(3Z)-6-(4-HYDROXY-3-METHOXYPHENYL)-3-(1H-PYRROL-2-YLMETHYLENE)-1,3-DIHYDRO-2H-INDOL-2-ONE

Identification

Name
(3Z)-6-(4-HYDROXY-3-METHOXYPHENYL)-3-(1H-PYRROL-2-YLMETHYLENE)-1,3-DIHYDRO-2H-INDOL-2-ONE
Accession Number
DB07078
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: 332.3526
Monoisotopic: 332.116092388
Chemical Formula
C20H16N2O3
InChI Key
AYSXURJZVXBSRV-WJDWOHSUSA-N
InChI
InChI=1S/C20H16N2O3/c1-25-19-10-13(5-7-18(19)23)12-4-6-15-16(11-14-3-2-8-21-14)20(24)22-17(15)9-12/h2-11,21,23H,1H3,(H,22,24)/b16-11-
IUPAC Name
(3Z)-6-(4-hydroxy-3-methoxyphenyl)-3-(1H-pyrrol-2-ylmethylidene)-2,3-dihydro-1H-indol-2-one
SMILES
COC1=CC(=CC=C1O)C1=CC2=C(C=C1)\C(=C\C1=CC=CN1)C(=O)N2

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USerine/threonine-protein kinase Chk1Not 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
10125830
PubChem Substance
99443549
ChemSpider
8301349
BindingDB
14649
ChEMBL
CHEMBL202930
HET
43A
PDB Entries
2ayp

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 Solubility0.0458 mg/mLALOGPS
logP3.49ALOGPS
logP3.45ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)9.82ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area74.35 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity97.95 m3·mol-1ChemAxon
Polarizability36.55 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.7148
Caco-2 permeable+0.5278
P-glycoprotein substrateSubstrate0.5134
P-glycoprotein inhibitor INon-inhibitor0.6708
P-glycoprotein inhibitor IIInhibitor0.568
Renal organic cation transporterNon-inhibitor0.8629
CYP450 2C9 substrateNon-substrate0.7955
CYP450 2D6 substrateNon-substrate0.7916
CYP450 3A4 substrateSubstrate0.5795
CYP450 1A2 substrateInhibitor0.8549
CYP450 2C9 inhibitorInhibitor0.9098
CYP450 2D6 inhibitorNon-inhibitor0.6885
CYP450 2C19 inhibitorInhibitor0.6524
CYP450 3A4 inhibitorInhibitor0.8979
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8871
Ames testAMES toxic0.7321
CarcinogenicityNon-carcinogens0.9233
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.8881 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9941
hERG inhibition (predictor II)Non-inhibitor0.53
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 methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
Methoxyphenols
Direct Parent
Methoxyphenols
Alternative Parents
Indolines / Phenoxy compounds / Anisoles / Methoxybenzenes / 1-hydroxy-2-unsubstituted benzenoids / Alkyl aryl ethers / Substituted pyrroles / Heteroaromatic compounds / Secondary carboxylic acid amides / Lactams
show 6 more
Substituents
Methoxyphenol / Indole or derivatives / Dihydroindole / Phenoxy compound / Anisole / Phenol ether / Methoxybenzene / Alkyl aryl ether / 1-hydroxy-2-unsubstituted benzenoid / Monocyclic benzene moiety
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activity
Specific Function
Serine/threonine-protein kinase which is required for checkpoint-mediated cell cycle arrest and activation of DNA repair in response to the presence of DNA damage or unreplicated DNA. May also nega...
Gene Name
CHEK1
Uniprot ID
O14757
Uniprot Name
Serine/threonine-protein kinase Chk1
Molecular Weight
54433.115 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 15:18 / Updated on December 01, 2017 15:45