1.0 2016-10-03 18:32:13 UTC 2020-06-04 19:49:43 UTC BMDB0012095 BMDB12095 SM(d22:0/20:1(11Z)) SM(D18:0/24:1(15Z)), also known as C24:1DH sphingomyelin or SM(D18:0/24:1), 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. Thus, SM(D18:0/24:1(15Z)) is considered to be a phosphosphingolipid lipid molecule. SM(D18:0/24:1(15Z)) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Sphingomyelin N-(11Z-Eicosenoyl)-1-phosphocholine-docosasphinganine Sphingomyelin(D22:0/20:1(11Z)) N-(11Z-Eicosenoyl)-1-phosphocholine-docosadihydrosphingosine N-(11Z-Eicosenoyl)-1-phosphocholine-docosad-erythro-sphinganine C47H95N2O6P 815.259 814.692775785 (2-{[(2S)-3-hydroxy-2-[(11Z)-icos-11-enamido]docosyl phosphono]oxy}ethyl)trimethylazanium (2-{[(2S)-3-hydroxy-2-[(11Z)-icos-11-enamido]docosyl phosphono]oxy}ethyl)trimethylazanium CCCCCCCCCCCCCCCCCCCC(O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCC\C=C/CCCCCCCC InChI=1S/C47H95N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-46(50)45(44-55-56(52,53)54-43-42-49(3,4)5)48-47(51)41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h21,23,45-46,50H,6-20,22,24-44H2,1-5H3,(H-,48,51,52,53)/b23-21-/t45-,46?/m0/s1 RQSNQPLHLROUTM-ORMDINQLSA-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. Organic compounds Lipids and lipid-like molecules Sphingolipids Phosphosphingolipids Phosphosphingolipids Amines Carboximidic acids Dialkyl phosphates Hydrocarbon derivatives Organic oxides Organic salts Organic zwitterions Organopnictogen compounds Phosphocholines Propargyl-type 1,3-dipolar organic compounds Secondary alcohols Tetraalkylammonium salts Alcohol Aliphatic acyclic compound Alkyl phosphate Amine Carboximidic acid Carboximidic acid derivative Dialkyl phosphate Hydrocarbon derivative Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic salt Organic zwitterion Organonitrogen compound Organooxygen compound Organopnictogen compound Phosphocholine Phosphoric acid ester Propargyl-type 1,3-dipolar organic compound Quaternary ammonium salt Secondary alcohol Sphingoid-1-phosphate or derivatives Tetraalkylammonium salt Aliphatic acyclic compounds Solid logp 6.23 ALOGPS logs -7.50 ALOGPS logp 10.38 ChemAxon pka_strongest_acidic 1.87 ChemAxon pka_strongest_basic -1 ChemAxon iupac (2-{[(2S)-3-hydroxy-2-[(11Z)-icos-11-enamido]docosyl phosphono]oxy}ethyl)trimethylazanium ChemAxon average_mass 815.259 ChemAxon mono_mass 814.692775785 ChemAxon smiles CCCCCCCCCCCCCCCCCCCC(O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCCCC\C=C/CCCCCCCC ChemAxon formula C47H95N2O6P ChemAxon inchi InChI=1S/C47H95N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-38-40-46(50)45(44-55-56(52,53)54-43-42-49(3,4)5)48-47(51)41-39-37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h21,23,45-46,50H,6-20,22,24-44H2,1-5H3,(H-,48,51,52,53)/b23-21-/t45-,46?/m0/s1 ChemAxon inchikey RQSNQPLHLROUTM-ORMDINQLSA-N ChemAxon polar_surface_area 107.92 ChemAxon refractivity 250.9 ChemAxon polarizability 104.99 ChemAxon rotatable_bond_count 44 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 Specdb::MsMs 1220134 Specdb::MsMs 1220135 Specdb::MsMs 1220136 Specdb::MsMs 1335826 Specdb::MsMs 1335827 Specdb::MsMs 1335828 Milk 3.1 +/- 0.1 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 3.5 +/- 0.1 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 4.34 +/- 0.02 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 Milk 3.57 +/- 0.02 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 FDB098085 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)