Livestock Metabolome Database: Showing metabocard for Prostaglandin E2 (LMDB00307)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:46:57 UTC

Update Date

2016-07-20 20:59:47 UTC

Lmdb

LMDB00307

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Prostaglandin E2

Description

The naturally occurring prostaglandin E2 (PGE2) is known in medicine as dinoprostone. 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 is also the prostaglandin that ultimately induces fever. 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(15S)-Prostaglandin e2	ChEBI
(5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oic acid	ChEBI
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoate	ChEBI
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoate	ChEBI
(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-enoic acid	ChEBI
Dinoproston	ChEBI
Dinoprostona	ChEBI
Dinoprostone	ChEBI
Dinoprostonum	ChEBI
PGE2	ChEBI
Prepidil	ChEBI
Propess	ChEBI
Prostin e2	ChEBI
Cervidil	Kegg
(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,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)-11a,15-Dihydroxy-9-oxoprost-13-enoate	Generator
(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acid	Generator
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acid	Generator
(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)-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-oxoprosta-5,13-dienoic 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
(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoate	Generator
(-)-Prostaglandin e2	HMDB
(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
5-trans-PGE2	HMDB
Glandin	HMDB
L-Prostaglandin e2	HMDB
Minprositin e2	HMDB
Minprostin e2	HMDB
Prostaglandin e	HMDB
Prostaglandin e2alpha	HMDB
Prostarmon e	HMDB
Prostin	HMDB
e2, Prostaglandin	HMDB
Prepidil gel	HMDB
alpha, Prostaglandin e2	HMDB
e2 alpha, Prostaglandin	HMDB
e2alpha, Prostaglandin	HMDB
alpha, PGE2	HMDB
Prostenon	HMDB
Gel, prepidil	HMDB
PGE2 alpha	HMDB
PGE2alpha	HMDB
Prostaglandin e2 alpha	HMDB

Chemical Formula

C₂₀H₃₂O₅

Average Molecular Weight

352.4651

Monoisotopic Molecular Weight

352.224974134

IUPAC Name

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

Traditional Name

dinoprostone

CAS Registry Number

363-24-6

SMILES

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

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)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1

InChI Key

XEYBRNLFEZDVAW-ARSRFYASSA-N

Chemical Taxonomy

Description

This compound 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

Substituents

Prostaglandin skeleton
Long-chain fatty acid
Hydroxy fatty acid
Cyclopentanol
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Ketone
Cyclic ketone
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

prostaglandins E (CHEBI:15551 )
Prostaglandins (C00584 )
Prostaglandins (LMFA03010003 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.31	ALOGPS
logP	3.23	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	99.44 m³·mol⁻¹	ChemAxon
Polarizability	41 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 3 TMS)	splash10-0059-4920000000-6108934d406ea4062761	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0059-4920000000-6108934d406ea4062761	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a73-5395000000-02aad995307bb6a67f94	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0ufu-9100850000-7394ff4333bcac154ae5	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 20V, Negative	splash10-00yi-0398000000-41c3a62b076046d87381	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 25V, Negative	splash10-00di-0495000000-df406a9e4cc995523a7e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 30V, Negative	splash10-00dr-0592000000-928e66269ab2854faa42	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 35V, Negative	splash10-00dr-0590000000-b364a55fc0598d9265b5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 40V, Negative	splash10-00dr-0890000000-b3a25d975f2a38d7e49f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 45V, Negative	splash10-0079-0960000000-c67461d3bd965cbf289c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 50V, Negative	splash10-000i-0920000000-830ad149a4fe8f36e211	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 55V, Negative	splash10-07br-0910000000-35e5bd204c947e2c4bcc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT (4000Q TRAP, Applied Biosystems) 60V, Negative	splash10-05fs-0900000000-573b0c5a4593210b387a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00yi-0398000000-612bce8f105beae0c5f2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00di-0495000000-78584a9b664c5155b473	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00dr-0592000000-b37d658cf7b0d590aad4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00dr-0590000000-985f93ab468aa6a8a1b8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-00dr-0890000000-5757ca5e8720a47086dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-0079-0960000000-c67461d3bd965cbf289c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-000i-0920000000-830ad149a4fe8f36e211	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-07br-0910000000-35e5bd204c947e2c4bcc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QIT , negative	splash10-05fs-0900000000-573b0c5a4593210b387a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-0294000000-9d89acbe9e631d718a4b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0019000000-31e36b1c042e1f53c0af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014r-2197000000-e7ed45d4821537db0598	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0lmv-9110000000-b4cb6476f830b7047f38	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0019000000-a8c5f8d16d784c75721a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kar-2159000000-92926ade35f53b386f30	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9421000000-f62f4a6586c94d0d622e	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Ruminal Fluid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details

External Links

DrugBank ID

DB00917

HMDB ID

HMDB0001220

FooDB ID

FDB022498

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

35424

BioCyc ID

5Z13E-15S-1115-DIHYDROXY-9-OXOPROS

METLIN ID

6089

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB23855

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Harizi H, Gualde N: Pivotal role of PGE2 and IL-10 in the cross-regulation of dendritic cell-derived inflammatory mediators. Cell Mol Immunol. 2006 Aug;3(4):271-7. [16978535 ]

Showing metabocard for Prostaglandin E2 (LMDB00307)

Structure for LMDB00307 (Prostaglandin E2)