(1S)-2-(1H-INDOL-3-YL)-1-{[(5-ISOQUINOLIN-6-YLPYRIDIN-3-YL)OXY]METHYL}ETHYLAMINE

Identification

Name
(1S)-2-(1H-INDOL-3-YL)-1-{[(5-ISOQUINOLIN-6-YLPYRIDIN-3-YL)OXY]METHYL}ETHYLAMINE
Accession Number
DB06959
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: 394.4684
Monoisotopic: 394.179361346
Chemical Formula
C25H22N4O
InChI Key
BUCZDJYEOAQTHL-KEKNWZKVSA-N
InChI
InChI=1S/C25H22N4O/c26-22(10-21-14-29-25-4-2-1-3-24(21)25)16-30-23-11-20(13-28-15-23)17-5-6-19-12-27-8-7-18(19)9-17/h1-9,11-15,21-22H,10,16,26H2/t21?,22-/m0/s1
IUPAC Name
(2S)-1-(3H-indol-3-yl)-3-{[5-(isoquinolin-6-yl)pyridin-3-yl]oxy}propan-2-amine
SMILES
[H][[email protected]@](N)(COC1=CN=CC(=C1)C1=CC2=CC=NC=C2C=C1)CC1([H])C=NC2=CC=CC=C12

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UcAMP-dependent protein kinase catalytic subunit alphaNot AvailableHuman
UcAMP-dependent protein kinase inhibitor alphaNot 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
11840906
PubChem Substance
99443430
ChemSpider
10015411
HET
2EA
PDB Entries
2f7e

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 Solubility0.00032 mg/mLALOGPS
logP3.33ALOGPS
logP2.99ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)13.74ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area73.39 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity119.38 m3·mol-1ChemAxon
Polarizability43.48 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9913
Caco-2 permeable-0.606
P-glycoprotein substrateNon-substrate0.5745
P-glycoprotein inhibitor INon-inhibitor0.8381
P-glycoprotein inhibitor IIInhibitor0.628
Renal organic cation transporterInhibitor0.5669
CYP450 2C9 substrateNon-substrate0.8403
CYP450 2D6 substrateNon-substrate0.665
CYP450 3A4 substrateNon-substrate0.5803
CYP450 1A2 substrateInhibitor0.9566
CYP450 2C9 inhibitorInhibitor0.5981
CYP450 2D6 inhibitorInhibitor0.7951
CYP450 2C19 inhibitorInhibitor0.728
CYP450 3A4 inhibitorInhibitor0.8872
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9277
Ames testNon AMES toxic0.5101
CarcinogenicityNon-carcinogens0.8942
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4553 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9545
hERG inhibition (predictor II)Non-inhibitor0.6472
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 isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Isoquinolines and derivatives
Sub Class
Not Available
Direct Parent
Isoquinolines and derivatives
Alternative Parents
3-alkylindoles / Aralkylamines / Alkyl aryl ethers / Pyridines and derivatives / Benzenoids / Heteroaromatic compounds / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Monoalkylamines / Imines
show 1 more
Substituents
Isoquinoline / 3-alkylindole / Indole / Indole or derivatives / Alkyl aryl ether / Aralkylamine / Pyridine / Benzenoid / Heteroaromatic compound / Ether
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Phosphorylates a large number of substrates in the cytoplasm and the nucleus. Regulates the abundance of compartmentalized pools of its regulatory subunits through phosphorylation of PJA2 which bin...
Gene Name
PRKACA
Uniprot ID
P17612
Uniprot Name
cAMP-dependent protein kinase catalytic subunit alpha
Molecular Weight
40589.38 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Protein kinase a catalytic subunit binding
Specific Function
Extremely potent competitive inhibitor of cAMP-dependent protein kinase activity, this protein interacts with the catalytic subunit of the enzyme after the cAMP-induced dissociation of its regulato...
Gene Name
PKIA
Uniprot ID
P61925
Uniprot Name
cAMP-dependent protein kinase inhibitor alpha
Molecular Weight
7988.435 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 15:44