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Identification
Name2-Deoxy-2,3-Dehydro-N-Acetyl-Neuraminic Acid
Accession NumberDB03991  (EXPT01111)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 291.2546
Monoisotopic: 291.095416525
Chemical FormulaC11H17NO8
InChI KeyJINJZWSZQKHCIP-CUZACWQJSA-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,2S)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
SMILES
CC(=O)N[C@@H]1[C@@H](O)C=C(O[[email protected]]1[[email protected]](O)[C@@H](O)CO)C(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Hemagglutinin-neuraminidaseProteinunknownNot AvailableHPIV-3P12564 details
SialidaseProteinunknownNot AvailableMicromonospora viridifaciensQ02834 details
NeuraminidaseProteinunknownNot AvailableInfluenza A virus (strain A/Tern/Australia/G70C/1975 H11N9)P03472 details
Hemagglutinin-neuraminidaseProteinunknownNot AvailableNDVP32884 details
Sialidase-2ProteinunknownNot AvailableHumanQ9Y3R4 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility65.2 mg/mLALOGPS
logP-2.2ALOGPS
logP-3.7ChemAxon
logS-0.65ALOGPS
pKa (Strongest Acidic)3.52ChemAxon
pKa (Strongest Basic)-0.41ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.55 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity64.11 m3·mol-1ChemAxon
Polarizability27.09 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyranoid amino acids and derivatives. These are compounds containing a (hydro)pyran ring bearing unprotected amino and carboxylic acid functionalities.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar acids and derivatives
Direct ParentPyranoid amino acids and derivatives
Alternative Parents
Substituents
  • Pyranoid amino acid
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Polyol
  • Carboxamide group
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available

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 trigger virion/cell membranes fusion (By similarity).Neuraminidase activity ensures the efficient spread of the virus by dissociating the mature virions from the neuraminic acid containing glycoproteins.
Gene Name:
HN
Uniprot ID:
P12564
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
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 release. Additionally helps virus spread through the circulation by further removing sialic acids from the cell surface. These cleavages prevent self-aggregation and ensure the efficient spread of th...
Gene Name:
NA
Uniprot ID:
P03472
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 trigger virion/cell membranes fusion (By similarity).Neuraminidase activity ensures the efficient spread of the virus by dissociating the mature virions from the neuraminic acid containing glycoproteins.
Gene Name:
HN
Uniprot ID:
P32884
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 ]
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
Molecular Weight:
42253.345 Da
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23