6-[4-(2-piperidin-1-ylethoxy)phenyl]-3-pyridin-4-ylpyrazolo[1,5-a]pyrimidine

Identification

Name
6-[4-(2-piperidin-1-ylethoxy)phenyl]-3-pyridin-4-ylpyrazolo[1,5-a]pyrimidine
Accession Number
DB08597
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
10K52CIC1Z
CAS number
Not Available
Weight
Average: 399.4882
Monoisotopic: 399.205910447
Chemical Formula
C24H25N5O
InChI Key
XHBVYDAKJHETMP-UHFFFAOYSA-N
InChI
InChI=1S/C24H25N5O/c1-2-12-28(13-3-1)14-15-30-22-6-4-19(5-7-22)21-16-26-24-23(17-27-29(24)18-21)20-8-10-25-11-9-20/h4-11,16-18H,1-3,12-15H2
IUPAC Name
4-(6-{4-[2-(piperidin-1-yl)ethoxy]phenyl}pyrazolo[1,5-a]pyrimidin-3-yl)pyridine
SMILES
C(CN1CCCCC1)OC1=CC=C(C=C1)C1=CN2N=CC(=C2N=C1)C1=CC=NC=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UActivin receptor type-1Not AvailableHuman
UPeptidyl-prolyl cis-trans isomerase FKBP1ANot 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
11524144
PubChem Substance
99445068
ChemSpider
9698930
BindingDB
50262685
ChEBI
78510
ChEMBL
CHEMBL478629
HET
TAK
PDB Entries
3aqv / 3h9r / 3q4t / 4c02

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 Solubility0.0148 mg/mLALOGPS
logP3.84ALOGPS
logP3.44ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)8.81ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area55.55 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity128.51 m3·mol-1ChemAxon
Polarizability45.75 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+0.9927
Caco-2 permeable-0.6108
P-glycoprotein substrateSubstrate0.6569
P-glycoprotein inhibitor IInhibitor0.6623
P-glycoprotein inhibitor IIInhibitor0.9217
Renal organic cation transporterInhibitor0.8216
CYP450 2C9 substrateNon-substrate0.8726
CYP450 2D6 substrateNon-substrate0.5888
CYP450 3A4 substrateSubstrate0.5562
CYP450 1A2 substrateInhibitor0.785
CYP450 2C9 inhibitorInhibitor0.6921
CYP450 2D6 inhibitorNon-inhibitor0.829
CYP450 2C19 inhibitorInhibitor0.6547
CYP450 3A4 inhibitorInhibitor0.67
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9129
Ames testNon AMES toxic0.6448
CarcinogenicityNon-carcinogens0.9059
BiodegradationNot ready biodegradable0.9972
Rat acute toxicity2.4667 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.8187
hERG inhibition (predictor II)Inhibitor0.5228
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 pyrazolo[1,5-a]pyrimidines. These are aromatic heterocyclic compounds containing a pyrazolo[3,4-d]pyrimidine ring system, which consists of a pyrazole ring fused to and sharing exactly one nitrogen atom with a pyrimidine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrazolopyrimidines
Sub Class
Pyrazolo[1,5-a]pyrimidines
Direct Parent
Pyrazolo[1,5-a]pyrimidines
Alternative Parents
Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Pyrimidines and pyrimidine derivatives / Pyridines and derivatives / Piperidines / Pyrazoles / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds
show 2 more
Substituents
Pyrazolo[1,5-a]pyrimidine / Phenoxy compound / Phenol ether / Alkyl aryl ether / Monocyclic benzene moiety / Benzenoid / Pyrimidine / Pyridine / Piperidine / Azole
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
piperidines, aromatic ether, pyridines, ring assembly, pyrazolopyrimidine (CHEBI:78510)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transmembrane receptor protein serine/threonine kinase activity
Specific Function
On ligand binding, forms a receptor complex consisting of two type II and two type I transmembrane serine/threonine kinases. Type II receptors phosphorylate and activate type I receptors which auto...
Gene Name
ACVR1
Uniprot ID
Q04771
Uniprot Name
Activin receptor type-1
Molecular Weight
57152.41 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
Type i transforming growth factor beta receptor binding
Specific Function
Keeps in an inactive conformation TGFBR1, the TGF-beta type I serine/threonine kinase receptor, preventing TGF-beta receptor activation in absence of ligand. Recruites SMAD7 to ACVR1B which prevent...
Gene Name
FKBP1A
Uniprot ID
P62942
Uniprot Name
Peptidyl-prolyl cis-trans isomerase FKBP1A
Molecular Weight
11950.665 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 15:33 / Updated on December 01, 2017 16:07