1.0 2018-09-13 16:16:46 UTC 2020-06-04 19:21:37 UTC BMDB0063567 BMDB63567 SM(d18:0/18:2(9Z,12Z)) SM(d18:0/18:2(9Z,12Z)) is a sphingomyelin (SM). Sphingomyelins are members of the class of compounds known as sphingolipids (SPs), or glycosylceramides. SPs are lipids containing a backbone of sphingoid bases (e.g. sphingosine or sphinganine) that are often covalently bound to a fatty acid derivative through N-acylation. SPs are found in cell membranes, particularly in peripheral nerve cells and the cells found in the central nervous system (including the brain and spinal cord). Sphingolipids are extremely versatile molecules that have functions controlling fundamental cellular processes such as cell division, differentiation, and cell death. Impairments associated with sphingolipid metabolism are associated with many common human diseases such as diabetes, various cancers, microbial infections, diseases of the cardiovascular and respiratory systems, Alzheimer’s disease and other neurological syndromes. The biosynthesis and catabolism of sphingolipids involves a large number of intermediate metabolites where many different enzymes are involved. Simple sphingolipids, which include the sphingoid bases and ceramides, make up the early products of the sphingolipid synthetic pathways, while complex sphingolipids may be formed by the addition of head groups to the ceramide template (Wikipedia). SM is the major sphingolipid in mammals it is found in animal cell membranes, especially in the membranous myelin sheath that surrounds some nerve cell axons. It usually consists of phosphocholine and ceramide, or a phosphoethanolamine head group. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. SM 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. In terms of its appearance and structure, SM(d18:0/18:2(9Z,12Z)) consists of a saturated 18-carbon sphingoid base with an attached unsaturated 9Z,12Z-octadecadienoyl fatty acid side chain. In most mammalian SPs, the 18-carbon sphingoid bases are predominant (PMID: 9759481). Sphingomyelin N-(9Z,12Z-Octadecadienoyl)-1-phosphocholine-sphinganine Sphingomyelin(D18:0/18:2(9Z,12Z)) N-(9Z,12Z-Octadecadienoyl)-1-phosphocholine-dihydrosphingosine N-(9Z,12Z-Octadecadienoyl)-1-phosphocholine-D-erythro-sphinganine C41H81N2O6P 729.081 728.583225334 (2-{[(2S,3R)-3-hydroxy-2-[(9Z,12Z)-octadeca-9,12-dienamido]octadecyl phosphono]oxy}ethyl)trimethylazanium (2-{[(2S,3R)-3-hydroxy-2-[(9Z,12Z)-octadeca-9,12-dienamido]octadecyl phosphono]oxy}ethyl)trimethylazanium [H][C@@](COP([O-])(=O)OCC[N+](C)(C)C)(NC(=O)CCCCCCC\C=C/C\C=C/CCCCC)[C@H](O)CCCCCCCCCCCCCCC InChI=1S/C41H81N2O6P/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/h14,16,20-21,39-40,44H,6-13,15,17-19,22-38H2,1-5H3,(H-,42,45,46,47)/b16-14-,21-20-/t39-,40+/m0/s1 LOHIJJRFCAEEGY-QPYJHBIRSA-N belongs to the class of organic compounds known as sphingomyelins. These are sphingolipids containing a backbone formed of an alcohol - sphingosine, a phosphate group, a choline and fatty acid chain. Organic compounds Lipids and lipid-like molecules Sphingolipids Phosphosphingolipids Sphingomyelins Amines Carbonyl compounds Dialkyl phosphates Hydrocarbon derivatives N-acyl amines Organic oxides Organic salts Organic zwitterions Organopnictogen compounds Phosphocholines Phosphoethanolamines Secondary alcohols Secondary carboxylic acid amides Tetraalkylammonium salts Alcohol Aliphatic acyclic compound Alkyl phosphate Amine Carbonyl group Carboxamide group Carboxylic acid derivative Ceramide phosphocholine Dialkyl phosphate Fatty acyl Fatty amide Hydrocarbon derivative N-acyl-amine 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 Quaternary ammonium salt Secondary alcohol Secondary carboxylic acid amide Tetraalkylammonium salt Aliphatic acyclic compounds Ceramide phosphocholines (sphingomyelins) logp 5.31 ALOGPS logs -7.41 ALOGPS logp 7.35 ChemAxon pka_strongest_acidic 1.87 ChemAxon pka_strongest_basic -1 ChemAxon iupac (2-{[(2S,3R)-3-hydroxy-2-[(9Z,12Z)-octadeca-9,12-dienamido]octadecyl phosphono]oxy}ethyl)trimethylazanium ChemAxon average_mass 729.081 ChemAxon mono_mass 728.583225334 ChemAxon smiles [H][C@@](COP([O-])(=O)OCC[N+](C)(C)C)(NC(=O)CCCCCCC\C=C/C\C=C/CCCCC)[C@H](O)CCCCCCCCCCCCCCC ChemAxon formula C41H81N2O6P ChemAxon inchi InChI=1S/C41H81N2O6P/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/h14,16,20-21,39-40,44H,6-13,15,17-19,22-38H2,1-5H3,(H-,42,45,46,47)/b16-14-,21-20-/t39-,40+/m0/s1 ChemAxon inchikey LOHIJJRFCAEEGY-QPYJHBIRSA-N ChemAxon polar_surface_area 107.92 ChemAxon refractivity 224.41 ChemAxon polarizability 91.2 ChemAxon rotatable_bond_count 37 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Milk 0.181 +/- 0.003 uM Commercial skim milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.163 +/- 0.002 uM Commercial 1% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.17 +/- 0.01 uM Commercial 2% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 0.21 +/- 0.01 uM Commercial 3.25% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 FDB097428 113381518 52931159 Dickson RC: Sphingolipid functions in Saccharomyces cerevisiae: comparison to mammals. Annu Rev Biochem. 1998;67:27-48. doi: 10.1146/annurev.biochem.67.1.27. 9759481