17-HDoHE (BioCAD00000023807)

blood

Metabolite Card

Formula: C22H32O3 (344.2351)
SMILES: CC\C=C/CC(O)\C=C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O

Synonyms [en]

17-HDoHE; (+/-)-17-hydroxy-4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoic acid; 17-Hydroxy-dha; 17-HDHA; (4Z,7Z,10Z,13Z,15E,19Z)-17-Hydroxydocosa-4,7,10,13,15,19-hexaenoic acid; (+/-)-17-hdohe

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

17-HDoHE. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000023807). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Docosahexaenoic acid (DHA) is a omega-3 essential fatty acid that reduces the incidence and severity of a number of diseases. Recently, a novel series of DHA-derived lipid mediators with potent protective actions has been identified. In this study we demonstrate that dietary amplification of these DHA-derived products protects the liver from necroinflammatory injury. In vitro, supplementation of hepatocytes with DHA significantly reduced hydrogen peroxide-induced DNA damage, evaluated by the "comet assay," and oxidative stress, determined by measurement of malondialdehyde levels. In vivo, dietary supplementation of mice with DHA ameliorated carbon tetrachloride-induced necroinflammatory damage. In addition, hepatic cyclooxygenase-2 expression and PGE2 levels were significantly reduced in mice fed DHA-enriched diets. In these animals, increased hepatic formation of DHA-derived lipid mediators (i.e., 17S-hydroxy-DHA (17S-HDHA) and protectin D1) was detected by HPLC-gas chromatography/mass spectrometry analysis. Consistent with these findings, synthetic 17-HDHA abrogated genotoxic and oxidative damage in hepatocytes and decreased TNF-alpha release and 5-lipoxygenase expression in macrophages. In a transactivation assay, 17-HDHA acted in a concentration-dependent manner as a PPARgamma agonist. Taken together, these findings identify a potential role for DHA-derived products, specifically 17S-HDHA and protectin D1, in mediating the protective effects of dietary DHA in necroinflammatory liver injury. (PMID: 17056761). This fatty acyl belongs to the main class of docosanoids. (Lipid Maps).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 90780-52-2
  • PubChem: 11046191
  • PubChem: 6439179
  • ChEBI: ChEBI:138640
  • ChEBI: ChEBI:72637
  • HMDB: HMDB0010213
  • LipidMaps: LMFA04000012
  • LipidMaps: LMFA04000032
  • NCBI MeSH: 17-hydroxy-4,7,10,13,15,19-docosahexaenoic acid
  • RefMet: RM0153416
  • RefMet: RM0153445
  • MoNA: UT000127
  • MoNA: UT000128
  • MoNA: UT000129
  • MoNA: UT000130
  • MoNA: UT000131
  • MoNA: UT000132
  • MoNA: UT000133
  • MoNA: UT000134
  • MoNA: UT000135
  • Metlin: METLIN_36447

Class / Ontology

Metabolic Network
ID EC Number Name
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
WikiPathways:WP5154 Docosahexaenoic acid oxylipin metabolism
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