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

Identification

Generic Name
4-{[(1R,2S)-1,2-dihydroxy-2-methyl-3-(4-nitrophenoxy)propyl]amino}-2-(trifluoromethyl)benzonitrile
DrugBank Accession Number
DB07421
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 411.3319
Monoisotopic: 411.104205252
Chemical Formula
C18H16F3N3O5
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAndrogen receptorNot 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 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
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Substituents
Alcohol / Alkanolamine / Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Allyl-type 1,3-dipolar organic compound / Amine / Aromatic homomonocyclic compound / Benzonitrile / C-nitro compound
show 26 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
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][C@](O)(NC1=CC(=C(C=C1)C#N)C(F)(F)F)[C@@](C)(O)COC1=CC=C(C=C1)[N+]([O-])=O

References

General References
Not Available
PubChem Compound
46937071
PubChem Substance
99443892
ChemSpider
25057164
ZINC
ZINC000039037416
PDBe Ligand
B66
PDB Entries
3b66

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 Solubility0.0107 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 Area128.65 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity96.45 m3·mol-1Chemaxon
Polarizability36.96 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

Targets

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Kind
Protein
Organism
Humans
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. [Article]

Drug created at September 15, 2010 21:21 / Updated at June 12, 2020 16:52