| Identification | Back Directory | [Name]
17(S)-HDoHE | [CAS]
92693-03-3 | [Synonyms]
17(S)-HDHA
17(S)-HDoHE
17(S)HDHA,17(S) HDHA
SWTYBBUBEPPYCX-YTQNUIGOSA-N
17(S)-hydroxy-4(Z),7(Z),10(Z),13(Z),15(E),19(Z)-docosahexaenoic acid
4,7,10,13,15,19-Docosahexaenoic acid, 17-hydroxy-, (4Z,7Z,10Z,13Z,15E,17S,19Z)- | [Molecular Formula]
C22H32O3 | [MDL Number]
MFCD18427951 | [MOL File]
92693-03-3.mol | [Molecular Weight]
344.49 |
| Chemical Properties | Back Directory | [storage temp. ]
Store at -20°C | [solubility ]
DMF: Miscible; DMSO: Miscible; Ethanol: Miscible; PBS (pH 7.2): 0.8 mg/ml | [form ]
ethanol solution | [InChIKey]
SWTYBBUBEPPYCX-YTQNUIGOSA-N | [SMILES]
CC/C=C\C[C@H](O)/C=C/C=C\C/C=C\C/C=C\C/C=C\CCC(O)=O |
| Hazard Information | Back Directory | [Description]
17(S)-HDHA is a hydroxy fatty acid formed from docosahexaenoic acid (DHA; ) by 15-lipoxygenase (15-LO) and is a precursor to 17(S)-resolvins.1,2 17(S)-HDHA inhibits platelet 12-LO (IC50 = 0.4 μM).2 It inhibits TNF-α-induced expression of IL1B in a human glial cell line (IC50 = ~0.5 nM).1 17(S)-HDHA (100 nM) inhibits NOD-, LRR-, and pyrin domain-containing protein 3 (NLRP3) inflammasome formation induced by homocysteine in podocytes.3 | [Uses]
17(S)-HDHA is a pro-resolving mediator (SPM). 17(S)-HDHA slightly activats PPARγ, PPARα and PPARδ[1]. | [Definition]
ChEBI: 17(S)-HDoHE is a polyunsaturated fatty acid that is (4Z,7Z,10Z,13Z,15E,19Z)-docosa-4,7,10,13,15,19-hexaenoic acid carrying a hydroxy substituent at the 17S-position. It is a metabolite of docosahexaenoic acid in human blood and mouse brain, and serves as a precursor to 17(S)-resolvins. It has a role as a mouse metabolite, an animal metabolite and a human xenobiotic metabolite. It is an enantiomer of a 17(R)-HDoHE. | [References]
1. Hong, S., Gronert, K., Devchand, P.R., et al. Novel docosatrienes and 17S-resolvins generated from docosahexaenoic acid in murine brain, human blood, and glial cells. Autacoids in anti-inflammation J. Biol. Chem. 278(17),14677-14687(2003).
2. Mitchell, P.D., Hallam, C., Hemsley, P.E., et al. Inhibition of platelet 12-lipoxygenase by hydroxy-fatty acids Biochem. Soc. Trans. 12,839-841(1984).
3. Li, G., Chen, Z., Bhat, O.M., et al. NLRP3 inflammasome as a novel target for docosahexaenoic acid metabolites to abrogate glomerular injury J. Lipid Res. 58(6),1080-1090(2017). |
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