Identification
Name4-{[(1R,2S)-1,2-dihydroxy-2-methyl-3-(4-nitrophenoxy)propyl]amino}-2-(trifluoromethyl)benzonitrile
Accession NumberDB07421
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 411.3319
Monoisotopic: 411.104205252
Chemical FormulaC18H16F3N3O5
InChI KeyINVUBEGZQHQAMY-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
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Androgen receptorProteinunknownNot AvailableHumanP10275 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as nitrophenyl ethers. These are aromatic compounds containing a nitrobenzene moiety that carries an ether group on the benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentNitrophenyl ethers
Alternative ParentsTrifluoromethylbenzenes / Phenylalkylamines / Phenoxy compounds / Phenol ethers / Benzonitriles / Nitroaromatic compounds / Secondary alkylarylamines / Alkyl aryl ethers / Tertiary alcohols / Propargyl-type 1,3-dipolar organic compounds
SubstituentsNitrophenyl ether / Trifluoromethylbenzene / Phenoxy compound / Nitroaromatic compound / Benzonitrile / Phenol ether / Phenylalkylamine / Alkyl aryl ether / Secondary aliphatic/aromatic amine / Tertiary alcohol
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot 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 factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
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 June 11, 2017 21:08