An EpEDE acid formed from DGLA, either by a strong oxidizing agent or by cytochrome P450 epoxygenases; biological properties are poorly understood.

5(Z),11(Z),14(Z)-Eicosatrienoic acid is a PUFA found in various natural sources including maritime pine (Pinus pinaster) seed oil (MPSO), gymnospermae leaves and seeds, and freshwater gastropods. A diet containing MPSO lowered HDL and ApoA1 levels in transgenic mice expressing human ApoA1. MPSO was…

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

A DHA epoxygenase metabolite found in rat brain and spinal cord that acts as a preferred substrate for sEH (Km = 3.2 µM); demonstrates antihyperalgesic activity in inflammatory and neuropathic pain models and potently inhibits angiogenesis and tumor growth in in vitro assays.

An internal standard for the quantification of trans-resveratrol by GC- or LC-MS.

A synthetic analog of natural PtdIns featuring C8:0 fatty acids at the sn-1 and sn-2 positions; contains the same inositol and DAG stereochemistry as the natural compound.

A cyanobacterial toxin that targets protein and glutathione synthesis in hepatocytes (IC50s = 1.3 and 2.4 µM, respectively), inhibits uridine monophosphate synthase complex activity (Ki = 10 µM), and induces DNA damage.

A proposed anti-inflammatory EPA metabolite that has been shown to promote inflammatory resolution in numerous disease models, including experimental colitis, asthma, atherosclerosis, type 2 diabetes, and HSV-1-induced stromal keratitis.

A major metabolite of PGD2 found in human and mouse urine at levels of approximately 1.5 and 8.1 ng/mg creatinine, respectively.

(±)12-HpETE is one of the six monohydroperoxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid (Item No. 90010) and consists of an equal mixture of the R and S isomers. Reduction of the hydroperoxide yields the more stable hydroxyl fatty acid (±)12-HETE (Item…

A major urinary metabolite of PGE2 that is excreted in guinea pig urine at a concentration range of 1.34-2.74.

8(S)-HETrE is a monohydroxy PUFA produced by rabbit neutrophil lipoxygenase when DGLA is used as a substrate. Although the biological activities of 8(S)-HETrE have not been well characterized, it is expected to behave similarly to 8(S)-HETE.

A microbial metabolite isolated from Streptomyces that is widely used as a selective inhibitor of the 20S proteasome.

An internal standard for the quantification of 2-AG by GC- or LC-MS.

A 13R,14S-dihydroxy DHA formed by recombinant human macrophage 12-LO and sEH co-incubated with DHA; reduces neutrophil infiltration in a mouse model of peritonitis and enhances human macrophage phagocytosis of zymosan A.

Key urinary metabolite of PGD2; represents approximately 1% and 4% of the infused radiolabeled dose in monkeys and humans, respectively.

An epoxygenase pathway product produced from EPA by CYP450 both in vitro and in vivo; its effects of remain to be determined.

Major β-oxidation product resulting from peroxisomal metabolism of 12(S)-HETE

An aspirin-triggered lipoxin that inhibits LTB4-induced chemotaxis, adherence, and transmigration of the neutrophils with twice the potency of LXA4 demonstrating activity in the nM range.

The L isomer of the biologically important D-myo-inositol-1,4,5-triphosphate; does not evoke a rise in intracellular calcium when added to cells.

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

11-trans LTC4 is a C-11 double bond isomer of LTC4. LTC4 undergoes slow temperature-dependent isomerization to 11-trans LTC4 during storage. 11-trans LTC4 is produced in smaller amounts relative to LTC4 in ionophore-stimulated HMC-1 cells (a human mast cell line) and equine eosinophils, but not in…

A stable analog of TXA2; unlike other TP receptor agonists, it inhibits platelet aggregation (IC₅₀ = 4-5 µM).

(±)11-HDHA is an autoxidation product of DHA in vitro. It is also produced from incubations of DHA in rat liver, brain, and intestinal microsomes. DHA is metabolized to 11(S)-HDHA by human platelets and canine retina. In addition to 11(S)-HDHA, 14(S)-HDHA is also produced by platelets.…

A non-enzymatic hydrolysis product of LTA4 with reduced activity compared to LTB4; also produced by oxidative decomposition of CysLTs such as LTC4 in the presence of myeloperoxidase and hypochlorous acid.

A synthetic analog of natural PtdIns containing C6:0 fatty acids at the sn-1 and sn-2 positions; contains the same inositol and DAG stereochemistry as the natural compound.

Largely acts a cell signaling intermediate; serving as substrate to produce IP5s, which can be further phosphorylated to produce Ins(1,2,3,4,5,6-)P6; also phosphorylated to produce phytic acid, which serves diverse roles in eukaryotic tissues; a poor activator of the Ins(1,4,5)-P3 receptor in vitro.

8-iso-17-phenyl PGF2β is an isomer of bimatoprost (free acid) that is epimerized at the 8 and 9 positions. There are no published reports on the biological activity of 8-iso-17-phenyl PGF2β.

An analog of (±)14(15)-EpEDE with greater lipid solubility than the free base.

An internal standard for quantification of 13,14-dihydro-15 (R,S)-hydroxy-16,16-difluoro-Prostaglandin E1, a metabolite of a bicyclic PGE1 derivative used in the treatment of chronic constipation, by GC- or LC-mass spectrometry (MS).

A positional isomer of LXA4 produced by the metabolism of 15-HETE or 15-HpETE by human leukocytes; inhibits PMV migration stimulated by LTB4 at a concentration of 10-7 M and inhibits LTB4-induced adhesion of PMNs with an IC₅₀ value of ~3 x 10-10 M.

Produced from Ins(1,2,3,5,6)P5 via a minor enzymatic phytate degradation pathway by K. terrigena; moderately effective in opening calcium channels relative to Ins(1,4,5)P3.