Identification

Generic Name
2-deoxy-2,3-dehydro-N-acetylneuraminic acid
DrugBank Accession Number
DB03991
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 291.2546
Monoisotopic: 291.095416525
Chemical Formula
C11H17NO8
Synonyms
  • Neu2en5Ac

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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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 AvailableHumans
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
Adverseeffects
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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
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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
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 41 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility65.2 mg/mLALOGPS
logP-2.2ALOGPS
logP-3.7ChemAxon
logS-0.65ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.55 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity64.11 m3·mol-1ChemAxon
Polarizability27.1 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

Targets

Drugtargets2
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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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
Details
5. Sialidase-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