1.0 2011-09-21 01:37:39 UTC 2015-07-21 06:59:22 UTC FDB028306 Lactosylcermide (d18:1/20:0) Lactosylceramide (d18:1/20:0) is a lactosylceramide or LacCer. Lactosylceramides are the most important and abundant of the diosylceramides. Lactosylceramides (LacCer) were originally called 'cytolipin H'. It is found in small amounts only in most animal tissues, but it has a number of significant biological functions and it is of great importance as the biosynthetic precursor of most of the neutral oligoglycosylceramides, sulfatides and gangliosides. In animal tissues, biosynthesis of lactosylceramide involves addition of the second monosaccharides unit (galactose) as its nucleotide derivative to monoglucosylceramide, catalysed by a specific beta-1,4-galactosyltransferase on the lumenal side of the Golgi apparatus. The glucosylceramide precursor must first cross from the cytosolic side of the membrane, possibly via the action of a flippase. The lactosylceramide produced can be further glycosylated or transferred to the plasma membrane. Lactosylceramide may assist in stabilizing the plasma membrane and activating receptor molecules in the special micro-domains or rafts, as with the cerebrosides. It may also have its own specialized function in the immunological system in that it is known to bind to specific bacteria. In addition, it is believed that a number of pro-inflammatory factors activate lactosylceramide synthase to generate lactosylceramide, which in turn activates "oxygen-sensitive" signalling pathways that affect such cellular processes as proliferation, adhesion, migration and angiogenesis. Dysfunctions in these pathways can affect several diseases of the cardiovascular system, cancer and inflammatory states, so lactosylceramide metabolism is a potential target for new therapeutic treatments. beta-D-Galactosyl-1,4-beta-D-glucosylceramide is the second to last step in the synthesis of N-Acylsphingosine and is converted from Glucosylceramide via the enzyme beta-1,4-galactosyltransferase 6(EC:2.4.1.-). It can be converted to Glucosylceramide via the enzyme beta-galactosidase (EC:3.2.1.23). [HMDB] C20 lactosyl ceramide D-Galactosyl-1-beta-delta-glucosylceramide delta-Galactosyl-1-beta-delta-glucosylceramide delta-Galactosyl-1,4er LacC,4-beta-D-glucosylceramide LacC,4-beta-delta-glucosylceramide LacCer(d18:1/20:0) Lactosyl ceramide (d18:1/20:0) N-(eicosanoyl)-1-b-lactosyl-sphing-4-enine N-(eicosanoyl)-1-beta-lactosyl-sphing-4-enine C50H95NO13 918.2882 917.680342131 N-[(2S,3R,4E)-1-{[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]icosanamide N-[(2S,3R,4E)-1-{[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]icosanamide [H][C@@](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)(NC(=O)CCCCCCCCCCCCCCCCCCC)[C@]([H])(O)\C=C\CCCCCCCCCCCCC InChI=1S/C50H95NO13/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-42(55)51-38(39(54)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2)37-61-49-47(60)45(58)48(41(36-53)63-49)64-50-46(59)44(57)43(56)40(35-52)62-50/h31,33,38-41,43-50,52-54,56-60H,3-30,32,34-37H2,1-2H3,(H,51,55)/b33-31+/t38-,39+,40+,41+,43-,44-,45+,46+,47+,48+,49+,50-/m0/s1 FGJIXPPBZNPEHW-CRMMDXJYSA-N belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. 6-aminopurines Organic compounds Organoheterocyclic compounds Imidazopyrimidines Purines and purine derivatives Aromatic heteropolycyclic compounds Aminopyrimidines and derivatives Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives Imidazoles Organopnictogen compounds Primary amines 6-aminopurine Amine Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Azole Heteroaromatic compound Hydrocarbon derivative Imidazole Organic nitrogen compound Organonitrogen compound Organopnictogen compound Primary amine Pyrimidine a small molecule methyladenine Solid logp 6.64 ALOGPS logs -5.30 ALOGPS solubility 4.58e-03 g/l ALOGPS logp 9.1 ChemAxon pka_strongest_acidic 11.92 ChemAxon pka_strongest_basic -3 ChemAxon iupac N-[(2S,3R,4E)-1-{[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxyoctadec-4-en-2-yl]icosanamide ChemAxon average_mass 918.2882 ChemAxon mono_mass 917.680342131 ChemAxon smiles [H][C@@](CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O)(NC(=O)CCCCCCCCCCCCCCCCCCC)[C@]([H])(O)\C=C\CCCCCCCCCCCCC ChemAxon formula C50H95NO13 ChemAxon inchi InChI=1S/C50H95NO13/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-42(55)51-38(39(54)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2)37-61-49-47(60)45(58)48(41(36-53)63-49)64-50-46(59)44(57)43(56)40(35-52)62-50/h31,33,38-41,43-50,52-54,56-60H,3-30,32,34-37H2,1-2H3,(H,51,55)/b33-31+/t38-,39+,40+,41+,43-,44-,45+,46+,47+,48+,49+,50-/m0/s1 ChemAxon inchikey FGJIXPPBZNPEHW-CRMMDXJYSA-N ChemAxon polar_surface_area 227.86 ChemAxon refractivity 249.01 ChemAxon polarizability 111.95 ChemAxon rotatable_bond_count 40 ChemAxon acceptor_count 13 ChemAxon donor_count 9 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 298873 Specdb::MsMs 298874 Specdb::MsMs 298875 Specdb::MsMs 340756 Specdb::MsMs 340757 Specdb::MsMs 340758 Specdb::MsMs 2293164 Specdb::MsMs 2293165 Specdb::MsMs 2293166 Specdb::MsMs 2645469 Specdb::MsMs 2645470 Specdb::MsMs 2645471 HMDB11593 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