2-deoxy-2,3-dehydro-N-acetylneuraminic acid
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Identification
- Generic Name
- 2-deoxy-2,3-dehydro-N-acetylneuraminic acid
- DrugBank Accession Number
- DB03991
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 291.2546
Monoisotopic: 291.095416525 - Chemical Formula
- C11H17NO8
- Synonyms
- Neu2en5Ac
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UHemagglutinin-neuraminidase Not Available HPIV-3 USialidase Not Available Micromonospora viridifaciens UNeuraminidase Not Available Influenza A virus (strain A/Tern/Australia/G70C/1975 H11N9) UHemagglutinin-neuraminidase Not Available NDV USialidase-2 Not Available Humans - 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
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as secondary alcohols. These are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Alcohols and polyols
- Direct Parent
- Secondary alcohols
- Alternative Parents
- Propargyl-type 1,3-dipolar organic compounds / Polyols / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Carboximidic acids / Primary alcohols / Organopnictogen compounds / Organonitrogen compounds / Organic oxides show 2 more
- Substituents
- Aliphatic heteromonocyclic compound / Carbonyl group / Carboximidic acid / Carboximidic acid derivative / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic 1,3-dipolar compound / Organic nitrogen compound show 9 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- N-acetylneuraminic acids (CHEBI:28062)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- QR7675ZK8X
- CAS number
- 24967-27-9
- InChI Key
- JINJZWSZQKHCIP-UFGQHTETSA-N
- InChI
- InChI=1S/C11H17NO8/c1-4(14)12-8-5(15)2-7(11(18)19)20-10(8)9(17)6(16)3-13/h2,5-6,8-10,13,15-17H,3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,8+,9+,10+/m0/s1
- IUPAC Name
- (2R,3R,4S)-3-acetamido-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
- SMILES
- [H][C@]1(OC(=C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO
References
- General References
- Not Available
- External Links
- PubChem Compound
- 65309
- PubChem Substance
- 46505061
- ChemSpider
- 58795
- BindingDB
- 4706
- ChEBI
- 28062
- ChEMBL
- CHEMBL96712
- ZINC
- ZINC000004096465
- PDBe Ligand
- DAN
- PDB Entries
- 1e8v / 1eus / 1f8b / 1ivf / 1ms0 / 1ms1 / 1ms8 / 1mz6 / 1n1t / 1n1v … show 46 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 65.2 mg/mL ALOGPS logP -2.2 ALOGPS logP -3.7 Chemaxon logS -0.65 ALOGPS pKa (Strongest Acidic) 3.32 Chemaxon pKa (Strongest Basic) -1.4 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 156.55 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 64.11 m3·mol-1 Chemaxon Polarizability 27.1 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 - 0.6158 Blood Brain Barrier - 0.9228 Caco-2 permeable - 0.7714 P-glycoprotein substrate Non-substrate 0.6597 P-glycoprotein inhibitor I Non-inhibitor 0.8042 P-glycoprotein inhibitor II Non-inhibitor 0.9652 Renal organic cation transporter Non-inhibitor 0.969 CYP450 2C9 substrate Non-substrate 0.7571 CYP450 2D6 substrate Non-substrate 0.8588 CYP450 3A4 substrate Non-substrate 0.6034 CYP450 1A2 substrate Non-inhibitor 0.9621 CYP450 2C9 inhibitor Non-inhibitor 0.9396 CYP450 2D6 inhibitor Non-inhibitor 0.9626 CYP450 2C19 inhibitor Non-inhibitor 0.934 CYP450 3A4 inhibitor Non-inhibitor 0.984 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9847 Ames test Non AMES toxic 0.7051 Carcinogenicity Non-carcinogens 0.9689 Biodegradation Ready biodegradable 0.9307 Rat acute toxicity 1.6959 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9803 hERG inhibition (predictor II) Non-inhibitor 0.9634
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-03k9-9540000000-6ebea9c8871fdfa5155b Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0feg-0190000000-deff17b172a11cc746d4 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0pir-0690000000-c247471e3a390b0a55d9 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0gz9-3690000000-00450433d614ee75c93f Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-02ou-2920000000-5bb8230afd2fed7f139e Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-01qi-1970000000-8059aa7db5d9b7918143 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0pe9-4910000000-41b9b7dcbf85c5ab6051 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 174.8203596 predictedDarkChem Lite v0.1.0 [M-H]- 173.3820596 predictedDarkChem Lite v0.1.0 [M-H]- 167.42049 predictedDeepCCS 1.0 (2019) [M+H]+ 177.1183596 predictedDarkChem Lite v0.1.0 [M+H]+ 175.2809596 predictedDarkChem Lite v0.1.0 [M+H]+ 169.3159 predictedDeepCCS 1.0 (2019) [M+Na]+ 175.6783596 predictedDarkChem Lite v0.1.0 [M+Na]+ 174.6973596 predictedDarkChem Lite v0.1.0 [M+Na]+ 175.2131 predictedDeepCCS 1.0 (2019)
Targets
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1. 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
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. DetailsNeuraminidase
- Kind
- Protein
- Organism
- Influenza A virus (strain A/Tern/Australia/G70C/1975 H11N9)
- Pharmacological action
- Unknown
- General Function
- Metal ion binding
- Specific Function
- Catalyzes the removal of terminal sialic acid residues from viral and cellular glycoconjugates. Cleaves off the terminal sialic acids on the glycosylated HA during virus budding to facilitate virus...
- Gene Name
- NA
- Uniprot ID
- P03472
- Uniprot Name
- Neuraminidase
- Molecular Weight
- 52468.405 Da
References
4. DetailsHemagglutinin-neuraminidase
- Kind
- Protein
- Organism
- NDV
- 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
- P32884
- Uniprot Name
- Hemagglutinin-neuraminidase
- Molecular Weight
- 63141.66 Da
References
5. DetailsSialidase-2
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Exo-alpha-(2->8)-sialidase activity
- Specific Function
- Catalyzes the removal of sialic acid (N-acetylneuraminic acid) moities from glycoproteins, oligosaccharides and gangliosides.
- Gene Name
- NEU2
- Uniprot ID
- Q9Y3R4
- Uniprot Name
- Sialidase-2
- Molecular Weight
- 42253.345 Da
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52