5-[(E)-(5-CHLORO-2-OXO-1,2-DIHYDRO-3H-INDOL-3-YLIDENE)METHYL]-N-[2-(DIETHYLAMINO)ETHYL]-2,4-DIMETHYL-1H-PYRROLE-3-CARBOXAMIDE

Identification

Name
5-[(E)-(5-CHLORO-2-OXO-1,2-DIHYDRO-3H-INDOL-3-YLIDENE)METHYL]-N-[2-(DIETHYLAMINO)ETHYL]-2,4-DIMETHYL-1H-PYRROLE-3-CARBOXAMIDE
Accession Number
DB08009
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
1C7AZL970U
CAS number
Not Available
Weight
Average: 414.928
Monoisotopic: 414.182253835
Chemical Formula
C22H27ClN4O2
InChI Key
XPLJEFSRINKZLC-ATVHPVEESA-N
InChI
InChI=1S/C22H27ClN4O2/c1-5-27(6-2)10-9-24-22(29)20-13(3)19(25-14(20)4)12-17-16-11-15(23)7-8-18(16)26-21(17)28/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28)/b17-12-
IUPAC Name
5-{[(3Z)-5-chloro-2-oxo-2,3-dihydro-1H-indol-3-ylidene]methyl}-N-[2-(diethylamino)ethyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide
SMILES
CCN(CC)CCNC(=O)C1=C(C)NC(\C=C2/C(=O)NC3=C2C=C(Cl)C=C3)=C1C

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCalcium/calmodulin-dependent protein kinase type 1GNot 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
5329103
PubChem Substance
99444480
ChemSpider
4486265
BindingDB
4815
ChEBI
132084
ChEMBL
CHEMBL13485
HET
J60
PDB Entries
2jam / 2xik / 3hzt / 4nzw

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 Solubility0.022 mg/mLALOGPS
logP3.64ALOGPS
logP3.39ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)11.27ChemAxon
pKa (Strongest Basic)9.04ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.23 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity120.85 m3·mol-1ChemAxon
Polarizability46.59 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9939
Blood Brain Barrier+0.7508
Caco-2 permeable-0.5756
P-glycoprotein substrateSubstrate0.8543
P-glycoprotein inhibitor IInhibitor0.555
P-glycoprotein inhibitor IIInhibitor0.5644
Renal organic cation transporterNon-inhibitor0.7079
CYP450 2C9 substrateNon-substrate0.8447
CYP450 2D6 substrateNon-substrate0.7768
CYP450 3A4 substrateSubstrate0.6781
CYP450 1A2 substrateInhibitor0.5183
CYP450 2C9 inhibitorNon-inhibitor0.6229
CYP450 2D6 inhibitorNon-inhibitor0.6475
CYP450 2C19 inhibitorNon-inhibitor0.5682
CYP450 3A4 inhibitorInhibitor0.5613
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7506
Ames testNon AMES toxic0.57
CarcinogenicityNon-carcinogens0.7637
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6664 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7828
hERG inhibition (predictor II)Inhibitor0.7771
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 indolines. These are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indolines
Direct Parent
Indolines
Alternative Parents
Pyrrole carboxamides / Substituted pyrroles / Aryl chlorides / Benzenoids / Vinylogous amides / Heteroaromatic compounds / Trialkylamines / Secondary carboxylic acid amides / Amino acids and derivatives / Lactams
show 6 more
Substituents
Dihydroindole / Pyrrole-3-carboxamide / Pyrrole-3-carboxylic acid or derivatives / Aryl chloride / Aryl halide / Substituted pyrrole / Benzenoid / Pyrrole / Heteroaromatic compound / Vinylogous amide
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Calmodulin-dependent protein kinase activity
Specific Function
Calcium/calmodulin-dependent protein kinase belonging to a proposed calcium-triggered signaling cascade. In vitro phosphorylates transcription factor CREB1 (By similarity).
Gene Name
CAMK1G
Uniprot ID
Q96NX5
Uniprot Name
Calcium/calmodulin-dependent protein kinase type 1G
Molecular Weight
53086.475 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 15:27 / Updated on December 01, 2017 15:59