Compound: PALMITOYLCARNITINE
SMILES: O=C(OC(C[N+](C)(C)C)CC(=O)[O-])CCCCCCCCCCCCCCC
InChIKey: XOMRRQXKHMYMOC-UHFFFAOYSA-N
Synonyms: PALMITOYLCARNITINE, 1935-18-8, Palmitylcarnitine, 3-hexadecanoyloxy-4-(trimethylazaniumyl)butanoate, U8K6DKA8V2, DTXSID90895028, 1-Propanaminium, 3-carboxy-N,N,N-trimethyl-2-((1-oxohexadecyl)oxy)-, inner salt, RefChem:905514, (+-)-Palmitoyl carnitine, DTXCID101324587, O-palmitoylcarnitine, (+/-)-palmitoyl carnitine, O-hexadecanoylcarnitine, PALMITOYL-CARNITINE, 3-(hexadecanoyloxy)-4-(trimethylazaniumyl)butanoate, 1-Propanaminium,3-carboxy-N,N,N-trimethyl-2-[(1-oxohexadecyl)oxy]-, inner salt, CHEBI:73067, 3-(hexadecanoyloxy)-4-(trimethylammonio)butanoate, palmitoyl-dl-carnitine, C23H45NO4, UNII-U8K6DKA8V2, MFCD00152152, carnitine palmitate, hexadecanoylcarnitines, Acylcarnitine C16:0, DL-PALMITOYLCARNITINE, PALMITYL-DL-CARNITINE, PALMITOYL DL-CARNITINE, SCHEMBL115183, CHEMBL301722, orb1992734, O-HEXADECANOYL-DL-CARNITINE, BDBM50230701, LMFA07070098, AKOS027326556, EBC-616081, PALMITOYL CARNITINE, (+/-)-, AC(16:0), FP172246, HY-126357, CS-0102941, 3-hexadecanoyloxy-4-(trimethylammonio)butanoate, H61236, ( inverted exclamation mark_)-Palmitoyl carnitine, Q7128408, (+-)-3-Carboxy-N,N,N-trimethyl-2-((1-oxohexadecyl)oxy)-1-propanaminium inner salt, 1-Propanaminium, 3-carboxy-N,N,N-trimethyl-2-((1-oxohexadecyl)oxy)-, inner salt, (+-)-, AMMONIUM, (3-CARBOXY-2-HYDROXYPROPYL)TRIMETHYL-, HYDROXIDE, INNER SALT, PALMITATE, PALMITIC ACID, ESTER WITH (3-CARBOXY-2-HYDROXYPROPYL)TRIMETHYLAMMONIUM HYDROXIDE INNER SALT
Theoretical properties:
molecular_formula: C23H45NO4
molecular_weight: 399.6 g/mol
exact_mass: 399.33485892 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 19
heavy_atom_count: 28
topological_polar_surface_area: 66.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: O-palmitoylcarnitine is an O-acylcarnitine having palmitoyl (hexadecanoyl) as the acyl substituent. It has a role as a metabolite. It is functionally related to a hexadecanoic acid.
chebi: An <em>O</em>-acylcarnitine having palmitoyl (hexadecanoyl) as the acyl substituent.
chembl: Palmitoyl-carnitine is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 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.