Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 01:38:53 UTC |
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Update date | 2015-07-21 06:59:24 UTC |
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Primary ID | FDB028381 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | SM(d17:1/24:0) |
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Description | Sphingomyelin (d17:1/24:0) or SM(d17:1/24:0) is a sphingomyelin. Sphingomyelin (SM or SPH) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. It usually consists of phosphorylcholine and ceramide. SM(18:1/16:0) consists of oleic acid attached to the C1 position and palmitic acid attached to the C2 position. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SPH has a ceramide core (sphingosine bonded to a fatty acid via an amide linkage). In addition it contains one polar head group, which is either phosphocholine or phosphoethanolamine. The plasma membrane of cells is highly enriched in sphingomyelin and is considered largely to be found in the exoplasmic leaflet of the cell membrane. However, there is some evidence that there may also be a sphingomyelin pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down sphingomyelin into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be sphingomyelin present there. Sphingomyelin can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme Sphingomyelinase, which causes the accumulation of Sphingomyelin in spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. SMs play a role in signal transduction.
Sphingomyelins are synthesized by the transfer of phosphorylcholine from phosphatidylcholine to a ceramide in a reaction catalyzed by sphingomyelin synthase. [HMDB] |
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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 | C46H94N2O6P |
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IUPAC name | {[(2S,3R,4E)-3-hydroxy-2-tetracosanamidoheptadec-4-en-1-yl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid |
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InChI Identifier | InChI=1S/C46H93N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-28-30-32-34-36-38-40-46(50)47-44(43-54-55(51,52)53-42-41-48(3,4)5)45(49)39-37-35-33-31-29-19-17-15-13-11-9-7-2/h37,39,44-45,49H,6-36,38,40-43H2,1-5H3,(H-,47,50,51,52)/p+1/b39-37+/t44-,45+/m0/s1 |
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InChI Key | NBEKBSIOEMQZTN-NMIJJABPSA-O |
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Isomeric SMILES | CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@]([H])(COP(O)(=O)OCC[N+](C)(C)C)[C@]([H])(O)\C=C\CCCCCCCCCCCC |
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Average Molecular Weight | 802.2221 |
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Monoisotopic Molecular Weight | 801.684950262 |
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Classification |
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Description | Belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative. |
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Kingdom | Organic compounds |
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Super Class | Organic nitrogen compounds |
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Class | Organonitrogen compounds |
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Sub Class | Quaternary ammonium salts |
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Direct Parent | Phosphocholines |
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Alternative Parents | |
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Substituents | - Phosphocholine
- Phosphoethanolamine
- Dialkyl phosphate
- Fatty amide
- N-acyl-amine
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- Tetraalkylammonium salt
- Carboxamide group
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxylic acid derivative
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- Amine
- Alcohol
- Organic oxide
- Organic salt
- Hydrocarbon derivative
- Organic cation
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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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 | Not Available |
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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 | splash10-0uyr-6021319410-cbacd799a19b61f7c0c3 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0gb9-3162209100-ee02a772befac1fefa15 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01bi-9077002100-9d1dc446ba89d19037db | 2017-09-01 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 24768060 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 52931214 |
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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 | HMDB11695 |
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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 | |
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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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