenoylcarnitine	C[N+](C)(C)C[C@H](CC([O-])=O)OC(=O)C=C	1877.6	Standard polar	33892256
Propenoylcarnitine	C[N+](C)(C)C[C@H](CC([O-])=O)OC(=O)C=C	1252.6	Standard non polar	33892256
Propenoylcarnitine	C[N+](C)(C)C[C@H](CC([O-])=O)OC(=O)C=C	1407.3	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 - Propenoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-9000000000-75fc08c3d27feb518327	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Propenoylcarnitine 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 - Propenoylcarnitine 10V, Positive-QTOF	splash10-066v-2930000000-454a580179166d0507bb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propenoylcarnitine 20V, Positive-QTOF	splash10-052f-3900000000-b50c527fe3c21e151579	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propenoylcarnitine 40V, Positive-QTOF	splash10-0pi0-9400000000-4054ae16ebec41595115	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propenoylcarnitine 10V, Negative-QTOF	splash10-03di-4190000000-363b169cd979e9082c96	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propenoylcarnitine 20V, Negative-QTOF	splash10-0nt9-6940000000-be8367f8d194c1c16d97	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propenoylcarnitine 40V, Negative-QTOF	splash10-0uk9-9000000000-81ec5a1bdf939e2a5454	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propenoylcarnitine 10V, Positive-QTOF	splash10-014i-0090000000-d39d73fb6e9c04d728f3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propenoylcarnitine 20V, Positive-QTOF	splash10-00kr-9050000000-40bf40a4e27ee0de0686	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Propenoylcarnitine 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	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Saliva
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	0.040-0.140 uM	Adult (>18 years old)	Both	Normal	The Metabolo...	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Feces	Detected and Quantified	0.16 +/- 0.08 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.1 +/- 0.04 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Saliva	Detected and Quantified	0.037 +/- 0.004 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	0.003 (0.001-0.006) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.0-0.06 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.01(0.01-0.05) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.02(0.0-0.06) 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	0.0253 (0.00163) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029297

KNApSAcK ID

Not Available

Chemspider ID

30776693

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

86076

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 Propenoylcarnitine (HMDB0013124)

MOL for HMDB0013124 (Propenoylcarnitine)

3D MOL for HMDB0013124 (Propenoylcarnitine)

3D SDF for HMDB0013124 (Propenoylcarnitine)

3D-SDF for HMDB0013124 (Propenoylcarnitine)

PDB for HMDB0013124 (Propenoylcarnitine)

3D PDB for HMDB0013124 (Propenoylcarnitine)

SMILES for HMDB0013124 (Propenoylcarnitine)

INCHI for HMDB0013124 (Propenoylcarnitine)

Structure for HMDB0013124 (Propenoylcarnitine)

3D Structure for HMDB0013124 (Propenoylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra