2[4-BROMO-2-FLUOROPHENYL)METHYL]-6-FLUOROSPIRO[ISOQUINOLINE-4-(1H),3'-PYRROLIDINE]-1,2',3,5'(2H)-TETRONE

Identification

Name
2[4-BROMO-2-FLUOROPHENYL)METHYL]-6-FLUOROSPIRO[ISOQUINOLINE-4-(1H),3'-PYRROLIDINE]-1,2',3,5'(2H)-TETRONE
Accession Number
DB07450
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: 449.202
Monoisotopic: 447.987025907
Chemical Formula
C19H11BrF2N2O4
InChI Key
BMHZAHGTGIZZCT-LJQANCHMSA-N
InChI
InChI=1S/C19H11BrF2N2O4/c20-10-2-1-9(14(22)5-10)8-24-16(26)12-4-3-11(21)6-13(12)19(18(24)28)7-15(25)23-17(19)27/h1-6H,7-8H2,(H,23,25,27)/t19-/m1/s1
IUPAC Name
(4R)-2-[(4-bromo-2-fluorophenyl)methyl]-6-fluoro-2,3-dihydro-1H-spiro[isoquinoline-4,3'-pyrrolidine]-1,2',3,5'-tetrone
SMILES
FC1=CC=C2C(=O)N(CC3=CC=C(Br)C=C3F)C(=O)[[email protected]]3(CC(=O)NC3=O)C2=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAldose reductaseNot 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
447950
PubChem Substance
99443921
ChemSpider
394897
BindingDB
50038843
ChEMBL
CHEMBL292963
HET
BFI
PDB Entries
1pwl

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 Solubility0.012 mg/mLALOGPS
logP2.42ALOGPS
logP2.5ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)8.43ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.55 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.73 m3·mol-1ChemAxon
Polarizability36.95 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9907
Blood Brain Barrier+0.9583
Caco-2 permeable-0.538
P-glycoprotein substrateNon-substrate0.5058
P-glycoprotein inhibitor IInhibitor0.5514
P-glycoprotein inhibitor IINon-inhibitor0.8302
Renal organic cation transporterNon-inhibitor0.662
CYP450 2C9 substrateNon-substrate0.8841
CYP450 2D6 substrateNon-substrate0.7935
CYP450 3A4 substrateSubstrate0.599
CYP450 1A2 substrateNon-inhibitor0.7476
CYP450 2C9 inhibitorNon-inhibitor0.7107
CYP450 2D6 inhibitorNon-inhibitor0.8624
CYP450 2C19 inhibitorNon-inhibitor0.6033
CYP450 3A4 inhibitorNon-inhibitor0.6566
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.565
Ames testNon AMES toxic0.7013
CarcinogenicityNon-carcinogens0.854
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4178 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9883
hERG inhibition (predictor II)Non-inhibitor0.7893
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 benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Isoquinolines and derivatives
Sub Class
Benzylisoquinolines
Direct Parent
Benzylisoquinolines
Alternative Parents
1,3-isoquinolinediones / Isoquinolones and derivatives / Tetrahydroisoquinolines / Bromobenzenes / Fluorobenzenes / Pyrrolidine-2-ones / Aryl bromides / Aryl fluorides / N-substituted carboxylic acid imides / N-unsubstituted carboxylic acid imides
show 10 more
Substituents
Benzylisoquinoline / 1,3-isoquinolinedione / Isoquinolone / Tetrahydroisoquinoline / Bromobenzene / Fluorobenzene / Halobenzene / Aryl bromide / Aryl fluoride / Aryl halide
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Details
1. Aldose reductase
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Glyceraldehyde oxidoreductase activity
Specific Function
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name
AKR1B1
Uniprot ID
P15121
Uniprot Name
Aldose reductase
Molecular Weight
35853.125 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 15:51