sialic acid
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Basic Info
| Common Name | Sialic acid(F01172) |
| 2D Structure | |
| FRCD ID | F01172 |
| CAS Number | 131-48-6 |
| PubChem CID | 906 |
| Formula | C11H19NO9 |
| IUPAC Name | 5-acetamido-2,4-dihydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid |
| InChI Key | SQVRNKJHWKZAKO-UHFFFAOYSA-N |
| 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) |
| Canonical SMILES | CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)O)O |
| Isomeric SMILES | CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)O)O |
| Synonyms |
Type IV
NANA
Lactaminic acid
131-48-6
NSC111756
Neuraminic acid, N-acetyl-
O-sialic acid
489-46-3
sialic acid
N-Acetylneuraminic Acid, Synthetic
|
| Classifies |
Predicted: Veterinary Drug
|
| Update Date | Nov 13, 2018 16:49 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Carbohydrates and carbohydrate conjugates |
| Intermediate Tree Nodes | Sugar acids and derivatives - Sugar amino acids and derivatives - Pyranoid amino acids and derivatives - Neuraminic acids and derivatives - N-acylneuraminic acids and derivatives |
| Direct Parent | N-acylneuraminic acids |
| Alternative Parents |
|
| Molecular Framework | Aliphatic heteromonocyclic compounds |
| 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 |
| Description | This compound belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 309.271 |
| Hydrogen Bond Donor Count | 7 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 5 |
| Complexity | 403 |
| Monoisotopic Mass | 309.106 |
| Exact Mass | 309.106 |
| XLogP | -3.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 21 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 6 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.9161 |
| Human Intestinal Absorption | HIA- | 0.8356 |
| Caco-2 Permeability | Caco2- | 0.8086 |
| P-glycoprotein Substrate | Non-substrate | 0.6951 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8950 |
| Non-inhibitor | 0.9498 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9723 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5735 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7533 |
| CYP450 2D6 Substrate | Non-substrate | 0.8571 |
| CYP450 3A4 Substrate | Non-substrate | 0.6255 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9719 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9592 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9722 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9583 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9869 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9893 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9956 |
| Non-inhibitor | 0.9696 | |
| AMES Toxicity | Non AMES toxic | 0.7858 |
| Carcinogens | Non-carcinogens | 0.9652 |
| Fish Toxicity | Low FHMT | 0.9483 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6335 |
| Honey Bee Toxicity | Low HBT | 0.7333 |
| Biodegradation | Ready biodegradable | 0.8474 |
| Acute Oral Toxicity | III | 0.4967 |
| Carcinogenicity (Three-class) | Non-required | 0.7334 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.6352 | LogS |
| Caco-2 Permeability | -0.4900 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.6429 | LD50, mol/kg |
| Fish Toxicity | 2.3264 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.5565 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Automation aided optimization of cloning, expression and purification of enzymes of the bacterial sialic acid catabolic and sialylation pathways enzymes forstructural studies. | Microb Biotechnol | 2018 Mar | 29345069 |
| Sialic acid involves in the interaction between ovomucin and hemagglutinin andinfluences the antiviral activity of ovomucin. | Int J Biol Macromol | 2018 Jul 30 | 30071221 |
| Pathogenesis and management of adenoviral keratoconjunctivitis. | Infect Drug Resist | 2018 Jul 17 | 30046247 |
| Characterization of edible bird's nest of different production, species andgeographical origins using nutritional composition, physicochemical propertiesand antioxidant activities. | Food Res Int | 2018 Jul | 29803459 |
| NanI Sialidase Can Support the Growth and Survival of Clostridium perfringensStrain F4969 in the Presence of Sialyated Host Macromolecules (Mucin) or Caco-2Cells. | Infect Immun | 2018 Jan 22 | 29203541 |
| Enzymatic properties of β-N-acetylglucosaminidases. | Appl Microbiol Biotechnol | 2018 Jan | 29143882 |
| C-source metabolic profilings of foodborne Shiga-toxin producing E. coli match serogroup differentiations and highlight functional adaptations. | Int J Food Microbiol | 2018 Feb 2 | 29217302 |
| NAction! How Can Neuraminidase-Based Immunity Contribute to Better InfluenzaVirus Vaccines? | MBio | 2018 Apr 3 | 29615508 |
| Solid-Phase Chemical Modification for Sialic Acid Linkage Analysis: Applicationto Glycoproteins of Host Cells Used in Influenza Virus Propagation. | Anal Chem | 2017 Sep 5 | 28792205 |
| Linear polysialoside outperforms dendritic analogs for inhibition of influenzavirus infection in vitro and in vivo. | Biomaterials | 2017 Sep | 28550754 |
| Bifidobacterium bifidum Extracellular Sialidase Enhances Adhesion to the Mucosal Surface and Supports Carbohydrate Assimilation. | MBio | 2017 Oct 3 | 28974612 |
| Insights into genetic diversity and biological propensities of potentiallyzoonotic avian influenza H9N2 viruses circulating in Egypt. | Virology | 2017 Nov | 28863277 |
| Variability in H9N2 haemagglutinin receptor-binding preference and the pH offusion. | Emerg Microbes Infect | 2017 Mar 22 | 28325922 |
| Dietary Human Milk Oligosaccharides but Not Prebiotic Oligosaccharides IncreaseCirculating Natural Killer Cell and Mesenteric Lymph Node Memory T CellPopulations in Noninfected and Rotavirus-Infected Neonatal Piglets. | J Nutr | 2017 Jun | 28490677 |
| In vitro generation of polysialylated cervical mucins by bacterialpolysialyltransferases to counteract cytotoxicity of extracellular histones. | FEBS J | 2017 Jun | 28371406 |
| Effect of Leaf Surface Chemical Properties on Efficacy of Sanitizer for RotavirusInactivation. | Appl Environ Microbiol | 2016 Sep 30 | 27520815 |
| Lipooligosaccharide locus classes and putative virulence genes among chicken and human Campylobacter jejuni isolates. | BMC Microbiol | 2016 Nov 21 | 27871232 |
| NMR analysis on the sialic acid-binding mechanism of an R-type lectin mutant bynatural evolution-mimicry. | FEBS Lett | 2016 Jun | 27172906 |
| The biofilm matrix of Campylobacter jejuni determined by fluorescence lectin-binding analysis. | Biofouling | 2016 | 27097059 |
| High fat diet-induced inflammation and oxidative stress are attenuated byN-acetylneuraminic acid in rats. | J Biomed Sci | 2015 Oct 24 | 26498218 |