Jump To Section:

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

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2009-11-02 23:32:58 UTC

Update Date

2023-05-30 20:55:50 UTC

HMDB ID

HMDB0013128

Secondary Accession Numbers

HMDB13128

Metabolite Identification

Common Name

Valerylcarnitine

Description

Valerylcarnitine is an acylcarnitine. More specifically, it is an valeric 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. Valerylcarnitine is therefore classified as a short chain AC. As a short-chain acylcarnitine valerylcarnitine 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 valerylcarnitine is elevated in the blood or plasma of individuals with exudative age-related macular degeneration (PMID: 32120889 ), type 2 Diabetes Mellitus (PMID: 31782507 , PMID: 20111019 ), obesity (PMID: 20111019 ), acute cerebral infarction (PMID: 29265114 ), diastolic heart failure (PMID: 26010610 ), systolic heart failure (PMID: 26010610 ). It is also decreased in the blood or plasma of individuals with pregnancy (PMID: 24704061 - in serum of pregnant women with fetus with CHD). Valerylcarnitine can also be found cerebrospinal fluid (CSF), and urine. 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

HMDB0013128
     RDKit          3D
Valerylcarnitine
 41 40  0  0  0  0  0  0  0  0999 V2000
    6.3840   -0.2730   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1295    0.3775    0.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8832   -0.2021   -0.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6915    0.5065    0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4159    0.0352   -0.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3893   -0.8654   -1.0791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2251    0.5764    0.2309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0596    0.1553   -0.2680 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7286    1.4176   -0.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    2.0895   -1.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1182    1.6605   -2.2657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4486    3.2872   -2.3746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8092   -0.4067    0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1178   -0.9022    0.6410 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.1932   -1.6367   -0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3892   -1.8774    1.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1697    0.0594    0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1575   -0.9863   -0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0604    0.5245   -0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9154   -0.8027    0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1501    1.4861    0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0685    0.2108    1.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8345   -1.2832   -0.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9219   -0.0085   -1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636    0.3534    1.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8451    1.6016    0.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852   -0.5987   -1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7444    1.2308   -1.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130    2.1045    0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0569    3.9012   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854    0.3738    1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1908   -1.2726    1.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9988   -2.4248   -0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4912   -1.0158   -1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2297   -2.1097   -0.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2386   -2.5167    1.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4652   -2.4048    1.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6814   -1.2542    2.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6667    0.1054   -0.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9464   -0.2734    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7846    1.0580    0.9892 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  6
  9 28  1  0
  9 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
M  CHG  1  14   1
M  END


  Mrv1652307072020082D          

 17 16  0  0  0  0            999 V2000
   -1.3585   -0.1994    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6442   -0.6128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0705   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4985   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2122   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9262   -0.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0705    0.6253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3585    0.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0728    1.0359    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -2.7910    0.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0728    1.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9262    1.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0667   -0.6231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0667   -1.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3524   -1.8612    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.7788   -1.8612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  6  0  0  0
  1 14  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 17  2  0  0  0  0
 15 16  1  0  0  0  0
M  CHG  2  10   1  16  -1
M  END
> <DATABASE_ID>
HMDB0013128

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H23NO4/c1-5-6-7-12(16)17-10(8-11(14)15)9-13(2,3)4/h10H,5-9H2,1-4H3/t10-/m1/s1

> <INCHI_KEY>
VSNFQQXVMPSASB-SNVBAGLBSA-N

> <FORMULA>
C12H23NO4

> <MOLECULAR_WEIGHT>
245.319

> <EXACT_MASS>
245.162708225

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
26.841823176157295

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-(pentanoyloxy)-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
-1.90

> <JCHEM_LOGP>
-2.8567074608050786

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.342854326087013

> <JCHEM_PKA_STRONGEST_BASIC>
-7.057185135307671

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
86.4657

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-(pentanoyloxy)-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013128
     RDKit          3D
Valerylcarnitine
 41 40  0  0  0  0  0  0  0  0999 V2000
    6.3840   -0.2730   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1295    0.3775    0.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8832   -0.2021   -0.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6915    0.5065    0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4159    0.0352   -0.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3893   -0.8654   -1.0791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2251    0.5764    0.2309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0596    0.1553   -0.2680 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7286    1.4176   -0.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    2.0895   -1.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1182    1.6605   -2.2657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4486    3.2872   -2.3746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8092   -0.4067    0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1178   -0.9022    0.6410 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.1932   -1.6367   -0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3892   -1.8774    1.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1697    0.0594    0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1575   -0.9863   -0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0604    0.5245   -0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9154   -0.8027    0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1501    1.4861    0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0685    0.2108    1.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8345   -1.2832   -0.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9219   -0.0085   -1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636    0.3534    1.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8451    1.6016    0.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852   -0.5987   -1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7444    1.2308   -1.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130    2.1045    0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0569    3.9012   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854    0.3738    1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1908   -1.2726    1.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9988   -2.4248   -0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4912   -1.0158   -1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2297   -2.1097   -0.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2386   -2.5167    1.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4652   -2.4048    1.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6814   -1.2542    2.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6667    0.1054   -0.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9464   -0.2734    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7846    1.0580    0.9892 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  6
  9 28  1  0
  9 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
M  CHG  1  14   1
M  END

HEADER    PROTEIN                                 07-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JUL-20         0                                  
HETATM    1  C   UNK     0      -2.536  -0.372   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.203  -1.144   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.132  -0.372   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.465  -1.144   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.797  -0.372   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.129  -1.144   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.462  -0.372   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.132   1.167   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.536   1.167   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -3.869   1.934   0.000  0.00  0.00           N+1
HETATM   11  C   UNK     0      -5.210   1.163   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.869   3.474   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.462   2.854   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.858  -1.163   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.858  -2.702   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.525  -3.474   0.000  0.00  0.00           O-1
HETATM   17  O   UNK     0      -5.187  -3.474   0.000  0.00  0.00           O+0
CONECT    1    2    9   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    3                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    1   15                                                       
CONECT   15   14   17   16                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0013128
HETATM    1  C1  UNL     1       6.384  -0.273  -0.167  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.129   0.377   0.375  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.883  -0.202  -0.269  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.691   0.506   0.332  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.416   0.035  -0.209  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.389  -0.865  -1.079  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.225   0.576   0.231  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.060   0.155  -0.268  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.729   1.418  -0.749  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.959   2.089  -1.816  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.118   1.660  -2.266  1.00  0.00           O  
HETATM   12  O4  UNL     1      -1.449   3.287  -2.375  1.00  0.00           O  
HETATM   13  C9  UNL     1      -1.809  -0.407   0.917  1.00  0.00           C  
HETATM   14  N1  UNL     1      -3.118  -0.902   0.641  1.00  0.00           N1+
HETATM   15  C10 UNL     1      -3.193  -1.637  -0.614  1.00  0.00           C  
HETATM   16  C11 UNL     1      -3.389  -1.877   1.722  1.00  0.00           C  
HETATM   17  C12 UNL     1      -4.170   0.059   0.672  1.00  0.00           C  
HETATM   18  H1  UNL     1       6.158  -0.986  -0.986  1.00  0.00           H  
HETATM   19  H2  UNL     1       7.060   0.525  -0.563  1.00  0.00           H  
HETATM   20  H3  UNL     1       6.915  -0.803   0.650  1.00  0.00           H  
HETATM   21  H4  UNL     1       5.150   1.486   0.207  1.00  0.00           H  
HETATM   22  H5  UNL     1       5.068   0.211   1.462  1.00  0.00           H  
HETATM   23  H6  UNL     1       3.834  -1.283  -0.021  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.922  -0.009  -1.357  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.764   0.353   1.444  1.00  0.00           H  
HETATM   26  H9  UNL     1       2.845   1.602   0.188  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.885  -0.599  -1.032  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.744   1.231  -1.160  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.813   2.104   0.125  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.057   3.901  -1.847  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.885   0.374   1.706  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.191  -1.273   1.282  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.999  -2.425  -0.524  1.00  0.00           H  
HETATM   34  H17 UNL     1      -3.491  -1.016  -1.459  1.00  0.00           H  
HETATM   35  H18 UNL     1      -2.230  -2.110  -0.831  1.00  0.00           H  
HETATM   36  H19 UNL     1      -4.239  -2.517   1.475  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.465  -2.405   1.968  1.00  0.00           H  
HETATM   38  H21 UNL     1      -3.681  -1.254   2.607  1.00  0.00           H  
HETATM   39  H22 UNL     1      -4.667   0.105  -0.319  1.00  0.00           H  
HETATM   40  H23 UNL     1      -4.946  -0.273   1.389  1.00  0.00           H  
HETATM   41  H24 UNL     1      -3.785   1.058   0.989  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4   23   24
CONECT    4    5   25   26
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   13   27
CONECT    9   10   28   29
CONECT   10   11   11   12
CONECT   12   30
CONECT   13   14   31   32
CONECT   14   15   16   17
CONECT   15   33   34   35
CONECT   16   36   37   38
CONECT   17   39   40   41
END

HMDB0013128
     RDKit          3D
Valerylcarnitine
 41 40  0  0  0  0  0  0  0  0999 V2000
    6.3840   -0.2730   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1295    0.3775    0.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8832   -0.2021   -0.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6915    0.5065    0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4159    0.0352   -0.2093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3893   -0.8654   -1.0791 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2251    0.5764    0.2309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0596    0.1553   -0.2680 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7286    1.4176   -0.7495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    2.0895   -1.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1182    1.6605   -2.2657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4486    3.2872   -2.3746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8092   -0.4067    0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1178   -0.9022    0.6410 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.1932   -1.6367   -0.6137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3892   -1.8774    1.7223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1697    0.0594    0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1575   -0.9863   -0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0604    0.5245   -0.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9154   -0.8027    0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1501    1.4861    0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0685    0.2108    1.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8345   -1.2832   -0.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9219   -0.0085   -1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636    0.3534    1.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8451    1.6016    0.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8852   -0.5987   -1.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7444    1.2308   -1.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130    2.1045    0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0569    3.9012   -1.8472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8854    0.3738    1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1908   -1.2726    1.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9988   -2.4248   -0.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4912   -1.0158   -1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2297   -2.1097   -0.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2386   -2.5167    1.4747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4652   -2.4048    1.9681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6814   -1.2542    2.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6667    0.1054   -0.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9464   -0.2734    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7846    1.0580    0.9892 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  8 27  1  6
  9 28  1  0
  9 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
M  CHG  1  14   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Pentanoyl-L-carnitine	ChEBI
C5-Carnitine	HMDB
O-Valeroyl-L-carnitine	HMDB
Pentanoylcarnitine	HMDB
Valeryl L-carnitine	HMDB
Valeryl-L-carnitine	HMDB
Valerylcarnitine	HMDB

Chemical Formula

C₁₂H₂₃NO₄

Average Molecular Weight

245.319

Monoisotopic Molecular Weight

245.162708225

IUPAC Name

(3R)-3-(pentanoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

(3R)-3-(pentanoyloxy)-4-(trimethylammonio)butanoate

CAS Registry Number

40225-14-7

SMILES

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

InChI Identifier

InChI=1S/C12H23NO4/c1-5-6-7-12(16)17-10(8-11(14)15)9-13(2,3)4/h10H,5-9H2,1-4H3/t10-/m1/s1

InChI Key

VSNFQQXVMPSASB-SNVBAGLBSA-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
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid salt
Carboxylic acid derivative
Carboxylic acid
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

O-acyl-L-carnitine (CHEBI:85095 )
O-valeroylcarnitine (CHEBI:85095 )

Ontology

Physiological effect

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)
Cerebrospinal Fluid (CSF) (PMID: 22546835)

Excreta

Biofluid or Excreta

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

Cellular substructure

Organelle

Peroxisome (PMID: 35710135)

Cell

All cells and tissues (PMID: 35710135)

Source

Exogenous

Exogenous (HMDB: HMDB0013128)

Food

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)
Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Endogenous

Endogenous (HMDB: HMDB0013128)

Process

Not Available

Role

Biological role

Energy source (PMID: 35710135)

Industrial application

Pharmaceutical industry

Biomarker

Breast cancer ()
Diabetes mellitus type 2 ()
Cardiovascular disease ()
Renal cell carcinoma ()
Heart failure ()
Celiac disease ()
Inflammatory bowel disease ()
Pregnancy (MarkerDB: MDB00000850)
Obesity (MarkerDB: MDB00000850)
Isovaleric acidemia (MarkerDB: MDB00000850)

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	0.016 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-2.9	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.34	ChemAxon
pKa (Strongest Basic)	-7.1	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	9	ChemAxon
Refractivity	86.47 m³·mol⁻¹	ChemAxon
Polarizability	26.84 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]+	158.422	30932474
DeepCCS	[M-H]-	156.064	30932474
DeepCCS	[M-2H]-	188.947	30932474
DeepCCS	[M+Na]+	164.515	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Valerylcarnitine	CCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	2602.1	Standard polar	33892256
Valerylcarnitine	CCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	1457.3	Standard non polar	33892256
Valerylcarnitine	CCCCC(=O)O[C@H](CC(O)=O)C[N+](C)(C)C	1691.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Valerylcarnitine,1TMS,isomer #1	CCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C)C[N+](C)(C)C	1717.4	Semi standard non polar	33892256
Valerylcarnitine,1TBDMS,isomer #1	CCCCC(=O)O[C@H](CC(=O)O[Si](C)(C)C(C)(C)C)C[N+](C)(C)C	1943.5	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 - Valerylcarnitine 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 - Valerylcarnitine 10V, Positive-QTOF	splash10-0002-0090000000-a919a7a98ddb53d7bb2b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerylcarnitine 20V, Positive-QTOF	splash10-000j-9050000000-87beaf2642b8fc410f0c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valerylcarnitine 40V, Positive-QTOF	splash10-000i-9000000000-e9262cbaff8cb4ad0ba6	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	<0.400 uM	Not Specified	Not Specified	Normal	10832746	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.14 +/- 0.06 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	0.040-0.260 uM	Adult (>18 years old)	Both	Normal	The Metabolo...	details
Blood	Detected and Quantified	<0.600 uM	Not Specified	Not Specified	Normal	12837870	details
Blood	Detected and Quantified	0.16(0.04) uM	Adult (>18 years old)	Both	Normal	26010610	details
Blood	Detected and Quantified	0.46 uM	Newborn (0-30 days old)	Not Specified	Normal	15615815	details
Blood	Detected and Quantified	0.14 +/- 0.04 uM	Adult (>18 years old)	Both	Normal	28278231	details
Blood	Detected and Quantified	<0.310 uM	Not Specified	Not Specified	Normal	17945527	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.013 +/- 0.006 uM	Adult (>18 years old)	Not Specified	Normal	22546835	details
Feces	Detected and Quantified	0.21 +/- 0.09 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Feces	Detected and Quantified	0.14 +/- 0.06 nmol/g wet feces	Adult (>18 years old)	Both	Normal	27624970	details
Urine	Detected and Quantified	0.220 (0.037-0.440) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.10 (0.05-0.25) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	Analysis of 40 NI...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	<3.0 umol/mmol creatinine	Newborn (0-30 days old)	Not Specified	Normal	15615815	details
Urine	Detected and Quantified	0.9187 +/- 0.4397 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.02-0.29 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	32340350	details
Urine	Detected and Quantified	0.04(0.02-0.25) umol/mmol creatinine	Newborn (0-30 days old)	Female	Normal	32340350	details
Urine	Detected and Quantified	0.05(0.02-0.3) 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	27.300-48.200 uM	Not Specified	Not Specified	Isovaleric acidemia	12837870	details
Blood	Detected and Quantified	0.2(0.06) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	0.22(0.08) uM	Adult (>18 years old)	Both	Heart failure with reduced ejection fraction	26010610	details
Blood	Detected and Quantified	0.0845 (0.0722) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	0.1179 (0.0241) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Blood	Detected and Quantified	0.510-2.0800 uM	Newborn (0-30 days old)	Both	2-Methylbutyryl-CoA dehydrogenase deficiency (SBACDD)	17945527	details
Blood	Detected and Quantified	0.34 uM	Children (1-13 years old)	Male	2-Methylbutyryl-CoA dehydrogenase deficiency (SBACDD)	17945527	details
Blood	Detected and Quantified	0.089 +/- 0.041 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Blood	Detected and Quantified	0.096 +/- 0.031 uM	Children (1-13 years old)	Both	Obesity	Metabolomics reve...	details
Urine	Detected and Quantified	0.6537 +/- 0.7142 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	0.4795 +/- 0.3669 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Pregnancy
Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Obesity
Simone Wahl, Christina Holzapfel, Zhonghao Yu, Michaela Breier, Ivan Kondofersky, Christiane Fuchs, Paula Singmann, Cornelia Prehn, Jerzy Adamski, Harald Grallert, Thomas Illig, Rui Wang-Sattler, Thomas Reinehr (2013). Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children. Metabolomics.
Isovaleric acidemia
Matern D, He M, Berry SA, Rinaldo P, Whitley CB, Madsen PP, van Calcar SC, Lussky RC, Andresen BS, Wolff JA, Vockley J: Prospective diagnosis of 2-methylbutyryl-CoA dehydrogenase deficiency in the Hmong population by newborn screening using tandem mass spectrometry. Pediatrics. 2003 Jul;112(1 Pt 1):74-8. [PubMed:12837870 ]
Short/branched chain acyl-CoA dehydrogenase deficiency
Sass JO, Ensenauer R, Roschinger W, Reich H, Steuerwald U, Schirrmacher O, Engel K, Haberle J, Andresen BS, Megarbane A, Lehnert W, Zschocke J: 2-Methylbutyryl-coenzyme A dehydrogenase deficiency: functional and molecular studies on a defect in isoleucine catabolism. Mol Genet Metab. 2008 Jan;93(1):30-5. doi: 10.1016/j.ymgme.2007.09.002. Epub 2007 Oct 22. [PubMed:17945527 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

601665 (Obesity)
243500 (Isovaleric acidemia)
610006 (Short/branched chain acyl-CoA dehydrogenase deficiency)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029301

KNApSAcK ID

Not Available

Chemspider ID

17353685

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16226475

PDB ID

Not Available

ChEBI ID

85095

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000850

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Zordoky BN, Sung MM, Ezekowitz J, Mandal R, Han B, Bjorndahl TC, Bouatra S, Anderson T, Oudit GY, Wishart DS, Dyck JR: Metabolomic fingerprint of heart failure with preserved ejection fraction. PLoS One. 2015 May 26;10(5):e0124844. doi: 10.1371/journal.pone.0124844. eCollection 2015. [PubMed:26010610 ]
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 ]
Zhang X, Li Y, Liang Y, Sun P, Wu X, Song J, Sun X, Hong M, Gao P, Deng D: Distinguishing Intracerebral Hemorrhage from Acute Cerebral Infarction through Metabolomics. Rev Invest Clin. 2017 Nov-Dec;69(6):319-328. doi: 10.24875/RIC.17002348. [PubMed:29265114 ]
Mihalik SJ, Goodpaster BH, Kelley DE, Chace DH, Vockley J, Toledo FG, DeLany JP: Increased levels of plasma acylcarnitines in obesity and type 2 diabetes and identification of a marker of glucolipotoxicity. Obesity (Silver Spring). 2010 Sep;18(9):1695-700. doi: 10.1038/oby.2009.510. Epub 2010 Jan 28. [PubMed:20111019 ]
Chao de la Barca JM, Rondet-Courbis B, Ferre M, Muller J, Buisset A, Leruez S, Plubeau G, Mace T, Moureauzeau L, Chupin S, Tessier L, Blanchet O, Lenaers G, Procaccio V, Mirebeau-Prunier D, Simard G, Gohier P, Milea D, Reynier P: A Plasma Metabolomic Profiling of Exudative Age-Related Macular Degeneration Showing Carnosine and Mitochondrial Deficiencies. J Clin Med. 2020 Feb 27;9(3). pii: jcm9030631. doi: 10.3390/jcm9030631. [PubMed:32120889 ]
Sun Y, Gao HY, Fan ZY, He Y, Yan YX: Metabolomics Signatures in Type 2 Diabetes: A Systematic Review and Integrative Analysis. J Clin Endocrinol Metab. 2020 Apr 1;105(4). pii: 5645632. doi: 10.1210/clinem/dgz240. [PubMed:31782507 ]
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 Valerylcarnitine (HMDB0013128)

MOL for HMDB0013128 (Valerylcarnitine)

3D MOL for HMDB0013128 (Valerylcarnitine)

3D SDF for HMDB0013128 (Valerylcarnitine)

3D-SDF for HMDB0013128 (Valerylcarnitine)

PDB for HMDB0013128 (Valerylcarnitine)

3D PDB for HMDB0013128 (Valerylcarnitine)

SMILES for HMDB0013128 (Valerylcarnitine)

INCHI for HMDB0013128 (Valerylcarnitine)

Structure for HMDB0013128 (Valerylcarnitine)

3D Structure for HMDB0013128 (Valerylcarnitine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra