1.0 2011-09-21 00:15:11 UTC 2019-11-26 03:21:04 UTC FDB022515 Glucosamine 6-phosphate Glucosamine 6-phosphate is normally produced in endothelial cells via the de novo glucosamine synthesis by the enzyme fructose-6-phosphate amidotransferase and the modulation of this pathway by hyperglycemia and glutamine. glutamine-fructose-6-phosphate amidotransferase (GFAT) catalyzes the first committed step in the pathway for biosynthesis of hexosamines in mammals. A member of the N-terminal nucleophile class of amidotransferases, GFAT transfers the amino group from the L-glutamine amide to D-fructose 6-phosphate, producing glutamic acid and glucosamine 6-phosphate. As glucosamine inhibits endothelial nitric oxide synthesis it has important implications for impaired endothelium-dependent relaxation and vascular dysfunction in diabetes mellitus. (PMID 11270676, 11842094) [HMDB] 2-amino-2-Deoxy-6-O-ONO-a-D-glucopyranose 2-amino-2-Deoxy-6-O-ONO-alpha-D-glucopyranose 2-amino-2-Deoxy-6-O-ONO-α-D-glucopyranose 2-amino-2-Deoxy-D-glucose 6-ate 2-Amino-2-deoxy-D-glucose 6-phosphate 2-amino-2-Deoxyglucose 6-ate 2-Amino-2-deoxyglucose 6-phosphate 2-amino-D-Glucose-6-ate 2-Amino-D-glucose-6-phosphate a-D-Glucosamine 6-(dihydrogen ate) a-D-Glucosamine 6-(dihydrogen ic acid) alpha-D-Glucosamine 6-(dihydrogen ate) alpha-D-Glucosamine 6-(dihydrogen ic acid) D-Glucosamine 6-ate D-Glucosamine 6-phosphate D-Glucosamine ate D-Glucosamine phosphate D-Glucosamine-6-ate D-Glucosamine-6-phosphate Glucosamine 6 -ate Glucosamine 6 -phosphate GLUCOSAMINE 6-ATE GLUCOSAMINE 6-ic acid Glucosamine 6-Phosphate Glucosamine 6-phosphic acid Glucosamine-6-ate glucosamine-6-P glucosamine-6-phosphate Glucose-6-orate Glucose-6-oric acid Glucose-6-phosphorate Glucose-6-phosphoric acid Oric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester Phosphoric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester α-D-glucosamine 6-(dihydrogen ate) α-D-glucosamine 6-(dihydrogen ic acid) C6H14NO8P 259.151 259.045702941 {[(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid α-D-glucosamine 6-phosphate 3616-42-0 N[C@H]1[C@@H](O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O InChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6+/m1/s1 XHMJOUIAFHJHBW-UKFBFLRUSA-N belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups. Hexose phosphates Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds 1,2-aminoalcohols 1,2-diols Aminosaccharides Hemiacetals Hydrocarbon derivatives Monoalkyl phosphates Monoalkylamines Monosaccharide phosphates Organic oxides Organopnictogen compounds Oxacyclic compounds Oxanes Secondary alcohols 1,2-aminoalcohol 1,2-diol Alcohol Aliphatic heteromonocyclic compound Alkyl phosphate Amine Amino saccharide Hemiacetal Hexose phosphate Hydrocarbon derivative Monoalkyl phosphate Monosaccharide phosphate Organic nitrogen compound Organic oxide Organic phosphoric acid derivative Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Phosphoric acid ester Polyol Primary aliphatic amine Primary amine Secondary alcohol 2-amino-2-deoxy-D-glucopyranose 6-phosphate Solid logp -2.60 ALOGPS logs -0.87 ALOGPS solubility 3.48e+01 g/l ALOGPS logp -4.2 ChemAxon pka_strongest_acidic 1.22 ChemAxon pka_strongest_basic 8.23 ChemAxon iupac {[(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 259.151 ChemAxon mono_mass 259.045702941 ChemAxon smiles N[C@H]1[C@@H](O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O ChemAxon formula C6H14NO8P ChemAxon inchi InChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6+/m1/s1 ChemAxon inchikey XHMJOUIAFHJHBW-UKFBFLRUSA-N ChemAxon polar_surface_area 162.7 ChemAxon refractivity 48.45 ChemAxon polarizability 21.42 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Amino Sugar Metabolism SMP00045 map00520 Glutamate Metabolism SMP00072 map00250 Specdb::NmrTwoD 1060 Specdb::NmrTwoD 1610 Specdb::CMs 3064 Specdb::CMs 37995 Specdb::CMs 173973 Specdb::NmrOneD 1669 Specdb::NmrOneD 4741 Specdb::NmrOneD 4742 Specdb::NmrOneD 9002 Specdb::NmrOneD 9003 Specdb::NmrOneD 9004 Specdb::NmrOneD 9005 Specdb::NmrOneD 9006 Specdb::NmrOneD 9007 Specdb::NmrOneD 9008 Specdb::NmrOneD 9009 Specdb::NmrOneD 9010 Specdb::NmrOneD 9011 Specdb::NmrOneD 9012 Specdb::NmrOneD 9013 Specdb::NmrOneD 9014 Specdb::NmrOneD 9015 Specdb::NmrOneD 9016 Specdb::NmrOneD 9017 Specdb::NmrOneD 9018 Specdb::NmrOneD 9019 Specdb::NmrOneD 9020 Specdb::NmrOneD 9021 Specdb::MsMs 1484 Specdb::MsMs 1485 Specdb::MsMs 1486 Specdb::MsMs 5120 Specdb::MsMs 5121 Specdb::MsMs 5122 Specdb::MsMs 179409 Specdb::MsMs 179410 Specdb::MsMs 179411 Specdb::MsMs 181737 Specdb::MsMs 181738 Specdb::MsMs 181739 Specdb::MsMs 439039 Specdb::MsMs 447960 Specdb::MsMs 447961 Specdb::MsMs 2247031 Specdb::MsMs 2247243 Specdb::MsMs 2322739 Specdb::MsMs 2322740 Specdb::MsMs 2322741 Specdb::MsMs 2615931 Specdb::MsMs 2615932 Specdb::MsMs 2615933 HMDB01254 15873 GLP #<Reference:0x000055ce3055e2a0> #<Reference:0x000055ce3055dfd0> 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 Milk (Cow) Type 2 specific 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 Glucokinase P35557 GCK Glucosamine 6-phosphate N-acetyltransferase Q96EK6 GNPNAT1 Glucosamine-6-phosphate isomerase 2 Q8TDQ7 GNPDA2 Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 1 Q06210 GFPT1 Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2 O94808 GFPT2 Hexokinase-1 P19367 HK1 Hexokinase-2 P52789 HK2 Hexokinase-3 P52790 HK3 Putative N-acetylglucosamine-6-phosphate deacetylase Q9Y303 AMDHD2