3-[3-(2,3-Dihydroxy-Propylamino)-Phenyl]-4-(5-Fluoro-1-Methyl-1h-Indol-3-Yl)-Pyrrole-2,5-Dione

Identification

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Name
3-[3-(2,3-Dihydroxy-Propylamino)-Phenyl]-4-(5-Fluoro-1-Methyl-1h-Indol-3-Yl)-Pyrrole-2,5-Dione
Accession Number
DB01772  (EXPT01170)
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: 409.4103
Monoisotopic: 409.143784348
Chemical Formula
C22H20FN3O4
InChI Key
RPGZQOOZHIEPJW-HNNXBMFYSA-N
InChI
InChI=1S/C22H20FN3O4/c1-26-10-17(16-8-13(23)5-6-18(16)26)20-19(21(29)25-22(20)30)12-3-2-4-14(7-12)24-9-15(28)11-27/h2-8,10,15,24,27-28H,9,11H2,1H3,(H,25,29,30)/t15-/m0/s1
IUPAC Name
3-(3-{[(2S)-2,3-dihydroxypropyl]amino}phenyl)-4-(5-fluoro-1-methyl-1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione
SMILES
[H][C@@](O)(CO)CNC1=CC=CC(=C1)C1=C(C(=O)NC1=O)C1=CN(C)C2=CC=C(F)C=C12

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlycogen synthase kinase-3 betaNot 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
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
448238
PubChem Substance
46504930
ChemSpider
395103
HET
DFN
PDB Entries
1r0e

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 Solubility0.0455 mg/mLALOGPS
logP2.16ALOGPS
logP1.32ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.47ChemAxon
pKa (Strongest Basic)3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area103.59 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity110.9 m3·mol-1ChemAxon
Polarizability42.09 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9766
Blood Brain Barrier-0.5778
Caco-2 permeable-0.6586
P-glycoprotein substrateSubstrate0.6482
P-glycoprotein inhibitor INon-inhibitor0.8044
P-glycoprotein inhibitor IINon-inhibitor0.7456
Renal organic cation transporterNon-inhibitor0.9198
CYP450 2C9 substrateNon-substrate0.8301
CYP450 2D6 substrateNon-substrate0.8224
CYP450 3A4 substrateSubstrate0.5425
CYP450 1A2 substrateNon-inhibitor0.8571
CYP450 2C9 inhibitorNon-inhibitor0.7907
CYP450 2D6 inhibitorNon-inhibitor0.8925
CYP450 2C19 inhibitorNon-inhibitor0.8513
CYP450 3A4 inhibitorNon-inhibitor0.9283
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8289
Ames testNon AMES toxic0.6806
CarcinogenicityNon-carcinogens0.8256
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6963 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9791
hERG inhibition (predictor II)Inhibitor0.7804
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 n-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 1-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
N-alkylindoles
Direct Parent
N-alkylindoles
Alternative Parents
Indoles / Aniline and substituted anilines / Phenylalkylamines / Secondary alkylarylamines / Maleimides / Aryl fluorides / N-methylpyrroles / N-unsubstituted carboxylic acid imides / Pyrrolines / Heteroaromatic compounds
show 13 more
Substituents
N-alkylindole / Indole / Aniline or substituted anilines / Phenylalkylamine / Secondary aliphatic/aromatic amine / Maleimide / N-methylpyrrole / Monocyclic benzene moiety / Aryl halide / Substituted pyrrole
show 30 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Constitutively active protein kinase that acts as a negative regulator in the hormonal control of glucose homeostasis, Wnt signaling and regulation of transcription factors and microtubules, by pho...
Gene Name
GSK3B
Uniprot ID
P49841
Uniprot Name
Glycogen synthase kinase-3 beta
Molecular Weight
46743.865 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. 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 June 13, 2005 07:24 / Updated on June 04, 2019 05:22