Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 20:36:50 UTC |
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Update Date | 2016-11-09 01:22:15 UTC |
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Accession Number | CHEM040424 |
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Identification |
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Common Name | SM(d18:1/24:0) |
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Class | Small Molecule |
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Description | SM(d18:1/24:0) or SM(d18:1/24:0) is a sphingomyelin. SM(d18:1/24:0) (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, SM(d18:1/24:0) 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(d18:1/24:0) 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(d18:1/24:0) pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down SM(d18:1/24:0) into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be SM(d18:1/24:0) present there. SM(d18:1/24:0) 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(d18:1/24:0) 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(d18:1/24:0) 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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SPH(D18:1/24:0) | HMDB | Sphingomyelin (D18:1/24:0) | HMDB | Sphingomyelin | HMDB | N-(Tetracosanoyl)-1-phosphocholine-sphing-4-enine | HMDB | Sphingomyelin(D18:1/24:0) | HMDB | N-(Tetracosanoyl)-1-phosphocholine-sphingosine | HMDB | N-(Tetracosanoyl)-1-phosphocholine-D-erythro-sphingosine | HMDB | N-(Tetracosanoyl)-1-phosphocholine-4-sphingenine | HMDB | N-(Tetracosanoyl)-1-phosphocholine-D-sphingosine | HMDB | N-(Tetracosanoyl)-1-phosphocholine-sphingenine | HMDB | N-(Tetracosanoyl)-1-phosphocholine-erythro-4-sphingenine | HMDB | 24:0 Sphingomyelin | HMDB | C24-Sphingomyelin | HMDB | Lignoceroyl sphingomyelin | HMDB | SM d18:1/24:0 | HMDB | SM(d18:1/24:0) | HMDB | Sphingomyelin (d18:1,C24:0) | HMDB | Sphingomyelin C24:0 | HMDB |
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Chemical Formula | C47H96N2O6P |
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Average Molecular Mass | 816.249 g/mol |
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Monoisotopic Mass | 815.701 g/mol |
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CAS Registry Number | Not Available |
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IUPAC Name | {[(2S,3R,4E)-3-hydroxy-2-tetracosanamidooctadec-4-en-1-yl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid |
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Traditional Name | [(2S,3R,4E)-3-hydroxy-2-tetracosanamidooctadec-4-en-1-yl]oxy(2-(trimethylammonio)ethoxy)phosphinic acid |
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SMILES | CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@]([H])(COP(O)(=O)OCC[N+](C)(C)C)[C@]([H])(O)\C=C\CCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C47H95N2O6P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-26-27-29-31-33-35-37-39-41-47(51)48-45(44-55-56(52,53)54-43-42-49(3,4)5)46(50)40-38-36-34-32-30-28-19-17-15-13-11-9-7-2/h38,40,45-46,50H,6-37,39,41-44H2,1-5H3,(H-,48,51,52,53)/p+1/b40-38+/t45-,46+/m0/s1 |
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InChI Key | QEDPUVGSSDPBMD-XTAIVQBESA-O |
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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 salt
- Amine
- Alcohol
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- 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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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 | Not Available |
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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 | HMDB0011697 |
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FooDB ID | FDB028383 |
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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 | 4446708 |
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ChEBI ID | Not Available |
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PubChem Compound ID | 5283595 |
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Kegg Compound ID | Not Available |
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YMDB ID | YMDB01549 |
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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 | 1. Ding J, Sorensen CM, Jaitly N, Jiang H, Orton DJ, Monroe ME, Moore RJ, Smith RD, Metz TO: Application of the accurate mass and time tag approach in studies of the human blood lipidome. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Aug 15;871(2):243-52. doi: 10.1016/j.jchromb.2008.04.040. Epub 2008 May 7. | 2. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. | 3. Hannun YA: The sphingomyelin cycle and the second messenger function of ceramide. J Biol Chem. 1994 Feb 4;269(5):3125-8. | 4. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. | 5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. | 6. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. | 7. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. | 8. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. | 9. Phospholipids Handbook | 10. The lipid handbook with CD-ROM |
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