NAV

9-Amino-2-deoxy-2,3-dehydro-n-acetyl-neuraminic acid

Identification

Generic Name
9-Amino-2-deoxy-2,3-dehydro-n-acetyl-neuraminic acid
DrugBank Accession Number
DB04227
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 290.2698
Monoisotopic: 290.11140094
Chemical Formula
C11H18N2O7
Synonyms
  • (6R)-5-Acetamido-6-[(1R,2R)-3-amino-1,2-dihydroxypropyl]-2,6-anhydro-3,5-dideoxy-L-threo-hex-2-enonic acid
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNeuraminidaseNot AvailableInfluenza A virus (strain A/Tern/Australia/G70C/1975 H11N9)
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
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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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 1,3-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C3 atom.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
1,3-aminoalcohols
Alternative Parents
Acetamides / Secondary carboxylic acid amides / Secondary alcohols / Amino acids / 1,2-aminoalcohols / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides
show 3 more
Substituents
1,2-aminoalcohol / 1,3-aminoalcohol / Acetamide / Alcohol / Aliphatic heteromonocyclic compound / Amino acid / Amino acid or derivatives / Carbonyl group / Carboxamide group / Carboxylic acid
show 13 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
VJTPBNUXDULDQD-UFGQHTETSA-N
InChI
InChI=1S/C11H18N2O7/c1-4(14)13-8-5(15)2-7(11(18)19)20-10(8)9(17)6(16)3-12/h2,5-6,8-10,15-17H,3,12H2,1H3,(H,13,14)(H,18,19)/t5-,6+,8+,9+,10+/m0/s1
IUPAC Name
(2R,3R,4S)-2-[(1R,2R)-3-amino-1,2-dihydroxypropyl]-3-acetamido-4-hydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid
SMILES
[H]N([H])C[C@@H](O)[C@@H](O)[C@]1([H])OC(=C[C@H](O)[C@H]1N([H])C(C)=O)C(O)=O

References

General References
Not Available
PubChem Compound
445534
PubChem Substance
46504947
ChemSpider
393149
ChEMBL
CHEMBL140830
ZINC
ZINC000005884079
PDBe Ligand
9AM
PDB Entries
1f8d / 8gfq

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 Solubility47.6 mg/mLALOGPS
logP-2.8ALOGPS
logP-6.1Chemaxon
logS-0.79ALOGPS
pKa (Strongest Acidic)3.17Chemaxon
pKa (Strongest Basic)9.21Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area162.34 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity65.77 m3·mol-1Chemaxon
Polarizability27.17 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6959
Blood Brain Barrier-0.9326
Caco-2 permeable-0.7836
P-glycoprotein substrateNon-substrate0.5317
P-glycoprotein inhibitor INon-inhibitor0.8263
P-glycoprotein inhibitor IINon-inhibitor0.9689
Renal organic cation transporterNon-inhibitor0.9693
CYP450 2C9 substrateNon-substrate0.8172
CYP450 2D6 substrateNon-substrate0.8429
CYP450 3A4 substrateNon-substrate0.6454
CYP450 1A2 substrateNon-inhibitor0.962
CYP450 2C9 inhibitorNon-inhibitor0.9468
CYP450 2D6 inhibitorNon-inhibitor0.9632
CYP450 2C19 inhibitorNon-inhibitor0.9229
CYP450 3A4 inhibitorNon-inhibitor0.9833
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9902
Ames testNon AMES toxic0.7007
CarcinogenicityNon-carcinogens0.9562
BiodegradationReady biodegradable0.63
Rat acute toxicity1.8519 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9887
hERG inhibition (predictor II)Non-inhibitor0.9592
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-MSsplash10-00e9-9230000000-988671c890573aa649b7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-006y-0090000000-5e0356c25e3d771c459c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004r-2390000000-bcf97a8744213e31420a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001r-1940000000-4a12b5d42adaba35ced9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-008a-0490000000-4bfb8cc08c0dc6a1802d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00yl-2930000000-d454a91868dc8b13897d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pei-3920000000-8117340ec31f70401f2e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-168.59258
predicted
DeepCCS 1.0 (2019)
[M+H]+170.48799
predicted
DeepCCS 1.0 (2019)
[M+Na]+176.3821
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Neuraminidase
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]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52