N-hydroxy-4-({4-[4-(trifluoromethyl)phenoxy]phenyl}sulfonyl)tetrahydro-2H-pyran-4-carboxamide

Identification

Generic Name
N-hydroxy-4-({4-[4-(trifluoromethyl)phenoxy]phenyl}sulfonyl)tetrahydro-2H-pyran-4-carboxamide
DrugBank Accession Number
DB06945
Background

N-hydroxy-4-({4-[4-(trifluoromethyl)phenoxy]phenyl}sulfonyl)tetrahydro-2H-pyran-4-carboxamide is a solid. This compound belongs to the diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. This substance is known to target a disintegrin and metalloproteinase with thrombospondin motifs 5.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 445.41
Monoisotopic: 445.080692618
Chemical Formula
C19H18F3NO6S
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UA disintegrin and metalloproteinase with thrombospondin motifs 5Not AvailableHumans
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 diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylethers
Direct Parent
Diphenylethers
Alternative Parents
Diarylethers / Trifluoromethylbenzenes / Benzenesulfonyl compounds / Phenoxy compounds / Phenol ethers / Oxanes / Sulfones / Hydroxamic acids / Dialkyl ethers / Oxacyclic compounds
show 7 more
Substituents
Alkyl fluoride / Alkyl halide / Aromatic heteromonocyclic compound / Benzenesulfonyl group / Carbonyl group / Carboxylic acid derivative / Dialkyl ether / Diaryl ether / Diphenylether / Ether
show 19 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
FOSWRYKPHVPIDJ-UHFFFAOYSA-N
InChI
InChI=1S/C19H18F3NO6S/c20-19(21,22)13-1-3-14(4-2-13)29-15-5-7-16(8-6-15)30(26,27)18(17(24)23-25)9-11-28-12-10-18/h1-8,25H,9-12H2,(H,23,24)
IUPAC Name
N-hydroxy-4-{4-[4-(trifluoromethyl)phenoxy]benzenesulfonyl}oxane-4-carboxamide
SMILES
ONC(=O)C1(CCOCC1)S(=O)(=O)C1=CC=C(OC2=CC=C(C=C2)C(F)(F)F)C=C1

References

General References
Not Available
PubChem Compound
9933197
PubChem Substance
99443416
ChemSpider
8108825
BindingDB
50348671
ChEMBL
CHEMBL1229868
ZINC
ZINC000024177188
PDBe Ligand
294
PDB Entries
3b8z

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 Solubility0.0441 mg/mLALOGPS
logP2.36ALOGPS
logP2.51Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)8.66Chemaxon
pKa (Strongest Basic)-3.6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area101.93 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity100.21 m3·mol-1Chemaxon
Polarizability38.91 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9739
Blood Brain Barrier+0.8865
Caco-2 permeable-0.6119
P-glycoprotein substrateNon-substrate0.6052
P-glycoprotein inhibitor IInhibitor0.5551
P-glycoprotein inhibitor IINon-inhibitor0.808
Renal organic cation transporterNon-inhibitor0.8
CYP450 2C9 substrateNon-substrate0.7399
CYP450 2D6 substrateNon-substrate0.7981
CYP450 3A4 substrateSubstrate0.5332
CYP450 1A2 substrateNon-inhibitor0.691
CYP450 2C9 inhibitorNon-inhibitor0.6678
CYP450 2D6 inhibitorNon-inhibitor0.8613
CYP450 2C19 inhibitorNon-inhibitor0.6224
CYP450 3A4 inhibitorInhibitor0.5432
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6834
Ames testNon AMES toxic0.5611
CarcinogenicityNon-carcinogens0.7036
BiodegradationNot ready biodegradable0.9886
Rat acute toxicity2.5365 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9652
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000b-2104900000-9060ba31feebf6c638ac
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udl-0009800000-749ceb1875e2a5c68a66
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-7219600000-e36bf796c74820911dd4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-0002900000-69e6a1fd7b046a5bce1a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-4932200000-fd5adf842b1f67949242
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-002s-7049200000-1255a6a36ddb65c2b265
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]-196.66566
predicted
DeepCCS 1.0 (2019)
[M+H]+199.02367
predicted
DeepCCS 1.0 (2019)
[M+Na]+205.11684
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Cleaves aggrecan, a cartilage proteoglycan, and may be involved in its turnover. May play an important role in the destruction of aggrecan in arthritic diseases. May play a role in proteolytic proc...
Gene Name
ADAMTS5
Uniprot ID
Q9UNA0
Uniprot Name
A disintegrin and metalloproteinase with thrombospondin motifs 5
Molecular Weight
101716.955 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 21:17 / Updated at June 12, 2020 16:52