1.0 2011-09-21 00:30:27 UTC 2017-03-11 23:00:24 UTC FDB023476 Trihexosylceramide (d18:1/24:1(15Z)) Trihexosylceramide is a glycosphingolipid which contains a trisaccharide (galactose-galactose-glucose) moiety bound in glycosidic linkage to the hydroxyl group of ceramide as the polar head group. It accumulates in tissue due to a defect in ceramide trihexosidase and is the cause of angiokeratoma corporis diffusum (Fabry disease). Although normal human colonic epithelial cells lack the glycosphingolipid globotriaosylceramide (Gb(3)), this molecule is highly expressed in metastatic colon cancer (PubMed ID 16365318 ) [HMDB] Gal-alpha1->4Gal-beta1->4Glc-beta1->1'Cer(d18:1/24:1 C60H111NO18 1134.5192 1133.780115753 (15E)-N-[(4E)-1-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3-hydroxyoctadec-4-en-2-yl]tetracos-15-enamide (15E)-N-[(4E)-1-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3-hydroxyoctadec-4-en-2-yl]tetracos-15-enamide 71965-57-6 CCCCCCCCCCCCC\C=C\C(O)C(COC1OC(CO)C(OC2OC(CO)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)C(O)C1O)NC(=O)CCCCCCCCCCCCC\C=C\CCCCCCCC InChI=1S/C60H111NO18/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-48(66)61-43(44(65)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2)42-74-58-54(72)51(69)56(46(40-63)76-58)79-60-55(73)52(70)57(47(41-64)77-60)78-59-53(71)50(68)49(67)45(39-62)75-59/h17-18,35,37,43-47,49-60,62-65,67-73H,3-16,19-34,36,38-42H2,1-2H3,(H,61,66)/b18-17+,37-35+ FZLJBZZCTNZGFA-YOPMPTLHSA-N belongs to the class of organic compounds known as glycosyl-n-acylsphingosines. Glycosyl-N-acylsphingosines are compounds containing a sphingosine linked to a simple glucosyl moiety. Glycosyl-N-acylsphingosines Organic compounds Lipids and lipid-like molecules Sphingolipids Glycosphingolipids Aliphatic heteromonocyclic compounds Acetals Alkyl glycosides Carbonyl compounds Hydrocarbon derivatives N-acyl amines O-glycosyl compounds Oligosaccharides Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Secondary carboxylic acid amides Acetal Alcohol Aliphatic heteromonocyclic compound Alkyl glycoside Carbonyl group Carboxamide group Carboxylic acid derivative Fatty acyl Fatty acyl glycoside Fatty amide Glycosyl compound Glycosyl-n-acylsphingosine Hydrocarbon derivative N-acyl-amine O-glycosyl compound Oligosaccharide Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol Secondary carboxylic acid amide Solid logp 5.91 ALOGPS logs -5.09 ALOGPS solubility 9.15e-03 g/l ALOGPS logp 8.75 ChemAxon pka_strongest_acidic 11.76 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (15E)-N-[(4E)-1-[(5-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3-hydroxyoctadec-4-en-2-yl]tetracos-15-enamide ChemAxon average_mass 1134.5192 ChemAxon mono_mass 1133.780115753 ChemAxon smiles CCCCCCCCCCCCC\C=C\C(O)C(COC1OC(CO)C(OC2OC(CO)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)C(O)C1O)NC(=O)CCCCCCCCCCCCC\C=C\CCCCCCCC ChemAxon formula C60H111NO18 ChemAxon inchi InChI=1S/C60H111NO18/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-48(66)61-43(44(65)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2)42-74-58-54(72)51(69)56(46(40-63)76-58)79-60-55(73)52(70)57(47(41-64)77-60)78-59-53(71)50(68)49(67)45(39-62)75-59/h17-18,35,37,43-47,49-60,62-65,67-73H,3-16,19-34,36,38-42H2,1-2H3,(H,61,66)/b18-17+,37-35+ ChemAxon inchikey FZLJBZZCTNZGFA-YOPMPTLHSA-N ChemAxon polar_surface_area 307.01 ChemAxon refractivity 300.94 ChemAxon polarizability 134.69 ChemAxon rotatable_bond_count 46 ChemAxon acceptor_count 18 ChemAxon donor_count 12 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 2332250 Specdb::MsMs 2332251 Specdb::MsMs 2332252 Specdb::MsMs 2630828 Specdb::MsMs 2630829 Specdb::MsMs 2630830 HMDB04883 #<Reference:0x000055ce320faa18> #<Reference:0x000055ce320fa838> #<Reference:0x000055ce320fa680> #<Reference:0x000055ce320fa4c8> #<Reference:0x000055ce320fa310> #<Reference:0x000055ce320fa158> #<Reference:0x000055ce320f9f28> #<Reference:0x000055ce320f9d48> #<Reference:0x000055ce320f9b90> #<Reference:0x000055ce320f99d8> #<Reference:0x000055ce320f97f8> #<Reference:0x000055ce320f9640> #<Reference:0x000055ce320f93e8> #<Reference:0x000055ce320f91b8> 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 Acid ceramidase Q13510 ASAH1 Alkaline ceramidase 1 Q8TDN7 ACER1 Alkaline ceramidase 2 Q5QJU3 ACER2 Alpha-galactosidase A P06280 GLA Antigen-presenting glycoprotein CD1d P15813 CD1D Beta-1,3-galactosyltransferase 5 Q9Y2C3 B3GALT5 Beta-hexosaminidase subunit alpha P06865 HEXA Beta-hexosaminidase subunit beta P07686 HEXB Ceramide glucosyltransferase Q16739 UGCG Ceramide synthase 1 P27544 CERS1 Collagen type IV alpha-3-binding protein Q9Y5P4 COL4A3BP Epididymal secretory protein E1 P61916 NPC2 Galactocerebrosidase P54803 GALC Ganglioside GM2 activator P17900 GM2A Glucosylceramidase P04062 GBA GPI ethanolamine phosphate transferase 1 O95427 PIGN GPI ethanolamine phosphate transferase 2 Q5H8A4 PIGG GPI ethanolamine phosphate transferase 3 Q8TEQ8 PIGO GPI mannosyltransferase 1 Q9H3S5 PIGM GPI mannosyltransferase 2 Q9NUD9 PIGV GPI mannosyltransferase 3 Q92521 PIGB GPI mannosyltransferase 4 Q86VD9 PIGZ GPI transamidase component PIG-S Q96S52 PIGS GPI transamidase component PIG-T Q969N2 PIGT GPI-anchor transamidase Q92643 PIGK Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase Q9BYG0 B3GNT5 Lactosylceramide 4-alpha-galactosyltransferase Q9NPC4 A4GALT N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase Q9Y2B2 PIGL Neutral ceramidase Q9NR71 ASAH2 Non-lysosomal glucosylceramidase Q9HCG7 GBA2 Phosphatidylinositol glycan anchor biosynthesis class U protein Q9H490 PIGU Phosphatidylinositol N-acetylglucosaminyltransferase subunit A P37287 PIGA Phosphatidylinositol N-acetylglucosaminyltransferase subunit C Q92535 PIGC Phosphatidylinositol N-acetylglucosaminyltransferase subunit H Q14442 PIGH Phosphatidylinositol N-acetylglucosaminyltransferase subunit P P57054 PIGP Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q Q9BRB3 PIGQ Phosphatidylinositol N-acetylglucosaminyltransferase subunit Y Q3MUY2 PIGY Phosphatidylinositol-glycan biosynthesis class F protein Q07326 PIGF Phosphatidylinositol-glycan biosynthesis class W protein Q7Z7B1 PIGW Phosphatidylinositol-glycan biosynthesis class X protein Q8TBF5 PIGX Putative neutral ceramidase C P0C7U2 ASAH2C Sphingomyelin phosphodiesterase P17405 SMPD1 T-cell surface glycoprotein CD1e, membrane-associated P15812 CD1E