S-3-(4-FLUOROPHENOXY)-2-HYDROXY-2-METHYL-N-[4-NITRO-3-(TRIFLUOROMETHYL)PHENYL]PROPANAMIDE

Identification

Name
S-3-(4-FLUOROPHENOXY)-2-HYDROXY-2-METHYL-N-[4-NITRO-3-(TRIFLUOROMETHYL)PHENYL]PROPANAMIDE
Accession Number
DB07769
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: 402.2971
Monoisotopic: 402.083884388
Chemical Formula
C17H14F4N2O5
InChI Key
KJMFOTCDISOHDX-INIZCTEOSA-N
InChI
InChI=1S/C17H14F4N2O5/c1-16(25,9-28-12-5-2-10(18)3-6-12)15(24)22-11-4-7-14(23(26)27)13(8-11)17(19,20)21/h2-8,25H,9H2,1H3,(H,22,24)/t16-/m0/s1
IUPAC Name
(2S)-3-(4-fluorophenoxy)-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
SMILES
C[[email protected]](O)(COC1=CC=C(F)C=C1)C(=O)NC1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAndrogen receptorNot AvailableHuman
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
5288215
PubChem Substance
99444240
ChemSpider
4450421
BindingDB
18663
ChEMBL
CHEMBL124718
HET
FHM
PDB Entries
2ax7 / 2ax8 / 2axa

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 Solubility0.00121 mg/mLALOGPS
logP2.69ALOGPS
logP3.64ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)11.77ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area104.38 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity91.15 m3·mol-1ChemAxon
Polarizability34.2 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9381
Blood Brain Barrier-0.5752
Caco-2 permeable-0.5863
P-glycoprotein substrateSubstrate0.5434
P-glycoprotein inhibitor IInhibitor0.5067
P-glycoprotein inhibitor IINon-inhibitor0.8812
Renal organic cation transporterNon-inhibitor0.9601
CYP450 2C9 substrateNon-substrate0.7895
CYP450 2D6 substrateNon-substrate0.8274
CYP450 3A4 substrateSubstrate0.5543
CYP450 1A2 substrateInhibitor0.5237
CYP450 2C9 inhibitorNon-inhibitor0.5196
CYP450 2D6 inhibitorNon-inhibitor0.7976
CYP450 2C19 inhibitorInhibitor0.5234
CYP450 3A4 inhibitorNon-inhibitor0.678
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6551
Ames testNon AMES toxic0.6008
CarcinogenicityNon-carcinogens0.6627
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5361 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9607
hERG inhibition (predictor II)Non-inhibitor0.7387
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 trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Trifluoromethylbenzenes
Direct Parent
Trifluoromethylbenzenes
Alternative Parents
Anilides / Nitrobenzenes / N-arylamides / Nitroaromatic compounds / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Fluorobenzenes / Aryl fluorides / Tertiary alcohols
show 10 more
Substituents
Trifluoromethylbenzene / Nitrobenzene / Anilide / Phenoxy compound / Nitroaromatic compound / N-arylamide / Phenol ether / Alkyl aryl ether / Fluorobenzene / Halobenzene
show 28 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Details
1. Androgen receptor
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 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 15:25 / Updated on December 01, 2017 15:55