4-{[(1R,2S)-1,2-dihydroxy-2-methyl-3-(4-nitrophenoxy)propyl]amino}-2-(trifluoromethyl)benzonitrile

Identification

Name
4-{[(1R,2S)-1,2-dihydroxy-2-methyl-3-(4-nitrophenoxy)propyl]amino}-2-(trifluoromethyl)benzonitrile
Accession Number
DB07421
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: 411.3319
Monoisotopic: 411.104205252
Chemical Formula
C18H16F3N3O5
InChI Key
INVUBEGZQHQAMY-SJORKVTESA-N
InChI
InChI=1S/C18H16F3N3O5/c1-17(26,10-29-14-6-4-13(5-7-14)24(27)28)16(25)23-12-3-2-11(9-22)15(8-12)18(19,20)21/h2-8,16,23,25-26H,10H2,1H3/t16-,17+/m1/s1
IUPAC Name
4-{[(1R,2S)-1,2-dihydroxy-2-methyl-3-(4-nitrophenoxy)propyl]amino}-2-(trifluoromethyl)benzonitrile
SMILES
[H][[email protected]](O)(NC1=CC(=C(C=C1)C#N)C(F)(F)F)[[email protected]@](C)(O)COC1=CC=C(C=C1)[N+]([O-])=O

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
46937071
PubChem Substance
99443892
ChemSpider
25057164
HET
B66
PDB Entries
3b66

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 Solubility0.0107 mg/mLALOGPS
logP2.99ALOGPS
logP3.05ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)11.57ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area131.33 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity97.45 m3·mol-1ChemAxon
Polarizability36.92 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9515
Blood Brain Barrier-0.511
Caco-2 permeable-0.5705
P-glycoprotein substrateNon-substrate0.5497
P-glycoprotein inhibitor IInhibitor0.5089
P-glycoprotein inhibitor IINon-inhibitor0.8562
Renal organic cation transporterNon-inhibitor0.9498
CYP450 2C9 substrateNon-substrate0.7056
CYP450 2D6 substrateNon-substrate0.8103
CYP450 3A4 substrateSubstrate0.5495
CYP450 1A2 substrateNon-inhibitor0.5
CYP450 2C9 inhibitorNon-inhibitor0.5811
CYP450 2D6 inhibitorNon-inhibitor0.8019
CYP450 2C19 inhibitorInhibitor0.5069
CYP450 3A4 inhibitorNon-inhibitor0.5894
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5783
Ames testNon AMES toxic0.5999
CarcinogenicityNon-carcinogens0.7029
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5807 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9732
hERG inhibition (predictor II)Non-inhibitor0.689
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 nitrophenyl ethers. These are aromatic compounds containing a nitrobenzene moiety that carries an ether group on the benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Nitrobenzenes
Direct Parent
Nitrophenyl ethers
Alternative Parents
Trifluoromethylbenzenes / Phenylalkylamines / Phenoxy compounds / Phenol ethers / Benzonitriles / Nitroaromatic compounds / Secondary alkylarylamines / Alkyl aryl ethers / Tertiary alcohols / Propargyl-type 1,3-dipolar organic compounds
show 9 more
Substituents
Nitrophenyl ether / Trifluoromethylbenzene / Phenoxy compound / Nitroaromatic compound / Benzonitrile / Phenol ether / Phenylalkylamine / Alkyl aryl ether / Secondary aliphatic/aromatic amine / Tertiary alcohol
show 26 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

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 15:21 / Updated on December 01, 2017 15:50