1.02011-09-21 01:56:14 UTC2019-11-26 03:21:31 UTCFDB029463SM(d18:0/16:1(9Z)(OH))Sphingomyelin (d18:0/16:1(9Z)(OH)) or SM(d18:0/16:1(9Z)(OH))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, 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]C16:1-OH SphingomyelinC39H77N2O7P717.0116716.54683934(2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-3-hydroxyhexadec-9-enamido]octadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazanium(2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-3-hydroxyhexadec-9-enamido]octadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazaniumCCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CC(O)CCCCC\C=C/CCCCCCInChI=1S/C39H77N2O7P/c1-6-8-10-12-14-16-18-19-21-23-25-27-29-31-38(43)37(35-48-49(45,46)47-33-32-41(3,4)5)40-39(44)34-36(42)30-28-26-24-22-20-17-15-13-11-9-7-2/h17,20,29,31,36-38,42-43H,6-16,18-19,21-28,30,32-35H2,1-5H3,(H-,40,44,45,46)/b20-17-,31-29+/t36?,37-,38+/m0/s1LPHMSPONPQCKTL-FKUNDBCPSA-N 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.PhosphosphingolipidsOrganic compoundsLipids and lipid-like moleculesSphingolipidsPhosphosphingolipidsAliphatic acyclic compoundsAminesCarbonyl compoundsDialkyl phosphatesHydrocarbon derivativesN-acyl aminesOrganic oxidesOrganic saltsOrganic zwitterionsOrganopnictogen compoundsPhosphocholinesPhosphoethanolaminesSecondary alcoholsSecondary carboxylic acid amidesTetraalkylammonium saltsAlcoholAliphatic acyclic compoundAlkyl phosphateAmineCarbonyl groupCarboxamide groupCarboxylic acid derivativeDialkyl phosphateFatty acylFatty amideHydrocarbon derivativeN-acyl-amineOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganic phosphoric acid derivativeOrganic saltOrganic zwitterionOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPhosphocholinePhosphoethanolaminePhosphoric acid esterQuaternary ammonium saltSecondary alcoholSecondary carboxylic acid amideSphingoid-1-phosphate or derivativesTetraalkylammonium saltSolidlogp4.38logs-7.20solubility4.84e-05 g/llogp5.38pka_strongest_acidic1.86pka_strongest_basic-1.5iupac(2-{[(2S,3R,4E)-3-hydroxy-2-[(9Z)-3-hydroxyhexadec-9-enamido]octadec-4-en-1-yl phosphono]oxy}ethyl)trimethylazaniumaverage_mass717.0116mono_mass716.54683934smilesCCCCCCCCCCCCC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CC(O)CCCCC\C=C/CCCCCCformulaC39H77N2O7PinchiInChI=1S/C39H77N2O7P/c1-6-8-10-12-14-16-18-19-21-23-25-27-29-31-38(43)37(35-48-49(45,46)47-33-32-41(3,4)5)40-39(44)34-36(42)30-28-26-24-22-20-17-15-13-11-9-7-2/h17,20,29,31,36-38,42-43H,6-16,18-19,21-28,30,32-35H2,1-5H3,(H-,40,44,45,46)/b20-17-,31-29+/t36?,37-,38+/m0/s1inchikeyLPHMSPONPQCKTL-FKUNDBCPSA-Npolar_surface_area128.15refractivity216.57polarizability87.13rotatable_bond_count35acceptor_count5donor_count3physiological_charge0formal_charge0Specdb::CMs759030Specdb::CMs759031Specdb::CMs759032Specdb::CMs759033Specdb::CMs759034Specdb::CMs759035Specdb::CMs759036Specdb::CMs759037Specdb::CMs759038Specdb::MsMs291706Specdb::MsMs291707Specdb::MsMs291708Specdb::MsMs331696Specdb::MsMs331697Specdb::MsMs331698Specdb::MsMs2431501Specdb::MsMs2431502Specdb::MsMs2431503Specdb::MsMs2762764Specdb::MsMs2762765Specdb::MsMs2762766Specdb::MsMs2859422Specdb::MsMs2859423Specdb::MsMs2859424Specdb::MsMs2946873Specdb::MsMs2946874Specdb::MsMs2946875HMDB13463AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930Cow milk, pasteurized, vitamin A + D added, 0% fatType 2specificCow milk, pasteurized, vitamin A + D added, 1% fatType 2specificCow milk, pasteurized, vitamin A + D added, 2% fatType 2specificCow milk, pasteurized, vitamin D added, 3.25% fatType 2specificDeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823Antigen-presenting glycoprotein CD1dP15813CD1DBeta-1,3-galactosyltransferase 5Q9Y2C3B3GALT5Epididymal secretory protein E1P61916NPC2Ganglioside GM2 activatorP17900GM2AGPI ethanolamine phosphate transferase 1O95427PIGNGPI ethanolamine phosphate transferase 2Q5H8A4PIGGGPI ethanolamine phosphate transferase 3Q8TEQ8PIGOGPI mannosyltransferase 1Q9H3S5PIGMGPI mannosyltransferase 2Q9NUD9PIGVGPI mannosyltransferase 3Q92521PIGBGPI mannosyltransferase 4Q86VD9PIGZGPI transamidase component PIG-SQ96S52PIGSGPI transamidase component PIG-TQ969N2PIGTGPI-anchor transamidaseQ92643PIGKLactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferaseQ9BYG0B3GNT5N-acetylglucosaminyl-phosphatidylinositol de-N-acetylaseQ9Y2B2PIGLNon-lysosomal glucosylceramidaseQ9HCG7GBA2Phosphatidylcholine:ceramide cholinephosphotransferase 1Q86VZ5SGMS1Phosphatidylcholine:ceramide cholinephosphotransferase 2Q8NHU3SGMS2Phosphatidylinositol glycan anchor biosynthesis class U proteinQ9H490PIGUPhosphatidylinositol N-acetylglucosaminyltransferase subunit AP37287PIGAPhosphatidylinositol N-acetylglucosaminyltransferase subunit CQ92535PIGCPhosphatidylinositol N-acetylglucosaminyltransferase subunit HQ14442PIGHPhosphatidylinositol N-acetylglucosaminyltransferase subunit PP57054PIGPPhosphatidylinositol N-acetylglucosaminyltransferase subunit QQ9BRB3PIGQPhosphatidylinositol N-acetylglucosaminyltransferase subunit YQ3MUY2PIGYPhosphatidylinositol-glycan biosynthesis class F proteinQ07326PIGFPhosphatidylinositol-glycan biosynthesis class W proteinQ7Z7B1PIGWPhosphatidylinositol-glycan biosynthesis class X proteinQ8TBF5PIGXProactivator polypeptideP07602PSAPSphingomyelin phosphodiesteraseP17405SMPD1T-cell surface glycoprotein CD1e, membrane-associatedP15812CD1E