Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:32:32 UTC |
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Update date | 2017-10-04 22:50:50 UTC |
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Primary ID | FDB023622 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 8-Isoprostaglandin F2a |
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Description | 8-Isoprostaglandin F2a is an isoprostane and a potent renal vasoconstrictor. Isoprostanes are prostaglandin-like compounds that are produced in vivo in humans by a noncyclooxygenase mechanism involving free radical-catalyzed peroxidation of arachidonic acid. The formation of these prostanoids proceeds through bicyclic endoperoxide intermediates that are then reduced to form ring isoprostanes. Of considerable interest is that, in contradistinction to cyclooxygenase-derived prostaglandins, isoprostanes have been shown to be initially formed in situ, esterified to phospholipids, and subsequently released preformed, presumably by phospholipases. The fact that prostanoids are produced in vivo by a noncyclooxygenase mechanism is of considerable interest from a biochemical perspective. However, this may also be associated with biological ramifications since it has been shown that these compounds are capable of exerting potent biological activity. (PMID: 7825845, 17012140). 8-iso-prostaglandin F2A is a biomarker for the consumption of offal meat.
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] |
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CAS Number | 27415-26-5 |
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Structure | |
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Synonyms | Synonym | Source |
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(5Z,13E,15S)-9alpha,11alpha,15-trihydroxy-8beta-prosta-5,13-dien-1-oate | hmdb | (5Z,13E,15S)-9alpha,11alpha,15-trihydroxy-8beta-prosta-5,13-dien-1-oic acid | hmdb | 8-Epi PGF-2alpha | hmdb | 8-Epi-pgf2a | Generator | 8-epi-PGF2alpha | hmdb | 8-Epi-pgf2α | Generator | 8-Epi-prostaglandin F2a | Generator | 8-Epi-prostaglandin F2alpha | hmdb | 8-Epi-prostaglandin F2α | Generator | 8-Epiprostaglandin F2a | Generator | 8-Epiprostaglandin F2alpha | hmdb | 8-Epiprostaglandin F2α | Generator | 8-iso-PGF2a | hmdb | 8-Iso-pgf2a-iii | Generator | 8-iso-PGF2alpha | hmdb | 8-Iso-pgf2alpha-iii | ChEBI | 8-Iso-pgf2α | Generator | 8-Iso-pgf2α-iii | Generator | 8-Isoprostaglandin F2alpha | hmdb | 8-Isoprostaglandin F2α | Generator | 9,11,15-trihydroxy Prosta-5,13-dien-1-oate | hmdb | 9,11,15-trihydroxy Prosta-5,13-dien-1-oic acid | hmdb | 9,11,15-Trihydroxy-prosta-5,13-dien-1-oate | hmdb | 9,11,15-Trihydroxy-prosta-5,13-dien-1-oic acid | hmdb | 9S,11R,15S-trihydroxy-5Z,13E-prostadienoate | hmdb | 9S,11R,15S-trihydroxy-5Z,13E-prostadienoic acid | hmdb | 9S,11R,15S-trihydroxy-5Z,13E-prostadienoic acid-cyclo[8S,12R] | hmdb |
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Predicted Properties | |
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Chemical Formula | C20H34O5 |
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IUPAC name | 7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid |
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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/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/t15-,16-,17+,18-,19+/m0/s1 |
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InChI Key | PXGPLTODNUVGFL-QXCZDIPSSA-N |
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Isomeric SMILES | [H]C(=C[C@@]1([H])[C@]([H])(O)C[C@]([H])(O)[C@@]1([H])CC=CCCCC(O)=O)[C@@]([H])(O)CCCCC |
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Average Molecular Weight | 354.481 |
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Monoisotopic Molecular Weight | 354.240624198 |
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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
- Fatty acid
- Unsaturated fatty acid
- Cyclopentanol
- Cyclic alcohol
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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 |
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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 | 4445435 |
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ChEMBL ID | CHEMBL1592632 |
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KEGG Compound ID | C13809 |
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Pubchem Compound ID | 5282263 |
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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 | Not Available |
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HMDB ID | HMDB05083 |
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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 | Not Available |
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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 | Not Available |
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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 | Not Available |
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Pathways | Not Available |
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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 | Not Available |
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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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