N-acetyl-beta-neuraminic acid
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Identification
- Generic Name
- N-acetyl-beta-neuraminic acid
- DrugBank Accession Number
- DB04265
- Background
An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518)
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 309.2699
Monoisotopic: 309.105981211 - Chemical Formula
- C11H19NO9
- Synonyms
- (-)-N-acetyl-beta-neuraminic acid
- beta-sialic acid
- N-acetyl-beta-D-neuraminic acid
- N-acetyl-β-neuraminic acid
- β-Neu5Ac
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UTetanus toxin Not Available Clostridium tetani (strain Massachusetts / E88) USialidase Not Available Micromonospora viridifaciens UEndo-N-acetylneuraminidase Not Available Enterobacteria phage K1F UHemagglutinin-neuraminidase Not Available HPIV-3 - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- N-acylneuraminic acids
- Alternative Parents
- Neuraminic acids / C-glucuronides / C-glycosyl compounds / Pyrans / Alpha hydroxy acids and derivatives / Oxanes / Acetamides / Secondary carboxylic acid amides / Secondary alcohols / Hemiacetals show 10 more
- Substituents
- Acetamide / Alcohol / Aliphatic heteromonocyclic compound / Alpha-hydroxy acid / C-glucuronide / C-glycosyl compound / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative show 19 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- N-acetylneuraminic acid (CHEBI:45744)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- TIP79W5HPN
- CAS number
- 19342-33-7
- InChI Key
- SQVRNKJHWKZAKO-PFQGKNLYSA-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)/t5-,6+,7+,8+,9+,11-/m0/s1
- IUPAC Name
- (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
- 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
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000230
- PubChem Compound
- 445063
- PubChem Substance
- 46508038
- ChemSpider
- 392810
- BindingDB
- 50063302
- ChEBI
- 45744
- ChEMBL
- CHEMBL165084
- ZINC
- ZINC000003793840
- PDBe Ligand
- SLB
- PDB Entries
- 1dfq / 1e8u / 1fv2 / 1fv3 / 1v0f / 1v3c / 2ber / 2jhl / 2xa5 / 2xwi … show 35 more
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 227.0 mg/mL ALOGPS logP -2.8 ALOGPS logP -3.6 Chemaxon logS -0.13 ALOGPS pKa (Strongest Acidic) 3 Chemaxon pKa (Strongest Basic) -1.3 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 7 Chemaxon Polar Surface Area 176.78 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 63.78 m3·mol-1 Chemaxon Polarizability 27.82 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8356 Blood Brain Barrier - 0.9161 Caco-2 permeable - 0.8086 P-glycoprotein substrate Non-substrate 0.6951 P-glycoprotein inhibitor I Non-inhibitor 0.895 P-glycoprotein inhibitor II Non-inhibitor 0.9498 Renal organic cation transporter Non-inhibitor 0.9723 CYP450 2C9 substrate Non-substrate 0.7533 CYP450 2D6 substrate Non-substrate 0.8571 CYP450 3A4 substrate Non-substrate 0.6255 CYP450 1A2 substrate 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 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9893 Ames test Non AMES toxic 0.7858 Carcinogenicity Non-carcinogens 0.9652 Biodegradation Ready biodegradable 0.8474 Rat acute toxicity 1.6429 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9956 hERG inhibition (predictor II) Non-inhibitor 0.9696
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 178.2480514 predictedDarkChem Lite v0.1.0 [M-H]- 178.2954514 predictedDarkChem Lite v0.1.0 [M-H]- 166.70906 predictedDeepCCS 1.0 (2019) [M+H]+ 180.0256514 predictedDarkChem Lite v0.1.0 [M+H]+ 178.4909514 predictedDarkChem Lite v0.1.0 [M+H]+ 169.10461 predictedDeepCCS 1.0 (2019) [M+Na]+ 179.6914514 predictedDarkChem Lite v0.1.0 [M+Na]+ 179.1478514 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.01714 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsTetanus toxin
- Kind
- Protein
- Organism
- Clostridium tetani (strain Massachusetts / E88)
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Tetanus toxin acts by inhibiting neurotransmitter release. It binds to peripheral neuronal synapses, is internalized and moves by retrograde transport up the axon into the spinal cord where it can ...
- Gene Name
- tetX
- Uniprot ID
- P04958
- Uniprot Name
- Tetanus toxin
- Molecular Weight
- 150680.98 Da
References
2. DetailsSialidase
- Kind
- Protein
- Organism
- Micromonospora viridifaciens
- Pharmacological action
- Unknown
- General Function
- Exo-alpha-(2->8)-sialidase activity
- Specific Function
- To release sialic acids for use as carbon and energy sources for this non-pathogenic bacterium while in pathogenic microorganisms, sialidases have been suggested to be pathogenic factors.
- Gene Name
- nedA
- Uniprot ID
- Q02834
- Uniprot Name
- Sialidase
- Molecular Weight
- 68829.78 Da
References
3. DetailsEndo-N-acetylneuraminidase
- Kind
- Protein
- Organism
- Enterobacteria phage K1F
- Pharmacological action
- Unknown
- General Function
- Endo-alpha-(2,8)-sialidase activity
- Specific Function
- Responsible for initial absorption of the phage to the host bacterium. Degradation of the alpha-2,8-linked polysialic acid K1 capsule.
- Gene Name
- Not Available
- Uniprot ID
- Q04830
- Uniprot Name
- Endo-N-acetylneuraminidase
- Molecular Weight
- 102012.495 Da
References
4. DetailsHemagglutinin-neuraminidase
- Kind
- Protein
- Organism
- HPIV-3
- Pharmacological action
- Unknown
- General Function
- Exo-alpha-(2->8)-sialidase activity
- Specific Function
- Attaches the virus to sialic acid-containing cell receptors and thereby initiating infection. Binding of HN protein to the receptor induces a conformational change that allows the F protein to trig...
- Gene Name
- HN
- Uniprot ID
- P12564
- Uniprot Name
- Hemagglutinin-neuraminidase
- Molecular Weight
- 64329.845 Da
References
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52