2-Deoxy-2,3-Dehydro-N-Acetyl-Neuraminic Acid

Identification

Name
2-Deoxy-2,3-Dehydro-N-Acetyl-Neuraminic Acid
Accession Number
DB03991  (EXPT01111)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 291.2546
Monoisotopic: 291.095416525
Chemical Formula
C11H17NO8
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)-4-hydroxy-3-[(1-hydroxyethylidene)amino]-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
SMILES
[H][[email protected]@](O)(CO)[[email protected]@]([H])(O)[[email protected]]1([H])OC(=C[[email protected]]([H])(O)[[email protected]@]1([H])N=C(C)O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHemagglutinin-neuraminidaseNot AvailableHPIV-3
USialidaseNot AvailableMicromonospora viridifaciens
UNeuraminidaseNot AvailableInfluenza A virus (strain A/Tern/Australia/G70C/1975 H11N9)
UHemagglutinin-neuraminidaseNot AvailableNDV
USialidase-2Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
65309
PubChem Substance
46505061
ChemSpider
58795
BindingDB
4706
ChEBI
28062
ChEMBL
CHEMBL96712
HET
DAN
PDB Entries
1e8v / 1eus / 1f8b / 1ivf / 1ms0 / 1ms1 / 1ms8 / 1mz6 / 1n1t / 1n1v
show 35 more

Clinical Trials

Clinical Trials
Not Available

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
PropertyValueSource
Water Solubility24.0 mg/mLALOGPS
logP-1.9ALOGPS
logP-3ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)3.46ChemAxon
pKa (Strongest Basic)2.04ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area160.04 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity64.63 m3·mol-1ChemAxon
Polarizability27.19 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6158
Blood Brain Barrier-0.9228
Caco-2 permeable-0.7714
P-glycoprotein substrateNon-substrate0.6597
P-glycoprotein inhibitor INon-inhibitor0.8042
P-glycoprotein inhibitor IINon-inhibitor0.9652
Renal organic cation transporterNon-inhibitor0.969
CYP450 2C9 substrateNon-substrate0.7571
CYP450 2D6 substrateNon-substrate0.8588
CYP450 3A4 substrateNon-substrate0.6034
CYP450 1A2 substrateNon-inhibitor0.9621
CYP450 2C9 inhibitorNon-inhibitor0.9396
CYP450 2D6 inhibitorNon-inhibitor0.9626
CYP450 2C19 inhibitorNon-inhibitor0.934
CYP450 3A4 inhibitorNon-inhibitor0.984
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9847
Ames testNon AMES toxic0.7051
CarcinogenicityNon-carcinogens0.9689
BiodegradationReady biodegradable0.9307
Rat acute toxicity1.6959 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9803
hERG inhibition (predictor II)Non-inhibitor0.9634
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
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Substituents
Secondary alcohol / Carboximidic acid / Carboximidic acid derivative / Carboxylic acid derivative / Carboxylic acid / Monocarboxylic acid or derivatives / Polyol / Propargyl-type 1,3-dipolar organic compound / Organic 1,3-dipolar compound / Oxacycle
show 9 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
N-acetylneuraminic acids (CHEBI:28062)

Targets

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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Details
5. Sialidase-2
Kind
Protein
Organism
Human
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 on June 13, 2005 07:24 / Updated on December 01, 2017 15:21