Metabolite Card
Formula: C20H34O5 (354.2406)
SMILES: CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@H]1C\C=C/CCCC(O)=O
Synonyms [en]
9,11,15-Trihydroxy-prosta-5,13-dien-1-oic acid; 8-epi-prostaglandin F2alpha; 8-isoprostaglandin F2alpha; 8-isoprostane; 15-F2t-IsoP; 8-iso-PGF2alpha
Last reviewed on 2024-06-28.
Cite this Page
9,11,15-Trihydroxy-prosta-5,13-dien-1-oic acid. 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: BioCAD00000005668). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
8-Isoprostaglandin F2a is an isoprostane and a potent renal vasoconstrictor. Isoprostanes are prostaglandin-like compounds that are produced in vivo in humans by a noncyclooxygenase mechanism involving free radical-catalyzed peroxidation of arachidonic acid. The formation of these prostanoids proceeds through bicyclic endoperoxide intermediates that are then reduced to form ring isoprostanes. Of considerable interest is that, in contradistinction to cyclooxygenase-derived prostaglandins, isoprostanes have been shown to be initially formed in situ, esterified to phospholipids, and subsequently released preformed, presumably by phospholipases. The fact that prostanoids are produced in vivo by a noncyclooxygenase mechanism is of considerable interest from a biochemical perspective. However, this may also be associated with biological ramifications since it has been shown that these compounds are capable of exerting potent biological activity. (PMID: 7825845, 17012140). Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. 8-iso-prostaglandin F2A is a biomarker for the consumption of offal meat.
DBLinks
- CAS Registry Number: 27415-26-5
- PubChem CID: 5282263
- ChEBI: 34505
- HMDB: HMDB0005083
- LipidMaps: LMFA03110001
- KEGG: C13809
- BioCyc:
- NCBI MeSH: 8-epi-prostaglandin F2alpha
- Wikipedia:
Other DBLinks
- CAS Registry Number: 27415-26-5
- PubChem: 12314600
- PubChem: 5282263
- ChEBI: ChEBI:34505
- HMDB: HMDB0005083
- LipidMaps: LMFA03110001
- KEGG: C13809
- NCBI MeSH: 8-epi-prostaglandin F2alpha
- RefMet: RM0139514
- Metlin: METLIN_36375
- Coconut NaturalProduct: CNP0248684.12
Class / Ontology
- WishartLab ClassyFire: [Eicosanoids] Eicosanoids
- RefMet: [Isoprostanes] Isoprostanes
- LipidMaps: [Isoprostanes [FA0311]] Isoprostanes [FA0311]
- ChEBI: [CHEBI:34505] 8-epi-prostaglandin F2alpha
- Coconut NaturalProduct: [Isoprostanes] Isoprostanes
Taxonomy Source
Pathway Synthetic
| pathway id | name |
|---|---|
| WikiPathways:WP1075 | Folate metabolism |
| WikiPathways:WP3193 | Vitamin B12 metabolism |
| WikiPathways:WP15 | Selenium micronutrient network |
| WikiPathways:WP1533 | Vitamin B12 metabolism |
| WikiPathways:WP176 | Folate metabolism |
| WikiPathways:WP3257 | Selenium micronutrient network |