A potent and selective agonist of the human PGE2 receptor, EP4 with a Ki value of 0.38 nM and an EC50 value of 0.6 nM; induces thermal hyperalgesia when injected into guinea pig forepaw and increases vasodilation of human pulmonary vein.

A lipid peroxidation product derived from oxidized ω-6 PUFAs such as linoleic acid and arachidonic acid which is widely used as a marker of lipid peroxidation.

Spontaneously hypertensive rats fed a diet which includes γ-tocotrienol show significant reduction of systolic blood pressure and an increase of nitric oxide synthase activity in blood vessels. γ-Tocotrienol at 20 µM induces apoptosis of malignant sympathoadrenal (+SA) murine…

An elongation product of γ-linolenic acid (18:3), rapidly metabolized by fatty acid desaturases to produce arachidonic acid (20:4); metabolized through the cyclooxygenase pathway to produce 1-series prostaglandins; can reduce atopic dermatitis and atherosclerosis when added to the diet of mice.

A substrate for cPLA₂.

A more lipophilic, stabilized form of HPA.

A potent anti-mitotic drug that is 100-fold more active than resveratrol at inhibiting the growth of human colon cancer Caco-2 cells; inhibits tubulin polymerization in a dose-dependent manner (IC₅₀ = 4 μM) and enzymes involved in the synthesis of the polyamines, putrescine, and spermidine.

A minor alkaloid produced in plants of the Solanaceae family, including tobacco; detection in urine is used as an indicator of tobacco use; diminishes Aβ production, reduces the transcription and protein levels of β-secretase, and dose dependently inhibits NF-κB activation.

A naturally occurring phospholipid produced by cells upon inflammatory stimulation; less potent than PAF C-16 and PAF C-18 in the induction of neutrophil chemotaxis, but is equipotent to PAF C-16 and PAF C-18 in promoting eosinophil migration.

An inhibitor of Ras-mediated signaling that inhibits the growth of PANC-1 and U87 tumor cells with IC₅₀ values of 20 and 10 µM, respectively.

A natural monoacylglycerol that is metabolized by monoacylglycerol lipase; an agonist of GPR119 (EC₅₀ = 2.5 µM), stimulating the release of glucagon-like peptide-1 from intestinal L-cells.

3-HPA is an analog of AM404, which is a selective inhibitor of carrier-mediated transport of AEA. 3-HPA is metabolized by both COX-1 and COX-2 and also selectively and irreversibly inhibits COX-2 with an IC50 value of 2 µM.

A homolog of DHEA, characterized by the addition of an (R)-β-methyl group at the terminal ethanolamine carbon.

Ameliorates depression, reduces dopamine-induced neurotoxicity, and attenuates damage in a model of stroke; blocks autophagy, reduces inflammation, and inhibits apoptosis in isolated neurons and in brains; induces apoptosis in colon cancer cells.

A “hybrid” analog which incorporates components of both the AEA-like and dopaminergic neurotransmitter pathways; is nearly inactive as a TRPV1 ligand and fails to elicit hyperalgesic or nocifensive responses in vivo; exhibits an “entourage” effect at concentrations of 0.1-10…

A more lipid-soluble form of DPA amenable to analysis using gas chromatography; may serve as a prodrug, since it should facilitate uptake of DPA and then be hydrolyzed by esterases to generate the free acid after uptake into cells.

An EPA-containing MAG amide analog that inhibits the growth of human lung carcinoma A549 cells, producing 98.4% growth inhibition when applied at 3 µM; an analog of EPEA, a natural N-acylethanolamide that impacts aging and inflammation.

A natural sesquiterpene that inhibits the proliferation of a wide range of tumors and enhances the effects of various chemotherapies; 10-40 µg/ml dose-dependently induces apoptosis and cell cycle arrest in the G2/M phase in HepG2 cells, upregulating Fas/FasL expression.

An endogenous CB neurotransmitter that binds to both CB1 and CB2 receptors.

An endocannabinoid analog that does not bind to CB1, CB2, or TRPV1; at 5 mg/kg antagonizes the hypotensive effects of a 10 mg/kg IV bolus of abnormal cannabidiol (Abn-CBD) in an anesthetized rat blood pressure model; relaxes isolated rat mesenteric arteries and abdominal aorta, and increases the…

A homolog of EPEA, characterized by the addition of an (R)-α-methyl group at the methylene carbon adjacent to the amide nitrogen.

cis-4,10-13,16-Docosatetraenoic acid methyl ester is a long chain PUFA. It is a minor fatty acid component of rat testis lipids. The methyl ester is a neutral, more lipophilic form of the free acid.

PPHP is a substrate for the measurement of peroxidase enzymes. PPHP has been used to quantitate the peroxidase activity of COX-1 and COX-2.

A natural isothiocyanate which induces the expression of phase II detoxification enzymes and activates Nrf2, promoting the expression of antioxidant and phase II genes; acts as a quorum sensing inhibitor, blocking acyl-homoserine lactone signaling in P. aeruginosa without affecting growth…

The ethanolamine amide of DHA that has been detected in both brain and retina at concentrations similar to those for AEA; binds to the rat brain CB1 receptor (Ki = 324 nM), which is approximately 10-fold higher than the Ki for AEA; inhibits shaker-related voltage-gated potassium channels in brain…

NAM is a potent, irreversible inhibitor of MAGL or MAGL-like activity in rat cerebellar membranes, exhibiting an IC50 value of 140 nM. Inhibition of MAGL by the sulfhydryl-reactive maleimide group of NAM suggests a critical cysteine residue is present in the substrate-binding site of the enzyme.

Thioester analogs of glycerophospholipids, in combination with Ellman’s reagent, are convenient colorimetric substrates for the measurement of phospholipase activity. HEPC is a truncated analog of phosphatidylcholine with the entire sn-1 substituent deleted, and with a hexadecylthioester in…

An 8-aza-9-oxo-15-hydroxy saturated analog of PGE2; selectively binds the EP4 receptor (Ki = 35 nM) relative to the EP1, EP2, and EP3 receptors (Ki = 3,000, 2,000, and >3,000 nM, respectively); stimulates cAMP formation in excised mouse ovaries.

(+)-15(R)-Fluprostenol isopropyl ester is a prodrug (Travoprost) which is converted by esterase enzymatic activity in the cornea to yield the corresponding free acid. The free acid, (+)-15(R)-fluprostenol, is a potent FP receptor agonist. The 15(R)-epimers of most PGs are about 100 times less…

DAN-1 EE is a fluorescent indicator for the bioimaging of NO. DAN-1 EE is a cell permeable derivative of DAN, a molecule which has been used extensively in the quantitation of nitrate and nitrite using fluorescence spectroscopy. Upon entry into the cell, DAN-1 EE is transformed into the less cell…

A potent, stable, and selective agonist analog of AEA with a Ki value of 2.2 nM at the isolated rat CB1 receptor; 325 times more potent at the CB1 receptor compared with the CB2 receptor; induces hypothermia in mice with the same efficacy as AEA, in spite of its much higher affinity for the CB1…

Unnatural C-15 epimer of Travoprost.