Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:14:56 UTC |
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Update date | 2019-11-26 03:21:03 UTC |
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Primary ID | FDB022498 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Prostaglandin E2 |
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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. |
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CAS Number | 363-24-6 |
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Structure | |
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Synonyms | Synonym | Source |
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(-)-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 |
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Predicted Properties | |
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Chemical Formula | C20H32O5 |
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IUPAC name | 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid |
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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 |
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InChI Key | XEYBRNLFEZDVAW-DODZYUBVSA-N |
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Isomeric SMILES | [H]C(=C[C@@]1([H])[C@]([H])(O)CC(=O)[C@]1([H])CC=CCCCC(O)=O)[C@@]([H])(O)CCCCC |
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Average Molecular Weight | 352.4651 |
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Monoisotopic Molecular Weight | 352.224974134 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Eicosanoids |
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Direct Parent | Prostaglandins and related compounds |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | Not Available |
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External Links |
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ChemSpider ID | 4444059 |
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ChEMBL ID | CHEMBL548 |
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KEGG Compound ID | C00584 |
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Pubchem Compound ID | 5280360 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00917 |
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HMDB ID | HMDB01220 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | 35424 |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Dinoprostone |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Prostaglandin E synthase | PTGES | O14684 | Prostaglandin E2 receptor EP4 subtype | PTGER4 | P35408 | Carbonyl reductase [NADPH] 1 | CBR1 | P16152 | Carbonyl reductase [NADPH] 3 | CBR3 | O75828 | Prostaglandin E synthase 2 | PTGES2 | Q9H7Z7 | Prostaglandin E synthase 3 | PTGES3 | Q15185 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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