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(+/-)-palmitoyl carnitine

Structure via PubChem · Public domain (PubChem)

EntityQ7128408· pop 7· linked from 6 articles

(+/-)-palmitoyl carnitine

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Also 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

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
Sources (4)

via Wikidata · CC0

~3 min read

Encyclopedic overview

6 sections
Contents
  • 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.

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