fatty acid oxidation

12:0 N-Biotinyl fatty acid, a biotinylated derivative of lauric acid, serves as an intermediate for synthesizing N-biotinylated phenylarsonous acids.

Gemfibrozil (CI-719) interacts with peroxisome proliferator-activated receptors (PPARalpha) resulting in PPARalpha-mediated stimulation of fatty acid oxidation and an increase in lipoprotein lipase (LPL) synthesis. Gemfibrozil is a fibric acid derivative with hypolipidemic effects. This enhances triglyceride-rich lipoprotein clearance and reduces the expression of apolipoprotein C-III (apoC-III). The reduction in hepatic production of apoC-III result in the subsequent reduction of serum levels of very-low-density-lipoprotein cholesterol (VLDL-C). In addition, gemfibrozil-mediated PPARalpha stimulation of apoA-I and apoA-II expression results in an increase in high-density lipoprotein cholesterol (HDL-C).

Trans-2-butene-1,4-dicarboxylic acid (3-Hexenedioic Acid) is a normal human unsaturated dicarboxylic acid metabolite with increased excretion in patients with Dicarboxylic aciduria caused by fatty acid metabolism disorders The urinary excretion of Trans-2-butene-1,4-dicarboxylic acid is increased in conditions of augmented mobilization of fatty acids or inhibited fatty acid oxidation.

Tetradecylthioacetic acid is a synthetic fatty acid with a sulfur substitution in the β-position. This modification renders TTA unable to undergo complete β-oxidation and increases its biological activity, including activation of peroxisome proliferator activated receptors (PPARs) with preference for PPARα.

Suberic acid (1,8-Octanedioic acid) is present in the urine of patients with fatty acid oxidation disorders. A metabolic breakdown product derived from oleic acid. Elevated levels of this unstaruated dicarboxylic acid are found in individuals with medium-chain acyl-CoA dehydrogenase deficiency (MCAD). Suberic acid is also associated with carnitine-acylcarnitine translocase deficiency, malonyl-Coa decarboxylase deficiency.

L-Carnitine (L(-)-Carnitine) is an amino acid derivative. L-Carnitine facilitates long-chain fatty acid entry into mitochondria, delivering substrate for oxidation and subsequent energy production. Fatty acids are utilized as an energy substrate in all tissues except the brain.

CVT-2738 (RS-94287) is a metabolite of Ranolazine. Ranolazine is a partial fatty acid oxidation (pFOX) inhibitor and anti-anginal drug.

Triheptanoin (IND 106011) is a fatty acid metabolic modulator. It potentially for the treatment of fatty acid oxidation disorders and GLUT1.

9-Oxononanoic Acid is an oxidized fatty acid, formed by the autoxidation of linoleic acid, which enhances phospholipase A2 (PLA2) activity and increases the production of thromboxane B2 in isolated human plasma.9-Oxononanoic Acid reduces hepatic neofatty acid synthesis and enhances the activity of rat hepatic carnitine palmitoyltransferase, a marker of β-oxidation. Activity.

Palmitoylcarnitine (Palmitoyl DL-carnitine) is a mitochondrial fatty acid oxidation intermediate that acts as a surfactant.

P053 is a potent, non-competitive, and selective ceramide synthase 1 (CerS1) inhibitor with an IC50 of 0.5 μM. It acts as an endogenous inhibitor of mitochondrial fatty acid oxidation in muscle and regulates whole-body adiposity[1].

Etomoxir sodium salt ((R)-Etomoxir sodium salt) is a carnitine palmitoyltransferase 1a (CPT-1a) inhibitor that blocks fatty acid synthesis. Etomoxir sodium salt has antitumor activity.

CP-640186 hydrochloride (CP 640186 HCl) is an isozyme-nonselective acetyl-CoA carboxylase (ACC) inhibitor, including rat liver ACC1 (IC50: 53 nM) and rat skeletal muscle ACC2 (IC50: 61 nM); with higher metabolic stability than CP-610431.

2-(2-Methylbenzamido)acetic acid (O-Toluric acid) is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. In certain cases, the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Methylhippuric acid is a metabolite of xylene which is an aromatic hydrocarbon widely used as a solvent.

N-Isovaleroylglycine (Isovaleroylglycine) is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases, the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine < -- > CoA + N-acylglycine. N-Isovaleroylglycine is a byproduct of the catabolism of the amino acid leucine. Accumulation of N-Isovaleroylglycine occurs in Isovaleric Acidemia (IVA).

BM-42304 is an inhibitor of fatty acid oxidation.

14-Pentadecenoic acid, a 15-carbon long-chain fatty acid with an alkene functional group on the terminal carbon of its aliphatic tail, has been observed to undergo oxidation due to the growth of M. cerificans at the expense of the parent alkene. This compound is utilized in the creation of fibrous scaffold biomaterials for tissue engineering purposes and in constructing metallomesogenic side-chain polymers for coating capillary columns in gas chromatography applications.

CP-640186 is an isozyme-nonselective Acetyl-CoA carboxylase (ACCase) inhibitor. The IC50s of CP-640186(CP 640186) is 53 nM and 61 nM for rat liver ACC1 and rat skeletal muscle ACC2 respectively.

Trimetazidine, an anti-ischemic (anti-anginal) metabolic agent, could improve myocardial glucose utilization through inhibition of long-chain 3-ketoacyl CoA thiolase activity and results in a reduction in fatty acid oxidation and a stimulation of glucose

Ninerafaxstat trihydrochloride shifts cellular metabolism to glucose oxidation from fatty acid oxidation. Ninerafaxstat trihydrochloride improves overall mitochondrial respiration and reduces fatty acid oxidation, thereby inhibiting the proliferation and growth of cancer cells.

Palmitoyl CoA lithium (Palmitoyl coenzyme A lithium) is a major component of fatty acids involved in the carnitine shuttle system, beta-oxidation, and the tricarboxylic acid cycle, and can be used to study metabolic disorders in the body.

Ajoene is a disulfide that has been found inA. sativumand has diverse biological activities, including antibacterial, anticancer, antiplatelet, and antioxidant properties.1,2,3,4It is active against Gram-positive (MICs = 5-160 µg/ml) and Gram-negative bacteria (MICs = 136-200 µg/ml), as well as yeasts (MICs = 10-20 µg/ml).1Ajoene is cytotoxic to mouse melanoma cells (IC50= 18 µM), as well as human colon, lung, mammary, and pancreatic cancer cells (IC50s = 7-41 µM).2It reduces tumor growth in a B16/BL6 mouse model of melanoma when administered at a dose of 25 mg/kg every other day and decreases the number of lung metastases when administered prior to tumor cell inoculation at doses ranging from 1-25 mg/kg. It inhibits ADP- or collagen-induced platelet aggregation in isolated baboon platelets when used at concentrations ranging from 75 to 150 µg/ml and in platelet-rich plasma isolated from baboons when administered at a dose of 25 mg/kg.3Ajoene (25 mg/kg) prevents thrombus formation on damaged arterial walls in heparinized pigs in anin situmodel of thrombogenesis.5It also reduces high-fat diet-induced hepatic steatosis, histopathological markers of liver damage, thiobarbituric acid reactive substances (TBARS) formation, and protein oxidation in a mouse model of non-alcoholic fatty liver disease (NAFLD).4 1.Naganawa, R., Iwata, N., Ishikawa, K., et al.Inhibition of microbial growth by ajoene, a sulfur-containing compound derived from garlicAppl. Environ. Microbiol.62(11)4238-4242(1996) 2.Taylor, P., Noriega, R., Farah, C., et al.Ajoene inhibits both primary tumor growth and metastasis of B16/BL6 melanoma cells in C57BL/6 miceCancer Lett.239(2)298-304(2006) 3.Teranishi, K., Apitz-Castro, R., Robson, S.C., et al.Inhibition of baboon platelet aggregation in vitro and in vivo by the garlic derivative, ajoeneXenotransplantation10(4)374-379(2003) 4.Han, C.Y., Ki, S.H., Kim, Y.W., et al.Ajoene, a stable garlic by-product, inhibits high fat diet-induced hepatic steatosis and oxidative injury through LKB1-dependent AMPK activationAntioxid. Redox Signal.14(2)187-202(2011) 5.Apitz-Castro, R., Badimon, J.J., and Badimon, L.A garlic derivative, ajoene, inhibits platelet deposition on severely damaged vessel wall in an in vivo porcine experimental modelThromb. Res.75(3)243-249(1994)

L-Carnitine-d9 is a deuterated compound of L-Carnitine. L-Carnitine has a CAS number of 541-15-1. L(-)-Carnitine is an amino acid derivative. L(-)-Carnitine facilitates long-chain fatty acid entry into mitochondria, delivering substrate for oxidation and subsequent energy production. Fatty acids are utilized as an energy substrate in all tissues except the brain.

(±)5-HETE, a monohydroxy fatty acid, emerges from the non-enzymatic oxidation of arachidonic acid and is one of six such derivatives. Its methyl ester variant exhibits no unique biological activity and serves as a provided standard. This methyl ester can also be present in oxidatively degraded polyunsaturated fatty acid (PUFA) methyl esters.

Palmoxirate sodium hydrate is a potent inhibitor of long-chain fatty acid oxidation.

Nervonic acid (Selacholeic acid) is a long chain unsaturated fatty acid that is enriched in sphingomyelin. It consists of choline, sphingosine, phosphoric acid, and fatty acid. Nervonic acid may enhance the brain functions and prevent demyelination (Chemical Land21). Research shows that there is negative relationship between nervonic acid and obesity-related risk factors. Demyelination in adrenoleukodystrophy (ALD) is associated with an accumulation of very long chain saturated fatty acids stemming from a genetic defect in the peroxisomal beta oxidation system responsible for the chain shortening of these fatty acids. Sphingolipids from post mortem ALD brain have decreased levels of nervonic acid, 24:1(n-9), and increased levels of stearic acid, 18:0.

Octanoic acid-13C is intended for use as an internal standard for the quantification of octanoic acid by GC- or LC-MS. Octanoic acid is a medium-chain saturated fatty acid. It has been found in Teleme cheeses made from goat, ovine, or bovine milk.1 Octanoic acid is active against the bacteria S. mutans, S. gordonii, F. nucleatum, and P. gingivalis (IC80s = <125, <125, 1,403, and 2,294 μM, respectively).2 Levels of octanoic acid are increased in the plasma of patients with medium-chain acyl-CoA dehydrogenase (MCAD) deficiency, an inborn error of fatty acid metabolism characterized by hypoketotic hypoglycemia, medium-chain dicarboxylic aciduria, and intolerance to fasting.3,4 |1. Mallatou, H., Pappa, E., and Massouras, T. Changes in free fatty acids during ripening of Teleme cheese made with ewes', goats', cows' or a mixture of ewes' and goats' milk. Int. Dairy J. 13(1-3), 211-219 (2003).|2. Hyang, C.B., Alimova, Y., Myers, T.M., et al. Short- and medium-chain fatty acids exhibit antimicrobial activity for oral microorganisms. Arch. Oral Biol. 56(7), 650-654 (2011).|3. Onkenhout, W., Venizelos, V., van der Poel, P.F.H., et al. Identification and quantification of intermediates of unsaturated fatty acid metabolism in plasma of patients with fatty acid oxidation disorders. Clin. Chem. 41(10), 1467-1474 (1995).|4. Rinaldo, P., O'Shea, J.J., Coates, P.M., et al. Medium-chain acyl-CoA dehydrogenase deficiency. Diagnosis by stable-isotope dilution measurement of urinary n-hexanoylglycine and 3-phenylpropionylglycine. N. Engl. J. Med. 319(20), 1308-1313 (1988).

(±)9-HODE is one of the two racemic monohydroxy fatty acids resulting from the non-enzymatic oxidation of linoleic acid. Approximately equal proportions of both isomers are found in mitochondrial and plasma membranes of rabbit reticulocytes. [1][2] Oxidized LDL contains significant amounts of esterified 9- and 13-HpODEs and HODEs. [3][4]

9(S),12(S),13(S)-TriHOME is a linoleic acid-derived oxylipin that has diverse biological activities.1,2,3,4It has been found in various plants and is produced in human eosinophils in a 15-lipoxygenase-dependent, soluble epoxide hydrolase-independent manner.1,59(S),12(S)13(S)-TriHOME inhibits antigen-induced β-hexosaminidase release from RBL-2H3 mast cells (IC50= 28.7 μg ml).2It inhibits LPS-induced nitric oxide (NO) production in BV-2 microglia (IC50= 40.95 μM).3In vivo, 9(S),12(S),13(S)-TriHOME (1 g animal) enhances the antiviral IgA and IgG antibody responses induced by a nasal influenza hemagglutinin (HA) vaccine by 5.2- and 2-fold, respectively, in mice.4 1.Hamberg, M., and Hamberg, G.Peroxygenase-catalyzed fatty acid epoxidation in cereal seeds: Sequential oxidation of linoleic acid into 9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acidPlant Physiol.110(3)807-815(1996) 2.Hong, S.S., and Oh, J.S.Inhibitors of antigen-induced degranulation of RBL-2H3 cells isolated from wheat branJ. Korean Soc. Appl. Biol. Chem.5569-74(2012) 3.Kim, C.S., Kwon, O.W., Kim, S.Y., et al.Five new oxylipins from Chaenomeles sinensisLipids49(11)1151-1159(2014) 4.Shirahata, T., Sunazuka, T., Yoshida, K., et al.Total synthesis, elucidation of absolute stereochemistry, and adjuvant activity of trihydroxy fatty acidsTetrahedron62(40)9483-9496(2006) 5.Fuchs, D., Tang, X., Johnsson, A.-K., et al.Eosinophils synthesize trihydroxyoctadecenoic acids (TriHOMEs) via a 15-lipoxygenase dependent processBiochim. Biophys. Acta Mol. Cell Biol. Lipids1865(4)158611(2020)

Octanoyl coenzyme A (octanoyl-CoA) is a medium-chain acyl CoA and a metabolic intermediate in mitochondrial fatty acid β-oxidation. Levels of octanoyl-CoA are increased in the liver of patients with Reye's syndrome and β-oxidation of octanoyl-CoA by medium-chain acyl CoA dehydrogenase (MCADH) is decreased in patients with MCADH deficiency (MCD). Octanoyl-CoA inhibits citrate synthase and glutamate dehydrogenase.

9(S)-HpOTrE, a monohydroperoxy polyunsaturated fatty acid, is produced by the action of 5-lipoxygenase (5-LO) on α-linolenic acid. It can be metabolized to colnelenic acid by a divinyl ether synthase activity found in garlic and potato microsomal fractions. 9(S)-HpOTrE also serves as a substrate for further oxidation by both soybean and potato LOs, resulting in 9,16-dihydroperoxy acid formation. The suicide inactivation of LOs when 9(S)-HpOTrE is used as a substrate is thought to occur via the formation of an unstable epoxide.

Nε,Nε,Nε-Trimethyllysine chloride (Lys(Me)3-OH Chloride) is a methylated derivative of lysine, found in histone proteins and serves as a coenzyme in fatty acid oxidation. It is a precursor for carnitine, generated by S-adenosyl-L-methionine on lysine residues. Upon proteolysis, it is converted to 3-hydroxy-6-N-trimethyllysine by mitochondrial 6-N-trimethyllysine dioxygenase, initiating carnitine biosynthesis.

(±)17-HDHA is an autoxidation product of docosahexaenoic acid in vitro. It is also produced from incubations of DHA in rat liver, brain, and intestinal microsomes. 17(S)-HDHA could be produced by enzymatic oxidation of DHA using soybean lipoxygenase (LO) and is the putative product of mammalian 15-LOs. 17(S)-HDHA was shown to be an inhibitor of U-46619 -induced rabbit and rat aortic smooth muscle contraction with IC50 values of 4.9 and 7.2 μM, respectively. (±)17-HDHA is a potential marker of oxidative stress in brain and retina where DHA is an abundant polyunsaturated fatty acid.

Malonyl CoA serves as a substrate in fatty acid biosynthesis while inhibiting fatty acid oxidation. It also acts as a reversible inhibitor of mitochondrial carnitine palmitoyltransferase (CPT) 1 [1] [2].

(±)5-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid. It contains equal amounts of 5(S)-HETE and 5(R)-HETE. (±)5-HETE induces the aggregation of isolated neutrophils with an IC50 value of 200 nM.[1]

Docosapentaenoic acid (DPA) is a ω-3 fatty acid found in fish oils. 17-oxo-7(Z),10(Z),13(Z),15(E),19(Z)-docosapentaenoic acid is a metabolite of lipoxygenase-mediated oxidation of DPA that is produced endogenously by aspirin-enhanced COX-2 activity. It has been shown to activate Nrf2-dependent antioxidant gene expression, to act as a PPARγ agonist (EC50 = ~200 nM), and to inhibit pro-inflammatory cytokine and nitric oxide production at biological concentration ranges (5-25 μM).

10,12-Tricosadiynoic acid is a highly selective and orally active inhibitor of acyl-CoA oxidase-1 (ACOX1), which can treat high-fat diet- or obesity-induced metabolic diseases by improving mitochondrial lipid and ROS metabolism.

(±)8-HEPE is produced by the non-enzymatic oxidation of EPA, containing equal amounts of 8(S)-HEPE and 8(R)-HEPE. The ability of (±)8-HEPE to induce hatching of E. modestus and B. balanoides eggs is probably due to the presence of the 8(R) isomer within the racemic mixture.[1][2]

Carnitine palmitoyltransferase 2 (CPT2), an enzyme involved in fatty acid oxidation, serves as a prognostic biomarker for colorectal cancer (CRC). Overexpression of CPT2 activates phosphorylated p53, enhancing its expression, which in turn suppresses tumor growth and induces apoptosis. Conversely, a deficiency in CPT2 leads to the prevalent hereditary disorder of long-chain fatty acid oxidation in skeletal muscle. Additionally, the downregulation of CPT2 correlates strongly with the advancement of multiple cancers, highlighting its importance in cancer research [1] [2].

Demethyleneberberine, which is composed of a potential antioxidant structure, could penetrate the membrane of mitochondria and accumulate in mitochondria either in vitro or in vivo.Demethyleneberberine suppresses CYP2E1, hypoxia inducible factor α, and inducible nitric oxide synthase, which contributes to oxidative stress and restored sirtuin 1/AMP-activated protein kinase/peroxisome proliferator-activated receptor-γ coactivator-1α pathway-associated fatty acid oxidation in chronic ethanol-fed mice.

Ninerafaxstat hifts cellular metabolism from fatty acid oxidation to glucose oxidation.Ninerafaxstat decreases fatty acid oxidation and improve overall mitochondrial respiration.Ninerafaxstat inhibit the growth and proliferation of cancer cells [1].

(±)10-HDHA is an autoxidation product of docosahexaenoic acid (DHA) in vitro.[1][2] It is also produced from incubations of DHA in rat liver, brain, and intestinal microsomes.[3][4][5] (±)10-HDHA is a potential marker of oxidative stress in brain and retina where DHA is an abundant polyunsaturated fatty acid. Reference：[1]. VanRollins, M., and Murphy, R.C. Autooxidation of docosahexaenoic acid: Analysis of ten isomers of hydroxydocosahexaenoate. J. Lipid Res. 25(5), 507-517 (1984).[2]. Reynaud, D., Thickitt, C.P., and Pace-Asciak, C.R. Facile preparation and structural determination of monohydroxy derivatives of docosahexaenoic acid (HDoHE) by α-tocopherol-directed autoxidation. Anal. Biochem. 214(1), 165-170 (1993).[3]. VanRollins, M., Baker, R.C., Sprecher, H., et al. Oxidation of docosahexaenoic acid by rat liver microsomes. J. Biol. Chem. 259(9), 5776-5783 (1984).[4]. Yamane, M., Abe, A., and Yamane, S. High-performance liquid chromatography-thermospray mass spectrometry of epoxy polyunsaturated fatty acids and epoxyhydroxy polyunsaturated fatty acids from an incubation mixture of rat tissue homogenate. J. Chromatogr. 652(2), 123-136 (1994).[5]. Kim, H.Y., Karanian, J.W., Shingu, T., et al. Sterochemical analysis of hydroxylated docosahexaenoates produced by human platelets and rat brain homogenate. Prostaglandins 40(5), 473-490 (1990).

8(S)-HEPE is a monohydroxy fatty acid produced by lipoxygenase oxidation of EPA. While it promotes barnacle egg hatching at 10 nM, its role as the natural egg hatching factor is not definitively established.

Peroxisome proliferator-activated receptors (PPARs) α, δ, γ are ligand-activated nuclear transcription factors involved in the regulation of energy homeostasis as well as insulin sensitivity and glucose metabolism. Pharmacologies of PPARδ receptor agonists, though relatively obscure, have recently been reported to elevate high-density lipoprotein (HDL) cholesterol and lower plasma triglyceride (TG) levels in obese insulin resistant rhesus monkeys. CAY10592 is a full PPARδ agonist (EC50 = 30 nM) in a fatty acid oxidation assay of rat L6 muscle cells with desirable oral pharmacokinetic properties. In a transactivation assay using human PPAR receptors, CAY10592 acts as a selective partial PPARδ agonist (EC50 = 53 nM) with no effect on PPARα or PPARγ activity up to 30 μM. Chronic treatment of high fat fed ApoB100/CETP-transgenic mice with CAY10592 at a dose of 20 mg/kg increases HDL levels, decreases LDL and TG levels, and improves insulin sensitivity.

Carnitine facilitates the transport of fatty acids into the mitochondria to be used in fatty acid metabolism. It does so by accepting acyl groups from fatty acids complexed with coenzyme A, which yields esterified carnitine or acylcarnitines that enable the transport of fatty acyl groups into the inner mitochondrial matrix. β-Oxidation of fatty acids in mitochondria is inhibited by uncoupling conditions, thus changes in circulating levels of various acylcarnitines have been used to identify alterations in metabolic state.[1] [2] Arachidonoyl-L-carnitine formed from carnitine conjugated to arachidonic acid .

1. Tiliroside (Tribuloside) shows anticarcinogenic activity. 2. Tiliroside shows hepatoprotective activity. 3. Tiliroside shows antioxidant and anti-inflammatory activity, can inhibit neuroinflammation in neurodegenerative disorders. 4. Tiliroside has anti-diabetic effect, are at least partially mediated through inhibitory effects on carbohydrate digestion and glucose uptake in the gastrointestinal tract. 5. Tiliroside and gnaphaliin are antioxidants against in vitro Cu(2+)-induced LDL oxidation in the same order of magnitude compared to that of the reference drug, probucol. 6. Tiliroside enhances fatty acid oxidation via the enhancement adiponectin signaling associated with the activation of both AMP-activated protein kinase and peroxisome proliferator-activated receptor α and ameliorates obesity-induced metabolic disorders.

Dodecanoylcarnitine ((-)-Lauroylcarnitine) has been associated with disturbances in fatty acid oxidation, and the use of Dodecanoylcarnitine resulted in an increase in the permeability of salmon calcitonin.

Mavodelpar (REN001), a selective PPARδ agonist, effectively suppresses glomerular injury and renal fibrosis. It is utilized in the research of primary mitochondrial myopathies (PMM) and long-chain fatty acid oxidation disorders (LC-FAOD).

Methyl Linolenate (Linolenic acid methyl ester) is a polyunsaturated fattly acid (PUFA). It is used in studies on the mechanisms and prevention of oxidation/peroxidation of unsaturated fatty acids.

(±)13-HODE is one of the two racemic monohydroxy fatty acids resulting from the non-enzymatic oxidation of linoleic acid. It is the principle hydroxylated fatty acid in human psoriatic skin scales, with a mean concentration of 17 ng/mg.[1]