1.0 2016-09-30 22:27:07 UTC 2020-06-04 20:56:29 UTC BMDB0000230 BMDB00230 N-Acetylneuraminic acid N-Acetylneuraminic acid, also known as N-acetylneuraminate or sialic acid, belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. N-Acetylneuraminic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. N-Acetylneuraminic acid exists in all living organisms, ranging from bacteria to humans. N-Acetylneuraminic acid participates in a number of enzymatic reactions, within cattle. In particular, N-Acetylneuraminic acid can be biosynthesized from N-acetylmannosamine and phosphoenolpyruvic acid; which is catalyzed by the enzyme sialic acid synthase. In addition, N-Acetylneuraminic acid can be converted into N-acetylmannosamine and pyruvic acid; which is mediated by the enzyme N-acetylneuraminate lyase. In cattle, N-acetylneuraminic acid is involved in the metabolic pathway called the amino sugar metabolism pathway. N-Acetylneuraminic acid is a potentially toxic compound. N-Acetylneuraminic acid has been found to be associated with several diseases known as sialidosis, normosomatic type, irritable bowel syndrome, ulcerative colitis, and colorectal cancer; also n-acetylneuraminic acid has been linked to the inborn metabolic disorders including salla disease. 5-N-ACETYL-BETA-D-neuraminIC ACID beta-Neu5ac 5-N-ACETYL-b-D-neuraminate 5-N-ACETYL-b-D-neuraminic acid 5-N-ACETYL-beta-D-neuraminate 5-N-ACETYL-β-D-neuraminate 5-N-ACETYL-β-D-neuraminic acid b-Neu5ac Β-neu5ac N-Acetylneuraminate 5-(Acetylamino)-3,5-dideoxy-D-glycero-b-D-galacto-2-nonulopyranosonate 5-(Acetylamino)-3,5-dideoxy-D-glycero-b-D-galacto-2-nonulopyranosonic acid 5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonate 5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid 5-(Acetylamino)-3,5-dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonate 5-(Acetylamino)-3,5-dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonic acid 5-(Acetylamino)-3,5-dideoxy-delta-glycero-delta-galacto-2-nonulosonate 5-(Acetylamino)-3,5-dideoxy-delta-glycero-delta-galacto-2-nonulosonic acid 5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonate 5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acid 5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulosonate 5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulosonic acid 5-N-Acetyl-beta-delta-neuraminic acid 5-N-Acetyl-D-neuraminate 5-N-Acetyl-D-neuraminic acid 5-N-Acetyl-delta-neuraminate 5-N-Acetyl-delta-neuraminic acid 5-N-Acetylneuraminate 5-N-Acetylneuraminic acid Aceneuramate Aceneuramic acid Acetylneuraminate Acetylneuraminic acid b-5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulopyranosonate b-5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulopyranosonic acid b-Sialic acid beta-5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulopyranosonate beta-5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulopyranosonic acid beta-Sialic acid Lactaminate Lactaminic acid N-Acetyl-b-D-neuraminate N-Acetyl-b-D-neuraminic acid N-Acetyl-b-neuraminate N-Acetyl-beta-delta-neuraminate N-Acetyl-beta-delta-neuraminic acid N-Acetyl-beta-neuraminate N-Acetyl-D-neuraminate N-Acetyl-D-neuraminic acid N-Acetyl-delta-neuraminate N-Acetyl-delta-neuraminic acid N-Acetyl-neuraminate N-Acetyl-neuraminic acid N-Acetylneuramate N-Acetylneuramic acid N-Acetylsialate N-Acetylsialic acid NAN NANA Neu5ac Sialic acid Acid, sialic Acid, N-acetylneuraminic N Acetylneuraminic acid N-Acetyl-beta-D-neuraminic acid N-Acetyl-beta-neuraminic acid N-Acetyl-β-D-neuraminic acid N-Acetyl-β-neuraminic acid N-Acetylneuraminic acid C11H19NO9 309.2699 309.105981211 (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid β-neu5ac 19342-33-7 [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-PFQGKNLYSA-N belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates N-acylneuraminic acids Acetamides Alpha hydroxy acids and derivatives C-glucuronides C-glycosyl compounds Carbonyl compounds Carboxylic acids Hemiacetals Hydrocarbon derivatives Monocarboxylic acids and derivatives Neuraminic acids Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Pyrans Secondary alcohols Secondary carboxylic acid amides Acetamide Alcohol Aliphatic heteromonocyclic compound Alpha-hydroxy acid C-glucuronide C-glycosyl compound Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Glycosyl compound Hemiacetal Hydrocarbon derivative Hydroxy acid Monocarboxylic acid or derivatives N-acylneuraminic acid Neuraminic acid Organic nitrogen compound Organic oxide Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Polyol Primary alcohol Pyran Secondary alcohol Secondary carboxylic acid amide Aliphatic heteromonocyclic compounds N-acetylneuraminic acid Solid melting_point 186 °C logp -2.78 ALOGPS logs -0.13 ALOGPS logp -3.6 ChemAxon pka_strongest_acidic 3 ChemAxon pka_strongest_basic -1.3 ChemAxon iupac (2S,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-PFQGKNLYSA-N ChemAxon polar_surface_area 176.78 ChemAxon refractivity 63.78 ChemAxon polarizability 27.82 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 9 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 1 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Amino Sugar Metabolism SMP0087175 Specdb::NmrTwoD 1002 Specdb::NmrTwoD 1225 Specdb::CMs 1973 Specdb::CMs 2042 Specdb::CMs 2056 Specdb::CMs 8816 Specdb::CMs 31091 Specdb::CMs 31092 Specdb::CMs 31093 Specdb::CMs 37374 Specdb::CMs 135662 Specdb::CMs 143396 Specdb::NmrOneD 1247 Specdb::NmrOneD 143090 Specdb::NmrOneD 143091 Specdb::NmrOneD 143092 Specdb::NmrOneD 143093 Specdb::NmrOneD 143094 Specdb::NmrOneD 143095 Specdb::NmrOneD 143096 Specdb::NmrOneD 143097 Specdb::NmrOneD 143098 Specdb::NmrOneD 143099 Specdb::NmrOneD 143100 Specdb::NmrOneD 143101 Specdb::NmrOneD 143102 Specdb::NmrOneD 143103 Specdb::NmrOneD 143104 Specdb::NmrOneD 143105 Specdb::NmrOneD 143106 Specdb::NmrOneD 143107 Specdb::NmrOneD 143108 Specdb::NmrOneD 143109 Specdb::MsMs 385 Specdb::MsMs 386 Specdb::MsMs 387 Specdb::MsMs 262038 Specdb::MsMs 262039 Specdb::MsMs 262040 Specdb::MsMs 281970 Specdb::MsMs 281971 Specdb::MsMs 281972 Specdb::MsMs 2257252 Specdb::MsMs 2257346 Specdb::MsMs 2259259 Specdb::MsMs 2259295 Specdb::MsMs 2392438 Specdb::MsMs 2392439 Specdb::MsMs 2392440 Specdb::MsMs 2569712 Specdb::MsMs 2569713 Specdb::MsMs 2569714 Adrenal Gland Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Brain Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Milk 462.379 uM Raw . mid lactation The N-acetyl neuraminic-acid content of the milk of various species Journal of Dairy Research (1973), 40: 421-425 Cambridge University Press doi: 10.1017/S0022029900014795 (About doi) Milk 32.334 - 42.0345 uM Raw milk. Average over the milking season International Dairy Journal: Volume 14, Issue 7, July 2004, Pages 571-579 Milk Commercial, conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8 Milk Detected but not quantified in conventional whole milk Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 Neuron Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Placenta Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Prostate Tissue Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Testis Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 C19910 392810 DB04265 445063 45744 N-Acetylneuraminic acid Yamamoto, Toshihiro; Teshima, Tadashi; Inami, Kaoru; Shiba, Tetsuo. Synthesis of sialic acid through aldol condensation of glucose with oxalacetic acid. Tetrahedron Letters (1992), 33(3), 325-8. International Dairy Journal: Volume 14, Issue 7, July 2004, Pages 571-579 Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 The N-acetyl neuraminic-acid content of the milk of various species Journal of Dairy Research (1973), 40: 421-425 Cambridge University Press doi: 10.1017/S0022029900014795 (About doi) BMDBP00109 N-acetylneuraminate lyase Q29RY9 NPL Enzyme BMDBP00789 N-acylneuraminate cytidylyltransferase Q3SZM5 CMAS Enzyme BMDBP00951 Sialidase-3 O97859 NEU3 Enzyme BMDBP00952 Sialidase-1 A6BMK7 NEU1 Enzyme BMDBP02181 Selectin P A6QPF9 SELP Enzyme BMDBP02182 C-C chemokine receptor type 5 Q2HJ17 CCR5 Enzyme BMDBP02868 N-acetylneuraminate synthase Q1RMX7 NANS Enzyme