2-chloro-4-{[(1R,3Z,7S,7aS)-7-hydroxy-1-(trifluoromethyl)tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-ylidene]amino}-3-methylbenzonitrile

Identification

Name
2-chloro-4-{[(1R,3Z,7S,7aS)-7-hydroxy-1-(trifluoromethyl)tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-ylidene]amino}-3-methylbenzonitrile
Accession Number
DB08088
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: 359.731
Monoisotopic: 359.064838997
Chemical Formula
C15H13ClF3N3O2
InChI Key
KALFKWQLCWAXJO-RNSKTZJQSA-N
InChI
InChI=1S/C15H13ClF3N3O2/c1-7-9(3-2-8(6-20)11(7)16)21-14-22-5-4-10(23)12(22)13(24-14)15(17,18)19/h2-3,10,12-13,23H,4-5H2,1H3/b21-14-/t10-,12-,13+/m0/s1
IUPAC Name
4-{[(1R,3Z,7S,7aS)-7-hydroxy-1-(trifluoromethyl)-hexahydropyrrolo[1,2-c][1,3]oxazol-3-ylidene]amino}-2-chloro-3-methylbenzonitrile
SMILES
N#CC1=CC=C(\N=C2/O[[email protected]@]([H])(C(F)(F)F)[[email protected]]3([H])[[email protected]](O)([H])CCN23)C(C)=C1Cl

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
11428356
PubChem Substance
99444559
ChemSpider
9603232
BindingDB
29320
ChEMBL
CHEMBL484726
HET
LGB
PDB Entries
3g0w

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 Solubility0.0826 mg/mLALOGPS
logP3.86ALOGPS
logP3.35ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)14.43ChemAxon
pKa (Strongest Basic)4.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area68.85 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity82.54 m3·mol-1ChemAxon
Polarizability31.94 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9904
Blood Brain Barrier+0.9368
Caco-2 permeable+0.5
P-glycoprotein substrateNon-substrate0.6102
P-glycoprotein inhibitor INon-inhibitor0.7059
P-glycoprotein inhibitor IINon-inhibitor0.7488
Renal organic cation transporterNon-inhibitor0.6698
CYP450 2C9 substrateNon-substrate0.6363
CYP450 2D6 substrateNon-substrate0.7709
CYP450 3A4 substrateSubstrate0.6614
CYP450 1A2 substrateInhibitor0.5421
CYP450 2C9 inhibitorNon-inhibitor0.5559
CYP450 2D6 inhibitorNon-inhibitor0.8434
CYP450 2C19 inhibitorInhibitor0.5678
CYP450 3A4 inhibitorNon-inhibitor0.8852
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6798
Ames testNon AMES toxic0.6131
CarcinogenicityNon-carcinogens0.8499
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6110 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7526
hERG inhibition (predictor II)Non-inhibitor0.7873
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 benzonitriles. These are organic compounds containing a benzene bearing a nitrile substituent.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzonitriles
Direct Parent
Benzonitriles
Alternative Parents
Toluenes / Chlorobenzenes / Aryl chlorides / Pyrrolidines / Oxazolidines / Secondary alcohols / Isoureas / Propargyl-type 1,3-dipolar organic compounds / Oxacyclic compounds / Azacyclic compounds
show 6 more
Substituents
Benzonitrile / Chlorobenzene / Halobenzene / Toluene / Aryl chloride / Aryl halide / Oxazolidine / Pyrrolidine / Isourea / Secondary alcohol
show 20 more
Molecular Framework
Aromatic heteropolycyclic 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 15:28 / Updated on December 01, 2017 16:00