1.0 2011-04-11 17:01:42 UTC 2015-07-21 06:56:17 UTC FDB021811 Uridine diphosphategalactose Uridine diphosphategalactose (UDPgal) is a nucleoside diphosphate sugar which can be epimerized into UDPglucose for entry into the mainstream of carbohydrate metabolism. UDPgal is a pivotal compound in the metabolism of galactose. UDPgal is a product of the galactose-l-phosphate uridyl transferase (EC 2.7.7.10) reaction but may also be made from Glucose-l-P, involving uridine diphosphate galactose-4-epimerase (EC 5.1.3.2). UDPgal is the necessary galactosyl donor of galactose in the metabolism to incorporate it into complex oligosaccharides, glycoproteins and glycolipids (galactosides). Defective galactosylation of complex glycoconjugates exists in tissues from galactosemic patients. There is a tendency for galactosemic red cell UDPgal to be in the low normal range with a high uridine diphosphate glucose to UDP-gal ratio. This may reflect an inability of red cell UDPgal-4'-epimerase to maintain a normal ratio and consequently higher levels of UDPgal. In the more complex white blood cells and cultured fibroblasts, the UDPgal content and the uridine diphosphate glucose to UDPgal ratio of galactosemics are normal. Therefore, defective galactosylation observed in galactosemic fibroblasts must result from a defect in the transfer of galactose from UDPgal to these moieties. (PMID: 2122114, 7671968) [HMDB] UDP-a-D-Galactopyranose UDP-a-D-Galactose UDP-alpha-D-Galactopyranose UDP-alpha-delta-Galactose UDP-delta-Galactopyranose UDP-delta-Galactose UDP-α-D-galactopyranose UDPgalactose Uridine 5'-(alpha-D-galactopyranosyl pyroate) Uridine 5'-(alpha-delta-galactopyranosyl pyroate) Uridine 5'-[3-(D-galactopyranosyl) dihydrogen diate] Uridine 5'-diate galactose Uridine 5'-diogalactose Uridine 5'-pyroate a-D-galactopyranosyl ester Uridine 5'-pyroate a-D-galactosyl ester Uridine 5'-pyroate a-delta-galactopyranosyl ester Uridine 5'-pyroate a-delta-galactosyl ester Uridine 5'-pyroate alpha-D-galactosyl ester Uridine 5'-pyroate alpha-delta-galactosyl ester Uridine 5'-pyroate D-galactosyl ester Uridine diate galactose Uridine diate-D-galactose Uridine diate-delta-galactose Uridine diate-galactose Uridine diic acid galactose Uridine diogalactose Uridine pyroate a-D-galactopyranosyl ester Uridine pyroate a-delta-galactopyranosyl ester Uridine pyroate alpha-D-galactopyranosyl ester Uridine pyroate alpha-delta-galactopyranosyl ester Uridine pyroogalactose Uridinediate galactose Uridinediogalactose C15H24N2O17P2 566.3018 566.055020376 [({[3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid {[3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid 2956-16-3 OCC1OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=CC(O)=NC2=O)C(O)C(O)C1O InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25) HSCJRCZFDFQWRP-UHFFFAOYSA-N belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Pyrimidine nucleotide sugars Organic compounds Nucleosides, nucleotides, and analogues Pyrimidine nucleotides Pyrimidine nucleotide sugars Aromatic heteromonocyclic compounds Azacyclic compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Hydropyrimidines Lactams Monoalkyl phosphates Monosaccharide phosphates Organic oxides Organic pyrophosphates Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Pentose phosphates Polyols Primary alcohols Pyrimidine ribonucleoside diphosphates Pyrimidones Secondary alcohols Tetrahydrofurans Ureas Vinylogous amides Alcohol Alkyl phosphate Aromatic heteromonocyclic compound Azacycle Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Hydropyrimidine Lactam Monoalkyl phosphate Monosaccharide Monosaccharide phosphate N-glycosyl compound Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organic pyrophosphate Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Oxane Pentose phosphate Pentose-5-phosphate Phosphoric acid ester Polyol Primary alcohol Pyrimidine Pyrimidine nucleotide sugar Pyrimidine ribonucleoside diphosphate Pyrimidone Secondary alcohol Tetrahydrofuran Urea Vinylogous amide Solid logp -1.25 ALOGPS logs -1.34 ALOGPS solubility 2.60e+01 g/l ALOGPS logp -4.6 ChemAxon pka_strongest_acidic 1.73 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac [({[3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid ChemAxon average_mass 566.3018 ChemAxon mono_mass 566.055020376 ChemAxon smiles OCC1OC(OP(O)(=O)OP(O)(=O)OCC2OC(C(O)C2O)N2C=CC(O)=NC2=O)C(O)C(O)C1O ChemAxon formula C15H24N2O17P2 ChemAxon inchi InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25) ChemAxon inchikey HSCJRCZFDFQWRP-UHFFFAOYSA-N ChemAxon polar_surface_area 295.03 ChemAxon refractivity 106.78 ChemAxon polarizability 47.04 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 15 ChemAxon donor_count 9 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Galactose Metabolism SMP00043 map00052 Lactose Synthesis SMP00444 Nucleotide Sugars Metabolism SMP00010 map00520 Specdb::NmrOneD 4572 Specdb::NmrOneD 241708 Specdb::NmrOneD 241709 Specdb::NmrOneD 241710 Specdb::NmrOneD 241711 Specdb::NmrOneD 241712 Specdb::NmrOneD 241713 Specdb::NmrOneD 241714 Specdb::NmrOneD 241715 Specdb::NmrOneD 241716 Specdb::NmrOneD 241717 Specdb::NmrOneD 241718 Specdb::NmrOneD 241719 Specdb::NmrOneD 241720 Specdb::NmrOneD 241721 Specdb::NmrOneD 241722 Specdb::NmrOneD 241723 Specdb::NmrOneD 241724 Specdb::NmrOneD 241725 Specdb::NmrOneD 241726 Specdb::NmrOneD 241727 Specdb::CMs 994419 Specdb::CMs 994420 Specdb::CMs 994421 Specdb::CMs 994422 Specdb::CMs 994423 Specdb::CMs 994424 Specdb::CMs 994425 Specdb::CMs 994426 Specdb::CMs 994427 Specdb::CMs 994428 Specdb::CMs 994429 Specdb::CMs 994430 Specdb::CMs 994431 Specdb::CMs 994432 Specdb::CMs 994433 Specdb::CMs 994434 Specdb::CMs 994435 Specdb::CMs 994436 Specdb::CMs 994437 Specdb::CMs 994438 Specdb::CMs 994439 Specdb::CMs 994440 Specdb::CMs 994441 Specdb::CMs 994442 Specdb::CMs 994443 HMDB00302 GDU #<Reference:0x000055ce31fda070> #<Reference:0x000055ce31fd9eb8> #<Reference:0x000055ce31fd9d00> #<Reference:0x000055ce31fd9b48> #<Reference:0x000055ce31fd9990> #<Reference:0x000055ce31fd97d8> #<Reference:0x000055ce31fd9620> 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 2-hydroxyacylsphingosine 1-beta-galactosyltransferase Q16880 UGT8 Alpha-lactalbumin P00709 LALBA Beta-1,3-galactosyltransferase 4 O96024 B3GALT4 Lactosylceramide 4-alpha-galactosyltransferase Q9NPC4 A4GALT