Palmitoylcarnitine
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IUPAC name
3-(palmitoyloxy)-4-(trimethylammonio)butanoate
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Identifiers | |
3D model (
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ChEMBL | |
ChemSpider | |
MeSH | Palmitoylcarnitine |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C23H45NO4 | |
Molar mass | 399.608 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Palmitoylcarnitine is an
Structure
Palmitoylcarnitine contains the saturated fatty acid known as palmitic acid (C16:0) which is bound to the β-hydroxy group of the carnitine. The core carnitine structure, consisting of butanoate with a quaternary ammonium attached to C4 and hydroxy group at C3, is a common molecular backbone for the transfer of multiple long chain fatty acids in the TCA cycle.
Function
Energy Generation
Palmitoylcarnitine is one molecule in a family of ester derivatives of carnitine that are utilized in the TCA cycle to generate energy. The beta oxidation yields 7 NADH, 7 FADH2, and 8 Acetyl-CoA chains. This Acetyl-CoA generates 3 NADH, 1 FADH2, and 1 GTP for every molecule in the TCA cycle. Each NADH generates 2.5 ATP in the ETC and FADH2 generates 1.5 ATP. This totals to 108 ATP, but 2 ATP are consumed to generate the initial Palmitoyl-CoA, leaving a net gain of 106 ATP.[citation needed]
Clinical Significance
Palmitoylcarnitine has demonstrated potential as a diagnostic marker in newborns for the medical condition of primary carnitine deficiency.[3]
Levels of palmitoylcarnitine (palcar) demonstrated significant correlation with dihydrotestosterone (DHT) and its effects in prostate cancer models, suggesting a similar role between the two molecules.[4]
See also
References
- ISBN 978-0-12-417044-5
- PMID 1055387.
- PMID 32521959.
- PMID 27403764.