NAV

(2R)-2-{[(4-FLUORO-3-METHYLPHENYL)SULFONYL]AMINO}-N-HYDROXY-2-TETRAHYDRO-2H-PYRAN-4-YLACETAMIDE

Identification

Generic Name
(2R)-2-{[(4-FLUORO-3-METHYLPHENYL)SULFONYL]AMINO}-N-HYDROXY-2-TETRAHYDRO-2H-PYRAN-4-YLACETAMIDE
DrugBank Accession Number
DB07290
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 346.374
Monoisotopic: 346.099870623
Chemical Formula
C14H19FN2O5S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ULethal factorNot AvailableBacillus anthracis
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 benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonamides
Direct Parent
Benzenesulfonamides
Alternative Parents
Alpha amino acids and derivatives / Benzenesulfonyl compounds / Toluenes / Fluorobenzenes / Oxanes / Organosulfonamides / Aryl fluorides / Aminosulfonyl compounds / Hydroxamic acids / Oxacyclic compounds
show 7 more
Substituents
Alpha-amino acid or derivatives / Aminosulfonyl compound / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Benzenesulfonamide / Benzenesulfonyl group / Carbonyl group / Carboxylic acid derivative / Dialkyl ether
show 23 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
LUCFRFDOOYLALP-CYBMUJFWSA-N
InChI
InChI=1S/C14H19FN2O5S/c1-9-8-11(2-3-12(9)15)23(20,21)17-13(14(18)16-19)10-4-6-22-7-5-10/h2-3,8,10,13,17,19H,4-7H2,1H3,(H,16,18)/t13-/m1/s1
IUPAC Name
(2R)-2-(4-fluoro-3-methylbenzenesulfonamido)-N-hydroxy-2-(oxan-4-yl)acetamide
SMILES
[H][C@@](NS(=O)(=O)C1=CC(C)=C(F)C=C1)(C1CCOCC1)C(=O)NO

References

General References
Not Available
PubChem Compound
4369384
PubChem Substance
99443761
ChemSpider
3571962
BindingDB
8503
ChEMBL
CHEMBL204593
ZINC
ZINC000003818457
PDBe Ligand
915
PDB Entries
1yqy

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 Solubility1.16 mg/mLALOGPS
logP0.12ALOGPS
logP0.76Chemaxon
logS-2.5ALOGPS
pKa (Strongest Acidic)8.68Chemaxon
pKa (Strongest Basic)-4.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area104.73 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity81.08 m3·mol-1Chemaxon
Polarizability32.84 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7826
Blood Brain Barrier-0.6963
Caco-2 permeable-0.6156
P-glycoprotein substrateSubstrate0.6174
P-glycoprotein inhibitor INon-inhibitor0.5494
P-glycoprotein inhibitor IINon-inhibitor0.9838
Renal organic cation transporterNon-inhibitor0.9157
CYP450 2C9 substrateNon-substrate0.6038
CYP450 2D6 substrateNon-substrate0.8053
CYP450 3A4 substrateNon-substrate0.5588
CYP450 1A2 substrateNon-inhibitor0.775
CYP450 2C9 inhibitorNon-inhibitor0.6427
CYP450 2D6 inhibitorNon-inhibitor0.8762
CYP450 2C19 inhibitorNon-inhibitor0.5772
CYP450 3A4 inhibitorNon-inhibitor0.7271
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8092
Ames testNon AMES toxic0.6022
CarcinogenicityNon-carcinogens0.8001
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5334 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9684
hERG inhibition (predictor II)Inhibitor0.5
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-MSsplash10-054o-4692000000-7d2d7d1b71cc423ddbe4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0119000000-55977906421e5ac2586f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dj-0109000000-68386794b390ee6e7a3e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-1390000000-77209a3140c0a59f44b2
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03xr-2297000000-322889fb5aa21b9acb6e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0btd-5902000000-ab9f482e6e26898d1a09
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0mvl-6944000000-93bf9e28f22832de74cf
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]-169.74536
predicted
DeepCCS 1.0 (2019)
[M+H]+172.14091
predicted
DeepCCS 1.0 (2019)
[M+Na]+178.49843
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Lethal factor
Kind
Protein
Organism
Bacillus anthracis
Pharmacological action
Unknown
General Function
Metallopeptidase activity
Specific Function
One of the three proteins composing the anthrax toxin, the agent which infects many mammalian species and that may cause death. LF is the lethal factor that, when associated with PA, causes death. ...
Gene Name
lef
Uniprot ID
P15917
Uniprot Name
Lethal factor
Molecular Weight
93769.58 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:20 / Updated at June 12, 2020 16:52