Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2013-05-01 17:29:40 UTC |
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Update Date | 2021-09-14 15:47:04 UTC |
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HMDB ID | HMDB0060041 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 11b-PGE2 |
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Description | 11b-PGE2 is a prostaglandins. 15-series prostaglandins (PGE2) and isoprostanes (isoPGE2) are robust biomarkers of oxidative stress, possess potent biological activity, and may be derived through cyclooxygenase or free radical pathways. Thus, their quantification is critical in understanding many biological process. Major brain PGE2/PGD2/isoPGE2 includes PGE2, entPGE2, 8-isoPGE2, 11b-PGE2, PGD2, and 15(R)-PGD2. (PMID: 21317107 ) |
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Structure | CCCCC[C@H](O)\C=C\[C@H]1[C@@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O 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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19-/m0/s1 |
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Synonyms | Value | Source |
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11b-Pge2 | Generator | 11Β-pge2 | Generator |
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Chemical Formula | C20H32O5 |
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Average Molecular Weight | 352.4651 |
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Monoisotopic Molecular Weight | 352.224974134 |
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IUPAC Name | (5Z)-7-[(1R,2R,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid |
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Traditional Name | 11β-prostaglandin E2 |
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CAS Registry Number | Not Available |
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SMILES | CCCCC[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/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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19-/m0/s1 |
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InChI Key | XEYBRNLFEZDVAW-YUOXZBOXSA-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 | Not Available |
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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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11b-PGE2,1TMS,isomer #1 | CCCCC[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 | 2825.3 | Semi standard non polar | 33892256 | 11b-PGE2,1TMS,isomer #2 | CCCCC[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 | 2760.1 | Semi standard non polar | 33892256 | 11b-PGE2,1TMS,isomer #3 | CCCCC[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 | 2777.3 | Semi standard non polar | 33892256 | 11b-PGE2,1TMS,isomer #4 | CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@@H]1O | 2792.8 | Semi standard non polar | 33892256 | 11b-PGE2,1TMS,isomer #5 | CCCCC[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 | 2715.1 | Semi standard non polar | 33892256 | 11b-PGE2,2TMS,isomer #1 | CCCCC[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 | 2722.0 | Semi standard non polar | 33892256 | 11b-PGE2,2TMS,isomer #2 | CCCCC[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 | 2783.0 | Semi standard non polar | 33892256 | 11b-PGE2,2TMS,isomer #3 | CCCCC[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 | 2827.1 | Semi standard non polar | 33892256 | 11b-PGE2,2TMS,isomer #4 | CCCCC[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 | 2726.3 | Semi standard non polar | 33892256 | 11b-PGE2,2TMS,isomer #5 | CCCCC[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 | 2721.7 | Semi standard non polar | 33892256 | 11b-PGE2,2TMS,isomer #6 | CCCCC[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 | 2793.1 | Semi standard non polar | 33892256 | 11b-PGE2,2TMS,isomer #7 | CCCCC[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 | 2747.3 | Semi standard non polar | 33892256 | 11b-PGE2,2TMS,isomer #8 | CCCCC[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 | 2787.4 | Semi standard non polar | 33892256 | 11b-PGE2,2TMS,isomer #9 | CCCCC[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 | 2724.3 | Semi standard non polar | 33892256 | 11b-PGE2,3TMS,isomer #1 | CCCCC[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 | 2711.5 | Semi standard non polar | 33892256 | 11b-PGE2,3TMS,isomer #2 | CCCCC[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 | 2781.6 | Semi standard non polar | 33892256 | 11b-PGE2,3TMS,isomer #3 | CCCCC[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 | 2743.2 | Semi standard non polar | 33892256 | 11b-PGE2,3TMS,isomer #4 | CCCCC[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 | 2800.8 | Semi standard non polar | 33892256 | 11b-PGE2,3TMS,isomer #5 | CCCCC[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 | 2734.4 | Semi standard non polar | 33892256 | 11b-PGE2,3TMS,isomer #6 | CCCCC[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 | 2774.0 | Semi standard non polar | 33892256 | 11b-PGE2,3TMS,isomer #7 | CCCCC[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 | 2733.4 | Semi standard non polar | 33892256 | 11b-PGE2,4TMS,isomer #1 | CCCCC[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 | 2794.8 | Semi standard non polar | 33892256 | 11b-PGE2,4TMS,isomer #1 | CCCCC[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 | 2871.7 | Standard non polar | 33892256 | 11b-PGE2,4TMS,isomer #1 | CCCCC[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 | 2843.1 | Standard polar | 33892256 | 11b-PGE2,4TMS,isomer #2 | CCCCC[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 | 2769.5 | Semi standard non polar | 33892256 | 11b-PGE2,4TMS,isomer #2 | CCCCC[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 | 2714.3 | Standard non polar | 33892256 | 11b-PGE2,4TMS,isomer #2 | CCCCC[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 | 2917.3 | Standard polar | 33892256 | 11b-PGE2,1TBDMS,isomer #1 | CCCCC[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 | 3071.9 | Semi standard non polar | 33892256 | 11b-PGE2,1TBDMS,isomer #2 | CCCCC[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 | 2962.4 | Semi standard non polar | 33892256 | 11b-PGE2,1TBDMS,isomer #3 | CCCCC[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 | 3031.5 | Semi standard non polar | 33892256 | 11b-PGE2,1TBDMS,isomer #4 | CCCCC[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 | 3056.6 | Semi standard non polar | 33892256 | 11b-PGE2,1TBDMS,isomer #5 | CCCCC[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 | 2956.7 | Semi standard non polar | 33892256 | 11b-PGE2,2TBDMS,isomer #1 | CCCCC[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 | 3207.8 | Semi standard non polar | 33892256 | 11b-PGE2,2TBDMS,isomer #2 | CCCCC[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 | 3289.1 | Semi standard non polar | 33892256 | 11b-PGE2,2TBDMS,isomer #3 | CCCCC[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 | 3290.5 | Semi standard non polar | 33892256 | 11b-PGE2,2TBDMS,isomer #4 | CCCCC[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 | 3207.1 | Semi standard non polar | 33892256 | 11b-PGE2,2TBDMS,isomer #5 | CCCCC[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 | 3197.1 | Semi standard non polar | 33892256 | 11b-PGE2,2TBDMS,isomer #6 | CCCCC[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 | 3236.4 | Semi standard non polar | 33892256 | 11b-PGE2,2TBDMS,isomer #7 | CCCCC[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 | 3198.7 | Semi standard non polar | 33892256 | 11b-PGE2,2TBDMS,isomer #8 | CCCCC[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 | 3275.5 | Semi standard non polar | 33892256 | 11b-PGE2,2TBDMS,isomer #9 | CCCCC[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 | 3205.0 | Semi standard non polar | 33892256 | 11b-PGE2,3TBDMS,isomer #1 | CCCCC[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 | 3438.1 | Semi standard non polar | 33892256 | 11b-PGE2,3TBDMS,isomer #2 | CCCCC[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 | 3460.1 | Semi standard non polar | 33892256 | 11b-PGE2,3TBDMS,isomer #3 | CCCCC[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 | 3450.1 | Semi standard non polar | 33892256 | 11b-PGE2,3TBDMS,isomer #4 | CCCCC[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 | 3520.4 | Semi standard non polar | 33892256 | 11b-PGE2,3TBDMS,isomer #5 | CCCCC[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 | 3460.0 | Semi standard non polar | 33892256 | 11b-PGE2,3TBDMS,isomer #6 | CCCCC[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 | 3464.0 | Semi standard non polar | 33892256 | 11b-PGE2,3TBDMS,isomer #7 | CCCCC[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 | 3450.9 | Semi standard non polar | 33892256 | 11b-PGE2,4TBDMS,isomer #1 | CCCCC[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 | 3648.3 | Semi standard non polar | 33892256 | 11b-PGE2,4TBDMS,isomer #1 | CCCCC[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 | 3490.1 | Standard non polar | 33892256 | 11b-PGE2,4TBDMS,isomer #1 | CCCCC[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 | 3150.4 | Standard polar | 33892256 | 11b-PGE2,4TBDMS,isomer #2 | CCCCC[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 | 3645.5 | Semi standard non polar | 33892256 | 11b-PGE2,4TBDMS,isomer #2 | CCCCC[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 | 3215.8 | Standard non polar | 33892256 | 11b-PGE2,4TBDMS,isomer #2 | CCCCC[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 | 3179.9 | Standard polar | 33892256 |
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General References | - Quehenberger O, Armando AM, Brown AH, Milne SB, Myers DS, Merrill AH, Bandyopadhyay S, Jones KN, Kelly S, Shaner RL, Sullards CM, Wang E, Murphy RC, Barkley RM, Leiker TJ, Raetz CR, Guan Z, Laird GM, Six DA, Russell DW, McDonald JG, Subramaniam S, Fahy E, Dennis EA: Lipidomics reveals a remarkable diversity of lipids in human plasma. J Lipid Res. 2010 Nov;51(11):3299-305. doi: 10.1194/jlr.M009449. Epub 2010 Jul 29. [PubMed:20671299 ]
- Brose SA, Thuen BT, Golovko MY: LC/MS/MS method for analysis of E(2) series prostaglandins and isoprostanes. J Lipid Res. 2011 Apr;52(4):850-9. doi: 10.1194/jlr.D013441. Epub 2011 Feb 10. [PubMed:21317107 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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