| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-07-13 19:42:31 UTC |
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| Update Date | 2016-09-23 18:44:42 UTC |
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| Lmdb | LMDB00107 |
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| Secondary Accession Numbers | None |
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| Metabolite Identification |
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| Common Name | N-Acetylneuraminic acid |
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| Description | N-Acetylneuraminic acid (NeuAc) or sialic acid is an acetyl derivative of the amino sugar neuraminic acid. It occurs in many glycoproteins, glycolipids, and polysaccharides in both mammals and bacteria. The most abundant sialic acid, NeuAc, is synthesized in vivo from N-acetylated D-mannosamine (ManNAc) or D-glucosamine (GlcNAc). NeuAc and its activated form, CMP-NeuAc, are biosynthesized in five consecutive reactions: UDP-N-acetylglucosamine (UDP-GlcNAc) N-acetylmannosamine (ManNAc) ManNAc 6-phosphate NeuAc 9-phosphate NeuAc CMP-NeuAc. CMP-NeuAc is transported into the Golgi apparatus and, with the aid of specific sialyltransferases, added onto nonreducing positions on oligosaccharide chains of glycoproteins and glycolipids. NeuAc is widely distributed throughout animal tissues and found in several fluids, including serum, cerebrospinal fluid, saliva, urine, amniotic fluid, and breast milk. It is found in high levels in the brain, adrenal glands, and the heart. Serum and urine levels of the free acid are elevated in individuals suffering from renal failure. Serum and saliva Neu5Ac levels are also elevated in alcoholics. A disorder known as Salla disease or infantile NeuAc storage disease is also characterized by high serum and urine levels of this compound. The negative charge of is responsible for the slippery feel of saliva and mucins coating the body's organs. This particular sialic acid is known to act as a "decoy" for invading pathogens. Along with involvement in preventing infections (mucus associated with mucous membranes ó mouth, nose, GI, respiratory tract), Neu5Ac acts as a receptor for influenza viruses, allowing attachment to mucous cells via hemagglutinin (an early step in acquiring influenzavirus infection). NeuAc is also becoming known as an agent necessary for mediating ganglioside distribution and structures in the brain. Sialic acid (SA) is an N-acetylated derivative of neuraminic acid that is an abundant terminal monosaccharide of glycoconjugates. Normal animal serum SA is largely bound to glycoproteins or glycolipids (Total sialic acid, TSA, 1.5-2.5 mmol/L), with small amounts of free SA (1-3 umol/L). Negatively charged SA units stabilize glycoprotein conformation in cell surface receptors to increase cell rigidity. This enables signal recognition and adhesion to ligands, antibodies, enzymes and microbes. SA residues are antigenic determinant residues in carbohydrate chains of glycolipids and glycoproteins, chemical messengers in tissue and body fluids, and may regulate glomeruli basement membrane permeability. Sialic acids are structurally unique nine-carbon keto sugars occupying the interface between the host and commensal or pathogenic microorganisms. An important function of host sialic acid is to regulate innate immunity. Sialic acid is the moiety most actively recycled for metabolic purposes in the salvage pathways in glycosphingolipid metabolism. Sialic acid is indispensable for the neuritogenic activities of gangliosides constituents which are unique in that a sialic acid directly binds to the glucose of the cerebroside, they are mutually connected in tandem, and some are located in the internal parts of the sugar chain. Sialylation (sialic acid linked to galactose, N-acetylgalactosamine, or linked to another sialic acid) represents one of the most frequently occurring terminations of the oligosaccharide chains of glycoproteins and glycolipids. The biosynthesis of the various linkages is mediated by the different members of the sialyltransferase family. (PMID: 11425186 , 11287396 , 12770781 , 16624269 , 12510390 , 15007099 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| 5-N-ACETYL-BETA-D-neuraminIC ACID | ChEBI | | beta-Neu5ac | ChEBI | | 5-N-ACETYL-b-D-neuraminate | Generator | | 5-N-ACETYL-b-D-neuraminic acid | Generator | | 5-N-ACETYL-beta-D-neuraminate | Generator | | 5-N-ACETYL-β-D-neuraminate | Generator | | 5-N-ACETYL-β-D-neuraminic acid | Generator | | b-Neu5ac | Generator | | Β-neu5ac | Generator | | N-Acetylneuraminate | Generator | | 5-(Acetylamino)-3,5-dideoxy-D-glycero-b-D-galacto-2-nonulopyranosonate | HMDB | | 5-(Acetylamino)-3,5-dideoxy-D-glycero-b-D-galacto-2-nonulopyranosonic acid | HMDB | | 5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonate | HMDB | | 5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid | HMDB | | 5-(Acetylamino)-3,5-dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonate | HMDB | | 5-(Acetylamino)-3,5-dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonic acid | HMDB | | 5-(Acetylamino)-3,5-dideoxy-delta-glycero-delta-galacto-2-nonulosonate | HMDB | | 5-(Acetylamino)-3,5-dideoxy-delta-glycero-delta-galacto-2-nonulosonic acid | HMDB | | 5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonate | HMDB | | 5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acid | HMDB | | 5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulosonate | HMDB | | 5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulosonic acid | HMDB | | 5-N-Acetyl-beta-delta-neuraminic acid | HMDB | | 5-N-Acetyl-D-neuraminate | HMDB | | 5-N-Acetyl-D-neuraminic acid | HMDB | | 5-N-Acetyl-delta-neuraminate | HMDB | | 5-N-Acetyl-delta-neuraminic acid | HMDB | | 5-N-Acetylneuraminate | HMDB | | 5-N-Acetylneuraminic acid | HMDB | | Aceneuramate | HMDB | | Aceneuramic acid | HMDB | | Acetylneuraminate | HMDB | | Acetylneuraminic acid | HMDB | | b-5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulopyranosonate | HMDB | | b-5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulopyranosonic acid | HMDB | | b-Sialic acid | HMDB | | beta-5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulopyranosonate | HMDB | | beta-5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulopyranosonic acid | HMDB | | beta-Sialic acid | HMDB | | Lactaminate | HMDB | | Lactaminic acid | HMDB | | N-Acetyl-b-D-neuraminate | HMDB | | N-Acetyl-b-D-neuraminic acid | HMDB | | N-Acetyl-b-neuraminate | HMDB | | N-Acetyl-beta-delta-neuraminate | HMDB | | N-Acetyl-beta-delta-neuraminic acid | HMDB | | N-Acetyl-beta-neuraminate | HMDB | | N-Acetyl-D-neuraminate | HMDB | | N-Acetyl-D-neuraminic acid | HMDB | | N-Acetyl-delta-neuraminate | HMDB | | N-Acetyl-delta-neuraminic acid | HMDB | | N-Acetyl-neuraminate | HMDB | | N-Acetyl-neuraminic acid | HMDB | | N-Acetylneuramate | HMDB | | N-Acetylneuramic acid | HMDB | | N-Acetylsialate | HMDB | | N-Acetylsialic acid | HMDB | | NAN | HMDB | | NANA | HMDB | | Neu5ac | HMDB | | Sialic acid | HMDB | | Acid, sialic | HMDB | | Acid, N-acetylneuraminic | HMDB | | N Acetylneuraminic acid | HMDB | | N-Acetyl-beta-D-neuraminic acid | HMDB | | N-Acetyl-beta-neuraminic acid | HMDB | | N-Acetyl-β-D-neuraminic acid | HMDB | | N-Acetyl-β-neuraminic acid | HMDB | | N-Acetylneuraminic acid | HMDB |
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| Chemical Formula | C11H19NO9 |
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| Average Molecular Weight | 309.2699 |
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| Monoisotopic Molecular Weight | 309.105981211 |
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| IUPAC Name | (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid |
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| Traditional Name | β-neu5ac |
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| CAS Registry Number | 131-48-6 |
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| SMILES | CC(=O)N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)CO)C(O)=O |
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| InChI Identifier | 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 |
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| InChI Key | SQVRNKJHWKZAKO-PFQGKNLYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Carbohydrates and carbohydrate conjugates |
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| Direct Parent | N-acylneuraminic acids |
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| Alternative Parents | |
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| Substituents | - N-acylneuraminic acid
- Neuraminic acid
- C-glucuronide
- C-glycosyl compound
- Glycosyl compound
- Alpha-hydroxy acid
- Pyran
- Hydroxy acid
- Oxane
- Acetamide
- Carboxamide group
- Hemiacetal
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Polyol
- Alcohol
- Hydrocarbon derivative
- Organic nitrogen compound
- Organopnictogen compound
- Primary alcohol
- Organic oxide
- Carbonyl group
- Organonitrogen compound
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Status | Detected but not Quantified |
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| Origin | Not Available |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - GC-MS (7 TMS) | splash10-0fr2-1961000000-3acdbc4b39a5bf685996 | Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (6 TMS) | splash10-014j-0492000000-8e4279660c77b0c70a30 | Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 7 TMS) | splash10-00l6-1792200000-863a168c10243229e892 | Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0fr2-1961000000-3acdbc4b39a5bf685996 | Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-014j-0492000000-8e4279660c77b0c70a30 | Spectrum | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-00l6-1792200000-863a168c10243229e892 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0h2f-9660000000-f7a1f63f319c23f8e72a | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive | splash10-0zfr-4620249000-1d39f85a16504ef9ea46 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00di-0190000000-a3a5aaa2e10a6cfed08a | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0fk9-3900000000-7100e174e13e94736ae7 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00si-9300000000-1166885a787fd53086b0 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-000i-9100000000-260b6f27d6f3469ede2f | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-000i-9000000000-35b6da9206192d33828e | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9301000000-47798651a02647e16452 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-000i-9000000000-1096dd07227387a97604 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01ox-1091000000-11c42df33f8993522db0 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03kc-5090000000-5d0c74aa0d8a2c8d321c | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-9320000000-cfda0db8085e62f50516 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4j-3391000000-68ee32ef5e2ba6223c42 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-9110000000-9ae00577454ddf4db073 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9300000000-798cb916675bb1245a78 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03kc-0095000000-8f7746cc3f652b12033f | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-02tc-1392000000-3e251c9d2583e71f866a | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-7910000000-ba41b78e53cb934a9b19 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-3039000000-4348eff0515b0da3bc08 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a59-6290000000-5ac6f13cca0827ab0dd0 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4u-9100000000-ac22477eeca403481eff | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | Spectrum | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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| General References | - Dall'Olio F: The sialyl-alpha2,6-lactosaminyl-structure: biosynthesis and functional role. Glycoconj J. 2000 Oct;17(10):669-76. [11425186 ]
- Keppler OT, Horstkorte R, Pawlita M, Schmidt C, Reutter W: Biochemical engineering of the N-acyl side chain of sialic acid: biological implications. Glycobiology. 2001 Feb;11(2):11R-18R. [11287396 ]
- Tettamanti G, Bassi R, Viani P, Riboni L: Salvage pathways in glycosphingolipid metabolism. Biochimie. 2003 Mar-Apr;85(3-4):423-37. [12770781 ]
- Gopaul KP, Crook MA: Sialic acid: a novel marker of cardiovascular disease? Clin Biochem. 2006 Jul;39(7):667-81. Epub 2006 Apr 19. [16624269 ]
- Yamada K: [Chemo-pharmaceutical studies on the glycosphingolipid constituents from echinoderm, sea cucumbers, as the medicinal materials]. Yakugaku Zasshi. 2002 Dec;122(12):1133-43. [12510390 ]
- Vimr ER, Kalivoda KA, Deszo EL, Steenbergen SM: Diversity of microbial sialic acid metabolism. Microbiol Mol Biol Rev. 2004 Mar;68(1):132-53. [15007099 ]
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