(5Z,13E)-11alpha-Hydroxy-9,15-dioxoprost-5,13-dienoate (BioCAD00000000639)
Metabolite Card
Formula: C20H30O5 (350.2093)
SMILES: CCCCCC(=O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
Synonyms [en]
15-keto-prostaglandin E2; 15-keto-PGE2; 15-deoxy-15-oxo-prostaglandin E2; 15-oxo-PGE2; 15-ketoprostaglandin E2; 9,15-dioxo-11R-hydroxy-5Z,13E-prostadienoic acid
Last reviewed on 2024-06-28.
Cite this Page
(5Z,13E)-11alpha-Hydroxy-9,15-dioxoprost-5,13-dienoate. 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: BioCAD00000000639). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
15-keto-PGE2 is one of the prostaglandin E2 metabolites. (PMID 7190512). It is a degradation product produced by 15-hydroxy prostaglandin dehydrogenase (PGDH or 15-PGDH). Dinoprostone is a naturally occurring prostaglandin E2 (PGE2) and the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bone's mineralized matrix). PGE2 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, to induce uterine contractions and to activate platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus; decreasing T-cell proliferation and lymphocyte migration and activating the secretion of IL-1alpha and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC), and PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype. (PMID: 16978535). 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.
DBLinks
- CAS Registry Number: 26441-05-4
- PubChem CID: 5280719
- ChEBI: 15547
- HMDB: HMDB0003175
- LipidMaps: LMFA03010030
- KEGG: C04707
- BioCyc:
- NCBI MeSH: 15-ketoprostaglandin E2
- Wikipedia:
Other DBLinks
- CAS Registry Number: 26441-05-4
- PubChem: 5280719
- ChEBI: ChEBI:15547
- HMDB: HMDB0003175
- LipidMaps: LMFA03010030
- KEGG: C04707
- NCBI MeSH: 15-ketoprostaglandin E2
- RefMet: RM0153766
- Metlin: METLIN_2309
- Metlin: METLIN_36107
- Coconut NaturalProduct: CNP0270184.1
- Coconut NaturalProduct: CNP0270184.2
Class / Ontology
- WishartLab ClassyFire: [Eicosanoids] Eicosanoids
- RefMet: [Prostaglandins] Prostaglandins
- LipidMaps: [Prostaglandins [FA0301]] Prostaglandins [FA0301]
- ChEBI: [CHEBI:15547] 15-dehydro-prostaglandin E2
- Coconut NaturalProduct: [Isoprostanes] Isoprostanes
| ID | EC Number | Name |
|---|---|---|
| KEGG:R02580 | 1.1.1.141 | (5Z,13E)-(15S)-11alpha,15-dihydroxy-9-oxoprost-13-enoate:NAD+15-oxidoreductase |
| KEGG:R04556 | 1.3.1.48 | (5Z)-(15S)-11alpha-hydroxy-9,15-dioxoprostanoate:NAD+ delta13-oxidoreductase |
| KEGG:R04557 | 1.3.1.48 | (5Z)-(15S)-11alpha-hydroxy-9,15-dioxoprostanoate:NADP+ delta13-oxidoreductase |
Taxonomy Source
- Angelica tschimganica [ncbi taxid: 2831633]
- Dendrilla cactos [ncbi taxid: ]
- Gracilariopsis longissima [ncbi taxid: 172976]
- Gypsophila patrinii [ncbi taxid: 1137863]
- Homo sapiens [ncbi taxid: 9606]
- Litoria subglandulosa [ncbi taxid: ]
- Myrceugenia exsucca [ncbi taxid: 290080]
- Naganishia albida [ncbi taxid: 100951]
- Quercus lanceaefolia [ncbi taxid: ]
Pathway Synthetic
| pathway id | name |
|---|---|
| WikiPathways:WP4347 | Eicosanoid metabolism via cyclooxygenases (COX) |
| WikiPathways:WP374 | Prostaglandin synthesis and regulation |
| WikiPathways:WP995 | Prostaglandin synthesis and regulation |
| WikiPathways:WP4719 | Eicosanoid metabolism via cyclooxygenases (COX) |
| WikiPathways:WP5155 | Arachidonic acid (AA, ARA) oxylipin metabolism |
| WikiPathways:WP303 | Prostaglandin synthesis and regulation |
| WikiPathways:WP98 | Prostaglandin synthesis and regulation |