Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 15:12:02 UTC |
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Update Date | 2022-03-07 02:49:16 UTC |
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HMDB ID | HMDB0002664 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Prostaglandin E3 |
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Description | Prostaglandin E3 is from the cyclooxygenase metabolism of eicosapentaenoic acid.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 signalling pathways. |
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Structure | CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O 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/h3-4,6-7,12-13,15-17,19,21,23H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16+,17+,19+/m0/s1 |
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Synonyms | Value | Source |
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(5Z,11alpha,13E,15S,17Z)-11,15-Dihydroxy-9-oxoprosta-5,13,17-trien-1-Oic acid | ChEBI | 9-oxo-11R,15S-Dihydroxy-5Z,13E,17Z-prostatrienoic acid | ChEBI | PGE3 | ChEBI | (5Z,11a,13E,15S,17Z)-11,15-Dihydroxy-9-oxoprosta-5,13,17-trien-1-Oate | Generator | (5Z,11a,13E,15S,17Z)-11,15-Dihydroxy-9-oxoprosta-5,13,17-trien-1-Oic acid | Generator | (5Z,11alpha,13E,15S,17Z)-11,15-Dihydroxy-9-oxoprosta-5,13,17-trien-1-Oate | Generator | (5Z,11Α,13E,15S,17Z)-11,15-dihydroxy-9-oxoprosta-5,13,17-trien-1-Oate | Generator | (5Z,11Α,13E,15S,17Z)-11,15-dihydroxy-9-oxoprosta-5,13,17-trien-1-Oic acid | Generator | 9-oxo-11R,15S-Dihydroxy-5Z,13E,17Z-prostatrienoate | Generator | (-)-Prostaglandin e3 | HMDB | 7-[3-Hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-heptenoate | HMDB | 7-[3-Hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-heptenoic acid | HMDB | 7-[3-Hydroxy-2-(3-hydroxy-1,5-octadienyl)-5-oxocyclopentyl]-5-heptenoic acid stereoisomer | HMDB | delta(17)-PGE1 | HMDB | delta(17)-Prostaglandin e1 | HMDB | Prostaglandin e3 | MeSH |
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Chemical Formula | C20H30O5 |
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Average Molecular Weight | 350.4492 |
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Monoisotopic Molecular Weight | 350.20932407 |
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IUPAC Name | (5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5Z)-3-hydroxyocta-1,5-dien-1-yl]-5-oxocyclopentyl]hept-5-enoic acid |
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Traditional Name | (-)-prostaglandin E3 |
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CAS Registry Number | 802-31-3 |
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SMILES | CC\C=C/C[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O |
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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/h3-4,6-7,12-13,15-17,19,21,23H,2,5,8-11,14H2,1H3,(H,24,25)/b6-3-,7-4-,13-12+/t15-,16+,17+,19+/m0/s1 |
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InChI Key | CBOMORHDRONZRN-QLOYDKTKSA-N |
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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
- Cyclopentanol
- Fatty acid
- Unsaturated fatty acid
- Cyclic alcohol
- Ketone
- Cyclic ketone
- Secondary alcohol
- Carboxylic acid
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Organooxygen compound
- Carbonyl group
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Prostaglandin E3,1TMS,isomer #1 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C | 2887.8 | Semi standard non polar | 33892256 | Prostaglandin E3,1TMS,isomer #2 | CC/C=C\C[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O | 2805.2 | Semi standard non polar | 33892256 | Prostaglandin E3,1TMS,isomer #3 | CC/C=C\C[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C | 2796.9 | Semi standard non polar | 33892256 | Prostaglandin E3,1TMS,isomer #4 | CC/C=C\C[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O | 2813.9 | Semi standard non polar | 33892256 | Prostaglandin E3,1TMS,isomer #5 | CC/C=C\C[C@H](O)/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O | 2749.9 | Semi standard non polar | 33892256 | Prostaglandin E3,2TMS,isomer #1 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C | 2762.8 | Semi standard non polar | 33892256 | Prostaglandin E3,2TMS,isomer #2 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2799.7 | Semi standard non polar | 33892256 | Prostaglandin E3,2TMS,isomer #3 | CC/C=C\C[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O)O[Si](C)(C)C | 2851.9 | Semi standard non polar | 33892256 | Prostaglandin E3,2TMS,isomer #4 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C | 2748.9 | Semi standard non polar | 33892256 | Prostaglandin E3,2TMS,isomer #5 | CC/C=C\C[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C | 2754.6 | Semi standard non polar | 33892256 | Prostaglandin E3,2TMS,isomer #6 | CC/C=C\C[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C | 2803.1 | Semi standard non polar | 33892256 | Prostaglandin E3,2TMS,isomer #7 | CC/C=C\C[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O | 2762.5 | Semi standard non polar | 33892256 | Prostaglandin E3,2TMS,isomer #8 | CC/C=C\C[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O | 2782.3 | Semi standard non polar | 33892256 | Prostaglandin E3,2TMS,isomer #9 | CC/C=C\C[C@H](O)/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C | 2729.9 | Semi standard non polar | 33892256 | Prostaglandin E3,3TMS,isomer #1 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2739.8 | Semi standard non polar | 33892256 | Prostaglandin E3,3TMS,isomer #2 | CC/C=C\C[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C | 2800.7 | Semi standard non polar | 33892256 | Prostaglandin E3,3TMS,isomer #3 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C | 2754.1 | Semi standard non polar | 33892256 | Prostaglandin E3,3TMS,isomer #4 | CC/C=C\C[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O)O[Si](C)(C)C | 2807.7 | Semi standard non polar | 33892256 | Prostaglandin E3,3TMS,isomer #5 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2738.2 | Semi standard non polar | 33892256 | Prostaglandin E3,3TMS,isomer #6 | CC/C=C\C[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C | 2780.1 | Semi standard non polar | 33892256 | Prostaglandin E3,3TMS,isomer #7 | CC/C=C\C[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C | 2745.2 | Semi standard non polar | 33892256 | Prostaglandin E3,4TMS,isomer #1 | CC/C=C\C[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C | 2791.2 | Semi standard non polar | 33892256 | Prostaglandin E3,4TMS,isomer #1 | CC/C=C\C[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C | 2851.8 | Standard non polar | 33892256 | Prostaglandin E3,4TMS,isomer #1 | CC/C=C\C[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C | 2819.7 | Standard polar | 33892256 | Prostaglandin E3,4TMS,isomer #2 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2772.4 | Semi standard non polar | 33892256 | Prostaglandin E3,4TMS,isomer #2 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2678.6 | Standard non polar | 33892256 | Prostaglandin E3,4TMS,isomer #2 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 2876.7 | Standard polar | 33892256 | Prostaglandin E3,1TBDMS,isomer #1 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3127.1 | Semi standard non polar | 33892256 | Prostaglandin E3,1TBDMS,isomer #2 | CC/C=C\C[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O | 3013.3 | Semi standard non polar | 33892256 | Prostaglandin E3,1TBDMS,isomer #3 | CC/C=C\C[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C | 3048.5 | Semi standard non polar | 33892256 | Prostaglandin E3,1TBDMS,isomer #4 | CC/C=C\C[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O | 3080.2 | Semi standard non polar | 33892256 | Prostaglandin E3,1TBDMS,isomer #5 | CC/C=C\C[C@H](O)/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O | 2982.9 | Semi standard non polar | 33892256 | Prostaglandin E3,2TBDMS,isomer #1 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3245.1 | Semi standard non polar | 33892256 | Prostaglandin E3,2TBDMS,isomer #2 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3296.4 | Semi standard non polar | 33892256 | Prostaglandin E3,2TBDMS,isomer #3 | CC/C=C\C[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O)O[Si](C)(C)C(C)(C)C | 3308.1 | Semi standard non polar | 33892256 | Prostaglandin E3,2TBDMS,isomer #4 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3226.5 | Semi standard non polar | 33892256 | Prostaglandin E3,2TBDMS,isomer #5 | CC/C=C\C[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C | 3230.0 | Semi standard non polar | 33892256 | Prostaglandin E3,2TBDMS,isomer #6 | CC/C=C\C[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C | 3253.6 | Semi standard non polar | 33892256 | Prostaglandin E3,2TBDMS,isomer #7 | CC/C=C\C[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O | 3225.2 | Semi standard non polar | 33892256 | Prostaglandin E3,2TBDMS,isomer #8 | CC/C=C\C[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O | 3264.3 | Semi standard non polar | 33892256 | Prostaglandin E3,2TBDMS,isomer #9 | CC/C=C\C[C@H](O)/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C | 3208.5 | Semi standard non polar | 33892256 | Prostaglandin E3,3TBDMS,isomer #1 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3461.0 | Semi standard non polar | 33892256 | Prostaglandin E3,3TBDMS,isomer #2 | CC/C=C\C[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3464.8 | Semi standard non polar | 33892256 | Prostaglandin E3,3TBDMS,isomer #3 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C | 3461.9 | Semi standard non polar | 33892256 | Prostaglandin E3,3TBDMS,isomer #4 | CC/C=C\C[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O)O[Si](C)(C)C(C)(C)C | 3507.5 | Semi standard non polar | 33892256 | Prostaglandin E3,3TBDMS,isomer #5 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3448.8 | Semi standard non polar | 33892256 | Prostaglandin E3,3TBDMS,isomer #6 | CC/C=C\C[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C | 3464.2 | Semi standard non polar | 33892256 | Prostaglandin E3,3TBDMS,isomer #7 | CC/C=C\C[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C | 3457.8 | Semi standard non polar | 33892256 | Prostaglandin E3,4TBDMS,isomer #1 | CC/C=C\C[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3640.1 | Semi standard non polar | 33892256 | Prostaglandin E3,4TBDMS,isomer #1 | CC/C=C\C[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3485.5 | Standard non polar | 33892256 | Prostaglandin E3,4TBDMS,isomer #1 | CC/C=C\C[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3101.0 | Standard polar | 33892256 | Prostaglandin E3,4TBDMS,isomer #2 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3644.6 | Semi standard non polar | 33892256 | Prostaglandin E3,4TBDMS,isomer #2 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3213.0 | Standard non polar | 33892256 | Prostaglandin E3,4TBDMS,isomer #2 | CC/C=C\C[C@@H](/C=C/[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3127.8 | Standard polar | 33892256 |
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