1.0 2011-09-21 00:28:50 UTC 2015-07-21 06:57:39 UTC FDB023369 N-Acetylneuraminic acid 9-phosphate N-Acetylneuraminic acid 9-phosphate is an intermediate in the synthesis of Acetylneuraminic acid, a process occurring in the cytosolic fraction by the human enzyme N-Acetylneuraminic acid 9-phosphate (Neu5Ac 9-P) synthase, that catalyzes the synthesis of N-Acetylneuraminic acid 9-phosphate, in a reaction by the mechanism of aldol condensation of phosphoenolpyruvate (PEP) with sugar substrates, ManNAc-6-P (N-acetylmannosamine 6-phosphate) or Man-6-P (mannose 6-phosphate). N-Acetylneuraminic acid 9-phosphate is converted to N-Acetylneuraminic acid by the enzyme N-acetylneuraminate-9-phosphate phosphatase. (PMID: 16503877, 6093772) [HMDB] 5-(acetylamino)-3,5-Dideoxy-D-glycero-D-galacto-2-nonulosonic acid 9-(dihydrogen ate) 5-(acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-Nonulosonic acid 9-(dihydrogen phosphate) N-Acetyl- 9-(dihydrogen ate)-neuraminic acid N-acetyl- 9-(dihydrogen phosphate)-Neuraminic acid N-Acetyl-neuraminic acid-9-ate N-acetyl-Neuraminic acid-9-phosphate N-Acetylneuraminate 9-ate N-Acetylneuraminic acid 9-ic acid C11H20NO12P 389.2498 389.072311621 (4S,5R,6R)-6-[(1R,2R)-1,2-dihydroxy-3-(phosphonooxy)propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid (4S,5R,6R)-6-[(1R,2R)-1,2-dihydroxy-3-(phosphonooxy)propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid 37992-17-9 [H][C@]1(OC(O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)COP(O)(O)=O InChI=1S/C11H20NO12P/c1-4(13)12-7-5(14)2-11(19,10(17)18)24-9(7)8(16)6(15)3-23-25(20,21)22/h5-9,14-16,19H,2-3H2,1H3,(H,12,13)(H,17,18)(H2,20,21,22)/t5-,6+,7+,8+,9+,11?/m0/s1 SQMNIXJSBCSNCI-LUWBGTNYSA-N belongs to the class of organic compounds known as n-acylneuraminate-9-phosphates. These are neuraminic acids carrying an N-acyl substituent, as well as a phosphate group at the O9-position. N-acylneuraminate-9-phosphates Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aliphatic heteromonocyclic compounds Acetamides Alpha hydroxy acids and derivatives C-glucuronides C-glycosyl compounds Carbonyl compounds Carboxylic acids Hemiacetals Hydrocarbon derivatives Monoalkyl phosphates Monocarboxylic acids and derivatives Neuraminic acids Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Pyrans Secondary alcohols Secondary carboxylic acid amides Acetamide Alcohol Aliphatic heteromonocyclic compound Alkyl phosphate Alpha-hydroxy acid C-glucuronide C-glycosyl compound Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Glycosyl compound Hemiacetal Hydrocarbon derivative Hydroxy acid Monoalkyl phosphate Monocarboxylic acid or derivatives N-acylneuraminate-9-phosphate Neuraminic acid Organic nitrogen compound Organic oxide Organic phosphoric acid derivative Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Phosphoric acid ester Pyran Secondary alcohol Secondary carboxylic acid amide amino sugar phosphate Solid logp -2.57 ALOGPS logs -1.39 ALOGPS solubility 1.59e+01 g/l ALOGPS logp -3.7 ChemAxon pka_strongest_acidic 1.47 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac (4S,5R,6R)-6-[(1R,2R)-1,2-dihydroxy-3-(phosphonooxy)propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid ChemAxon average_mass 389.2498 ChemAxon mono_mass 389.072311621 ChemAxon smiles [H][C@]1(OC(O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)COP(O)(O)=O ChemAxon formula C11H20NO12P ChemAxon inchi InChI=1S/C11H20NO12P/c1-4(13)12-7-5(14)2-11(19,10(17)18)24-9(7)8(16)6(15)3-23-25(20,21)22/h5-9,14-16,19H,2-3H2,1H3,(H,12,13)(H,17,18)(H2,20,21,22)/t5-,6+,7+,8+,9+,11?/m0/s1 ChemAxon inchikey SQMNIXJSBCSNCI-LUWBGTNYSA-N ChemAxon polar_surface_area 223.31 ChemAxon refractivity 74.65 ChemAxon polarizability 32.62 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 11 ChemAxon donor_count 8 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 24608 Specdb::CMs 38759 Specdb::CMs 130397 Specdb::CMs 138131 Specdb::CMs 151720 Specdb::CMs 279858 Specdb::NmrOneD 48262 Specdb::NmrOneD 48263 Specdb::NmrOneD 48264 Specdb::NmrOneD 48265 Specdb::NmrOneD 48266 Specdb::NmrOneD 48267 Specdb::NmrOneD 48268 Specdb::NmrOneD 48269 Specdb::NmrOneD 48270 Specdb::NmrOneD 48271 Specdb::NmrOneD 48272 Specdb::NmrOneD 48273 Specdb::NmrOneD 48274 Specdb::NmrOneD 48275 Specdb::NmrOneD 48276 Specdb::NmrOneD 48277 Specdb::NmrOneD 48278 Specdb::NmrOneD 48279 Specdb::NmrOneD 48280 Specdb::NmrOneD 48281 Specdb::MsMs 320470 Specdb::MsMs 320471 Specdb::MsMs 320472 Specdb::MsMs 367843 Specdb::MsMs 367844 Specdb::MsMs 367845 Specdb::MsMs 2303820 Specdb::MsMs 2303821 Specdb::MsMs 2303822 Specdb::MsMs 2657983 Specdb::MsMs 2657984 Specdb::MsMs 2657985 HMDB04381 #<Reference:0x000055ce3346ad78> #<Reference:0x000055ce3346abc0> 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 Sialic acid synthase Q9NR45 NANS