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

Identification

Name
(2R)-2-{[(4-FLUORO-3-METHYLPHENYL)SULFONYL]AMINO}-N-HYDROXY-2-TETRAHYDRO-2H-PYRAN-4-YLACETAMIDE
Accession Number
DB07290
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 346.374
Monoisotopic: 346.099870623
Chemical Formula
C14H19FN2O5S
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][[email protected]@](NS(=O)(=O)C1=CC(C)=C(F)C=C1)(C1CCOCC1)C(=O)NO

Pharmacology

Indication
Not Available
Structured Indications
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
4369384
PubChem Substance
99443761
ChemSpider
3571962
BindingDB
8503
ChEMBL
CHEMBL204593
HET
915
PDB Entries
1yqy

Clinical Trials

Clinical Trials
Not Available

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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / Benzenesulfonamide / Benzenesulfonyl group / Fluorobenzene / Halobenzene / Toluene / Aryl fluoride / Aryl halide / Organosulfonic acid amide
show 23 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Details
1. 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. [PubMed:10592235]

Drug created on September 15, 2010 15:20 / Updated on December 01, 2017 15:48