15-KETOPROSTAGLANDIN E2

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H30O5
Molecular Weight	350.4492
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCC(=O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O

InChI

InChIKey=YRTJDWROBKPZNV-KMXMBPPJSA-N

InChI=1S/C20H30O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17-,19-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C20H30O5
Molecular Weight	350.4492
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	2
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29175486 | https://www.ncbi.nlm.nih.gov/pubmed/23542179 | https://www.ncbi.nlm.nih.gov/pubmed/26820738

15-Ketoprostaglandin E2 (15-keto PGE2) is a metabolite of prostaglandin E2 (PGE2) with reduced biological activity, which then by the action of prostaglandin reductase 2 (PTGR2) transforms into 13,14-dihydro-15-keto-PGE2, s a secondary metabolite without biological activity. Some experiments have shown that exists the therapeutic potential by targeting PTGR2/15-keto-PGE2 in pancreatic cancer. Besides, it is known, that 15-keto-PGE2 has higher affinity to the prostaglandin EP2 receptor than to the EP4 receptor. Some experiments also have revealed the key signaling cascade: 15-Hydroxyprostaglandin dehydrogenase (15-PGDH)/15-keto-PGE2-mediated activation of PPARγ and p21(WAF1/Cip1) in the regulation of the hepatocarcinogenesis and tumor progression.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin E2 receptor EP2 subtype 5 Target ID: P43116 Gene ID: 5732.0 Gene Symbol: PTGER2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/29175486	Agonist 2678
Peroxisome proliferator-activated receptor gamma 111 Target ID: P37231\|\|\|Q15179 Gene ID: 5468.0 Gene Symbol: PPARG Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23542179	Activator 1430
Prostaglandin reductase 2 1 Target ID: Q8N8N7 Gene ID: 145482.0 Gene Symbol: PTGR2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26820738	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Albumin-eicosanoid interactions. A model system to determine their attributes and inhibition.	1984 Mar 10	6698991
Quantitative high-performance liquid chromatography/electrospray ionization tandem mass spectrometric analysis of 2- and 3-series prostaglandins in cultured tumor cells.	2002 Sep 1	12234478
Chinese hamster monomeric carbonyl reductases of the short-chain dehydrogenase/reductase superfamily.	2009 Mar 16	18983989
A novel transporter of SLC22 family specifically transports prostaglandins and co-localizes with 15-hydroxyprostaglandin dehydrogenase in renal proximal tubules.	2010 Jul 16	20448048
Modulation of nitro-fatty acid signaling: prostaglandin reductase-1 is a nitroalkene reductase.	2013 Aug 30	23878198
15-Hydroxyprostaglandin dehydrogenase generation of electrophilic lipid signaling mediators from hydroxy ω-3 fatty acids.	2015 Feb 27	25586183
Human prostaglandin reductase 1 (PGR1): Substrate specificity, inhibitor analysis and site-directed mutagenesis.	2015 Jun 5	25619643

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

15-keto-prostaglandin E2 (15-keto-PGE2) induces p21WAF1/Cip1 gene transcription through PPAR gamma. Accordingly, treatment of the wild type Huh7 cells with 15-keto-PGE2 (10µM) significantly enhanced the p21 promoter reporter activity and this effect was abolished by PGR2 overexpression or GW9662 treatment (10µM). Treatment of wild type Huh7 cells with 15-keto-PGE2 (10µM) also enhanced PPAR gamma association with the p21 promoter DNA and the effect was blocked by the PPAR gamma antagonist GW9662 (10µM). Treatment of wild type Huh7 cells with the pharmacologic PPAR gamma agonist, ciglitazone, also increased PPAR gamma association with the p21 promoter. These observations demonstrate that 15-PGDH-derived 15-keto-PGE2 induces PPAR gamma association with the p21 promoter and enhances p21 transcription in hepatocellular carcinoma (HCC) cells.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 06:31:09 GMT 2023` Edited by `admin` on `Sat Dec 16 06:31:09 GMT 2023`
Record UNII	2S0F1FTK13
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

15-KETOPROSTAGLANDIN E2

Common Name

English

15-KETO PGE2

Common Name

English

15-DEHYDROPROSTAGLANDIN E2

Common Name

English

15-KETO-PROSTAGLANDIN E2

Common Name

English

DINOPROSTONE IMPURITY F [EP IMPURITY]

Common Name

English

DINOPROSTONE IMPURITY, 15-OXO-DINOPROSTONE- [USP IMPURITY]

Common Name

English

15-OXO-PGE2

Common Name

English

15-OXOPROSTAGLANDIN E2

Common Name

English

(Z)-7-((1R,2R,3R)-3-HYDROXY-2-((E)-3-OXO-OCT-1-ENYL)-5-OXOCYCLOPENTYL)HEPT-5-ENOIC ACID

Systematic Name

English

PROSTA-5,13-DIEN-1-OIC ACID, 11-HYDROXY-9,15-DIOXO-, (5Z,11.ALPHA.,13E)-

Systematic Name

English

15-OXO-DINOPROSTONE

Common Name

English

15-KETO-PGE2

Common Name

English

Code System Code Type Description

CHEBI

57400