Home Other Building Blocks PALMITOYL CARNITINE

PALMITOYL CARNITINE

CAS No.:
2364-67-2
Catalog Number:
AG00BVAG
Molecular Formula:
C23H45NO4
Molecular Weight:
399.6077
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Product Description
Catalog Number:
AG00BVAG
Chemical Name:
PALMITOYL CARNITINE
CAS Number:
2364-67-2
Molecular Formula:
C23H45NO4
Molecular Weight:
399.6077
MDL Number:
MFCD00152152
IUPAC Name:
(3R)-3-hexadecanoyloxy-4-(trimethylazaniumyl)butanoate
InChI:
InChI=1S/C23H45NO4/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(27)28-21(19-22(25)26)20-24(2,3)4/h21H,5-20H2,1-4H3/t21-/m1/s1
InChI Key:
XOMRRQXKHMYMOC-OAQYLSRUSA-N
SMILES:
CCCCCCCCCCCCCCCC(=O)O[C@@H](C[N+](C)(C)C)CC(=O)[O-]
UNII:
1G38O5K038
Properties
Complexity:
398  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
399.335g/mol
Formal Charge:
0
Heavy Atom Count:
28  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
399.616g/mol
Monoisotopic Mass:
399.335g/mol
Rotatable Bond Count:
19  
Topological Polar Surface Area:
66.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
7.7  
Literature
Title Journal
Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports 20180101
Hepatic toxicity of dronedarone in mice: role of mitochondrial β-oxidation. Toxicology 20140902
Lipidomic profiling reveals protective function of fatty acid oxidation in cocaine-induced hepatotoxicity. Journal of lipid research 20121101
Progression of type 2 diabetes in GK rats affects muscle and liver mitochondria differently: pronounced reduction of complex II flux is observed in liver only. American journal of physiology. Endocrinology and metabolism 20120815
Obesity augments the age-induced increase in mitochondrial capacity for H2O2 release in Zucker fatty rats. Acta physiologica (Oxford, England) 20120301
Measurement of precursor enrichment for calculating intramuscular triglyceride fractional synthetic rate. Journal of lipid research 20120101
Palmitoyl-DL-carnitine is a multitarget inhibitor of Pseudomonas aeruginosa biofilm development. Chembiochem : a European journal of chemical biology 20111216
Manifold effects of palmitoylcarnitine on endoplasmic reticulum metabolism: 11β-hydroxysteroid dehydrogenase 1, flux through hexose-6-phosphate dehydrogenase and NADPH concentration. The Biochemical journal 20110701
Ex vivo and in vivo diffusion of ropivacaine through spinal meninges: influence of absorption enhancers. International journal of pharmaceutics 20110214
Absorption enhancement effect of acylcarnitines through changes in tight junction protein in Caco-2 cell monolayers. Drug metabolism and pharmacokinetics 20110101
Urea-induced hypometabolism in the hibernating wood frog (Rana sylvatica) is not reflected in isolated mitochondria. Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology 20101101
Effects of acylcarnitines on efflux transporting system in Caco-2 cell monolayers. European journal of drug metabolism and pharmacokinetics 20100901
Comparison of amino acids and acylcarnitines assay methods used in newborn screening assays by tandem mass spectrometry. Clinica chimica acta; international journal of clinical chemistry 20100502
[The drug hypoxen--a new inhibitor of mitochondrial respiration and mitochondrial dehydrogenases]. Izvestiia Akademii nauk. Seriia biologicheskaia 20100101
The late Na+ current (INa) inhibitor ranolazine attenuates effects of palmitoyl-L-carnitine to increase late INa and cause ventricular diastolic dysfunction. The Journal of pharmacology and experimental therapeutics 20090801
Oxygen sensitivity of mitochondrial reactive oxygen species generation depends on metabolic conditions. The Journal of biological chemistry 20090612
Bezafibrate for an inborn mitochondrial beta-oxidation defect. The New England journal of medicine 20090219
The effect of hyperosmosis on paracellular permeability in Caco-2 cell monolayers. Bioscience, biotechnology, and biochemistry 20090201
Peroxidative damage of mitochondrial respiration is substrate-dependent. Physiological research 20090101
Liquid chromatography/mass spectrometry determination of endogenous plasma acetyl and palmitoyl carnitines as potential biomarkers of beta-oxidation in mice. Rapid communications in mass spectrometry : RCM 20081101
Deleterious action of FA metabolites on ATP synthesis: possible link between lipotoxicity, mitochondrial dysfunction, and insulin resistance. American journal of physiology. Endocrinology and metabolism 20080901
Different effects of palmitoyl-L-carnitine and palmitoyl-CoA on mitochondrial function in rat ventricular myocytes. American journal of physiology. Heart and circulatory physiology 20080701
The transcriptional coactivator PGC-1alpha is essential for maximal and efficient cardiac mitochondrial fatty acid oxidation and lipid homeostasis. American journal of physiology. Heart and circulatory physiology 20080701
Carnitine supplementation induces acylcarnitine production in tissues of very long-chain acyl-CoA dehydrogenase-deficient mice, without replenishing low free carnitine. Pediatric research 20080601
Biorelevant refinement of the Caco-2 cell culture model to assess efficacy of paracellular permeability enhancers. Journal of pharmaceutical sciences 20080501
Inhibition of palmityl carnitine oxidation in rat liver mitochondria by tert-butyl hydroperoxide. Physiological research 20080101
[The role of the functional state of kidney mitochondria in predisposition of hydronephrotic rabits to gentamicin nephrotoxicity]. Eksperimental'naia i klinicheskaia farmakologiia 20080101
[Destabilization of the cytosolic calcium level and cardiomyocyte death in the presence of long-chain fatty acid derivatives]. Biofizika 20080101
Flux control analysis of mitochondrial oxidative phosphorylation in rat skeletal muscle: pyruvate and palmitoyl-carnitine as substrates give different control patterns. European journal of applied physiology 20071201
Agonist potency at P2X7 receptors is modulated by structurally diverse lipids. British journal of pharmacology 20071001
Palmitoylcarnitine regulates estrification of lipids and promotes palmitoylation of GAP-43. FEBS letters 20070821
Reduced efficiency, but increased fat oxidation, in mitochondria from human skeletal muscle after 24-h ultraendurance exercise. Journal of applied physiology (Bethesda, Md. : 1985) 20070501
Modulation of tight junction properties relevant to fluid transport across rabbit corneal endothelium. Experimental eye research 20070401
Nitric oxide increases oxidative phosphorylation efficiency. Journal of bioenergetics and biomembranes 20070401
Influence of intensity of food restriction on skeletal muscle mitochondrial energy metabolism in rats. American journal of physiology. Endocrinology and metabolism 20060901
Skeletal muscle fat oxidation is increased in African-American and white women after 10 days of endurance exercise training. Obesity (Silver Spring, Md.) 20060701
Influence of propolis water solution on heart mitochondrial function. The Journal of pharmacy and pharmacology 20060501
Palmitoylcarnitine modulates interaction between protein kinase C betaII and its receptor RACK1. The FEBS journal 20060301
Measurement of stable isotopic enrichment and concentration of long-chain fatty acyl-carnitines in tissue by HPLC-MS. Journal of lipid research 20060201
High-precision isotopic analysis of palmitoylcarnitine by liquid chromatography/electrospray ionization ion-trap tandem mass spectrometry. Rapid communications in mass spectrometry : RCM 20060101
Whole-body heat shock protects the ischemic rat heart by stimulating mitochondria respiration. Canadian journal of physiology and pharmacology 20060101
Increased mitochondrial palmitoylcarnitine/carnitine countertransport by flavone causes oxidative stress and apoptosis in colon cancer cells. Cellular and molecular life sciences : CMLS 20051201
Comparison of (+)- and (-)-hemipalmitoylcarnitinium as inhibitors of hepatic mitochondrial carnitine palmitoyltransferases in diabetic rats. Medicinal chemistry (Shariqah (United Arab Emirates)) 20050901
Thyroid-hormone effects on putative biochemical pathways involved in UCP3 activation in rat skeletal muscle mitochondria. FEBS letters 20050314
Strategy for the isolation, derivatization, chromatographic separation, and detection of carnitine and acylcarnitines. Analytical chemistry 20050301
Cysteine-scanning mutagenesis of muscle carnitine palmitoyltransferase I reveals a single cysteine residue (Cys-305) is important for catalysis. The Journal of biological chemistry 20050211
Membrane transport of fatty acylcarnitine and free L-carnitine by rat liver microsomes. European journal of biochemistry 20040301
A comparison of in vitro acylcarnitine profiling methods for the diagnosis of classical and variant short chain acyl-CoA dehydrogenase deficiency. Clinica chimica acta; international journal of clinical chemistry 20031101
A novel mitochondrial carnitine-acylcarnitine translocase induced by partial hepatectomy and fasting. The Journal of biological chemistry 20031003
Effects of various absorption enhancers on transport of clodronate through Caco-2 cells. International journal of pharmaceutics 20030811
A novel action of palmitoyl-L-carnitine in human vascular endothelial cells. Journal of pharmacological sciences 20030701
Skeletal muscle mitochondrial oxidative capacity and uncoupling protein 3 are differently influenced by semistarvation and refeeding. FEBS letters 20030605
Fasting, lipid metabolism, and triiodothyronine in rat gastrocnemius muscle: interrelated roles of uncoupling protein 3, mitochondrial thioesterase, and coenzyme Q. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20030601
Fatty acid oxidation by skeletal muscle homogenates from morbidly obese black and white American women. Metabolism: clinical and experimental 20030601
Palmitoylcarnitine modulates palmitoylation of proteins: implication for differentiation of neural cells. Neurochemical research 20030401
[Analyses of Ca-related ion channel currents and their involvement in Ca mobilization in smooth muscle and endothelial cells]. Nihon yakurigaku zasshi. Folia pharmacologica Japonica 20030301
Interaction of palmitoylcarnitine with protein kinase C in neuroblastoma NB-2a cells. Neurochemistry international 20030101
Involvement of oxygen free radicals in the respiratory uncoupling induced by free calcium and ADP-magnesium in isolated cardiac mitochondria: comparing reoxygenation in cultured cardiomyocytes. Molecular and cellular biochemistry 20030101
Topology of superoxide production from different sites in the mitochondrial electron transport chain. The Journal of biological chemistry 20021122
Effects of in vivo treatment of rats with trimethyltin chloride on respiratory properties of rat liver mitochondria. Biochemical pharmacology 20020815
Palmitoylcarnitine modulates interaction protein kinase C delta-GAP-43. Biochemical and biophysical research communications 20020621
Effects of chronic caloric restriction on mitochondrial respiration in the ischemic reperfused rat heart. Molecular and cellular biochemistry 20020401
Tandem mass spectrometric assay for the determination of carnitine palmitoyltransferase II activity in muscle tissue. Analytical biochemistry 20020315
Screening for carnitine palmitoyltransferase II deficiency by tandem mass spectrometry. Journal of inherited metabolic disease 20020201
Relevance of fatty acid oxidation in regulation of the outer mitochondrial membrane permeability for ADP. FEBS letters 20011207
Modulation of P-glycoprotein activity in Calu-3 cells using steroids and beta-ligands. International journal of pharmaceutics 20011009
Effects of dietary polyunsaturated fatty acids and hepatic steatosis on the functioning of isolated working rat heart under normoxic conditions and during post-ischemic reperfusion. Molecular and cellular biochemistry 20010801
The effects of endurance training and exhaustive exercise on mitochondrial enzymes in tissues of the rat (Rattus norvegicus). Comparative biochemistry and physiology. Part A, Molecular & integrative physiology 20010401
Effects of arrhythmogenic lipid metabolites on the L-type calcium current of diabetic vs. non-diabetic rat hearts. Molecular and cellular biochemistry 20010401
Emotional distress induced rhabdomyolysis in an individual with carnitine palmitoly-transferase deficiency. Clinical and experimental rheumatology 20010101
Tetracycline-induced steatosis in primary canine hepatocyte cultures. Fundamental and applied toxicology : official journal of the Society of Toxicology 19971201
Effect of clofibrate treatment on acylcarnitine oxidation in isolated rat liver mitochondria. Medical biology 19790201
Properties