1-[3-({[(4-AMINO-5-FLUORO-2-METHYLQUINOLIN-3-YL)METHYL]THIO}METHYL)PHENYL]-2,2,2-TRIFLUOROETHANE-1,1-DIOL

Identification

Name
1-[3-({[(4-AMINO-5-FLUORO-2-METHYLQUINOLIN-3-YL)METHYL]THIO}METHYL)PHENYL]-2,2,2-TRIFLUOROETHANE-1,1-DIOL
Accession Number
DB07756
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: 426.428
Monoisotopic: 426.10251134
Chemical Formula
C20H18F4N2O2S
InChI Key
GPBGHVRNVGXPNM-UHFFFAOYSA-N
InChI
InChI=1S/C20H18F4N2O2S/c1-11-14(18(25)17-15(21)6-3-7-16(17)26-11)10-29-9-12-4-2-5-13(8-12)19(27,28)20(22,23)24/h2-8,27-28H,9-10H2,1H3,(H2,25,26)
IUPAC Name
1-[3-({[(4-amino-5-fluoro-2-methylquinolin-3-yl)methyl]sulfanyl}methyl)phenyl]-2,2,2-trifluoroethane-1,1-diol
SMILES
CC1=C(CSCC2=CC(=CC=C2)C(O)(O)C(F)(F)F)C(N)=C2C(F)=CC=CC2=N1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAcetylcholinesteraseNot 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
1723
PubChem Substance
99444227
ChemSpider
1660
BindingDB
10504
HET
FBQ
PDB Entries
1hbj

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 Solubility0.00422 mg/mLALOGPS
logP3.64ALOGPS
logP3.18ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)7.59ChemAxon
pKa (Strongest Basic)8.42ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.37 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity105.05 m3·mol-1ChemAxon
Polarizability40.02 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9897
Blood Brain Barrier+0.865
Caco-2 permeable+0.5146
P-glycoprotein substrateSubstrate0.558
P-glycoprotein inhibitor INon-inhibitor0.8453
P-glycoprotein inhibitor IINon-inhibitor0.8634
Renal organic cation transporterNon-inhibitor0.8053
CYP450 2C9 substrateNon-substrate0.8336
CYP450 2D6 substrateNon-substrate0.7637
CYP450 3A4 substrateNon-substrate0.6603
CYP450 1A2 substrateInhibitor0.736
CYP450 2C9 inhibitorNon-inhibitor0.7158
CYP450 2D6 inhibitorNon-inhibitor0.6893
CYP450 2C19 inhibitorNon-inhibitor0.6129
CYP450 3A4 inhibitorNon-inhibitor0.5843
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5646
Ames testNon AMES toxic0.6815
CarcinogenicityNon-carcinogens0.8841
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6550 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9714
hERG inhibition (predictor II)Non-inhibitor0.6353
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 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 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Aminoquinolines and derivatives
Direct Parent
4-aminoquinolines
Alternative Parents
Haloquinolines / Aminopyridines and derivatives / Methylpyridines / Aryl fluorides / Benzene and substituted derivatives / Heteroaromatic compounds / Fluorohydrins / Sulfenyl compounds / Azacyclic compounds / Dialkylthioethers
show 6 more
Substituents
4-aminoquinoline / Haloquinoline / Aminopyridine / Methylpyridine / Aryl fluoride / Aryl halide / Monocyclic benzene moiety / Benzenoid / Pyridine / Heteroaromatic compound
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Serine hydrolase activity
Specific Function
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name
ACHE
Uniprot ID
P22303
Uniprot Name
Acetylcholinesterase
Molecular Weight
67795.525 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