| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation date | 2011-09-21 00:28:25 UTC |
|---|
| Update date | 2015-07-21 06:57:39 UTC |
|---|
| Primary ID | FDB023345 |
|---|
| Secondary Accession Numbers | Not Available |
|---|
| Chemical Information |
|---|
| FooDB Name | 15-Keto-prostaglandin F2a |
|---|
| Description | 15-Keto-prostaglandin F2a is the oxidized product of prostaglandin F2a by 15-hydroxyprostaglandin dehydrogenase, which is present in lung, kidney, placenta and other tissues and catalyzes the NAD- or NADP-dependent dehydrogenation of 15-dydroxyl group. 15-Keto-prostaglandin F2a is further metabolized by its delta13-reduction, beta-oxidation and omega oxidation. The ultimate metabolite is 5a,7a-dihydroxy-11-keto-tetranorprosta-1,16-dioic acid, and excreted in urine. Prostaglandin F2a (PGF2) is one of the earliest discovered and most common prostaglandins is actively biosynthesized in various organs of mammals and exhibits a variety of biological activities, including contraction of pulmonary arteries. PGF2 is mainly synthesized directly from PGH2 by PGH2 9,11-endoperoxide reductase. A small amount of PGF2 is also produced from PGE2 by PGE2 9-ketoreductase. A PGF2 epimer has been reported to exhibit various biological activities, and its levels are increased in bronchoalveolar lavage fluid, plasma, and urine in patients with mastocytosis and bronchial asthma. PGF2 is synthesized from PGD2 by PGD2 11-ketoreductase. (PMID: 16475787, 184496, 5951401, 12432938)
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 | 35850-13-6 |
|---|
| Structure | |
|---|
| Synonyms | |
|---|
| Predicted Properties | |
|---|
| Chemical Formula | C20H32O5 |
|---|
| IUPAC name | 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooct-1-en-1-yl)cyclopentyl]hept-5-enoic acid |
|---|
| 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/h4,7,12-13,16-19,22-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/t16-,17-,18+,19-/m1/s1 |
|---|
| InChI Key | LOLJEILMPWPILA-AKHDSKFASA-N |
|---|
| Isomeric SMILES | [H][C@]1(O)C[C@@]([H])(O)[C@]([H])(C=CC(=O)CCCCC)[C@@]1([H])CC=CCCCC(O)=O |
|---|
| Average Molecular Weight | 352.4651 |
|---|
| Monoisotopic Molecular Weight | 352.224974134 |
|---|
| 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
- Alpha,beta-unsaturated ketone
- Enone
- Cyclic alcohol
- Acryloyl-group
- 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 | 4444410 |
|---|
| ChEMBL ID | Not Available |
|---|
| KEGG Compound ID | C05960 |
|---|
| Pubchem Compound ID | 5280887 |
|---|
| Pubchem Substance ID | Not Available |
|---|
| ChEBI ID | 28442 |
|---|
| Phenol-Explorer ID | Not Available |
|---|
| DrugBank ID | Not Available |
|---|
| HMDB ID | HMDB04240 |
|---|
| 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 | |
|---|
