2.0 2012-10-10 12:22:30 -0600 2015-09-16 14:50:11 -0600 ECMDB23217 M2MDB003607 N-Acetyl-alpha-neuraminate N-Acetyl-alpha-neuraminate is a sialic acid. Sialic acids are an important family of related 9-carbon sugars acids, present on the surface of many different cells and functioning in a wide range of different biological processes. They can be utilized by pathogens to evade the host immune response. N-acetylneuraminic acid is the most common sialic acid. A number of bacteria that can colonize humans (such as E. coli) make use of N-acetylneuraminic acid as a nutrient source. Production of the enzymes involved in N-acetylneuraminate degradation is induced by growth on sialic acid as the sole source of carbon, which is due to transcriptional regulation by the repressor NanR. (2R,4S,5R,6R)-5-acetamido-2,4-Dihydroxy-6-(1R,2R)-1,2,3-trihydroxypropyloxane-2-carboxylate (2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-(1R,2R)-1,2,3-trihydroxypropyloxane-2-carboxylic acid 5-(acetylamino)-3,5-dideoxy-D-glycero-a-D-galacto-2-Nonulopyranosonate 5-(acetylamino)-3,5-dideoxy-D-glycero-a-D-galacto-2-Nonulopyranosonic acid 5-(acetylamino)-3,5-Dideoxy-delta-glycero-a-delta-galacto-2-nonulopyranosonate 5-(acetylamino)-3,5-Dideoxy-delta-glycero-a-delta-galacto-2-nonulopyranosonic acid 5-(acetylamino)-3,5-dideoxy-delta-glycero-alpha-delta-galacto-2-Nonulopyranosonate 5-(acetylamino)-3,5-dideoxy-delta-glycero-alpha-delta-galacto-2-Nonulopyranosonic acid 5-(acetylamino)-3,5-Dideoxy-δ-glycero-a-δ-galacto-2-nonulopyranosonate 5-(acetylamino)-3,5-Dideoxy-δ-glycero-a-δ-galacto-2-nonulopyranosonic acid 5-(acetylamino)-3,5-Dideoxy-δ-glycero-α-δ-galacto-2-nonulopyranosonate 5-(acetylamino)-3,5-Dideoxy-δ-glycero-α-δ-galacto-2-nonulopyranosonic acid 5-acetamido-3,5-dideoxy-a-D-glycero-D-galacto-Nonulopyranosonate 5-acetamido-3,5-dideoxy-a-D-glycero-D-galacto-Nonulopyranosonic acid 5-acetamido-3,5-Dideoxy-a-delta-glycero-delta-galacto-nonulopyranosonate 5-acetamido-3,5-Dideoxy-a-delta-glycero-delta-galacto-nonulopyranosonic acid 5-acetamido-3,5-Dideoxy-a-δ-glycero-δ-galacto-nonulopyranosonate 5-acetamido-3,5-Dideoxy-a-δ-glycero-δ-galacto-nonulopyranosonic acid 5-acetamido-3,5-dideoxy-alpha-delta-glycero-delta-galacto-Nonulopyranosonate 5-acetamido-3,5-dideoxy-alpha-delta-glycero-delta-galacto-Nonulopyranosonic acid 5-acetamido-3,5-Dideoxy-α-δ-glycero-δ-galacto-nonulopyranosonate 5-acetamido-3,5-Dideoxy-α-δ-glycero-δ-galacto-nonulopyranosonic acid 8)-a-NeuNAC-(2->n 8)-alpha-NeuNAC-(2->n 8)-α-NeuNAC-(2->n a-Neu5ac a-Neu5ac-(2->8)N Alpha-Neu5Ac Alpha-Neu5Ac-(2->8)n N-Acetyl-a-D-neuraminate N-Acetyl-a-D-neuraminic acid N-Acetyl-a-delta-neuraminate N-Acetyl-a-delta-neuraminic acid N-Acetyl-a-neuraminate N-Acetyl-a-neuraminic acid N-Acetyl-a-δ-neuraminate N-Acetyl-a-δ-neuraminic acid N-Acetyl-alpha-delta-neuraminate N-Acetyl-alpha-delta-neuraminic acid N-Acetyl-alpha-neuraminic acid N-Acetyl-α-neuraminate N-Acetyl-α-neuraminic acid N-Acetyl-α-δ-neuraminate N-Acetyl-α-δ-neuraminic acid N-Acetylated a-(2->8)-linked homosialopolysaccharide N-acetylated alpha-(2->8)-linked homosialopolysaccharide N-Acetylated α-(2->8)-linked homosialopolysaccharide Poly-a-(2->8)-neu5ac Poly-a-(2->8)-neunac Poly-alpha-(2->8)-Neu5Ac Poly-alpha-(2->8)-NeuNAc Poly-α-(2->8)-neu5ac Poly-α-(2->8)-neunac Polyalpha-Neu5Ac-(2->8) α-Neu5ac α-Neu5ac-(2->8)N C11H19NO9 309.2699 309.105981211 (2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid N-acetylneuraminic acid 21646-00-4 [H][C@]1(O[C@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11+/m0/s1 SQVRNKJHWKZAKO-YRMXFSIDSA-N Solid logp -2.78 ALOGPS logs -0.13 ALOGPS solubility 2.27e+02 g/l ALOGPS logp -3.6 ChemAxon pka_strongest_acidic 3 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac (2R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid ChemAxon average_mass 309.2699 ChemAxon mono_mass 309.105981211 ChemAxon smiles [H][C@]1(O[C@](O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO ChemAxon formula C11H19NO9 ChemAxon inchi InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11+/m0/s1 ChemAxon inchikey SQVRNKJHWKZAKO-YRMXFSIDSA-N ChemAxon polar_surface_area 176.78 ChemAxon refractivity 63.78 ChemAxon polarizability 28.19 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 9 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 12640 Specdb::CMs 37757 Specdb::CMs 131847 Specdb::CMs 139581 Specdb::CMs 147132 Specdb::CMs 279584 Specdb::CMs 1075503 Specdb::CMs 1075504 Specdb::CMs 1075506 Specdb::CMs 1075508 Specdb::CMs 1075510 Specdb::CMs 1075512 Specdb::CMs 1075514 Specdb::CMs 1075516 Specdb::CMs 1075518 Specdb::CMs 1075520 Specdb::CMs 1075521 Specdb::CMs 1075523 Specdb::CMs 1075525 Specdb::CMs 1075527 Specdb::CMs 1075529 Specdb::CMs 1075531 Specdb::CMs 1075533 Specdb::CMs 1075535 Specdb::CMs 1075537 Specdb::MsMs 28334 Specdb::MsMs 28335 Specdb::MsMs 28336 Specdb::MsMs 34892 Specdb::MsMs 34893 Specdb::MsMs 34894 Specdb::MsMs 2746597 Specdb::MsMs 2746598 Specdb::MsMs 2746599 Specdb::MsMs 2932362 Specdb::MsMs 2932363 Specdb::MsMs 2932364 HMDB00773 444885 C19909 58770 Not Available SIA FDB022234 Thompson JA, Miles BS, Fennessey PV: Urinary organic acids quantitated by age groups in a healthy pediatric population. Clin Chem. 1977 Sep;23(9):1734-8. 890917 Baumberger, Franz; Vasella, Andrea. , Synthesis of N-acetylneuraminic acid and N-acetyl-4-epineuraminic acid. Helvetica Chimica Acta (1986), 69(5), 1205-15. N-acetylneuraminate epimerase P39371 NANM_ECOLI nanM http://ecmdb.ca/proteins/P39371.xml N-Acetyl-alpha-neuraminate > N-Acetylneuraminic acid