Record Information |
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Version | 2.0 |
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Created at | 2024-09-11 18:56:15 UTC |
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Updated at | 2024-09-11 18:56:16 UTC |
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NP-MRD ID | NP0338958 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 11-Epi-PGF2a |
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Description | 11-Epi-PGF2a 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. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. 11-Epi-PGF2a is an extremely weak basic (essentially neutral) compound (based on its pKa). 11-Epi-PGF2a can be biosynthesized from prostaglandin D2 through its interaction with the enzyme aldo-keto reductase family 1 member C3. 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. 11-Epi-PGF2alpha is converted from (5Z,13E)-(15S)-9alpha,15-Dihydroxy-11-oxoprosta-5,13-dienoate via the enzyme prostaglandin-F synthase (EC1.1.1.188). In humans, 11-epi-PGF2a is involved in mefenamic acid action pathway. Prostaglandins are eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. The PGs and TXs are collectively identified as prostanoids. 11-Epi-PGF2alpha is an intermediate in Arachidonic acid metabolism. |
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Structure | [H]C(=C[C@]1([H])C(CC=CCCCC(O)=O)C(O)C[C@]1([H])O)[C@@]([H])(O)CCCCC 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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Synonyms | Not Available |
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Chemical Formula | C20H34O5 |
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Average Mass | 354.4810 Da |
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Monoisotopic Mass | 354.24062 Da |
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IUPAC Name | 7-[(2R,3S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid |
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Traditional Name | 7-[(2R,3S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid |
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CAS Registry Number | Not Available |
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SMILES | [H]C(=C[C@]1([H])C(CC=CCCCC(O)=O)C(O)C[C@]1([H])O)[C@@]([H])(O)CCCCC |
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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-UVSIREBESA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Not Available |
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Chemical Taxonomy |
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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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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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