Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Predicted

Creation Date

2021-03-31 19:27:29 UTC

Update Date

2022-10-24 19:45:17 UTC

HMDB ID

HMDB0241653

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Hydroxyvalerylcarnitine

Description

4-Hydroxyvalerylcarnitine is an acylcarnitine. More specifically, it is an 4-hydroxypentanoic 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. 4-Hydroxyvalerylcarnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine 4-Hydroxyvalerylcarnitine 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 4-Hydroxyvalerylcarnitine is elevated in the blood or plasma of individuals with 3-hydroxy-3-methylglutaryl-coenzyme A lyase deficiency (PMID: 28583327 ) and holocarboxylase synthetase deficiency (PMID: 27114915 ). It is also decreased in the blood or plasma of individuals with psoriasis (PMID: 33391503 ). 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

HMDB0241653
     RDKit          3D
4-Hydroxyvalerylcarnitine
 32 31  0  0  0  0  0  0  0  0999 V2000
   -2.6302    2.5025    2.3500 C   0  0  0  0  0  1  0  0  0  0  0  0
   -2.9374    1.4209    1.4322 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.6481    1.9866    0.3143 C   0  0  0  0  0  1  0  0  0  0  0  0
   -3.7794    0.4840    2.1904 C   0  0  0  0  0  1  0  0  0  0  0  0
   -1.6853    0.8090    1.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7171    0.2016   -0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7198   -0.8775   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5537   -2.0497    0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3931   -2.9751    0.2561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115   -2.1322    1.2369 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.4209   -0.3632   -0.5521 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3934    0.0217   -1.5797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0271    0.9153   -2.3839 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7289   -0.5864   -1.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7539    0.3840   -1.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4935    0.5839    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5820   -0.6973    1.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5224    1.4324    0.7363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9455    1.6640    0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    0.1012    1.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8527    0.9567   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7684   -0.5117   -0.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5486   -1.2558   -1.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8313   -1.5807   -1.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8893   -0.6783   -2.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7691   -0.0162   -1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6958    1.3572   -1.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5046    1.0505    0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2081   -1.4516    0.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0710   -0.4902    2.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5934   -1.1390    1.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3661    0.9335    0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
 14 24  1  0
 14 25  1  0
 15 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
M  CHG  2   2   1  10  -1
M  RAD  3   1   2   3   2   4   2
M  END

  Mrv1652303312121272D          

 18 17  0  0  0  0            999 V2000
    1.0461   -0.2211    0.0000 C   0  0  0  0  0  1  0  0  0  0  0  0
    1.0461    0.6039    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.8711    0.6039    0.0000 C   0  0  0  0  0  1  0  0  0  0  0  0
    0.2211    0.6039    0.0000 C   0  0  0  0  0  1  0  0  0  0  0  0
    1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.9039    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  CHG  2   2   1  18  -1
M  END
> <DATABASE_ID>
HMDB0241653

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H15NO5/c1-9(14)5-6-12(17)18-10(7-11(15)16)8-13(2,3)4/h9-10,14H,5-8H2,1H3,(H,15,16)/q+1/p-1

> <INCHI_KEY>
LMUUCZFQHPIMJM-UHFFFAOYSA-M

> <FORMULA>
C12H14NO5

> <MOLECULAR_WEIGHT>
252.246

> <EXACT_MASS>
252.087197555

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.405349370511807

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
({3-carboxy-2-[(4-hydroxypentanoyl)oxy]propyl}dimethylazaniumyl)methylidyne

> <JCHEM_LOGP>
-4.709874191471746

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.311995237130517

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.22875951186784

> <JCHEM_PKA_STRONGEST_BASIC>
-2.517508302802943

> <JCHEM_POLAR_SURFACE_AREA>
86.66

> <JCHEM_REFRACTIVITY>
75.45080000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
({3-carboxy-2-[(4-hydroxypentanoyl)oxy]propyl}dimethylammonio)methylidyne

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0241653
     RDKit          3D
4-Hydroxyvalerylcarnitine
 32 31  0  0  0  0  0  0  0  0999 V2000
   -2.6302    2.5025    2.3500 C   0  0  0  0  0  1  0  0  0  0  0  0
   -2.9374    1.4209    1.4322 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.6481    1.9866    0.3143 C   0  0  0  0  0  1  0  0  0  0  0  0
   -3.7794    0.4840    2.1904 C   0  0  0  0  0  1  0  0  0  0  0  0
   -1.6853    0.8090    1.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7171    0.2016   -0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7198   -0.8775   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5537   -2.0497    0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3931   -2.9751    0.2561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115   -2.1322    1.2369 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.4209   -0.3632   -0.5521 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3934    0.0217   -1.5797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0271    0.9153   -2.3839 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7289   -0.5864   -1.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7539    0.3840   -1.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4935    0.5839    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5820   -0.6973    1.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5224    1.4324    0.7363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9455    1.6640    0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    0.1012    1.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8527    0.9567   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7684   -0.5117   -0.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5486   -1.2558   -1.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8313   -1.5807   -1.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8893   -0.6783   -2.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7691   -0.0162   -1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6958    1.3572   -1.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5046    1.0505    0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2081   -1.4516    0.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0710   -0.4902    2.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5934   -1.1390    1.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3661    0.9335    0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
 14 24  1  0
 14 25  1  0
 15 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
M  CHG  2   2   1  10  -1
M  RAD  3   1   2   3   2   4   2
M  END

HEADER    PROTEIN                                 31-MAR-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAR-21         0                                  
HETATM    1  C   UNK     0       1.953  -0.413   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.953   1.127   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       3.493   1.127   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.413   1.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.953   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.620   2.667   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.954   4.977   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.955   1.127   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.286   4.977   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.953   5.747   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.619   4.977   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.953   7.287   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    6   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0241653
HETATM    1  C1  UNL     1      -2.630   2.502   2.350  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.937   1.421   1.432  1.00  0.00           N1+
HETATM    3  C2  UNL     1      -3.648   1.987   0.314  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.779   0.484   2.190  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.685   0.809   1.044  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.717   0.202  -0.314  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.720  -0.877  -0.529  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.554  -2.050   0.346  1.00  0.00           C  
HETATM    9  O1  UNL     1      -3.393  -2.975   0.256  1.00  0.00           O  
HETATM   10  O2  UNL     1      -1.512  -2.132   1.237  1.00  0.00           O1-
HETATM   11  O3  UNL     1      -0.421  -0.363  -0.552  1.00  0.00           O  
HETATM   12  C8  UNL     1       0.393   0.022  -1.580  1.00  0.00           C  
HETATM   13  O4  UNL     1       0.027   0.915  -2.384  1.00  0.00           O  
HETATM   14  C9  UNL     1       1.729  -0.586  -1.794  1.00  0.00           C  
HETATM   15  C10 UNL     1       2.754   0.384  -1.199  1.00  0.00           C  
HETATM   16  C11 UNL     1       2.493   0.584   0.280  1.00  0.00           C  
HETATM   17  C12 UNL     1       2.582  -0.697   1.049  1.00  0.00           C  
HETATM   18  O5  UNL     1       3.522   1.432   0.736  1.00  0.00           O  
HETATM   19  H1  UNL     1      -0.946   1.664   0.987  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.318   0.101   1.781  1.00  0.00           H  
HETATM   21  H3  UNL     1      -1.853   0.957  -1.119  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.768  -0.512  -0.543  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.549  -1.256  -1.581  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.831  -1.581  -1.335  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.889  -0.678  -2.879  1.00  0.00           H  
HETATM   26  H8  UNL     1       3.769  -0.016  -1.332  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.696   1.357  -1.702  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.505   1.051   0.459  1.00  0.00           H  
HETATM   29  H11 UNL     1       3.208  -1.452   0.518  1.00  0.00           H  
HETATM   30  H12 UNL     1       3.071  -0.490   2.022  1.00  0.00           H  
HETATM   31  H13 UNL     1       1.593  -1.139   1.281  1.00  0.00           H  
HETATM   32  H14 UNL     1       4.366   0.934   0.559  1.00  0.00           H  
CONECT    1    2
CONECT    2    3    4    5
CONECT    5    6   19   20
CONECT    6    7   11   21
CONECT    7    8   22   23
CONECT    8    9    9   10
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   24   25
CONECT   15   16   26   27
CONECT   16   17   18   28
CONECT   17   29   30   31
CONECT   18   32
END

HMDB0241653
     RDKit          3D
4-Hydroxyvalerylcarnitine
 32 31  0  0  0  0  0  0  0  0999 V2000
   -2.6302    2.5025    2.3500 C   0  0  0  0  0  1  0  0  0  0  0  0
   -2.9374    1.4209    1.4322 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.6481    1.9866    0.3143 C   0  0  0  0  0  1  0  0  0  0  0  0
   -3.7794    0.4840    2.1904 C   0  0  0  0  0  1  0  0  0  0  0  0
   -1.6853    0.8090    1.0441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7171    0.2016   -0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7198   -0.8775   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5537   -2.0497    0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3931   -2.9751    0.2561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5115   -2.1322    1.2369 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.4209   -0.3632   -0.5521 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3934    0.0217   -1.5797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0271    0.9153   -2.3839 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7289   -0.5864   -1.7941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7539    0.3840   -1.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4935    0.5839    0.2801 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5820   -0.6973    1.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5224    1.4324    0.7363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9455    1.6640    0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    0.1012    1.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8527    0.9567   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7684   -0.5117   -0.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5486   -1.2558   -1.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8313   -1.5807   -1.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8893   -0.6783   -2.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7691   -0.0162   -1.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6958    1.3572   -1.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5046    1.0505    0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2081   -1.4516    0.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0710   -0.4902    2.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5934   -1.1390    1.2812 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3661    0.9335    0.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
 14 24  1  0
 14 25  1  0
 15 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
 17 30  1  0
 17 31  1  0
 18 32  1  0
M  CHG  2   2   1  10  -1
M  RAD  3   1   2   3   2   4   2
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₂H₁₄NO₅

Average Molecular Weight

252.246

Monoisotopic Molecular Weight

252.087197555

IUPAC Name

({3-carboxy-2-[(4-hydroxypentanoyl)oxy]propyl}dimethylazaniumyl)methylidyne

Traditional Name

({3-carboxy-2-[(4-hydroxypentanoyl)oxy]propyl}dimethylammonio)methylidyne

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H15NO5/c1-9(14)5-6-12(17)18-10(7-11(15)16)8-13(2,3)4/h9-10,14H,5-8H2,1H3,(H,15,16)/q+1/p-1

InChI Key

LMUUCZFQHPIMJM-UHFFFAOYSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Dicarboxylic acid or derivatives
Quaternary ammonium salt
Secondary alcohol
Carboxylic acid salt
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organic zwitterion
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

All cells and tissues (PMID: 35710135)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 35710135)

Excreta

Biofluid or Excreta

Urine (PMID: 35710135)

Cellular substructure

Cytoplasm (PMID: 35710135)
Mitochondrion matrix (PMID: 35710135)

Organelle

Peroxisome (PMID: 35710135)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

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	-4.7	ChemAxon
pKa (Strongest Acidic)	3.23	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	86.66 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	75.45 m³·mol⁻¹	ChemAxon
Polarizability	25.41 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]+	148.815	30932474
DeepCCS	[M-H]-	146.414	30932474
DeepCCS	[M-2H]-	180.494	30932474
DeepCCS	[M+Na]+	155.151	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxyvalerylcarnitine,1TMS,isomer #1	[C][N+]([C])([C])CC(CC(=O)[O-])OC(=O)CCC(C)O[Si](C)(C)C	1778.3	Semi standard non polar	33892256
4-Hydroxyvalerylcarnitine,1TBDMS,isomer #1	[C][N+]([C])([C])CC(CC(=O)[O-])OC(=O)CCC(C)O[Si](C)(C)C(C)(C)C	1992.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxyvalerylcarnitine 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 - 4-Hydroxyvalerylcarnitine 10V, Positive-QTOF	Not Available	2021-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvalerylcarnitine 20V, Positive-QTOF	Not Available	2021-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvalerylcarnitine 40V, Positive-QTOF	Not Available	2021-04-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvalerylcarnitine 10V, Positive-QTOF	splash10-03di-0090000000-2c59ab2896e0b309dfe2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvalerylcarnitine 20V, Positive-QTOF	splash10-01p9-9050000000-eeb1b523e2b808aebed0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxyvalerylcarnitine 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)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Acylcarnitine 4-Hydroxyvalerylcarnitine		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

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 ]
Grunert SC, Schlatter SM, Schmitt RN, Gemperle-Britschgi C, Mrazova L, Balci MC, Bischof F, Coker M, Das AM, Demirkol M, de Vries M, Gokcay G, Haberle J, Ucar SK, Lotz-Havla AS, Lucke T, Roland D, Rutsch F, Santer R, Schlune A, Staufner C, Schwab KO, Mitchell GA, Sass JO: 3-Hydroxy-3-methylglutaryl-coenzyme A lyase deficiency: Clinical presentation and outcome in a series of 37 patients. Mol Genet Metab. 2017 Jul;121(3):206-215. doi: 10.1016/j.ymgme.2017.05.014. Epub 2017 May 22. [PubMed:28583327 ]
Blazenovic I, Kind T, Sa MR, Ji J, Vaniya A, Wancewicz B, Roberts BS, Torbasinovic H, Lee T, Mehta SS, Showalter MR, Song H, Kwok J, Jahn D, Kim J, Fiehn O: Structure Annotation of All Mass Spectra in Untargeted Metabolomics. Anal Chem. 2019 Feb 5;91(3):2155-2162. doi: 10.1021/acs.analchem.8b04698. Epub 2019 Jan 16. [PubMed:30608141 ]
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 ]
Chen C, Hou G, Zeng C, Ren Y, Chen X, Peng C: Metabolomic profiling reveals amino acid and carnitine alterations as metabolic signatures in psoriasis. Theranostics. 2021 Jan 1;11(2):754-767. doi: 10.7150/thno.51154. eCollection 2021. [PubMed:33391503 ]
Donti TR, Blackburn PR, Atwal PS: Holocarboxylase synthetase deficiency pre and post newborn screening. Mol Genet Metab Rep. 2016 Apr 6;7:40-4. doi: 10.1016/j.ymgmr.2016.03.007. eCollection 2016 Jun. [PubMed:27114915 ]
Yu D, Zhou L, Xuan Q, Wang L, Zhao X, Lu X, Xu G: Strategy for Comprehensive Identification of Acylcarnitines Based on Liquid Chromatography-High-Resolution Mass Spectrometry. Anal Chem. 2018 May 1;90(9):5712-5718. doi: 10.1021/acs.analchem.7b05471. Epub 2018 Apr 20. [PubMed:29651844 ]
Yan X, Markey SP, Marupaka R, Dong Q, Cooper BT, Mirokhin YA, Wallace WE, Stein SE: Mass Spectral Library of Acylcarnitines Derived from Human Urine. Anal Chem. 2020 May 5;92(9):6521-6528. doi: 10.1021/acs.analchem.0c00129. Epub 2020 Apr 23. [PubMed:32271007 ]
Zuniga A, Li L: Ultra-high performance liquid chromatography tandem mass spectrometry for comprehensive analysis of urinary acylcarnitines. Anal Chim Acta. 2011 Mar 9;689(1):77-84. doi: 10.1016/j.aca.2011.01.018. Epub 2011 Jan 18. [PubMed:21338760 ]
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 ]

Showing metabocard for 4-Hydroxyvalerylcarnitine (HMDB0241653)

MOL for HMDB0241653 (4-Hydroxyvalerylcarnitine)

3D MOL for HMDB0241653 (4-Hydroxyvalerylcarnitine)

3D SDF for HMDB0241653 (4-Hydroxyvalerylcarnitine)

3D-SDF for HMDB0241653 (4-Hydroxyvalerylcarnitine)

PDB for HMDB0241653 (4-Hydroxyvalerylcarnitine)

3D PDB for HMDB0241653 (4-Hydroxyvalerylcarnitine)

SMILES for HMDB0241653 (4-Hydroxyvalerylcarnitine)

INCHI for HMDB0241653 (4-Hydroxyvalerylcarnitine)

Structure for HMDB0241653 (4-Hydroxyvalerylcarnitine)

3D Structure for HMDB0241653 (4-Hydroxyvalerylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra