(1S)-2-(1H-INDOL-3-YL)-1-[({5-[(E)-2-PYRIDIN-4-YLVINYL]PYRIDIN-3-YL}OXY)METHYL]ETHYLAMINE

Identification

Name
(1S)-2-(1H-INDOL-3-YL)-1-[({5-[(E)-2-PYRIDIN-4-YLVINYL]PYRIDIN-3-YL}OXY)METHYL]ETHYLAMINE
Accession Number
DB07107
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: 370.447
Monoisotopic: 370.179361346
Chemical Formula
C23H22N4O
InChI Key
SGHXFHRRWFLILP-XJDXJNMNSA-N
InChI
InChI=1S/C23H22N4O/c24-20(12-19-14-27-23-4-2-1-3-22(19)23)16-28-21-11-18(13-26-15-21)6-5-17-7-9-25-10-8-17/h1-11,13-15,20,27H,12,16,24H2/b6-5+/t20-/m0/s1
IUPAC Name
(2S)-1-(1H-indol-3-yl)-3-({5-[(E)-2-(pyridin-4-yl)ethenyl]pyridin-3-yl}oxy)propan-2-amine
SMILES
[H][[email protected]@](N)(COC1=CN=CC(\C=C\C2=CC=NC=C2)=C1)CC1=CNC2=C1C=CC=C2

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
6914613
PubChem Substance
99443578
ChemSpider
5290493
BindingDB
15022
ChEMBL
CHEMBL383541
HET
4EA
PDB Entries
2f7x

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 Solubility0.000753 mg/mLALOGPS
logP3.12ALOGPS
logP3.09ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)17.11ChemAxon
pKa (Strongest Basic)9.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area76.82 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity111.74 m3·mol-1ChemAxon
Polarizability41.93 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9876
Caco-2 permeable-0.6341
P-glycoprotein substrateSubstrate0.5567
P-glycoprotein inhibitor INon-inhibitor0.9097
P-glycoprotein inhibitor IINon-inhibitor0.5991
Renal organic cation transporterInhibitor0.5
CYP450 2C9 substrateNon-substrate0.8584
CYP450 2D6 substrateNon-substrate0.6492
CYP450 3A4 substrateNon-substrate0.6141
CYP450 1A2 substrateInhibitor0.8983
CYP450 2C9 inhibitorNon-inhibitor0.6688
CYP450 2D6 inhibitorInhibitor0.882
CYP450 2C19 inhibitorNon-inhibitor0.5205
CYP450 3A4 inhibitorInhibitor0.5933
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9013
Ames testNon AMES toxic0.6412
CarcinogenicityNon-carcinogens0.961
BiodegradationNot ready biodegradable0.997
Rat acute toxicity2.5676 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9059
hERG inhibition (predictor II)Non-inhibitor0.6195
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 3-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indoles
Direct Parent
3-alkylindoles
Alternative Parents
Aralkylamines / Alkyl aryl ethers / Substituted pyrroles / Pyridines and derivatives / Benzenoids / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents
3-alkylindole / Alkyl aryl ether / Aralkylamine / Pyridine / Substituted pyrrole / Benzenoid / Pyrrole / Heteroaromatic compound / Ether / Azacycle
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 15:46