Record Information |
---|
Version | 1.0 |
---|
Creation Date | 2016-05-25 18:31:28 UTC |
---|
Update Date | 2016-11-09 01:17:30 UTC |
---|
Accession Number | CHEM022402 |
---|
Identification |
---|
Common Name | SM(d18:1/18:0) |
---|
Class | Small Molecule |
---|
Description | SM(d18:1/18:0) (d18:1/18:0) or SM(d18:1/18:0) 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(18:1/18:0) consists of oleic acid attached to the C1 position and stearic acid attached to the C2 position. In humans, SM(d18:1/18:0) 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(d18:1/18:0) 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(d18:1/18:0) pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2 - an enzyme that breaks down SM(d18:1/18:0) into ceramide has been found to localise exclusively to the inner leaflet further suggesting that there may be SM(d18:1/18:0) present there. SM(d18:1/18:0) 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(d18:1/18:0) 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(d18:1/18:0) synthase. |
---|
Contaminant Sources | - FooDB Chemicals
- HMDB Contaminants - Urine
|
---|
Contaminant Type | Not Available |
---|
Chemical Structure | |
---|
Synonyms | Value | Source |
---|
N-(Octadecanoyl)-sphing-4-enine-1-phosphocholine | HMDB | N-Acyl-4-sphingenyl-1-O-phosphorylcholine | HMDB | N-Acyl-D-sphingosine-1-phosphocholine | HMDB | Sphingomyelin | HMDB | Sphingomyelin (D18:1/18:0) | HMDB | N-(Octadecanoyl)-1-phosphocholine-sphing-4-enine | HMDB | Sphingomyelin(D18:1/18:0) | HMDB | N-(Octadecanoyl)-1-phosphocholine-sphingosine | HMDB | N-(Octadecanoyl)-1-phosphocholine-D-erythro-sphingosine | HMDB | N-(Octadecanoyl)-1-phosphocholine-4-sphingenine | HMDB | N-(Octadecanoyl)-1-phosphocholine-D-sphingosine | HMDB | N-(Octadecanoyl)-1-phosphocholine-sphingenine | HMDB | N-(Octadecanoyl)-1-phosphocholine-erythro-4-sphingenine | HMDB |
|
---|
Chemical Formula | C41H84N2O6P |
---|
Average Molecular Mass | 732.089 g/mol |
---|
Monoisotopic Mass | 731.607 g/mol |
---|
CAS Registry Number | 85187-10-6 |
---|
IUPAC Name | {[(2S,3R,4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid |
---|
Traditional Name | [(2S,3R,4E)-3-hydroxy-2-octadecanamidooctadec-4-en-1-yl]oxy(2-(trimethylammonio)ethoxy)phosphinic acid |
---|
SMILES | CCCCCCCCCCCCCCCCCC(=O)N[C@@]([H])(COP(O)(=O)OCC[N+](C)(C)C)[C@]([H])(O)\C=C\CCCCCCCCCCCCC |
---|
InChI Identifier | InChI=1S/C41H83N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h32,34,39-40,44H,6-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/p+1/b34-32+/t39-,40+/m0/s1 |
---|
InChI Key | LKQLRGMMMAHREN-YJFXYUILSA-O |
---|
Chemical Taxonomy |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Sphingolipids |
---|
Sub Class | Phosphosphingolipids |
---|
Direct Parent | Phosphosphingolipids |
---|
Alternative Parents | |
---|
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
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | Not Available |
---|
Biological Properties |
---|
Status | Detected and Not Quantified |
---|
Origin | Not Available |
---|
Cellular Locations | Not Available |
---|
Biofluid Locations | Not Available |
---|
Tissue Locations | Not Available |
---|
Pathways | Not Available |
---|
Applications | Not Available |
---|
Biological Roles | Not Available |
---|
Chemical Roles | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Appearance | Not Available |
---|
Experimental Properties | Property | Value |
---|
Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
|
---|
Predicted Properties | |
---|
Spectra |
---|
Spectra | Spectrum Type | Description | Splash Key | View |
---|
LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-001i-0200000900-e97fc8b60f9884266fe8 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-001i-0900000000-6e6f0a8e64b4641256a7 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-001i-0900000000-57c2d6df417e54414b35 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
|
---|
Toxicity Profile |
---|
Route of Exposure | Not Available |
---|
Mechanism of Toxicity | Not Available |
---|
Metabolism | Not Available |
---|
Toxicity Values | Not Available |
---|
Lethal Dose | Not Available |
---|
Carcinogenicity (IARC Classification) | Not Available |
---|
Uses/Sources | Not Available |
---|
Minimum Risk Level | Not Available |
---|
Health Effects | Not Available |
---|
Symptoms | Not Available |
---|
Treatment | Not Available |
---|
Concentrations |
---|
| Not Available |
---|
External Links |
---|
DrugBank ID | Not Available |
---|
HMDB ID | HMDB0001348 |
---|
FooDB ID | FDB022570 |
---|
Phenol Explorer ID | Not Available |
---|
KNApSAcK ID | Not Available |
---|
BiGG ID | Not Available |
---|
BioCyc ID | Not Available |
---|
METLIN ID | 176 |
---|
PDB ID | Not Available |
---|
Wikipedia Link | Not Available |
---|
Chemspider ID | 4446701 |
---|
ChEBI ID | 17636 |
---|
PubChem Compound ID | 5283588 |
---|
Kegg Compound ID | C00550 |
---|
YMDB ID | YMDB01546 |
---|
ECMDB ID | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
MSDS | Not Available |
---|
General References | 1. Harzer K, Massenkeil G, Frohlich E: Concurrent increase of cholesterol, sphingomyelin and glucosylceramide in the spleen from non-neurologic Niemann-Pick type C patients but also patients possibly affected with other lipid trafficking disorders. FEBS Lett. 2003 Feb 27;537(1-3):177-81. | 2. He X, Chen F, McGovern MM, Schuchman EH: A fluorescence-based, high-throughput sphingomyelin assay for the analysis of Niemann-Pick disease and other disorders of sphingomyelin metabolism. Anal Biochem. 2002 Jul 1;306(1):115-23. | 3. Reichl D, Sterchi JM: Human peripheral lymph lipoproteins are enriched in sphingomyelin. Biochim Biophys Acta. 1992 Jul 9;1127(1):28-32. | 4. Nelson JC, Jiang XC, Tabas I, Tall A, Shea S: Plasma sphingomyelin and subclinical atherosclerosis: findings from the multi-ethnic study of atherosclerosis. Am J Epidemiol. 2006 May 15;163(10):903-12. Epub 2006 Apr 12. | 5. Chen H, Born E, Mathur SN, Johlin FC Jr, Field FJ: Sphingomyelin content of intestinal cell membranes regulates cholesterol absorption. Evidence for pancreatic and intestinal cell sphingomyelinase activity. Biochem J. 1992 Sep 15;286 ( Pt 3):771-7. | 6. Liu KZ, Mantsch HH: Simultaneous quantitation from infrared spectra of glucose concentrations, lactate concentrations, and lecithin/sphingomyelin ratios in amniotic fluid. Am J Obstet Gynecol. 1999 Mar;180(3 Pt 1):696-702. | 7. Horter MJ, Sondermann S, Reinecke H, Bogdanski J, Woltering A, Kerber S, Breithardt G, Assmann G, Von Eckardstein A: Associations of HDL phospholipids and paraoxonase activity with coronary heart disease in postmenopausal women. Acta Physiol Scand. 2002 Oct;176(2):123-30. | 8. Tanaka K, Nishizawa K, Yamamoto H, Naruto T, Izeki E, Taga T, Shimada M, Saeki Y: Analysis of very long-chain fatty acids and plasmalogen in the erythrocyte membrane: a simple method for the detection of peroxisomal disorders and discrimination between adrenoleukodystrophy and Zellweger syndrome. Neuropediatrics. 1990 Aug;21(3):119-23. | 9. Cribier S, Morrot G, Neumann JM, Devaux PF: Lateral diffusion of erythrocyte phospholipids in model membranes comparison between inner and outer leaflet components. Eur Biophys J. 1990;18(1):33-41. | 10. Nyberg L, Duan RD, Axelson J, Nilsson A: Identification of an alkaline sphingomyelinase activity in human bile. Biochim Biophys Acta. 1996 Mar 29;1300(1):42-8. | 11. Whitworth NS, Magann EF, Morrison JC: Evaluation of fetal lung maturity in diamniotic twins. Am J Obstet Gynecol. 1999 Jun;180(6 Pt 1):1438-41. | 12. de Oliveira JS, Zaharenko AJ, de Freitas JC, Konno K, de Andrade SA, Portaro FC, Richardson M, Sant'anna OA, Tambourgi DV: Caissarolysin I (Bcs I), a new hemolytic toxin from the Brazilian sea anemone Bunodosoma caissarum: purification and biological characterization. Biochim Biophys Acta. 2006 Mar;1760(3):453-61. Epub 2006 Jan 17. | 13. Omarini LP, Frank-Burkhardt SE, Seemayer TA, Mentha G, Terrier F: Niemann-Pick disease type C: nodular splenomegaly. Abdom Imaging. 1995 Mar-Apr;20(2):157-60. | 14. Berna L, Asfaw B, Conzelmann E, Cerny B, Ledvinova J: Determination of urinary sulfatides and other lipids by combination of reversed-phase and thin-layer chromatographies. Anal Biochem. 1999 May 1;269(2):304-11. | 15. He X, Chen F, Gatt S, Schuchman EH: An enzymatic assay for quantifying sphingomyelin in tissues and plasma from humans and mice with Niemann-Pick disease. Anal Biochem. 2001 Jun 15;293(2):204-11. | 16. Feki NC, Therond P, Couturier M, Limea G, Legrand A, Jouannet P, Auger J: Human sperm lipid content is modified after migration into human cervical mucus. Mol Hum Reprod. 2004 Feb;10(2):137-42. | 17. Wang C, Yang J, Gao P, Lu X, Xu G: Identification of phospholipid structures in human blood by direct-injection quadrupole-linear ion-trap mass spectrometry. Rapid Commun Mass Spectrom. 2005;19(17):2443-53. | 18. Otterbach B, Stoffel W: Acid sphingomyelinase-deficient mice mimic the neurovisceral form of human lysosomal storage disease (Niemann-Pick disease). Cell. 1995 Jun 30;81(7):1053-61. | 19. Haughey NJ, Cutler RG, Tamara A, McArthur JC, Vargas DL, Pardo CA, Turchan J, Nath A, Mattson MP: Perturbation of sphingolipid metabolism and ceramide production in HIV-dementia. Ann Neurol. 2004 Feb;55(2):257-67. | 20. Fujiwaki T, Yamaguchi S, Tasaka M, Sakura N, Taketomi T: Application of delayed extraction-matrix-assisted laser desorption ionization time-of-flight mass spectrometry for analysis of sphingolipids in pericardial fluid, peritoneal fluid and serum from Gaucher disease patients. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Aug 25;776(1):115-23. |
|
---|