MiMeDB: Showing metabocard for 9,12-Hexadecadienylcarnitine (MMDBc0033538)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:52:44 UTC

Update Date

2022-12-15 22:51:56 UTC

MiMeDB ID

MMDBc0033538

Metabolite Identification

Common Name

9,12-Hexadecadienylcarnitine

Description

9,12-Hexadecadienoylcarnitine is an acylcarnitine. More specifically, it is an 9,12-hexadecadienoic 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. 9,12-Hexadecadienoylcarnitine is therefore classified as a long chain AC. As a long-chain acylcarnitine 9,12-hexadecadienoylcarnitine 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. 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 ). 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

Synonyms

Not Available

Chemical Formula

C₂₃H₄₁NO₄

Average Molecular Weight

395.5759

Monoisotopic Molecular Weight

395.303558805

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

InChI Identifier

InChI=1S/C23H41NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(24(2,3)4)19-20-22(25)26/h7-8,10-11,21H,5-6,9,12-20H2,1-4H3/t21-/m0/s1

InChI Key

AHZCIODFJPNPKS-NRFANRHFSA-N

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Fungi	Ascomycota	1	Human Feces	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human	Detected and Quantified	0.01				Adult (>18 years old)	Both	Normal	HMDB	21359215	details
Human	Detected and Quantified			0.0	0.01	Newborn (0-30 days old)	Both	Normal	HMDB	32340350	details
Human	Detected and Quantified	0.0010		0.0005	0.0040	Adult (>18 years old)	Both	Normal	HMDB	24023812	details
Human	Detected and Quantified	0.11	0.04			Adult (>18 years old)	Both	Normal	HMDB	27624970	details
Human	Detected and Quantified	0.19	0.09			Adult (>18 years old)	Both	Normal	HMDB	27624970	details
Human	Detected and Quantified	0.011	0.002			Adult (>18 years old)	Both	Normal	HMDB	Zerihun T. Dame, Farid Aziat, Rupasri Mandal, Ram Krishnamurthy, Souhaila Bouatra, Shima Borzouie, An Chi Guo, Tanvir Sajed, Lu Deng, Hong Lin, Philip Liu, Edison Dong, David S. Wishart "The human saliva metabolome" Metabolomics (2015) DOI 10.1007/s11306-015-0840-5	details
Human	Detected and Quantified			0.0080	0.0250	Adult (>18 years old)	Both	Normal	HMDB	Molecular You (https://molecularyou.com)	details

External Links

Not Available

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Okun JG, Kolker S, Schulze A, Kohlmuller D, Olgemoller K, Lindner M, Hoffmann GF, Wanders RJ, Mayatepek E: A method for quantitative acylcarnitine profiling in human skin fibroblasts using unlabelled palmitic acid: diagnosis of fatty acid oxidation disorders and differentiation between biochemical phenotypes of MCAD deficiency. Biochim Biophys Acta. 2002 Oct 10;1584(2-3):91-8. doi: 10.1016/s1388-1981(02)00296-2. [PubMed:12385891 ]
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 ]
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. doi: 10.1194/jlr.R600022-JLR200. 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. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
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 ]
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 ]
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 ]
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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 9,12-Hexadecadienylcarnitine (MMDBc0033538)

MOL for #<Metabolite:0x000055b76dd65d60>

3D MOL for #<Metabolite:0x000055b76dd65d60>

3D SDF for #<Metabolite:0x000055b76dd65d60>

3D-SDF for #<Metabolite:0x000055b76dd65d60>

PDB for #<Metabolite:0x000055b76dd65d60>

3D PDB for #<Metabolite:0x000055b76dd65d60>

SMILES for #<Metabolite:0x000055b76dd65d60>

INCHI for #<Metabolite:0x000055b76dd65d60>

Structure for #<Metabolite:0x000055b76dd65d60>

3D Structure for #<Metabolite:0x000055b76dd65d60>