NAV

(2R,4S,5R,6R)-5-Acetamido-4-amino-6-(diethylcarbamoyl)oxane-2-carboxylic acid

Identification

Generic Name
(2R,4S,5R,6R)-5-Acetamido-4-amino-6-(diethylcarbamoyl)oxane-2-carboxylic acid
DrugBank Accession Number
DB02529
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 301.3388
Monoisotopic: 301.163770861
Chemical Formula
C13H23N3O5
Synonyms
Not Available
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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 pyranoid amino acids and derivatives. These are compounds containing a (hydro)pyran ring bearing unprotected amino and carboxylic acid functionalities.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Pyranoid amino acids and derivatives
Alternative Parents
Gamma amino acids and derivatives / C-glycosyl compounds / Pyrans / Oxanes / Tertiary carboxylic acid amides / Acetamides / Secondary carboxylic acid amides / Amino acids / Oxacyclic compounds / Monocarboxylic acids and derivatives
show 6 more
Substituents
Acetamide / Aliphatic heteromonocyclic compound / Amine / Amino acid / Amino acid or derivatives / C-glycosyl compound / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative
show 18 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
BULFTXGJKXVMER-LNFKQOIKSA-N
InChI
InChI=1S/C13H23N3O5/c1-4-16(5-2)12(18)11-10(15-7(3)17)8(14)6-9(21-11)13(19)20/h8-11H,4-6,14H2,1-3H3,(H,15,17)(H,19,20)/t8-,9+,10+,11+/m0/s1
IUPAC Name
(2R,4S,5R,6R)-4-amino-6-(diethylcarbamoyl)-5-acetamidooxane-2-carboxylic acid
SMILES
CCN(CC)C(=O)[C@@H]1O[C@H](C[C@H](N)[C@H]1NC(C)=O)C(O)=O

References

General References
Not Available
PubChem Compound
17753990
PubChem Substance
46508969
ChemSpider
16743980
ZINC
ZINC000033821311
PDBe Ligand
G28
PDB Entries
2qwg / 2qwj

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
logP-4.2Chemaxon
pKa (Strongest Acidic)3.63Chemaxon
pKa (Strongest Basic)9.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area121.96 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity73.37 m3·mol-1Chemaxon
Polarizability30.33 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6496
Blood Brain Barrier-0.9876
Caco-2 permeable-0.6929
P-glycoprotein substrateSubstrate0.7155
P-glycoprotein inhibitor INon-inhibitor0.8199
P-glycoprotein inhibitor IINon-inhibitor0.9847
Renal organic cation transporterNon-inhibitor0.9602
CYP450 2C9 substrateNon-substrate0.8859
CYP450 2D6 substrateNon-substrate0.7949
CYP450 3A4 substrateNon-substrate0.5344
CYP450 1A2 substrateNon-inhibitor0.9292
CYP450 2C9 inhibitorNon-inhibitor0.9228
CYP450 2D6 inhibitorNon-inhibitor0.9368
CYP450 2C19 inhibitorNon-inhibitor0.8653
CYP450 3A4 inhibitorNon-inhibitor0.9571
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9876
Ames testNon AMES toxic0.8119
CarcinogenicityNon-carcinogens0.8163
BiodegradationNot ready biodegradable0.9154
Rat acute toxicity2.2407 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9937
hERG inhibition (predictor II)Non-inhibitor0.91
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-MSsplash10-0udi-9770000000-c84accd896ff0e4d7b4c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-3e146be4d80f80961796
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0129000000-9b187f62be88bc1d95fc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ufr-0496000000-68f5a3af9450889ddb74
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ik9-2971000000-1ff53384eb92fa87c935
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-044i-2910000000-e9fdc751d5dc65a5e084
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pdi-5940000000-793b8dc7ae03e65eead7
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]-173.73845
predicted
DeepCCS 1.0 (2019)
[M+H]+176.13402
predicted
DeepCCS 1.0 (2019)
[M+Na]+182.04654
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 July 02, 2020 13:18