Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 01:30:55 UTC |
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Update date | 2015-07-21 06:59:15 UTC |
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Primary ID | FDB027851 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | CerP(d18:1/18:0) |
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Description | CerP(d18:1/18:0), also known as N-octadecanoyl-sphing-4-enine-1-phosphate, is a ceramide phosphate (CerP). Ceramide phosphates are members of the class of compounds known as sphingolipids (SPs), or glycosylceramides. SPs are lipids containing a backbone of sphingoid bases (e.g. sphingosine or sphinganine) that are often covalently bound to a fatty acid derivative through N-acylation. SPs are found in cell membranes, particularly in peripheral nerve cells and the cells found in the central nervous system (including the brain and spinal cord). Sphingolipids are extremely versatile molecules that have functions controlling fundamental cellular processes such as cell division, differentiation, and cell death. Impairments associated with sphingolipid metabolism are associated with many common human diseases such as diabetes, various cancers, microbial infections, diseases of the cardiovascular and respiratory systems, Alzheimer’s disease and other neurological syndromes. The biosynthesis and catabolism of sphingolipids involves a large number of intermediate metabolites where many different enzymes are involved. Simple sphingolipids, which include the sphingoid bases and ceramides, make up the early products of the sphingolipid synthetic pathways, while complex sphingolipids may be formed by the addition of head groups to the ceramide template (Wikipedia). In humans, ceramide phosphate are formed from ceramides by the action of a specific ceramide kinase (CerK) and can be dephosphorylated by phosphatidate phosphatase back to the ceramide. CerPs are an important metabolite of ceramide as it acts as a mediator of the inflammatory response. CerPs are also known to have a dual regulatory capacity acting as intracellular second messengers to regulate cell survival, or as extracellular receptor ligands to stimulate chemotaxis. Moreover, CerPs have been shown to be specific and potent inducers of arachidonic acid and prostanoid synthesis in cells through the translocation and activation of cytoplasmic phospholipase A2. In terms of its appearance and structure, CerP(d18:1/18:0) is a colorless solid that consists of an unsaturated 18-carbon sphingoid base with an attached saturated octadecanoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481). |
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CAS Number | Not Available |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C36H72NO6P |
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IUPAC name | {[(2S,3R,4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl]oxy}phosphonic acid |
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InChI Identifier | InChI=1S/C36H72NO6P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(39)37-34(33-43-44(40,41)42)35(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,34-35,38H,3-28,30,32-33H2,1-2H3,(H,37,39)(H2,40,41,42)/b31-29+/t34-,35+/m0/s1 |
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InChI Key | ZQQLMECVOXKFJK-NXCSZAMKSA-N |
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Isomeric SMILES | CCCCCCCCCCCCCCCCCC(=O)N[C@@]([H])(COP(=O)(O)O)[C@]([H])(O)\C=C\CCCCCCCCCCCCC |
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Average Molecular Weight | 645.9337 |
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Monoisotopic Molecular Weight | 645.509725553 |
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Classification |
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Description | Belongs to the class of organic compounds known as phosphosphingolipids. These are sphingolipids with a structure based on a sphingoid base that is attached to a phosphate head group. They differ from phosphonospingolipids which have a phosphonate head group. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Sphingolipids |
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Sub Class | Phosphosphingolipids |
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Direct Parent | Phosphosphingolipids |
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Alternative Parents | |
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Substituents | - Sphingoid-1-phosphate or derivatives
- Phosphoethanolamine
- Monoalkyl phosphate
- Fatty amide
- N-acyl-amine
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxamide group
- Carboxylic acid derivative
- Organic nitrogen compound
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Organic oxygen compound
- Alcohol
- Organopnictogen compound
- Hydrocarbon derivative
- Organic oxide
- 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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Physiological effect | Organoleptic effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | CerP(d18:1/18:0), TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | CerP(d18:1/18:0), TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | CerP(d18:1/18:0), TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | CerP(d18:1/18:0), TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | CerP(d18:1/18:0), TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | CerP(d18:1/18:0), TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | CerP(d18:1/18:0), "CerP(d18:1/18:0),1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0000197000-a4d61ca5d6c47d158f83 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001j-1100092000-64bcd7b593825ba2a80f | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014i-8690000000-bdfc25d8722174480461 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-2000009000-8300713cd59c69f96d37 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-002f-9000007000-0f5db15f8caea78936e2 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-a5e502a2627af2048a1f | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 4446696 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 5283583 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB10701 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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