MiMeDB: Showing metabocard for Tetradecenoylcarnitine (MMDBc0033537)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:52:42 UTC

Update Date

2024-04-30 20:12:08 UTC

Metabolite ID

MMDBc0033537

Metabolite Identification

Common Name

Tetradecenoylcarnitine

Description

cis-5-Tetradecenoylcarnitine is an acylcarnitine. More specifically, it is an cis-5-tetradecenoic 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 [Dambrova et al. 2021, Physiological Reviews], 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. cis-5-Tetradecenoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine cis-5-Tetradecenoylcarnitine is generally formed through esterification with long-chain fatty acids obtained from the diet. The main function of most long-chain acylcarnitines is to ensure long chain fatty acid transport into the mitochondria (PMID: 22804748 ). Altered levels of long-chain acylcarnitines can serve as useful markers for inherited disorders of long-chain fatty acid metabolism. In particular cis-5-Tetradecenoylcarnitine is elevated in the blood or plasma of individuals with very long-chain acyl-CoA dehydrogenase (VLACD) deficiency (PMID: 25843429 , PMID: 19327992 , PMID: 11433098 , PMID: 18670371 , PMID: 12828998 ), trifunctional protein (mitochondrial long-chain ketoacyl-coa thiolase) deficiency (PMID: 16423905 ), mitochondrial dysfunction in diabetes patients (PMID: 28726959 ), acadvl acyl-coa dehydrogenase very long chain deficiency (PMID: 29491033 ), nonalcoholic fatty liver disease (NAFLD) (PMID: 27211699 ), and insulin resistance type 2 diabetes (PMID: 24358186 ). Carnitine palmitoyltransferase I (CPT I, EC:2.3.1.21) is involved in the synthesis of long-chain acylcarnitines (more than C12) on the mitochondrial outer membrane. Elevated serum/plasma levels of long-chain acylcarnitines are not only markers for incomplete FA oxidation but also are indicators of altered carbohydrate and lipid metabolism. High serum concentrations of long-chain acylcarnitines in the postprandial or fed state are markers of insulin resistance and arise from insulin's inability to inhibit CPT-1-dependent fatty acid metabolism in muscles and the heart (PMID: 19073774 ). Increased intracellular content of long-chain acylcarnitines is thought to serve as a feedback inhibition mechanism of insulin action (PMID: 23258903 ). Defects in enzymes of the beta-oxidation pathway cause sudden, unexplained death in childhood, acute hepatic encephalopathy or liver failure, skeletal myopathy, and cardiomyopathy (PMID: 7479827 ). In healthy subjects, increased concentrations of insulin effectively inhibits long-chain acylcarnitine production. Several studies have also found increased levels of circulating long-chain acylcarnitines in chronic heart failure patients (PMID: 26796394 ). 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 at [Dambrova et al. 2021, Physiological Reviews].

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221920562D          

 26 25  0  0  0  0            999 V2000
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7151    5.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5881    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4131    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    6.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    6.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717    5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    7.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0006    5.8559    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   10.1427    7.5059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717    7.5059    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   10.1427    5.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717    5.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 13 14  1  4  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 19 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 17  1  0  0  0  0
 21 16  1  0  0  0  0
 22  2  1  0  0  0  0
 22  3  1  0  0  0  0
 22  4  1  0  0  0  0
 22 18  1  0  0  0  0
 23 20  2  0  0  0  0
 24 20  1  0  0  0  0
 25 21  2  0  0  0  0
 26 19  1  0  0  0  0
 26 21  1  0  0  0  0
M  CHG  2  22   1  24  -1
M  END


  Mrv1652305221920562D          

 26 25  0  0  0  0            999 V2000
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7151    5.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5881    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4131    6.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4283    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1427    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    6.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2862    6.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717    5.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    7.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8572    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0006    5.8559    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   10.1427    7.5059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717    7.5059    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   10.1427    5.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5717    5.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  2  0  0  0  0
 13 14  1  4  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 19 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 17  1  0  0  0  0
 21 16  1  0  0  0  0
 22  2  1  0  0  0  0
 22  3  1  0  0  0  0
 22  4  1  0  0  0  0
 22 18  1  0  0  0  0
 23 20  2  0  0  0  0
 24 20  1  0  0  0  0
 25 21  2  0  0  0  0
 26 19  1  0  0  0  0
 26 21  1  0  0  0  0
M  CHG  2  22   1  24  -1
M  END
> <DATABASE_ID>
MMDBc0033537

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H39NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-21(25)26-19(17-20(23)24)18-22(2,3)4/h12-13,19H,5-11,14-18H2,1-4H3

> <INCHI_KEY>
NNCBVXBBLABOCB-UHFFFAOYSA-N

> <FORMULA>
C21H39NO4

> <MOLECULAR_WEIGHT>
369.5387

> <EXACT_MASS>
369.287908741

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
44.52133344703289

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(tetradec-5-enoyloxy)-4-(trimethylazaniumyl)butanoate

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
0.7824888675282539

> <ALOGPS_LOGS>
-7.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.235690941127461

> <JCHEM_PKA_STRONGEST_BASIC>
-7.05730458065797

> <JCHEM_POLAR_SURFACE_AREA>
66.43

> <JCHEM_REFRACTIVITY>
128.9913

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(tetradec-5-enoyloxy)-4-(trimethylammonio)butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.602  10.161   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.498   9.597   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.038  12.265   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.266   4.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.599   4.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.933   4.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.933   6.311   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.267   7.081   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.267  11.701   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.934  11.701   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.600  10.931   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.267  13.241   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.267   8.621   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      24.268  10.931   0.000  0.00  0.00           N+1
HETATM   23  O   UNK     0      18.933  14.011   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      21.600  14.011   0.000  0.00  0.00           O-1
HETATM   25  O   UNK     0      18.933   9.391   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      21.600   9.391   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   22                                                            
CONECT    3   22                                                            
CONECT    4   22                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   21                                                       
CONECT   17   19   20                                                       
CONECT   18   19   22                                                       
CONECT   19   17   18   26                                                  
CONECT   20   17   23   24                                                  
CONECT   21   16   25   26                                                  
CONECT   22    2    3    4   18                                             
CONECT   23   20                                                            
CONECT   24   20                                                            
CONECT   25   21                                                            
CONECT   26   19   21                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

Synonyms

Not Available

Molecular Formula

C₂₁H₃₉NO₄

Average Mass

369.5387

Monoisotopic Mass

369.287908741

IUPAC Name

3-(tetradec-5-enoyloxy)-4-(trimethylazaniumyl)butanoate

Traditional Name

3-(tetradec-5-enoyloxy)-4-(trimethylammonio)butanoate

CAS Registry Number

835598-21-5

SMILES

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

InChI Identifier

InChI=1S/C21H39NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-21(25)26-19(17-20(23)24)18-22(2,3)4/h12-13,19H,5-11,14-18H2,1-4H3

InChI Key

NNCBVXBBLABOCB-UHFFFAOYSA-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

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.7e-05 g/L	ALOGPS
logP	0.48	ALOGPS
logP	0.78	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	4.24	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	17	ChemAxon
Refractivity	128.99 m³·mol⁻¹	ChemAxon
Polarizability	44.52 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-9210000000-0e252dd9fa20839689f3	2016-09-22	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0002288	Coenzyme A	L-Carnitine	Carnitine palmitoyltransferase 2	VMH	30371894
MMDBr0002289	Tetradecenoylcarnitine	Tetradecenoylcarnitine	Solute carrier family 25 (carnitine/acylcarnitine translocase), member 20	VMH	30371894
MMDBr0005080	L-Carnitine	Coenzyme A	Carnitine palmitoyltransferase 1a (liver)	VMH	19137688 15653102 12403251
MMDBr0005082	L-Carnitine	Coenzyme A	Carnitine palmitoyltransferase 1a (liver)	VMH	19327992 18670371 15466478 11433098
MMDBr0005365	Tetradecenoylcarnitine	Tetradecenoylcarnitine	Not Available	VMH	30371894
MMDBr0005368	Tetradecenoylcarnitine	Tetradecenoylcarnitine	Not Available	VMH	30371894
MMDBr0005744	Sodium	Sodium	Not Available	VMH	30371894
MMDBr0006719	Tetradecenoylcarnitine	Tetradecenoylcarnitine	Not Available	VMH	30371894
MMDBr0006720	Tetradecenoylcarnitine	Tetradecenoylcarnitine	Not Available	VMH	30371894
MMDBr0009763	L-Carnitine	Coenzyme A	Carnitine palmitoyltransferase 1a (liver)	VMH	30371894
MMDBr0009764	L-Carnitine	L-Carnitine	Solute carrier family 22 (organic cation transporter), member 1	VMH	30371894
MMDBr0009765	L-Carnitine	Coenzyme A	Carnitine palmitoyltransferase 2	VMH	30371894
MMDBr0009860	L-Carnitine	L-Carnitine	Solute carrier family 22 (organic cation/carnitine transporter), member 5	VMH	30371894
MMDBr0009861	L-Carnitine	Coenzyme A	Carnitine o-acetyltransferase	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Very long chain acyl-coa dehydrogenase deficiency	Increased	Association	Human Blood	HMDB	9034211
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Obesity	Slight Increase	Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Obesity	Slight Increase	Association	Human Blood	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929
Animal	Milk	Bos taurus	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Blood	Detected and Quantified	5.223		2.658	7.891	uM	Adult (>18 years old)	Both	Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD)	HMDB	9034211
Human Blood	Detected and Quantified	<1				uM	Newborn (0-30 days old)	Not Specified	Normal	HMDB	16950999
Human Blood	Detected and Quantified	0.03		0.03	0.04	uM	Newborn (0-30 days old)		Normal	HMDB	25754623
Human Blood	Detected and Quantified	0.032		0.005	0.097	uM	Children (1-13 years old)	Both	Normal	HMDB	9034211
Human Blood	Detected and Quantified	0.06	0.03			uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Blood	Detected and Quantified	0.08		0.06	0.11	uM	Infant (0-1 year old)		Normal	HMDB	25754623
Human Urine	Detected and Quantified	0.0039	0.0013			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Blood	Detected and Quantified	0.122	0.042			uM	Children (1-13 years old)	Both	Obesity	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Human Blood	Detected and Quantified	0.131	0.048			uM	Children (1-13 years old)	Both	Obesity	HMDB	Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children
Human Urine	Detected and Quantified	0.0038	0.0015			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Blood	Detected and Quantified			0.020	0.240	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)
Human Blood	Detected and Quantified			0.020	0.240	uM	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022796

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

57353952

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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Strauss AW, Powell CK, Hale DE, Anderson MM, Ahuja A, Brackett JC, Sims HF: Molecular basis of human mitochondrial very-long-chain acyl-CoA dehydrogenase deficiency causing cardiomyopathy and sudden death in childhood. Proc Natl Acad Sci U S A. 1995 Nov 7;92(23):10496-500. doi: 10.1073/pnas.92.23.10496. [PubMed:7479827 ]
Wood JC, Magera MJ, Rinaldo P, Seashore MR, Strauss AW, Friedman A: Diagnosis of very long chain acyl-dehydrogenase deficiency from an infant's newborn screening card. Pediatrics. 2001 Jul;108(1):E19. doi: 10.1542/peds.108.1.e19. [PubMed:11433098 ]
Shigematsu Y, Hirano S, Hata I, Tanaka Y, Sudo M, Tajima T, Sakura N, Yamaguchi S, Takayanagi M: Selective screening for fatty acid oxidation disorders by tandem mass spectrometry: difficulties in practical discrimination. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):63-72. doi: 10.1016/s1570-0232(03)00281-2. [PubMed:12828998 ]
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 ]
Das AM, Illsinger S, Lucke T, Hartmann H, Ruiter JP, Steuerwald U, Waterham HR, Duran M, Wanders RJ: Isolated mitochondrial long-chain ketoacyl-CoA thiolase deficiency resulting from mutations in the HADHB gene. Clin Chem. 2006 Mar;52(3):530-4. doi: 10.1373/clinchem.2005.062000. Epub 2006 Jan 19. [PubMed:16423905 ]
Tajima G, Sakura N, Shirao K, Okada S, Tsumura M, Nishimura Y, Ono H, Hasegawa Y, Hata I, Naito E, Yamaguchi S, Shigematsu Y, Kobayashi M: Development of a new enzymatic diagnosis method for very-long-chain Acyl-CoA dehydrogenase deficiency by detecting 2-hexadecenoyl-CoA production and its application in tandem mass spectrometry-based selective screening and newborn screening in Japan. Pediatr Res. 2008 Dec;64(6):667-72. doi: 10.1203/PDR.0b013e318187cc44. [PubMed:18670371 ]
Bruce CR, Hoy AJ, Turner N, Watt MJ, Allen TL, Carpenter K, Cooney GJ, Febbraio MA, Kraegen EW: Overexpression of carnitine palmitoyltransferase-1 in skeletal muscle is sufficient to enhance fatty acid oxidation and improve high-fat diet-induced insulin resistance. Diabetes. 2009 Mar;58(3):550-8. doi: 10.2337/db08-1078. Epub 2008 Dec 10. [PubMed:19073774 ]
Laforet P, Acquaviva-Bourdain C, Rigal O, Brivet M, Penisson-Besnier I, Chabrol B, Chaigne D, Boespflug-Tanguy O, Laroche C, Bedat-Millet AL, Behin A, Delevaux I, Lombes A, Andresen BS, Eymard B, Vianey-Saban C: Diagnostic assessment and long-term follow-up of 13 patients with Very Long-Chain Acyl-Coenzyme A dehydrogenase (VLCAD) deficiency. Neuromuscul Disord. 2009 May;19(5):324-9. doi: 10.1016/j.nmd.2009.02.007. Epub 2009 Mar 26. [PubMed:19327992 ]
Reuter SE, Evans AM: Carnitine and acylcarnitines: pharmacokinetic, pharmacological and clinical aspects. Clin Pharmacokinet. 2012 Sep 1;51(9):553-72. doi: 10.1007/BF03261931. [PubMed:22804748 ]
Schooneman MG, Vaz FM, Houten SM, Soeters MR: Acylcarnitines: reflecting or inflicting insulin resistance? Diabetes. 2013 Jan;62(1):1-8. doi: 10.2337/db12-0466. [PubMed:23258903 ]
Mai M, Tonjes A, Kovacs P, Stumvoll M, Fiedler GM, Leichtle AB: Serum levels of acylcarnitines are altered in prediabetic conditions. PLoS One. 2013 Dec 16;8(12):e82459. doi: 10.1371/journal.pone.0082459. eCollection 2013. [PubMed:24358186 ]
Hisahara S, Matsushita T, Furuyama H, Tajima G, Shigematsu Y, Imai T, Shimohama S: A heterozygous missense mutation in adolescent-onset very long-chain acyl-CoA dehydrogenase deficiency with exercise-induced rhabdomyolysis. Tohoku J Exp Med. 2015 Apr;235(4):305-10. doi: 10.1620/tjem.235.305. [PubMed:25843429 ]
Ahmad T, Kelly JP, McGarrah RW, Hellkamp AS, Fiuzat M, Testani JM, Wang TS, Verma A, Samsky MD, Donahue MP, Ilkayeva OR, Bowles DE, Patel CB, Milano CA, Rogers JG, Felker GM, O'Connor CM, Shah SH, Kraus WE: Prognostic Implications of Long-Chain Acylcarnitines in Heart Failure and Reversibility With Mechanical Circulatory Support. J Am Coll Cardiol. 2016 Jan 26;67(3):291-9. doi: 10.1016/j.jacc.2015.10.079. [PubMed:26796394 ]
Chen Y, Li C, Liu L, Guo F, Li S, Huang L, Sun C, Feng R: Serum metabonomics of NAFLD plus T2DM based on liquid chromatography-mass spectrometry. Clin Biochem. 2016 Sep;49(13-14):962-6. doi: 10.1016/j.clinbiochem.2016.05.016. Epub 2016 May 20. [PubMed:27211699 ]
Abu Bakar MH, Sarmidi MR: Association of cultured myotubes and fasting plasma metabolite profiles with mitochondrial dysfunction in type 2 diabetes subjects. Mol Biosyst. 2017 Aug 22;13(9):1838-1853. doi: 10.1039/c7mb00333a. [PubMed:28726959 ]
Lepori V, Muhlhause F, Sewell AC, Jagannathan V, Janzen N, Rosati M, Alves de Sousa FMM, Tschopp A, Schupbach G, Matiasek K, Tipold A, Leeb T, Kornberg M: A Nonsense Variant in the ACADVL Gene in German Hunting Terriers with Exercise Induced Metabolic Myopathy. G3 (Bethesda). 2018 May 4;8(5):1545-1554. doi: 10.1534/g3.118.200084. [PubMed:29491033 ]

Showing metabocard for Tetradecenoylcarnitine (MMDBc0033537)

MOL for #<Metabolite:0x00007f560841dc90>

3D MOL for #<Metabolite:0x00007f560841dc90>

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Structure for #<Metabolite:0x00007f560841dc90>

3D Structure for #<Metabolite:0x00007f560841dc90>