Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-27 00:13:49 UTC |
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Update Date | 2016-11-09 01:22:18 UTC |
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Accession Number | CHEM040631 |
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Identification |
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Common Name | SM(d18:1/12:0) |
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Class | Small Molecule |
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Description | SM(d18:1/12:0) (d18:1/12:0) or SM(d18:1/12:0) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. In humans, SM(d18:1/12:0) 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(d18:1/12:0) 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(d18:1/12:0) pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down SM(d18:1/12:0) into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be SM(d18:1/12:0) present there. SM(d18:1/12:0) 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(d18:1/12:0) 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(d18:1/12:0) synthase. |
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Contaminant Sources | |
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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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C12 Sphingomyelin | HMDB | N-(Dodecanoyl)-sphing-4-enine-1-phosphocholine | HMDB | N-Lauroyl-D-erythro-sphingosylphosphoryl choline | HMDB | Sphingomyelin | HMDB | N-(Dodecanoyl)-1-phosphocholine-sphing-4-enine | HMDB | Sphingomyelin(D18:1/12:0) | HMDB | N-(Dodecanoyl)-1-phosphocholine-sphingosine | HMDB | N-(Dodecanoyl)-1-phosphocholine-D-erythro-sphingosine | HMDB | N-(Dodecanoyl)-1-phosphocholine-4-sphingenine | HMDB | N-(Dodecanoyl)-1-phosphocholine-D-sphingosine | HMDB | N-(Dodecanoyl)-1-phosphocholine-sphingenine | HMDB | N-(Dodecanoyl)-1-phosphocholine-erythro-4-sphingenine | HMDB |
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Chemical Formula | C35H71N2O6P |
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Average Molecular Mass | 646.922 g/mol |
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Monoisotopic Mass | 646.505 g/mol |
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CAS Registry Number | Not Available |
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IUPAC Name | (2-{[(2S,3R,4E)-2-dodecanamido-3-hydroxyoctadec-4-en-1-yl phosphonato]oxy}ethyl)trimethylazanium |
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Traditional Name | (2-{[(2S,3R,4E)-2-dodecanamido-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)CCCCCCCCCCC |
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InChI Identifier | InChI=1S/C35H71N2O6P/c1-6-8-10-12-14-16-17-18-19-21-22-24-26-28-34(38)33(32-43-44(40,41)42-31-30-37(3,4)5)36-35(39)29-27-25-23-20-15-13-11-9-7-2/h26,28,33-34,38H,6-25,27,29-32H2,1-5H3,(H-,36,39,40,41)/b28-26+/t33-,34+/m0/s1 |
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InChI Key | HZCLJRFPXMKWHR-FEBLJDHQSA-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 | |
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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 GC-MS | Predicted GC-MS Spectrum - GC-MS ("SM(d18:1/12:0),1TMS,#1" TMS) - 70eV, Positive | Not Available | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0000119000-12f4f78497383af17795 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ur0-0000929000-cbbf7f7c9506460209a7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-0000911000-a347a0296da95f64c821 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000t-0600009000-9c9626f7c1d63d175cd9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000t-0600009000-9c9626f7c1d63d175cd9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-0900003000-e3fb6ca76868e3afa231 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0000109000-74d018f89dc6c564894e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0150-0000709000-9694df1aa7fbefb3e9da | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-0000902000-730d818f9723522cedd3 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0000009000-f1196e26f70d6c4e696c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0000029000-bf385d595383fb327983 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9103010000-f9506ae49d896ecfc7eb | 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 | HMDB0012096 |
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FooDB ID | FDB028763 |
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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 | 24846872 |
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ChEBI ID | 17636 |
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PubChem Compound ID | 44260123 |
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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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