N-[(2-Hydroxy-1-hydroxymethyl)ethyl]-11-oxo-9alpha,15s-dihydroxy-prosta-5z, 13e-dien-1-amide

2-Arachidonyl glycerol (2-AG) exhibits cannabinoid (CB) agonist activity at the CB₁ receptor,¹ is an important endogenous monoglyceride species,² and is thus considered to be the natural ligand for the CB₁ receptor. 2-AG can also be sequentially metabolized by COX-2 and specific PG synthases to form PG 2-glyceryl esters.³ In activated RAW 264.7 cells, PGD₂ 2-glyceryl ester is the primary product of 2-AG metabolism in the COX pathway.³ PGD₂ serinol amide (PGD₂-SA) is a stable analog of PGD₂ 2-glyceryl ester. Unlike PGD₂ 2-glyceryl ester and other fatty acyl 2-glyceryl esters, PGD₂-SA will not isomerize to the less active primary (1-glyceryl) ester. The biological activity of PGD₂-SA has not yet been determined.

Prostaglandin D2 serinol amide is a weak inhibitor of the hydrolysis of [3H]2-oleoylglycerol[1].

ChEBI: PGD2-dihydroxypropanylamine is a prostanoid.

1. Sugiura, T., Kodaka, T., Kondo, S., et al. Is the cannabinoid CB₁ receptor a 2-arachidonoylglycerol receptor Structural requirements for triggering a Ca²⁺ transient in NG108-15 cells J. Biochem. 122(4),890-895(1997).
2. Kondo, S., Kondo, H., Nakane, S., et al. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor agonist: Identification as one of the major species of monoacylglycerols in various rat tissues, and evidence for its generation through Ca²⁺-dependent and -independent mechanisms FEBS Lett. 429(2),152-156(1998).
3. Kozak, K.R., Crews, B.C., Morrow, J.D., et al. Metabolism of the endocannabinoids, 2-arachidonylgycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides J. Biol. Chem. 277(47),44877-44885(2002).