NAV

(2S)-1-(3H-Indol-3-yl)-3-{[5-(6-isoquinolinyl)-3-pyridinyl]oxy}-2-propanamine

Identification

Generic Name
(2S)-1-(3H-Indol-3-yl)-3-{[5-(6-isoquinolinyl)-3-pyridinyl]oxy}-2-propanamine
DrugBank Accession Number
DB06959
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 394.4684
Monoisotopic: 394.179361346
Chemical Formula
C25H22N4O
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UcAMP-dependent protein kinase catalytic subunit alphaNot AvailableHumans
UcAMP-dependent protein kinase inhibitor alphaNot 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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
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
3-alkylindole / Alkyl aryl ether / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Ether / Heteroaromatic compound / Hydrocarbon derivative
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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]N([H])[C@H](COC1=CN=CC(=C1)C1=CC2=C(C=C1)C=NC=C2)CC1C=NC2=CC=CC=C12

References

General References
Not Available
PubChem Compound
11840906
PubChem Substance
99443430
ChemSpider
10015411
PDBe Ligand
2EA
PDB Entries
2f7e

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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)14.15Chemaxon
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
Polarizability44.24 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

Targets

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Details1. cAMP-dependent protein kinase catalytic subunit alpha
Kind
Protein
Organism
Humans
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. [Article]
Details2. cAMP-dependent protein kinase inhibitor alpha
Kind
Protein
Organism
Humans
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. [Article]

Drug created at September 15, 2010 21:18 / Updated at June 12, 2020 16:52