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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 of 15-KETOPROSTAGLANDIN E2

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

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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Prostaglandin E2 receptor EP2 subtype
5
Target ID: P43116
Gene ID: 5732.0
Gene Symbol: PTGER2
Target Organism: Homo sapiens (Human)
Agonist
2752
Peroxisome proliferator-activated receptor gamma
118
Target ID: P37231|||Q15179
Gene ID: 5468.0
Gene Symbol: PPARG
Target Organism: Homo sapiens (Human)
Activator
1447
Prostaglandin reductase 2
1
Target ID: Q8N8N7
Gene ID: 145482.0
Gene Symbol: PTGR2
Target Organism: Homo sapiens (Human)
Substrate
661
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Albumin-eicosanoid interactions. A model system to determine their attributes and inhibition.
1984 Mar 10

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 Mon Mar 31 21:36:33 GMT 2025
Edited
by admin
on Mon Mar 31 21:36:33 GMT 2025
Record UNII
2S0F1FTK13
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
15-DEHYDROPROSTAGLANDIN E2
Preferred Name English
15-KETOPROSTAGLANDIN E2
Common Name English
15-KETO PGE2
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
Created by admin on Mon Mar 31 21:36:33 GMT 2025 , Edited by admin on Mon Mar 31 21:36:33 GMT 2025
PRIMARY
FDA UNII
2S0F1FTK13
Created by admin on Mon Mar 31 21:36:33 GMT 2025 , Edited by admin on Mon Mar 31 21:36:33 GMT 2025
PRIMARY
EPA CompTox
DTXSID401317991
Created by admin on Mon Mar 31 21:36:33 GMT 2025 , Edited by admin on Mon Mar 31 21:36:33 GMT 2025
PRIMARY
CAS
26441-05-4
Created by admin on Mon Mar 31 21:36:33 GMT 2025 , Edited by admin on Mon Mar 31 21:36:33 GMT 2025
PRIMARY
CHEBI
15547
Created by admin on Mon Mar 31 21:36:33 GMT 2025 , Edited by admin on Mon Mar 31 21:36:33 GMT 2025
PRIMARY
PUBCHEM
5280719
Created by admin on Mon Mar 31 21:36:33 GMT 2025 , Edited by admin on Mon Mar 31 21:36:33 GMT 2025
PRIMARY
Related Record Type Details
Structure of DINOPROSTONE
PARENT -> METABOLITE
Related Record Type Details
Structure of DINOPROSTONE
PARENT -> IMPURITY
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