Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-08-13 03:26:19 UTC |
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Update Date | 2022-03-07 02:49:19 UTC |
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HMDB ID | HMDB0003689 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Neuroprotectin D1 |
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Description | Neuroprotectin D1 is an autacoid protectin. Autacoids are chemical mediators including the families of resolvins and protectins, defined by their potent bioactions and novel chemical structures. They require enzymatic generation from docosanoids, oxygenated products from docosahexaenoic acid (DHA), which specifically possess a conjugated triene double-bond system in their structures, are denoted protectins. The protectins demonstrate anti-inflammatory and neuroprotective actions in vivo. Resolvins and protectins have specific stereoselective actions which evoke biological actions in the nanogram range in vivo and are natural exudate products. Resolvins and protectins as distinct chemical families join the lipoxins as potent agonists of endogenous anti-inflammation and are proresolving chemical mediators of interest in human disease as potential new approaches to treatment. The terms protectin and neuroprotectin [the term applied to protectin that is generated in the neural tissues] were introduced given the anti-inflammatory and protective actions of the 10,17-docosatriene in neural systems, stroke, and animal models of Alzheimer's disease. The prefix in neuroprotectin (NPD1) provides a local pathway address for the biosynthesis and action of this molecule. In recent years, investigators have recognized inflammation as playing a key role in many prevalent diseases not previously considered to be of inflammatory etiology. These include Alzheimer's disease, cardiovascular disease, and cancer, which now join those well-appreciated inflammatory disorders such as arthritis and periodontal disease. Identifying the molecular mechanism(s) that underlie the many reports of the benefits of dietary omega-3 PUFAs remains an important challenge for nutrition and medicine. Thus, that these new mediator families, resolvins and protectins, are biosynthesized from EPA and DHA, act locally, and possess potent, novel bioactions is of interest to researchers. (PMID: 17090225 ). |
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Structure | CC\C=C/C[C@H](O)\C=C/C=C/C=C/[C@H](O)C\C=C/C\C=C/CCC(O)=O InChI=1S/C22H32O4/c1-2-3-10-15-20(23)17-12-8-9-13-18-21(24)16-11-6-4-5-7-14-19-22(25)26/h3,5-13,17-18,20-21,23-24H,2,4,14-16,19H2,1H3,(H,25,26)/b7-5-,9-8+,10-3-,11-6-,17-12-,18-13+/t20-,21+/m0/s1 |
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Synonyms | Value | Source |
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(4Z,7Z,10R,11E,13E,15Z,17S,19Z)-10,17-Dihydroxydocosahexaenoic acid | ChEBI | (N)PD1 | ChEBI | (Neuro)protectin D1 | ChEBI | 10(R),17(S)-Dihydroxydocosa-4Z,7Z,11E,13E,15Z,19Z-hexaenoic acid | ChEBI | NPD1 | ChEBI | PD1 | ChEBI | (4Z,7Z,10R,11E,13E,15Z,17S,19Z)-10,17-Dihydroxydocosahexaenoate | Generator | 10(R),17(S)-Dihydroxydocosa-4Z,7Z,11E,13E,15Z,19Z-hexaenoate | Generator | 10R,17S-Dihydroxy-docosa-4Z,7Z,11E,13E,15Z,19Z-hexaenoate | HMDB | 10R,17S-Dihydroxy-docosa-4Z,7Z,11E,13E,15Z,19Z-hexaenoic acid | HMDB, MeSH | Protectin D1 | MeSH, HMDB | Neuroprotectin D1 | ChEBI |
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Chemical Formula | C22H32O4 |
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Average Molecular Weight | 360.4871 |
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Monoisotopic Molecular Weight | 360.230059512 |
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IUPAC Name | (4Z,7Z,10R,11E,13E,15Z,17S,19Z)-10,17-dihydroxydocosa-4,7,11,13,15,19-hexaenoic acid |
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Traditional Name | neuroprotectin D1 |
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CAS Registry Number | Not Available |
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SMILES | CC\C=C/C[C@H](O)\C=C/C=C/C=C/[C@H](O)C\C=C/C\C=C/CCC(O)=O |
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InChI Identifier | InChI=1S/C22H32O4/c1-2-3-10-15-20(23)17-12-8-9-13-18-21(24)16-11-6-4-5-7-14-19-22(25)26/h3,5-13,17-18,20-21,23-24H,2,4,14-16,19H2,1H3,(H,25,26)/b7-5-,9-8+,10-3-,11-6-,17-12-,18-13+/t20-,21+/m0/s1 |
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InChI Key | CRDZYJSQHCXHEG-SFVBTVKNSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. |
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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 | Fatty acids and conjugates |
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Direct Parent | Very long-chain fatty acids |
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Alternative Parents | |
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Substituents | - Very long-chain fatty acid
- Hydroxy fatty acid
- Unsaturated fatty acid
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Not Available | 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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Neuroprotectin D1,1TMS,isomer #1 | CC/C=C\C[C@@H](/C=C\C=C\C=C\[C@H](O)C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C | 3207.3 | Semi standard non polar | 33892256 | Neuroprotectin D1,1TMS,isomer #2 | CC/C=C\C[C@H](O)/C=C\C=C\C=C\[C@@H](C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C | 3208.7 | Semi standard non polar | 33892256 | Neuroprotectin D1,1TMS,isomer #3 | CC/C=C\C[C@H](O)/C=C\C=C\C=C\[C@H](O)C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C | 3090.1 | Semi standard non polar | 33892256 | Neuroprotectin D1,2TMS,isomer #1 | CC/C=C\C[C@@H](/C=C\C=C\C=C\[C@@H](C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C | 3262.1 | Semi standard non polar | 33892256 | Neuroprotectin D1,2TMS,isomer #2 | CC/C=C\C[C@@H](/C=C\C=C\C=C\[C@H](O)C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 3157.2 | Semi standard non polar | 33892256 | Neuroprotectin D1,2TMS,isomer #3 | CC/C=C\C[C@H](O)/C=C\C=C\C=C\[C@@H](C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C | 3149.6 | Semi standard non polar | 33892256 | Neuroprotectin D1,3TMS,isomer #1 | CC/C=C\C[C@@H](/C=C\C=C\C=C\[C@@H](C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3185.5 | Semi standard non polar | 33892256 | Neuroprotectin D1,1TBDMS,isomer #1 | CC/C=C\C[C@@H](/C=C\C=C\C=C\[C@H](O)C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C(C)(C)C | 3443.4 | Semi standard non polar | 33892256 | Neuroprotectin D1,1TBDMS,isomer #2 | CC/C=C\C[C@H](O)/C=C\C=C\C=C\[C@@H](C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C(C)(C)C | 3443.3 | Semi standard non polar | 33892256 | Neuroprotectin D1,1TBDMS,isomer #3 | CC/C=C\C[C@H](O)/C=C\C=C\C=C\[C@H](O)C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C | 3326.6 | Semi standard non polar | 33892256 | Neuroprotectin D1,2TBDMS,isomer #1 | CC/C=C\C[C@@H](/C=C\C=C\C=C\[C@@H](C/C=C\C/C=C\CCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3689.1 | Semi standard non polar | 33892256 | Neuroprotectin D1,2TBDMS,isomer #2 | CC/C=C\C[C@@H](/C=C\C=C\C=C\[C@H](O)C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3617.8 | Semi standard non polar | 33892256 | Neuroprotectin D1,2TBDMS,isomer #3 | CC/C=C\C[C@H](O)/C=C\C=C\C=C\[C@@H](C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3618.5 | Semi standard non polar | 33892256 | Neuroprotectin D1,3TBDMS,isomer #1 | CC/C=C\C[C@@H](/C=C\C=C\C=C\[C@@H](C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3901.6 | Semi standard non polar | 33892256 |
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