Levuglandin

Levuglandin E₂
Names
	IUPAC name (5Z,8R,9R,10E,12S)-8-acetyl-9-formyl-12- hydroxyheptadeca-5,10-dienoic acid
	Other names LGE2
Identifiers
CAS Number	91712-41-3;
3D model (JSmol)	Interactive image;
ChemSpider	4696839;
KEGG	C13807;
PubChem CID	5771742;
CompTox Dashboard (EPA)	DTXSID30429543 ;
	InChI InChI=1S/C20H32O5/c1-3-4-7-10-18(23)14-13-17(15-21)19(16(2)22)11-8-5-6-9-12-20(24)25/h5,8,13-15,17-19,23H,3-4,6-7,9-12H2,1-2H3,(H,24,25)/b8-5-,14-13+/t17-,18-,19-/m0/s1 Key: WJWAORNTZNRHBP-QNUMDXCLSA-N;
	SMILES CCCCC[C@@H](/C=C/[C@@H](C=O)[C@@H](C/C=C\CCCC(=O)O)C(=O)C)O;
Properties
Chemical formula	C20H32O5
Molar mass	352.465 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Levuglandin D₂
Names
	IUPAC name (5Z,8R,9R,10E,12S)-9-acetyl-8-formyl-12- hydroxyheptadeca-5,10-dienoic acid
Identifiers
CAS Number	91712-44-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	7827799 ;
KEGG	C13808 ;
PubChem CID	9548876;
CompTox Dashboard (EPA)	DTXSID30429543 ;
	InChI InChI=1S/C20H32O5/c1-3-4-7-11-18(23)13-14-19(16(2)22)17(15-21)10-8-5-6-9-12-20(24)25/h5,8,13-15,17-19,23H,3-4,6-7,9-12H2,1-2H3,(H,24,25)/b8-5-,14-13+/t17-,18-,19-/m0/s1 Key: MLLWPVVMXGUOHD-QNUMDXCLSA-N ;
	SMILES CCCCC[C@@H](/C=C/[C@H]([C@@H](C/C=C\CCCC(=O)O)C=O)C(=O)C)O;
Properties
Chemical formula	C20H32O5
Molar mass	352.465 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Levuglandins are reactive aldehydes formed by the spontaneous rearrangement of prostaglandin H (PGH). Enantiomerically pure levuglandin (LG) E₂ can also be formed through the cyclooxygenase (COX) pathway by a rearrangement of the prostaglandin (PG) endoperoxide PGH ₂. They are nonclassic eicosanoids. One species, levuglandin E₂, (LGE₂), forms neurotoxic adducts with amyloid beta. Levuglandins and isolevuglandins can damage proteins by covalent adduction, thereby interfering with their normal functions. These lipid-derived protein modifications may serve as dosimeters of oxidative injury. Elevated plasma levels of isoLG-protein epitopes are associated with atherosclerosis but are independent of total cholesterol, a classical risk factor.