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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2021-09-11 11:21:58 UTC

Update Date

2025-05-29 22:15:41 UTC

HMDB ID

HMDB0253155

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Hexenoylcarnitine

Description

Hexenoylcarnitine belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. In humans, hexenoylcarnitine is involved in the acylcarnitine 4-hexenoylcarnitine pathway. Hexenoylcarnitine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on Hexenoylcarnitine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Hexenoylcarnitine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Hexenoylcarnitine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0253155
     RDKit          3D
Hexenoylcarnitine
 41 40  0  0  0  0  0  0  0  0999 V2000
    3.7774    0.3924   -1.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3886    0.1798   -0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6335    0.8999    0.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2339    0.4818    0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405   -0.5052    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2965   -1.0069    0.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0546   -2.0319   -0.4548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7050   -0.4428    1.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4092    0.7213    1.8217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8099   -1.4827    2.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2304   -2.7723    1.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4114   -3.1234    1.5261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2683   -3.7579    1.4711 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.0860   -0.4600    0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3478    0.5532   -0.4045 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.8306    1.8037    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4875    0.0255   -1.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3148    0.7835   -1.3723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6855   -0.5574   -2.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8036    0.9098   -1.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4703    1.0577   -2.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4475   -0.9125   -0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4333    0.5596   -0.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5829    1.9841    0.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1963    0.8712    1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6644    1.0443    1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3255   -1.0400   -0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6693    1.5208    1.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5013   -1.1244    3.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1760   -1.6083    2.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8666   -0.4275    1.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1725   -1.4373    0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417    1.6689    1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8271    2.0830   -0.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1847    2.6746   -0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8875    0.9126   -1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1963   -0.3817   -0.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1225   -0.7031   -1.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151   -0.1179   -2.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789    1.1917   -1.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7368    1.5738   -2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 14 31  1  0
 14 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
 18 39  1  0
 18 40  1  0
 18 41  1  0
M  CHG  2  13  -1  15   1
M  END


  Mrv1652309112113222D          

 18 17  0  0  0  0            999 V2000
   -0.4125    2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.8875    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
  8 18  1  0  0  0  0
M  CHG  2  12  -1  14   1
M  END
> <DATABASE_ID>
HMDB0253155

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H23NO4/c1-5-6-7-8-11(15)13(18,9-12(16)17)10-14(2,3)4/h7-8,18H,5-6,9-10H2,1-4H3

> <INCHI_KEY>
JNTUUFYYQOWHEZ-UHFFFAOYSA-N

> <FORMULA>
C13H23NO4

> <MOLECULAR_WEIGHT>
257.33

> <EXACT_MASS>
257.162708225

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.67577240049446

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-4-oxo-3-[(trimethylazaniumyl)methyl]non-5-enoate

> <ALOGPS_LOGP>
-1.66

> <JCHEM_LOGP>
-2.819684736471746

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.448337177058825

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.3534853136493386

> <JCHEM_PKA_STRONGEST_BASIC>
-4.476832563125352

> <JCHEM_POLAR_SURFACE_AREA>
77.43

> <JCHEM_REFRACTIVITY>
92.68399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-4-oxo-3-[(trimethylammonio)methyl]non-5-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253155
     RDKit          3D
Hexenoylcarnitine
 41 40  0  0  0  0  0  0  0  0999 V2000
    3.7774    0.3924   -1.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3886    0.1798   -0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6335    0.8999    0.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2339    0.4818    0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405   -0.5052    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2965   -1.0069    0.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0546   -2.0319   -0.4548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7050   -0.4428    1.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4092    0.7213    1.8217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8099   -1.4827    2.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2304   -2.7723    1.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4114   -3.1234    1.5261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2683   -3.7579    1.4711 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.0860   -0.4600    0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3478    0.5532   -0.4045 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.8306    1.8037    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4875    0.0255   -1.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3148    0.7835   -1.3723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6855   -0.5574   -2.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8036    0.9098   -1.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4703    1.0577   -2.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4475   -0.9125   -0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4333    0.5596   -0.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5829    1.9841    0.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1963    0.8712    1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6644    1.0443    1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3255   -1.0400   -0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6693    1.5208    1.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5013   -1.1244    3.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1760   -1.6083    2.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8666   -0.4275    1.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1725   -1.4373    0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417    1.6689    1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8271    2.0830   -0.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1847    2.6746   -0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8875    0.9126   -1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1963   -0.3817   -0.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1225   -0.7031   -1.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151   -0.1179   -2.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789    1.1917   -1.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7368    1.5738   -2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 14 31  1  0
 14 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
 18 39  1  0
 18 40  1  0
 18 41  1  0
M  CHG  2  13  -1  15   1
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -0.770   5.128   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   3.795   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770   2.461   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770  -0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.770  -2.874   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.540  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.207  -3.080   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.874  -5.390   0.000  0.00  0.00           O-1
HETATM   13  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.874   0.770   0.000  0.00  0.00           N+1
HETATM   15  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.207   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.080  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13   18                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18    8                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0253155
HETATM    1  C1  UNL     1       3.777   0.392  -1.878  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.389   0.180  -0.528  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.634   0.900   0.514  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.234   0.482   0.751  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.641  -0.505   0.142  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.296  -1.007   0.277  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.055  -2.032  -0.455  1.00  0.00           O  
HETATM    8  C7  UNL     1      -0.705  -0.443   1.184  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.409   0.721   1.822  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.810  -1.483   2.340  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.230  -2.772   1.778  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.411  -3.123   1.526  1.00  0.00           O  
HETATM   13  O4  UNL     1      -0.268  -3.758   1.471  1.00  0.00           O1-
HETATM   14  C10 UNL     1      -2.086  -0.460   0.564  1.00  0.00           C  
HETATM   15  N1  UNL     1      -2.348   0.553  -0.405  1.00  0.00           N1+
HETATM   16  C11 UNL     1      -2.831   1.804   0.150  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.487   0.026  -1.204  1.00  0.00           C  
HETATM   18  C13 UNL     1      -1.315   0.783  -1.372  1.00  0.00           C  
HETATM   19  H1  UNL     1       3.686  -0.557  -2.423  1.00  0.00           H  
HETATM   20  H2  UNL     1       2.804   0.910  -1.783  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.470   1.058  -2.473  1.00  0.00           H  
HETATM   22  H4  UNL     1       4.448  -0.912  -0.296  1.00  0.00           H  
HETATM   23  H5  UNL     1       5.433   0.560  -0.525  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.583   1.984   0.195  1.00  0.00           H  
HETATM   25  H7  UNL     1       4.196   0.871   1.483  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.664   1.044   1.497  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.325  -1.040  -0.578  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.669   1.521   1.321  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.501  -1.124   3.113  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.176  -1.608   2.815  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.867  -0.428   1.329  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.172  -1.437   0.021  1.00  0.00           H  
HETATM   33  H15 UNL     1      -3.042   1.669   1.218  1.00  0.00           H  
HETATM   34  H16 UNL     1      -3.827   2.083  -0.304  1.00  0.00           H  
HETATM   35  H17 UNL     1      -2.185   2.675  -0.095  1.00  0.00           H  
HETATM   36  H18 UNL     1      -3.887   0.913  -1.739  1.00  0.00           H  
HETATM   37  H19 UNL     1      -4.196  -0.382  -0.451  1.00  0.00           H  
HETATM   38  H20 UNL     1      -3.122  -0.703  -1.928  1.00  0.00           H  
HETATM   39  H21 UNL     1      -1.215  -0.118  -2.020  1.00  0.00           H  
HETATM   40  H22 UNL     1      -0.379   1.192  -1.007  1.00  0.00           H  
HETATM   41  H23 UNL     1      -1.737   1.574  -2.070  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5    5   26
CONECT    5    6   27
CONECT    6    7    7    8
CONECT    8    9   10   14
CONECT    9   28
CONECT   10   11   29   30
CONECT   11   12   12   13
CONECT   14   15   31   32
CONECT   15   16   17   18
CONECT   16   33   34   35
CONECT   17   36   37   38
CONECT   18   39   40   41
END

HMDB0253155
     RDKit          3D
Hexenoylcarnitine
 41 40  0  0  0  0  0  0  0  0999 V2000
    3.7774    0.3924   -1.8780 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3886    0.1798   -0.5279 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6335    0.8999    0.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2339    0.4818    0.7507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405   -0.5052    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2965   -1.0069    0.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0546   -2.0319   -0.4548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7050   -0.4428    1.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4092    0.7213    1.8217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8099   -1.4827    2.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2304   -2.7723    1.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4114   -3.1234    1.5261 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2683   -3.7579    1.4711 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.0860   -0.4600    0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3478    0.5532   -0.4045 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.8306    1.8037    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4875    0.0255   -1.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3148    0.7835   -1.3723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6855   -0.5574   -2.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8036    0.9098   -1.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4703    1.0577   -2.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4475   -0.9125   -0.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4333    0.5596   -0.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5829    1.9841    0.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1963    0.8712    1.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6644    1.0443    1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3255   -1.0400   -0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6693    1.5208    1.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5013   -1.1244    3.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1760   -1.6083    2.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8666   -0.4275    1.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1725   -1.4373    0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0417    1.6689    1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8271    2.0830   -0.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1847    2.6746   -0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8875    0.9126   -1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1963   -0.3817   -0.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1225   -0.7031   -1.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151   -0.1179   -2.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789    1.1917   -1.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7368    1.5738   -2.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  3
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 14 31  1  0
 14 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
 18 39  1  0
 18 40  1  0
 18 41  1  0
M  CHG  2  13  -1  15   1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₂₃NO₄

Average Molecular Weight

257.33

Monoisotopic Molecular Weight

257.162708225

IUPAC Name

3-hydroxy-4-oxo-3-[(trimethylazaniumyl)methyl]non-5-enoate

Traditional Name

3-hydroxy-4-oxo-3-[(trimethylammonio)methyl]non-5-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H23NO4/c1-5-6-7-8-11(15)13(18,9-12(16)17)10-14(2,3)4/h7-8,18H,5-6,9-10H2,1-4H3

InChI Key

JNTUUFYYQOWHEZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-chain keto acids and derivatives

Alternative Parents

Substituents

Medium-chain keto acid
Gamma-keto acid
Amino fatty acid
Branched fatty acid
Hydroxy fatty acid
Acyloin
Beta-aminoketone
Fatty acyl
Unsaturated fatty acid
Acryloyl-group
Alpha-hydroxy ketone
Enone
Tetraalkylammonium salt
Quaternary ammonium salt
Tertiary alcohol
Alpha,beta-unsaturated ketone
Ketone
Carboxylic acid salt
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Organopnictogen compound
Organic salt
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-1.7	ALOGPS
logP	-2.8	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.35	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.43 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	92.68 m³·mol⁻¹	ChemAxon
Polarizability	27.68 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]+	156.4	30932474
DeepCCS	[M-H]-	154.042	30932474
DeepCCS	[M-2H]-	186.925	30932474
DeepCCS	[M+Na]+	162.493	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.6089 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.04 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1112.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	204.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	134.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	78.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	370.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	358.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	684.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	969.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	218.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1356.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	220.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	256.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	403.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	286.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	14.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hexenoylcarnitine	CCCC=CC(=O)C(O)(CC([O-])=O)C[N+](C)(C)C	2653.9	Standard polar	33892256
Hexenoylcarnitine	CCCC=CC(=O)C(O)(CC([O-])=O)C[N+](C)(C)C	1536.9	Standard non polar	33892256
Hexenoylcarnitine	CCCC=CC(=O)C(O)(CC([O-])=O)C[N+](C)(C)C	1748.5	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 - Hexenoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9100000000-6342887a45397e0ed758	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexenoylcarnitine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexenoylcarnitine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hexenoylcarnitine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details
Blood	Detected and Quantified	0.02 ± 0.01 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	0.03 ± 0.01 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	0.03 ± 0.01 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	0.03 ± 0.01 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	0.03 ± 0.01 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	0.03 ± 0 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	0.03 ± 0 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	0.03 ± 0.01 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details
Blood	Detected and Quantified	0.03 ± 0 uM	Adult (>18 years old)	Both	Normal	Quantitative comp...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

67497918

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129846791

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Hexenoylcarnitine (HMDB0253155)

MOL for HMDB0253155 (Hexenoylcarnitine)

3D MOL for HMDB0253155 (Hexenoylcarnitine)

3D SDF for HMDB0253155 (Hexenoylcarnitine)

3D-SDF for HMDB0253155 (Hexenoylcarnitine)

PDB for HMDB0253155 (Hexenoylcarnitine)

3D PDB for HMDB0253155 (Hexenoylcarnitine)

SMILES for HMDB0253155 (Hexenoylcarnitine)

INCHI for HMDB0253155 (Hexenoylcarnitine)

Structure for HMDB0253155 (Hexenoylcarnitine)

3D Structure for HMDB0253155 (Hexenoylcarnitine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra