A homolog of LOEA, characterized by the addition of an (S)-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.

A substrate for cPLA₂.

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

(+)-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…

A more lipophilic, stabilized form of HPA.

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 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 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 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 water soluble prodrug analog of AEA with similar activity to that of AEA in the growth inhibition of C6 glioma cells; also a structural variant of LPA, however, its effects on the various LPA receptors have not been tested.

A fatty acid amide derived from ricinoleic acid and methyl benzylamine that demonstrates potent growth inhibition of glioma (U251), breast (MCF-7), ovarian (NCI-ADR/RES and OVCAR-3), kidney (786-0), non-small cell lung (NCI-H460), and prostate (PC-3) cancer cells with a mean GI50 value of 6.9 µM.

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.

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…

An analog of AEA that potentiates the activity of endogenous AEA by blocking its re-uptake into presynaptic neurons; selectively inhibits the carrier-mediated transport of AEA without affecting anandamide hydrolysis; inhibits the transport of AEA with an IC₅₀ value of 1 µM in rat…

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

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.

Cloprostenol is a synthetic PGF2α analog and a potent FP receptor agonist. (+)-15-epi Cloprostenol is the 15(S), or 15β-hydroxy enantiomer of (+)-cloprostenol. This epimer is less active by several orders of magnitude as an FP receptor ligand when compared to 15(R)-cloprostenol. However,…

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.

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 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, 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…

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.

Modified with a carboxylic acid group terminating the C-16 alkyl chain, providing a convenient site for chemical crosslinking.

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

An internal standard for the quantification of oleoyl serotonin by GC- or LC-MS.

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

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.

Unnatural C-15 epimer of Travoprost.

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

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