Structure via PubChem · Public domain (PubChem)
levuglandin D2
Sign in to saveAlso known as 9,10-Seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoate, 9,10-Seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoic acid, LGD2
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. El
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Vinony's link graph records 4 inbound references to levuglandin D2, and connects out to digital object identifier, chemical formula and aldehydes.
It is catalogued under the topic Eicosanoids.
Vinony links it to 7 Wikipedia language editions.
Chemical data
- Formula
- C20H32O5
- Molecular weight
- 352.5 g/mol
- IUPAC name
- (5Z,8R,9R,10E,12S)-9-acetyl-8-formyl-12-hydroxyheptadeca-5,10-dienoic acid
- SMILES
- CCCCC[C@@H](/C=C/[C@H]([C@@H](C/C=C\CCCC(=O)O)C=O)C(=O)C)O
- InChIKey
- MLLWPVVMXGUOHD-QNUMDXCLSA-N
- XLogP
- 2.6
- Polar surface area
- 91.7 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 352.224974
Show 3 more facts
- isomeric SMILES
- CCCCC[C@@H](/C=C/[C@H]([C@@H](C/C=C\CCCC(=O)O)C=O)C(=O)C)O
- chemical formula
- C₂₀H₃₂O₅
- canonical SMILES
- CCCCCC(C=CC(C(CC=CCCCC(=O)O)C=O)C(=O)C)O
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- History
- 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.
==History== Though spontaneous rearrangements of PGH2 are known to generate prostaglandins (PG) PGD2 and PGE2. Prof. Robert Salomon at Case Western Reserve University discovered that a novel alternative rearrangement also occurs that producing two γ-ketoaldehydes and named them levuglandins LGD2 and LGE2 as they are derivatives of levulinaldehyde with prostanoid side chains.
Excerpted from Wikipedia’s “levuglandin D2” article, available under the CC BY-SA 4.0 licence.