| Identification | Back Directory | [Name]
N-[(2-HYDROXY-1-HYDROXYMETHYL)ETHYL]-11-OXO-9ALPHA,15S-DIHYDROXY-PROSTA-5Z, 13E-DIEN-1-AMIDE | [CAS]
851761-42-7 | [Synonyms]
PGD2-SA
PROSTAGLANDIN D2 SERINOL AMIDE
N-[(2-HYDROXY-1-HYDROXYMETHYL)ETHYL]-11-OXO-9ALPHA,15S-DIHYDROXY-PROSTA-5Z, 13E-DIEN-1-AMIDE
(Z)-N-(1,3-dihydroxypropan-2-yl)-7-[(1R,2R,5S)-5-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-3-oxocyclopentyl]hept-5-enamide | [Molecular Formula]
C23H39NO6 | [MDL Number]
MFCD08062228 | [MOL File]
851761-42-7.mol | [Molecular Weight]
425.56 |
| Chemical Properties | Back Directory | [Boiling point ]
686.2±55.0 °C(Predicted) | [density ]
1.172±0.06 g/cm3(Predicted) | [solubility ]
DMF: 25 mg/ml; DMSO: 25 mg/ml; Ethanol: 25 mg/ml; PBS (pH 7.2): 5 mg/ml | [pka]
13.86±0.60(Predicted) |
| Hazard Information | Back Directory | [Description]
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. | [Uses]
Prostaglandin D2 serinol amide is a weak inhibitor of the hydrolysis of [3H]2-oleoylglycerol[1]. | [Definition]
ChEBI: PGD2-dihydroxypropanylamine is a prostanoid. | [References]
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). |
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