| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation date | 2011-09-21 00:24:38 UTC |
|---|
| Update date | 2015-07-21 06:57:31 UTC |
|---|
| Primary ID | FDB023097 |
|---|
| Secondary Accession Numbers | Not Available |
|---|
| Chemical Information |
|---|
| FooDB Name | Prostaglandin D3 |
|---|
| Description | Prostaglandin D3 (PGD3) is a prostanoid that has been identified as an inhibitor of human platelet aggregation and as a modulator of autonomic nerve transmission. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 16986207, 6252026, 6952267, 4019112, 6945633
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] |
|---|
| CAS Number | 71902-47-1 |
|---|
| Structure | |
|---|
| Synonyms | |
|---|
| Predicted Properties | |
|---|
| Chemical Formula | C20H30O5 |
|---|
| IUPAC name | 7-[(1R,2R,5S)-5-hydroxy-2-[(3S)-3-hydroxyocta-1,5-dien-1-yl]-3-oxocyclopentyl]hept-5-enoic acid |
|---|
| InChI Identifier | 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/h3-4,6-7,12-13,15-18,21-22H,2,5,8-11,14H2,1H3,(H,24,25)/t15-,16+,17+,18-/m0/s1 |
|---|
| InChI Key | ANOICLBSJIMQTA-MLHJIOFPSA-N |
|---|
| Isomeric SMILES | [H]C(=C[C@@]1([H])C(=O)C[C@]([H])(O)[C@]1([H])CC=CCCCC(O)=O)[C@@]([H])(O)CC=CCC |
|---|
| Average Molecular Weight | 350.4492 |
|---|
| Monoisotopic Molecular Weight | 350.20932407 |
|---|
| Classification |
|---|
| 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 | |
|---|
| Substituents | - Prostaglandin skeleton
- Long-chain fatty acid
- Hydroxy fatty acid
- Fatty acid
- Unsaturated fatty acid
- Cyclopentanol
- Cyclic alcohol
- Cyclic ketone
- Secondary alcohol
- Ketone
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic homomonocyclic compound
|
|---|
| Molecular Framework | Aliphatic homomonocyclic compounds |
|---|
| External Descriptors | Not Available |
|---|
| Ontology |
|---|
| Ontology | No ontology term |
|---|
| Physico-Chemical Properties |
|---|
| Physico-Chemical Properties - Experimental | |
|---|
| Spectra |
|---|
| Spectra | Not Available |
|---|
| External Links |
|---|
| ChemSpider ID | 4445434 |
|---|
| ChEMBL ID | Not Available |
|---|
| KEGG Compound ID | C13802 |
|---|
| Pubchem Compound ID | 5282260 |
|---|
| Pubchem Substance ID | Not Available |
|---|
| ChEBI ID | 34939 |
|---|
| Phenol-Explorer ID | Not Available |
|---|
| DrugBank ID | Not Available |
|---|
| HMDB ID | HMDB03034 |
|---|
| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
|---|
| EAFUS ID | Not Available |
|---|
| Dr. Duke ID | Not Available |
|---|
| BIGG ID | Not Available |
|---|
| KNApSAcK ID | Not Available |
|---|
| HET ID | Not Available |
|---|
| Food Biomarker Ontology | Not Available |
|---|
| VMH ID | Not Available |
|---|
| Flavornet ID | Not Available |
|---|
| GoodScent ID | Not Available |
|---|
| SuperScent ID | Not Available |
|---|
| Wikipedia ID | Not Available |
|---|
| Phenol-Explorer Metabolite ID | Not Available |
|---|
| Duplicate IDS | Not Available |
|---|
| Old DFC IDS | Not Available |
|---|
| Associated Foods |
|---|
|
| Biological Effects and Interactions |
|---|
| Health Effects / Bioactivities | Not Available |
|---|
| Enzymes | Not Available |
|---|
| Pathways | Not Available |
|---|
| Metabolism | Not Available |
|---|
| Biosynthesis | Not Available |
|---|
| Organoleptic Properties |
|---|
| Flavours | Not Available |
|---|
| Files |
|---|
| MSDS | Not Available |
|---|
| References |
|---|
| Synthesis Reference | Not Available |
|---|
| General Reference | Not Available |
|---|
| Content Reference | |
|---|
