1.0 2011-09-21 00:38:11 UTC 2015-07-21 06:57:58 UTC FDB023993 Isoglobotriaose Isoglobotriaose is a glycosphingolipid found in mammalian tissues; nonepithelial residue in the intestine, spleen, and spleen microsomes. (PMID: 7053385, 893368, 4690582) Globotriaosylceramide receptors bind to Verotoxin 1 (VT1) B subunits from Escherichia coli eliciting human vascular disease as a consequence of specific binding to these receptors on endothelial cell surfaces. (PMID: 10361298, 10353828) Globotriaosylceramides accumulate in patients with Fabry disease. Fabry disease is a X-linked metabolic disorder caused by a deficiency of alpha-galactosidase leading to the systemic accumulation of glycosphingolipids with alpha-galactosyl moieties; glycolipid deposition in endothelial cells leads to renal failure and cardiac and cerebrovascular disease. (PMID: 10339603) [HMDB] alpha-D-Galp-(1-4)-beta-D-Galp-(1-4)-D-Glc alpha-delta-Galp-(1-4)-beta-delta-Galp-(1-4)-delta-Glc Globoisotriaose Isoglobotriaose Isoglobotriglycosylceramide O-alpha-D-galactopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)- D-Glucose O-alpha-delta-galactopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)- D-Glucose C19H34O15 502.4643 502.189770418 (2R,3R,4R,5R)-4-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(1S,2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxy}oxan-2-yl]oxy}-2,3,5,6-tetrahydroxyhexanal isoglobotriaose 41744-59-6 [H][C@@](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O[C@@]2([H])C[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H]1O)([C@H](O)CO)[C@H](O)[C@@H](O)C=O InChI=1S/C19H34O15/c20-2-6-1-9(13(28)15(30)11(6)26)32-18-14(29)10(5-23)33-19(16(18)31)34-17(8(25)4-22)12(27)7(24)3-21/h3,6-20,22-31H,1-2,4-5H2/t6-,7+,8-,9+,10-,11+,12-,13+,14+,15+,16-,17-,18+,19+/m1/s1 DRRWNKCTTZUPPM-FBSSLUAZSA-N belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. Fatty acyl glycosides of mono- and disaccharides Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acyl glycosides Aliphatic heteromonocyclic compounds Acetals Alkyl glycosides Alpha-hydroxyaldehydes Beta-hydroxy aldehydes Cyclitols and derivatives Cyclohexanols Dialkyl ethers Disaccharides Fatty alcohols Hydrocarbon derivatives O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Polyols Primary alcohols Acetal Alcohol Aldehyde Aliphatic heteromonocyclic compound Alkyl glycoside Alpha-hydroxyaldehyde Beta-hydroxy aldehyde Carbonyl group Cyclic alcohol Cyclitol or derivatives Cyclohexanol Dialkyl ether Disaccharide Ether Fatty acyl glycoside of mono- or disaccharide Fatty alcohol Glycosyl compound Hydrocarbon derivative O-glycosyl compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Polyol Primary alcohol Secondary alcohol Solid logp -2.94 ALOGPS logs -0.42 ALOGPS solubility 1.93e+02 g/l ALOGPS logp -7.2 ChemAxon pka_strongest_acidic 11.62 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac (2R,3R,4R,5R)-4-{[(2S,3R,4S,5S,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-{[(1S,2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxy}oxan-2-yl]oxy}-2,3,5,6-tetrahydroxyhexanal ChemAxon average_mass 502.4643 ChemAxon mono_mass 502.189770418 ChemAxon smiles [H][C@@](O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O[C@@]2([H])C[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H]1O)([C@H](O)CO)[C@H](O)[C@@H](O)C=O ChemAxon formula C19H34O15 ChemAxon inchi InChI=1S/C19H34O15/c20-2-6-1-9(13(28)15(30)11(6)26)32-18-14(29)10(5-23)33-19(16(18)31)34-17(8(25)4-22)12(27)7(24)3-21/h3,6-20,22-31H,1-2,4-5H2/t6-,7+,8-,9+,10-,11+,12-,13+,14+,15+,16-,17-,18+,19+/m1/s1 ChemAxon inchikey DRRWNKCTTZUPPM-FBSSLUAZSA-N ChemAxon polar_surface_area 267.29 ChemAxon refractivity 105.91 ChemAxon polarizability 47.58 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 15 ChemAxon donor_count 11 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 301912 Specdb::MsMs 301913 Specdb::MsMs 301914 Specdb::MsMs 344521 Specdb::MsMs 344522 Specdb::MsMs 344523 Specdb::MsMs 2840955 Specdb::MsMs 2840956 Specdb::MsMs 2840957 Specdb::MsMs 2865234 Specdb::MsMs 2865235 Specdb::MsMs 2865236 Specdb::CMs 16213 Specdb::CMs 39052 Specdb::CMs 168694 Specdb::CMs 168696 Specdb::CMs 168698 Specdb::CMs 168700 Specdb::CMs 280640 Specdb::NmrOneD 81352 Specdb::NmrOneD 81353 Specdb::NmrOneD 81354 Specdb::NmrOneD 81355 Specdb::NmrOneD 81356 Specdb::NmrOneD 81357 Specdb::NmrOneD 81358 Specdb::NmrOneD 81359 Specdb::NmrOneD 81360 Specdb::NmrOneD 81361 Specdb::NmrOneD 81362 Specdb::NmrOneD 81363 Specdb::NmrOneD 81364 Specdb::NmrOneD 81365 Specdb::NmrOneD 81366 Specdb::NmrOneD 81367 Specdb::NmrOneD 81368 Specdb::NmrOneD 81369 Specdb::NmrOneD 81370 Specdb::NmrOneD 81371 HMDB06598 #<Reference:0x000055ce31ebdf98> #<Reference:0x000055ce31ebddb8> #<Reference:0x000055ce31ebdbb0> #<Reference:0x000055ce31ebd9f8> #<Reference:0x000055ce31ebd818> #<Reference:0x000055ce31ebd610> 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