1.0 2011-09-21 00:14:43 UTC 2015-07-21 06:57:14 UTC FDB022482 N,N'-Diacetylchitobiosyldiphosphodolichol Diacetylchitobiosyldiphosphodolichol is an intermediate in the N-glycan biosynthesis, a series of reactions catalyzed by the enzymes chitobiosyldiphosphodolichol beta-mannosyltransferases (EC 2.4.1.141, EC 2.4.1.142). (KEGG) This compound and its corresponding enzymes are implicated in Congenital disorders of glycosylation (CDGs) , that comprise a group of multisystem diseases with mostly severe psychomotor and mental retardation. Type I CDG comprises those disorders in which there are defects that affect biosynthesis of dolichol-linked oligosaccharides in the cytosol or the endoplasmic reticulum (ER), as well as defects involving the transfer of oligosaccharides onto nascent glycoproteins. Type II CDG comprises all defects of further trimming and elongation of N-linked oligosaccharides in the ER and Golgi. (OMIM 608540) [HMDB] Chitobiosyldiodolichol N,N'-diacetylchitobiosyldiodolichol C28H50N2O19P2 780.6461 780.248300452 [(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-(carboxyamino)-4-hydroxy-6-{[hydroxy({hydroxy[(3,7,10-trimethylundeca-6,9-dien-1-yl)oxy]phosphoryl}oxy)phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]carbamic acid (2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-(carboxyamino)-4-hydroxy-6-{[hydroxy([hydroxy((3,7,10-trimethylundeca-6,9-dien-1-yl)oxy)phosphoryl]oxy)phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-ylcarbamic acid [H][C@]1(CO)O[C@@]([H])(O[C@]2([H])[C@@]([H])(CO)O[C@@]([H])(OP(O)(=O)OP(O)(=O)OCCC(C)CCC=C(C)CC=C(C)C)[C@]([H])(NC(O)=O)[C@@]2([H])O)[C@]([H])(NC(O)=O)[C@@]([H])(O)[C@]1([H])O InChI=1S/C28H50N2O19P2/c1-14(2)8-9-15(3)6-5-7-16(4)10-11-44-50(40,41)49-51(42,43)48-26-20(30-28(38)39)23(35)24(18(13-32)46-26)47-25-19(29-27(36)37)22(34)21(33)17(12-31)45-25/h6,8,16-26,29-35H,5,7,9-13H2,1-4H3,(H,36,37)(H,38,39)(H,40,41)(H,42,43)/t16?,17-,18-,19-,20-,21-,22-,23-,24-,25+,26+/m1/s1 YBYNXPYEWMVKMB-WKFMSSQESA-N belongs to the class of organic compounds known as disaccharide phosphates. These are disaccharides carrying one or more phosphate group on a sugar unit. Disaccharide phosphates Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Acetals Carbamic acids Carbonyl compounds Hydrocarbon derivatives Monoalkyl phosphates Monocyclic monoterpenoids O-glycosyl compounds Organic carbonic acids and derivatives Organic oxides Organic pyrophosphates Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Primary alcohols Secondary alcohols Acetal Alcohol Aliphatic heteromonocyclic compound Alkyl phosphate Carbamic acid Carbamic acid derivative Carbonic acid derivative Carbonyl group Disaccharide phosphate Glycosyl compound Hydrocarbon derivative Monoalkyl phosphate Monocyclic monoterpenoid Monoterpenoid O-glycosyl compound Organic nitrogen compound Organic oxide Organic phosphoric acid derivative Organic pyrophosphate Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Phosphoric acid ester Primary alcohol Secondary alcohol Solid logp 0.38 ALOGPS logs -2.51 ALOGPS solubility 2.43e+00 g/l ALOGPS logp -0.014 ChemAxon pka_strongest_acidic 1.73 ChemAxon pka_strongest_basic -3.5 ChemAxon iupac [(2S,3R,4R,5S,6R)-2-{[(2R,3S,4R,5R,6S)-5-(carboxyamino)-4-hydroxy-6-{[hydroxy({hydroxy[(3,7,10-trimethylundeca-6,9-dien-1-yl)oxy]phosphoryl}oxy)phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]carbamic acid ChemAxon average_mass 780.6461 ChemAxon mono_mass 780.248300452 ChemAxon smiles [H][C@]1(CO)O[C@@]([H])(O[C@]2([H])[C@@]([H])(CO)O[C@@]([H])(OP(O)(=O)OP(O)(=O)OCCC(C)CCC=C(C)CC=C(C)C)[C@]([H])(NC(O)=O)[C@@]2([H])O)[C@]([H])(NC(O)=O)[C@@]([H])(O)[C@]1([H])O ChemAxon formula C28H50N2O19P2 ChemAxon inchi InChI=1S/C28H50N2O19P2/c1-14(2)8-9-15(3)6-5-7-16(4)10-11-44-50(40,41)49-51(42,43)48-26-20(30-28(38)39)23(35)24(18(13-32)46-26)47-25-19(29-27(36)37)22(34)21(33)17(12-31)45-25/h6,8,16-26,29-35H,5,7,9-13H2,1-4H3,(H,36,37)(H,38,39)(H,40,41)(H,42,43)/t16?,17-,18-,19-,20-,21-,22-,23-,24-,25+,26+/m1/s1 ChemAxon inchikey YBYNXPYEWMVKMB-WKFMSSQESA-N ChemAxon polar_surface_area 329.79 ChemAxon refractivity 171.9 ChemAxon polarizability 72.35 ChemAxon rotatable_bond_count 19 ChemAxon acceptor_count 16 ChemAxon donor_count 11 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon HMDB01196 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 Chitobiosyldiphosphodolichol beta-mannosyltransferase Q9BT22 ALG1 UDP-N-acetylglucosamine transferase subunit ALG13 homolog Q9NP73 ALG13