An ester of the free acid that is less water soluble, but more amenable for the formulation of stearidonate-containing diets and dietary supplements.

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.

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 reversible, competitive thrombin inhibitor (Ki = 5 nM) that shows selectivity for thrombin over other clotting pathway enzymes.

Oleyloxyethyl phosphorylcholine is an inhibitor of PLA2 with an IC₅₀ value of 6.2 µM for porcine pancreatic PLA2.

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 structural analog of capsaicin, which is the noxious active component of hot peppers of the Capsicum genus, and the amide of vanillylamine and oleic acid; acts as an agonist at TRPV1, inducing desensitization analgesia in rat and mouse models of pain; potentiates the agonist activity of…

Thioetheramide-PC is a structurally modified phospholipid that functions as a competitive, reversible inhibitor of sPLA2. The IC₅₀ value for thioetheramide-PC is 2 µM at a substrate concentration of 0.5 mM. In addition to binding to the catalytic site of sPLA2, thioetheramide-PC…

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.

A substrate for cPLA₂.

A more lipophilic, stabilized form of HPA.

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

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.

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…

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

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.

An isomer of Vitamin E that has less potent antioxidant properties than α-tocotrienol.

An alkaloid metabolite of nicotine as well as a major product of its pyrolysis; binds comparably to CYP2A6 and CYP2A13 (Kis = 7.5 and 5.6 µM, respectively), but appears to more effectively inactivate CYP2A6.

DGLA is a metabolite produced by chain elongation of the essential fatty acid γ-linolenic acid. Ethyl DGLA is an esterified version of the free acid which is less water soluble, but more ammenable for the formulation of DGLA-containing diets and dietary supplements. DGLA has been advanced as…

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 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…

A potent inhibitor of HCV infection (EC₅₀ = 17 nM) that displays low cytotoxicity of virally-infected human hepatoma Huh7.5.1 cells (CC₅₀ = 21.3 µM); displays good pharmacokinetics in mice when delivered intraperitoneally, with preferential liver distribution without…

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…

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.

Unnatural C-15 epimer of Travoprost.

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 minor impurity produced in the synthesis of (+)-cloprostenol; 20-fold less active than (+)-cloprostenol in terminating pregnancy in the hamster.

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 selective calcium ionophore that mobilizes intracellular calcium stores. It is used as a research tool to raise the intracellular level of calcium, to study calcium transport across biological membranes, and to stimulate the intracellular production of cytokines.

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

Travoprost is the Alcon trade name for fluprostenol isopropyl ester, an F-series prostaglandin analog which has been approved for use as an ocular hypotensive drug. Fluprostenol isopropyl ester is a prodrug which is converted by esterase enzymatic activity in the cornea to yield the corresponding…

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