| Identification | Back Directory | [Name]
13,14-DIHYDRO-15-KETO PROSTAGLANDIN E2 | [CAS]
363-23-5 | [Synonyms]
PGEM
13,14-Dihydro-15-keto-PGE2
CUJMXIQZWPZMNQ-XYYGWQPLSA-N
15-keto-13,14-dihydroprostaglandine2
13,14-dihydro-15-oxo-prostaglandin E2
13,14-DIHYDRO-15-KETO PROSTAGLANDIN E2
13,14-Dihydro-15-ketoprostaglandinE2 solution
9,15-DIOXO-11ALPHA-HYDROXY-PROST-5Z-EN-1-OIC ACID
(5Z)-11α-Hydroxy-9,15-dioxoprosta-5-ene-1-oic acid
(5Z,11α)-11-Hydroxy-9,15-dioxoprost-5-en-1-oic acid
13,14-dihydro-15-keto Prostaglandin E2 MaxSpecStandard
13,14-dihydro-15-keto Prostaglandin E2 Lipid Maps MS Standard
(E)-7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid | [Molecular Formula]
C20H32O5 | [MDL Number]
MFCD00135217 | [MOL File]
363-23-5.mol | [Molecular Weight]
352.47 |
| Chemical Properties | Back Directory | [Boiling point ]
538.1±45.0 °C(Predicted) | [density ]
1.086±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C | [solubility ]
DMF: >100 mg/ml
DMSO: >100 mg/ml
Ethanol: >100 mg/mlPBS (pH 7.2): >5 mg/ml | [form ]
Liquid | [pka]
4.75±0.10(Predicted) | [color ]
Colorless to light yellow |
| Hazard Information | Back Directory | [Description]
13,14-dihydro-15-keto Prostaglandin E2 (13,14-dihydro-15-keto PGE2) is a metabolite of PGE2 and the primary PGE2 metabolite in plasma. It is formed from PGE2 via a 15-keto PGE2 intermediate by 15-oxo-PG Δ13 reductase. Unlike PGE2, 13,14-dihydro-15-keto PGE2 does not bind effectively to the PGE2 receptors EP2 and EP4 expressed in CHO cells (Kis = 12 and 57 μM, respectively) or induce adenylate cyclase activity in the same cells (EC50s = >18 and >38 μM, respectively). Levels of 13,14-dihydro-15-keto PGE2 are increased in the plasma of women in the third trimester of pregnancy and in women during and immediately after labor and delivery. Levels of 13,14-dihydro-15-keto PGE2 levels are decreased in tumor tissue compared to adjacent non-cancerous tissue isolated from patients with non-small cell lung cancer (NSCLC). | [Uses]
13,14-Dihydro-15-ketoPGE2 is a primary metabolite of PGE2 in plasma. | [Definition]
ChEBI: The 13,14-dihydro derivative of 15-oxo-prostaglandin E2. | [References]
[1] P. HUSSLEIN H. S. Concentration of 13,14-dihydro-15-keto-prostaglandin E2 in the maternal peripheral plasma during labour of spontaneous onset[J]. Bjog-An International Journal of Obstetrics and Gynaecology, 1984, 91 3: 228-231. DOI: 10.1111/j.1471-0528.1984.tb04757.x
[2] DUNCAN HUGHES. NAD+-dependent 15-hydroxyprostaglandin dehydrogenase regulates levels of bioactive lipids in non-small cell lung cancer.[J]. Cancer prevention research (Philadelphia, Pa.), 2008, 1 4: 241-249. DOI: 10.1158/1940-6207.capr-08-0055
[3] JOVANA MARIC PHD , PHD Gerd G M Nerea Ferreirós PhD, PHD Danielle F M, et al. Cytokine-induced endogenous production of prostaglandin D2 is essential for human group 2 innate lymphoid cell activation[J]. Journal of Allergy and Clinical Immunology, 2019, 143 6: Pages 2202-2214.e5. DOI: 10.1016/j.jaci.2018.10.069 |
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