Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-27 01:18:01 UTC |
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Update Date | 2016-11-09 01:22:26 UTC |
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Accession Number | CHEM041264 |
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Identification |
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Common Name | SM(d18:0/22:3(10Z,13Z,16Z)) |
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Class | Small Molecule |
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Description | SM(d18:0/22:3(10Z,13Z,16Z)) (d18:0/22:3(10Z,13Z,16Z)) or SM (d18:0/22:3(10Z,13Z,16Z)) 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. In humans, SM(d18:0/22:3(10Z,13Z,16Z)) 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 SM(d18:0/22:3(10Z,13Z,16Z)) 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 SM(d18:0/22:3(10Z,13Z,16Z)) pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down SM(d18:0/22:3(10Z,13Z,16Z)) into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be SM(d18:0/22:3(10Z,13Z,16Z)) present there. SM(d18:0/22:3(10Z,13Z,16Z)) 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 SM(d18:0/22:3(10Z,13Z,16Z)) 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 SM(d18:0/22:3(10Z,13Z,16Z)) synthase. |
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Contaminant Sources | - FooDB Chemicals
- HMDB Contaminants - Urine
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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C22:3 Sphingomyelin | HMDB | N-(15Z-Tetracosenoyl)-sphing-4-enine-1-phosphocholine | HMDB | Sphingomyelin | MetBuilder | N-(10Z,13Z,16Z-Docosenoyl)-1-phosphocholine-sphinganine | MetBuilder | Sphingomyelin(D18:0/22:3(10Z,13Z,16Z)) | MetBuilder | N-(10Z,13Z,16Z-Docosenoyl)-1-phosphocholine-dihydrosphingosine | MetBuilder | N-(10Z,13Z,16Z-Docosenoyl)-1-phosphocholine-D-erythro-sphinganine | MetBuilder |
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Chemical Formula | C45H85N2O6P |
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Average Molecular Mass | 781.140 g/mol |
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Monoisotopic Mass | 780.615 g/mol |
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CAS Registry Number | Not Available |
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IUPAC Name | (2-{[(2S,3R,4E)-2-[(10Z,13Z,16Z)-docosa-10,13,16-trienamido]-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium |
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Traditional Name | (2-{[(2S,3R,4E)-2-[(10Z,13Z,16Z)-docosa-10,13,16-trienamido]-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium |
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SMILES | CCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCC\C=C/C\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C45H85N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-27-29-31-33-35-37-39-45(49)46-43(42-53-54(50,51)52-41-40-47(3,4)5)44(48)38-36-34-32-30-28-26-19-17-15-13-11-9-7-2/h14,16,20-21,23-24,36,38,43-44,48H,6-13,15,17-19,22,25-35,37,39-42H2,1-5H3,(H-,46,49,50,51)/b16-14-,21-20-,24-23-,38-36+/t43-,44+/m0/s1 |
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InChI Key | YTQGMICAWXIKQI-OIMFMVRSSA-N |
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Chemical Taxonomy |
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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
- Phosphocholine
- Phosphoethanolamine
- Dialkyl phosphate
- Fatty amide
- N-acyl-amine
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Fatty acyl
- Alkyl phosphate
- Tetraalkylammonium salt
- Quaternary ammonium salt
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxamide group
- Carboxylic acid derivative
- Organic zwitterion
- Alcohol
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- Amine
- Organic salt
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001s-6021191400-557ab4f38846192585b9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-2161191000-e8ddd0e535990eddb776 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0019-7092002100-416f5929569024596c7e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0000002900-b481cc5dc0793e7568ae | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-2025149400-92a80422f0b7499c6608 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0059-9137020000-98df2cfb2cd00650eab4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0600000900-439c211144ee1643a11e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0600000900-439c211144ee1643a11e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-0900000300-0be8560f723dfe5abeb2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0000001900-f50cae3af91435376f21 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ue0-0000007900-e5e7b187daad04a4b8f9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-0000039300-7d0b50ab5745ea11438f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0000000900-d0a8ce956fa8a5c76189 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0000001900-8ba6482033b3c0fcd8fb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9010301000-5aad112432764041bbc3 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0000001190-447388101896927c60d3 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ur0-0000009290-6006512be3a0badac22e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-0000039110-df7ab7feb7903afd44d9 | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0013468 |
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FooDB ID | FDB029468 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | Not Available |
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BioCyc ID | Not Available |
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METLIN ID | Not Available |
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PDB ID | Not Available |
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Wikipedia Link | Not Available |
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Chemspider ID | Not Available |
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ChEBI ID | 90002 |
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PubChem Compound ID | 53481789 |
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Kegg Compound ID | C00550 |
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YMDB ID | Not Available |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | |
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