1.0 2011-09-21 01:44:21 UTC 2015-07-21 06:59:31 UTC FDB028751 LysoSM(d18:0) Sphingomyelin (d18:0/0:0) or LysoSM(d18:0)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. 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] SM(d18:0/0:0) Sphinganine-1-ocholine sphinganine-1-phosphocholine Sphingomyelin(d18:0/0:0) C23H51N2O5P 466.6352 466.353559264 (2-{[(2S,3R)-2-amino-3-hydroxyoctadecyl phosphonato]oxy}ethyl)trimethylazanium (2-{[(2S,3R)-2-amino-3-hydroxyoctadecyl phosphonato]oxy}ethyl)trimethylazanium CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)COP([O-])(=O)OCC[N+](C)(C)C InChI=1S/C23H51N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h22-23,26H,5-21,24H2,1-4H3/t22-,23+/m0/s1 GSEOJHIBPQRSNH-XZOQPEGZSA-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. Phosphosphingolipids Organic compounds Lipids and lipid-like molecules Sphingolipids Phosphosphingolipids Aliphatic acyclic compounds 1,2-aminoalcohols Dialkyl phosphates Hydrocarbon derivatives Monoalkylamines Organic oxides Organic salts Organic zwitterions Organopnictogen compounds Phosphocholines Phosphoethanolamines Secondary alcohols Tetraalkylammonium salts 1,2-aminoalcohol Alcohol Aliphatic acyclic compound Alkyl phosphate Amine Dialkyl phosphate Hydrocarbon derivative Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic salt Organic zwitterion Organonitrogen compound Organooxygen compound Organopnictogen compound Phosphocholine Phosphoethanolamine Phosphoric acid ester Primary aliphatic amine Primary amine Quaternary ammonium salt Secondary alcohol Sphingoid-1-phosphate or derivatives Tetraalkylammonium salt Lysosphingomyelins and lysoglycosphingolipids Solid logp 1.72 ALOGPS logs -5.87 ALOGPS solubility 7.04e-04 g/l ALOGPS logp -0.047 ChemAxon pka_strongest_acidic 1.83 ChemAxon pka_strongest_basic 9.73 ChemAxon iupac (2-{[(2S,3R)-2-amino-3-hydroxyoctadecyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon average_mass 466.6352 ChemAxon mono_mass 466.353559264 ChemAxon smiles CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)COP([O-])(=O)OCC[N+](C)(C)C ChemAxon formula C23H51N2O5P ChemAxon inchi InChI=1S/C23H51N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h22-23,26H,5-21,24H2,1-4H3/t22-,23+/m0/s1 ChemAxon inchikey GSEOJHIBPQRSNH-XZOQPEGZSA-N ChemAxon polar_surface_area 104.84 ChemAxon refractivity 139.1 ChemAxon polarizability 56.39 ChemAxon rotatable_bond_count 22 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 39811 Specdb::CMs 132975 Specdb::CMs 140709 Specdb::MsMs 2831980 Specdb::MsMs 2831981 Specdb::MsMs 2831982 Specdb::MsMs 2850028 Specdb::MsMs 2850029 Specdb::MsMs 2850030 Specdb::NmrOneD 95338 Specdb::NmrOneD 95339 Specdb::NmrOneD 95340 Specdb::NmrOneD 95341 Specdb::NmrOneD 95342 Specdb::NmrOneD 95343 Specdb::NmrOneD 95344 Specdb::NmrOneD 95345 Specdb::NmrOneD 95346 Specdb::NmrOneD 95347 Specdb::NmrOneD 95348 Specdb::NmrOneD 95349 Specdb::NmrOneD 95350 Specdb::NmrOneD 95351 Specdb::NmrOneD 95352 Specdb::NmrOneD 95353 Specdb::NmrOneD 95354 Specdb::NmrOneD 95355 Specdb::NmrOneD 95356 Specdb::NmrOneD 95357 HMDB12082 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Non-lysosomal glucosylceramidase Q9HCG7 GBA2 Proactivator polypeptide P07602 PSAP Sphingomyelin phosphodiesterase P17405 SMPD1