FComEx: Prostaglandin E2 (PC000907)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:19 UTC

Update date

2017-01-19 02:36:40 UTC

FoodComEx ID

PC000907

FoodDB Record

FDB022498

Chemical Information

Name

Prostaglandin E2

Description

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, induction of uterine contractions and of 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-1α 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) 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 signaling pathways. [HMDB]. Prostaglandin E2 is found in many foods, some of which are common sage, nanking cherry, colorado pinyon, and sweet basil.

CAS Number

363-24-6

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(-)-Prostaglandin E2	hmdb
(15S)-Prostaglandin e2	ChEBI
(5Z,11a,13e,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oate	Generator
(5Z,11a,13e,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oic acid	Generator
(5Z,11alpha,13e,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oate	Generator
(5Z,11alpha,13e,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oic acid	ChEBI
(5Z,11α,13e,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-Oate	Generator
(5Z,11α,13e,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-Oic acid	Generator
(5Z,13E,15S)-11-alpha,15-dihydroxy-9-oxoprost-5,13-dienoate	hmdb
(5Z,13E,15S)-11-alpha,15-dihydroxy-9-oxoprost-5,13-dienoic acid	hmdb
(5Z,13e)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoate	Generator
(5Z,13e)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acid	Generator
(5Z,13e)-(15S)-11a,15-Dihydroxy-9-oxoprosta-5,13-dienoate	Generator
(5Z,13e)-(15S)-11a,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid	Generator
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate	hmdb
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acid	hmdb
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoate	hmdb
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoic acid	hmdb
(5Z,13e)-(15S)-11α,15-dihydroxy-9-oxoprost-13-enoate	Generator
(5Z,13e)-(15S)-11α,15-dihydroxy-9-oxoprost-13-enoic acid	Generator
(5Z,13e)-(15S)-11α,15-dihydroxy-9-oxoprosta-5,13-dienoate	Generator
(5Z,13e)-(15S)-11α,15-dihydroxy-9-oxoprosta-5,13-dienoic acid	Generator
(e,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoate	Generator
(e,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acid	ChEBI
(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoate	Generator
(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic acid	ChEBI
5-trans-PGE2	hmdb
Dinoproston	ChEBI
Dinoprostona	ChEBI
Dinoprostone	hmdb
Dinoprostonum	hmdb
Glandin	hmdb
l-Prostaglandin E2	hmdb
Minprositin E2	hmdb
Minprostin E2	hmdb
PGE2	hmdb
Prepidil	hmdb
Propess	ChEBI
Prostaglandin E	hmdb
Prostaglandin E2	hmdb
Prostaglandin E2alpha	hmdb
Prostarmon E	hmdb
Prostin	hmdb
Prostin E2	hmdb

Chemical Formula

C20H32O5

IUPAC name

7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid

InChI Identifier

InChI=1S/C20H32O5/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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/t15-,16+,17+,19+/m0/s1

InChI Key

XEYBRNLFEZDVAW-DODZYUBVSA-N

Isomeric SMILES

[H]C(=C[C@@]1([H])[C@]([H])(O)CC(=O)[C@]1([H])CC=CCCCC(O)=O)[C@@]([H])(O)CCCCC

Average Molecular Weight

352.4651

Monoisotopic Molecular Weight

352.224974134

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents