1.0 2011-09-21 00:08:55 UTC 2015-07-21 06:56:59 UTC FDB022130 Glucosylgalactosyl hydroxylysine Glucosylgalactosyl hydroxylysine is a Glycoside of hydroxylysine. Hydroxylation of lysine is an important post-translational modification of collagen, (PMID 10928217) a reaction catalyzed by the enzyme Lysyl hydroxylase (EC 1.14.11.4) forming hydroxylysine in collagens and other proteins with collagen-like amino acid sequences, by the hydroxylation of lysine residues in X-lys-gly sequences. The hydroxylysine residues formed in the lysyl hydroxylase reaction have 2 important functions: first, their hydroxy groups serve as sites of attachment for carbohydrate units, either the monosaccharide galactose or the disaccharide glucosylgalactose; and second, they are essential for the stability of the intermolecular collagen crosslinks. (OMIM 153454) Hydroxylysine-deficient skin collagen is manifested in Ehlers-Danlos syndrome, type VIA, A heritable disorder of connective tissue (PMID 5016372) [HMDB] 1,2alpha-Glucosylgalactosyl-O-hydroxylysine 2-O-a-D-Glucopyranosyl-O-b-D-galactopyranosylhydroxylysine 2-O-alpha-D-Glucopyranosyl-O-beta-D-galactopyranosylhydroxylysine 2-O-alpha-delta-Glucopyranosyl-O-beta-delta-galactopyranosylhydroxylysine 5-[O-a-D-Glucopyranosyl-(1->2)-b-D-galactopyranosyloxy]-L-lysine 5-[O-alpha-D-Glucopyranosyl-(1->2)-beta-D-galactopyranosyloxy]-L-lysine 5-[O-alpha-delta-Glucopyranosyl-(1->2)-beta-delta-galactopyranosyloxy]-L-lysine Glucopyranosylgalactopyranosylhydroxylysine Glucosido-galactosyl-hydroxylysine Glucosyl galactosyl-d-hydroxylysine Glucosyl galactosyl-delta-hydroxylysine Glucosylgalactosyl hydroxylysine Glucosylgalactosylhydroxylysine Hydroxylysine-galactose-glucose Hydroxylysine-glucose-galactose L-5-((2-O-alpha-D-glucopyranosyl-beta-D-galactopyranosyl)oxy)-Lysine L-5-((2-O-alpha-delta-glucopyranosyl-beta-delta-galactopyranosyl)oxy)-Lysine C18H34N2O13 486.4682 486.206089184 (2S)-2,6-diamino-5-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}hexanoic acid (2S)-2,6-diamino-5-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}hexanoic acid 32448-35-4 NCC(CC[C@H](N)C(O)=O)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)C(O)[C@H]1O InChI=1S/C18H34N2O13/c19-3-6(1-2-7(20)16(28)29)30-18-15(13(26)11(24)9(5-22)32-18)33-17-14(27)12(25)10(23)8(4-21)31-17/h6-15,17-18,21-27H,1-5,19-20H2,(H,28,29)/t6?,7-,8+,9+,10+,11-,12?,13-,14+,15+,17+,18+/m0/s1 UTIRJVJBKWSIOX-SRMFCGEKSA-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 Amino acids Amino fatty acids Carbonyl compounds Carboxylic acids Disaccharides Heterocyclic fatty acids Hydrocarbon derivatives Hydroxy fatty acids L-alpha-amino acids Medium-chain fatty acids Monoalkylamines Monocarboxylic acids and derivatives O-glycosyl compounds Organic oxides Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Secondary alcohols Acetal Alcohol Aliphatic heteromonocyclic compound Alpha-amino acid Alpha-amino acid or derivatives Amine Amino acid Amino acid or derivatives Amino fatty acid Carbonyl group Carboxylic acid Carboxylic acid derivative Disaccharide Fatty acid Fatty acyl glycoside of mono- or disaccharide Glycosyl compound Heterocyclic fatty acid Hydrocarbon derivative Hydroxy fatty acid L-alpha-amino acid Medium-chain fatty acid Monocarboxylic acid or derivatives O-glycosyl compound Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Oxane Polyol Primary alcohol Primary aliphatic amine Primary amine Secondary alcohol Solid logp -3.61 ALOGPS logs -0.77 ALOGPS solubility 8.22e+01 g/l ALOGPS logp -8 ChemAxon pka_strongest_acidic 1.76 ChemAxon pka_strongest_basic 9.8 ChemAxon iupac (2S)-2,6-diamino-5-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}hexanoic acid ChemAxon average_mass 486.4682 ChemAxon mono_mass 486.206089184 ChemAxon smiles NCC(CC[C@H](N)C(O)=O)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)C(O)[C@H]1O ChemAxon formula C18H34N2O13 ChemAxon inchi InChI=1S/C18H34N2O13/c19-3-6(1-2-7(20)16(28)29)30-18-15(13(26)11(24)9(5-22)32-18)33-17-14(27)12(25)10(23)8(4-21)31-17/h6-15,17-18,21-27H,1-5,19-20H2,(H,28,29)/t6?,7-,8+,9+,10+,11-,12?,13-,14+,15+,17+,18+/m0/s1 ChemAxon inchikey UTIRJVJBKWSIOX-SRMFCGEKSA-N ChemAxon polar_surface_area 267.87 ChemAxon refractivity 104 ChemAxon polarizability 46.29 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 15 ChemAxon donor_count 10 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 52740 Specdb::MsMs 52741 Specdb::MsMs 52742 Specdb::MsMs 111414 Specdb::MsMs 111415 Specdb::MsMs 111416 Specdb::MsMs 1448412 Specdb::MsMs 2840538 Specdb::MsMs 2840539 Specdb::MsMs 2840540 Specdb::MsMs 2864907 Specdb::MsMs 2864908 Specdb::MsMs 2864909 Specdb::NmrOneD 7142 Specdb::NmrOneD 7143 Specdb::NmrOneD 7144 Specdb::NmrOneD 7145 Specdb::NmrOneD 7146 Specdb::NmrOneD 7147 Specdb::NmrOneD 7148 Specdb::NmrOneD 7149 Specdb::NmrOneD 7150 Specdb::NmrOneD 7151 Specdb::NmrOneD 7152 Specdb::NmrOneD 7153 Specdb::NmrOneD 7154 Specdb::NmrOneD 7155 Specdb::NmrOneD 7156 Specdb::NmrOneD 7157 Specdb::NmrOneD 7158 Specdb::NmrOneD 7159 Specdb::NmrOneD 7160 Specdb::NmrOneD 7161 Specdb::CMs 24480 Specdb::CMs 37639 Specdb::CMs 154024 Specdb::CMs 163814 Specdb::CMs 163816 Specdb::CMs 163818 Specdb::CMs 163820 Specdb::CMs 163822 Specdb::CMs 163824 Specdb::CMs 163826 Specdb::CMs 163829 Specdb::CMs 163831 Specdb::CMs 163833 Specdb::CMs 163835 Specdb::CMs 163837 Specdb::CMs 163839 Specdb::CMs 163841 Specdb::CMs 163843 Specdb::CMs 163845 Specdb::CMs 163847 Specdb::CMs 163849 Specdb::CMs 163851 Specdb::CMs 163853 Specdb::CMs 163855 Specdb::CMs 163857 HMDB00585 #<Reference:0x000055ce3282d880> #<Reference:0x000055ce3282d2e0> #<Reference:0x000055ce3282ce80> #<Reference:0x000055ce3282c930> #<Reference:0x000055ce3282c480> #<Reference:0x000055ce3282bf58> #<Reference:0x000055ce3282baf8> #<Reference:0x000055ce3282b620> #<Reference:0x000055ce3282b198> #<Reference:0x000055ce3282ad38> #<Reference:0x000055ce3282a860> #<Reference:0x000055ce3282a3d8> 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