| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation date | 2011-09-21 00:29:25 UTC |
|---|
| Update date | 2015-07-21 06:57:41 UTC |
|---|
| Primary ID | FDB023404 |
|---|
| Secondary Accession Numbers | Not Available |
|---|
| Chemical Information |
|---|
| FooDB Name | 13,14-Dihydro-15-keto PGF2a |
|---|
| Description | 13,14-dihydro-15-keto PGF2a E1 is an isoprostane. The isoprostanes embody a vast family of novel prostaglandin-like lipids that are produced by nonenzymatic peroxidation of arachidonic acid (AA) in response to free radicals and reactive oxygen species. Although free AA is required for the formation of prostaglandins by cyclooxygenases, the isoprostanes can be generated nonenzymatically from esterified AA in membrane phospholipids before being released by a phospholipase(s). Another dissimilarity is that isoprostanes feature side chains that are almost exclusively orientated cis relative to the cyclopentane ring and are therefore distinct from the prostaglandins, which always have side chains in the trans configuration. Nevertheless, isoprostanes are isomeric with prostaglandins and have been given the prefix D-, E-, and F{alpha}- to denote the prostane ring shared with PGD2, PGE2, and PGF2{alpha} respectively. An additional level of complexity is that peroxidation of AA can occur at one of any of four carbon atoms producing regioisomers, the so-called 5-, 12-, 8-, and 15-series isoprostanes, each consisting of eight racemic diastereomers. Thus, a total of 64 isomers can be generated for each of the D-, E-, and F{alpha}-ring isoprostanes. (PMID: 15528403)
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 | 27376-76-7 |
|---|
| Structure | |
|---|
| Synonyms | |
|---|
| Predicted Properties | |
|---|
| Chemical Formula | C20H34O5 |
|---|
| IUPAC name | 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid |
|---|
| InChI Identifier | InChI=1S/C20H34O5/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/h4,7,16-19,22-23H,2-3,5-6,8-14H2,1H3,(H,24,25)/t16-,17-,18+,19-/m1/s1 |
|---|
| InChI Key | VKTIONYPMSCHQI-AKHDSKFASA-N |
|---|
| Isomeric SMILES | [H][C@@]1(O)C[C@]([H])(O)[C@]([H])(CC=CCCCC(O)=O)[C@@]1([H])CCC(=O)CCCCC |
|---|
| Average Molecular Weight | 354.481 |
|---|
| Monoisotopic Molecular Weight | 354.240624198 |
|---|
| 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
- Cyclopentanol
- Fatty acid
- Unsaturated fatty acid
- Cyclic alcohol
- Ketone
- Secondary alcohol
- Carboxylic acid
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- 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 | 4446166 |
|---|
| ChEMBL ID | Not Available |
|---|
| KEGG Compound ID | Not Available |
|---|
| Pubchem Compound ID | 5283039 |
|---|
| Pubchem Substance ID | Not Available |
|---|
| ChEBI ID | Not Available |
|---|
| Phenol-Explorer ID | Not Available |
|---|
| DrugBank ID | Not Available |
|---|
| HMDB ID | HMDB04685 |
|---|
| 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 | show |
|---|
| References |
|---|
| Synthesis Reference | Not Available |
|---|
| General Reference | Not Available |
|---|
| Content Reference | |
|---|
