NAV

(3R,4R,5S,6R)-6-Fluoro-3,4,5-trihydroxytetrahydro-2H-pyran-2-olate

Identification

Generic Name
(3R,4R,5S,6R)-6-Fluoro-3,4,5-trihydroxytetrahydro-2H-pyran-2-olate
DrugBank Accession Number
DB03586
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 167.1124
Monoisotopic: 167.035576571
Chemical Formula
C5H8FO5
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
UAlpha-xylosidaseNot AvailableEscherichia coli (strain K12)
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 monosaccharides. These are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Monosaccharides
Alternative Parents
Oxanes / Secondary alcohols / Fluorohydrins / Polyols / Oxacyclic compounds / Organofluorides / Organic oxides / Hydrocarbon derivatives / Alkyl fluorides / Alkoxides
show 1 more
Substituents
Alcohol / Aliphatic heteromonocyclic compound / Alkoxide / Alkyl fluoride / Alkyl halide / Fluorohydrin / Halohydrin / Hydrocarbon derivative / Monosaccharide / Organic anion
show 8 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
CSWSGZBYLQUXQI-ZAMRNKCBSA-N
InChI
InChI=1S/C5H8FO5/c6-4-2(8)1(7)3(9)5(10)11-4/h1-5,7-9H/q-1/t1-,2-,3+,4-,5?/m0/s1
IUPAC Name
(3R,4R,5S,6R)-6-fluoro-3,4,5-trihydroxyoxan-2-olate
SMILES
[H][C@]1(F)OC([O-])[C@H](O)[C@@H](O)[C@@H]1O

References

General References
Not Available
PubChem Compound
5289591
PubChem Substance
46505913
ChemSpider
4451525
PDBe Ligand
XYF
PDB Entries
1xsk

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 Solubility441.0 mg/mLALOGPS
logP-1.5ALOGPS
logP-1.9Chemaxon
logS0.38ALOGPS
pKa (Strongest Acidic)11.18Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area92.98 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity40.16 m3·mol-1Chemaxon
Polarizability13.09 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9561
Blood Brain Barrier+0.8283
Caco-2 permeable-0.5814
P-glycoprotein substrateNon-substrate0.7023
P-glycoprotein inhibitor INon-inhibitor0.9715
P-glycoprotein inhibitor IINon-inhibitor0.9927
Renal organic cation transporterNon-inhibitor0.946
CYP450 2C9 substrateNon-substrate0.8823
CYP450 2D6 substrateNon-substrate0.8743
CYP450 3A4 substrateNon-substrate0.7221
CYP450 1A2 substrateNon-inhibitor0.9072
CYP450 2C9 inhibitorNon-inhibitor0.9196
CYP450 2D6 inhibitorNon-inhibitor0.9214
CYP450 2C19 inhibitorNon-inhibitor0.9242
CYP450 3A4 inhibitorNon-inhibitor0.8018
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9471
Ames testNon AMES toxic0.8669
CarcinogenicityNon-carcinogens0.9151
BiodegradationNot ready biodegradable0.8176
Rat acute toxicity2.3763 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9702
hERG inhibition (predictor II)Non-inhibitor0.9617
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 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-127.926994
predicted
DeepCCS 1.0 (2019)
[M+H]+130.08237
predicted
DeepCCS 1.0 (2019)
[M+Na]+137.02852
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Alpha-xylosidase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Xyloglucan 1,6-alpha-xylosidase activity
Specific Function
Can catalyze the transfer of alpha-xylosyl residue from alpha-xyloside to xylose, glucose, mannose, fructose, maltose, isomaltose, nigerose, kojibiose, sucrose and trehalose.
Gene Name
yicI
Uniprot ID
P31434
Uniprot Name
Alpha-xylosidase
Molecular Weight
88078.905 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