Structure via PubChem · Public domain (PubChem)
(+/-)-palmitoyl carnitine
Sign in to saveAlso known as 3-(hexadecanoyloxy)-4-(trimethylammonio)butanoate, O-hexadecanoylcarnitine, hexadecanoylcarnitines, palmitoylcarnitine, hexadecanoylcarnitine
Palmitoylcarnitine is an ester derivative of carnitine involved in the metabolism of fatty acids. During the tricarboxylic acid cycle (TCA), fatty acids undergo a process known as β-oxidation to produce energy in the form of ATP. β-oxidation occurs primarily within mitochondria, however the mitochondrial membrane prevents the entry of long chain fatty acids (>C10), so the conversion of fatty acids such as palmitic acid is key. Palmitic acid is brought to the cell and once inside the cytoplasm is first converted to Palmitoyl-CoA. Palmitoyl-CoA has the ability to freely pass the outer mitochondr
Chemical data
- Formula
- C23H45NO4
- Molecular weight
- 399.6 g/mol
- IUPAC name
- 3-hexadecanoyloxy-4-(trimethylazaniumyl)butanoate
- SMILES
- CCCCCCCCCCCCCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C
- InChIKey
- XOMRRQXKHMYMOC-UHFFFAOYSA-N
- XLogP
- 7.7
- Polar surface area
- 66.4 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
2,330 papers- Targeting carnitine palmitoyl transferase 1A (CPT1A) induces ferroptosis and synergizes with immunotherapy in lung cancer.Signal transduction and targeted therapy · 2024
- Palmitoyl-L-carnitine induces tau phosphorylation and mitochondrial dysfunction in neuronal cells.PloS one · 2024
- The Carnitine Palmitoyl-Transferase 2 Cascade Hypothesis for Alzheimer's Disease.Journal of Alzheimer's disease : JAD · 2024
- Carnitine palmitoyl-transferase 1A is potentially involved in bovine herpesvirus 1 productive infection.Veterinary microbiology · 2024
- The role of carnitine palmitoyl transferase 2 in the progression of salt-sensitive hypertension.American journal of physiology. Cell physiology · 2025
via PubMed
Wikidata facts
- Mass
- 399.335
Show 3 more facts
- chemical formula
- C₂₃H₄₅NO₄
- canonical SMILES
- CCCCCCCCCCCCCCCC(=O)OC(CC(=O)[O-])C[N+](C)(C)C
- subject has role
- vitamin B
via Wikidata · CC0
~3 min read
Encyclopedic overview
6 sectionsContents
- Structure
- Function
- Energy Generation
- Clinical Significance
- See also
- References
Palmitoylcarnitine is an ester derivative of carnitine involved in the metabolism of fatty acids. During the tricarboxylic acid cycle (TCA), fatty acids undergo a process known as β-oxidation to produce energy in the form of ATP. β-oxidation occurs primarily within mitochondria, however the mitochondrial membrane prevents the entry of long chain fatty acids (>C10), so the conversion of fatty acids such as palmitic acid is key. Palmitic acid is brought to the cell and once inside the cytoplasm is first converted to Palmitoyl-CoA. Palmitoyl-CoA has the ability to freely pass the outer mitochondrial membrane, but the inner membrane is impermeable to the Acyl-CoA and thioester forms of various long-chain fatty acids such as palmitic acid. The palmitoyl-CoA is then enzymatically transformed into palmitoylcarnitine via the Carnitine O-palmitoyltransferase family. The palmitoylcarnitine is then actively transferred into the inner membrane of the mitochondria via the carnitine-acylcarnitine translocase. Once inside the inner mitochondrial membrane, the same Carnitine O-palmitoyltransferase family is then responsible for transforming the palmitoylcarnitine back to the palmitoyl-CoA form.
== Structure == alt=Palmitic acid consists of a 16-carbon chain starting from a carboxylic acid|left|thumb|194x194px|Chemical Structure of Palmitic Acid 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.
Excerpted from Wikipedia’s “(+/-)-palmitoyl carnitine” article, available under the CC BY-SA 4.0 licence.