(2R)-2-AMINO-3,3,3-TRIFLUORO-N-HYDROXY-2-{[(4-PHENOXYPHENYL)SULFONYL]METHYL}PROPANAMIDE

Identification

Generic Name
(2R)-2-AMINO-3,3,3-TRIFLUORO-N-HYDROXY-2-{[(4-PHENOXYPHENYL)SULFONYL]METHYL}PROPANAMIDE
DrugBank Accession Number
DB07246
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 404.361
Monoisotopic: 404.065376905
Chemical Formula
C16H15F3N2O5S
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UMatrix metalloproteinase-9Not 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
Adverseeffects
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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 / Alpha amino acids and derivatives / Benzenesulfonyl compounds / Phenoxy compounds / Phenol ethers / Sulfones / Hydroxamic acids / Organopnictogen compounds / Organofluorides / Organic oxides
show 4 more
Substituents
Alkyl fluoride / Alkyl halide / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aromatic homomonocyclic compound / Benzenesulfonyl group / Carbonyl group / Carboxylic acid derivative / Diaryl ether
show 19 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
MKRPIBSCGZAUCH-OAHLLOKOSA-N
InChI
InChI=1S/C16H15F3N2O5S/c17-16(18,19)15(20,14(22)21-23)10-27(24,25)13-8-6-12(7-9-13)26-11-4-2-1-3-5-11/h1-9,23H,10,20H2,(H,21,22)/t15-/m1/s1
IUPAC Name
(2R)-2-amino-3,3,3-trifluoro-N-hydroxy-2-[(4-phenoxybenzenesulfonyl)methyl]propanamide
SMILES
N[C@](CS(=O)(=O)C1=CC=C(OC2=CC=CC=C2)C=C1)(C(=O)NO)C(F)(F)F

References

General References
Not Available
PubChem Compound
16129579
PubChem Substance
99443717
ChemSpider
17286395
ZINC
ZINC000016052326
PDBe Ligand
7MR
PDB Entries
2ow1

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 Solubility0.0258 mg/mLALOGPS
logP2.4ALOGPS
logP1.58ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)8.6ChemAxon
pKa (Strongest Basic)1.86ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.72 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity88.59 m3·mol-1ChemAxon
Polarizability34.11 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9332
Blood Brain Barrier+0.5316
Caco-2 permeable-0.6328
P-glycoprotein substrateNon-substrate0.5489
P-glycoprotein inhibitor INon-inhibitor0.7372
P-glycoprotein inhibitor IINon-inhibitor0.9336
Renal organic cation transporterNon-inhibitor0.914
CYP450 2C9 substrateNon-substrate0.7373
CYP450 2D6 substrateNon-substrate0.8053
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.7386
CYP450 2C9 inhibitorNon-inhibitor0.7332
CYP450 2D6 inhibitorNon-inhibitor0.8511
CYP450 2C19 inhibitorNon-inhibitor0.5775
CYP450 3A4 inhibitorInhibitor0.5829
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.654
Ames testNon AMES toxic0.5819
CarcinogenicityNon-carcinogens0.5811
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4969 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9972
hERG inhibition (predictor II)Non-inhibitor0.6917
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

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
May play an essential role in local proteolysis of the extracellular matrix and in leukocyte migration. Could play a role in bone osteoclastic resorption. Cleaves KiSS1 at a Gly-|-Leu bond. Cleaves...
Gene Name
MMP9
Uniprot ID
P14780
Uniprot Name
Matrix metalloproteinase-9
Molecular Weight
78457.51 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 on September 15, 2010 21:19 / Updated on June 12, 2020 16:52