2-amino-4-[2,4-dichloro-5-(2-pyrrolidin-1-ylethoxy)phenyl]-N-ethylthieno[2,3-d]pyrimidine-6-carboxamide

Identification

Name
2-amino-4-[2,4-dichloro-5-(2-pyrrolidin-1-ylethoxy)phenyl]-N-ethylthieno[2,3-d]pyrimidine-6-carboxamide
Accession Number
DB06969
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: 480.411
Monoisotopic: 479.094951109
Chemical Formula
C21H23Cl2N5O2S
InChI Key
WJUNQSYQHHIVFX-UHFFFAOYSA-N
InChI
InChI=1S/C21H23Cl2N5O2S/c1-2-25-19(29)17-10-13-18(26-21(24)27-20(13)31-17)12-9-16(15(23)11-14(12)22)30-8-7-28-5-3-4-6-28/h9-11H,2-8H2,1H3,(H,25,29)(H2,24,26,27)
IUPAC Name
2-amino-4-{2,4-dichloro-5-[2-(pyrrolidin-1-yl)ethoxy]phenyl}-N-ethylthieno[2,3-d]pyrimidine-6-carboxamide
SMILES
CCNC(=O)C1=CC2=C(N=C(N)N=C2S1)C1=C(Cl)C=C(Cl)C(OCCN2CCCC2)=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHeat shock protein HSP 90-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
25210273
PubChem Substance
99443440
ChemSpider
24629112
BindingDB
33237
ChEMBL
CHEMBL563327
HET
2KL
PDB Entries
2wi7

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 Solubility0.00249 mg/mLALOGPS
logP4.6ALOGPS
logP4.21ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)13.9ChemAxon
pKa (Strongest Basic)8.03ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.37 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity125.57 m3·mol-1ChemAxon
Polarizability49.78 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9059
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.6836
P-glycoprotein inhibitor IInhibitor0.5946
P-glycoprotein inhibitor IIInhibitor0.6394
Renal organic cation transporterInhibitor0.5069
CYP450 2C9 substrateNon-substrate0.8312
CYP450 2D6 substrateNon-substrate0.8116
CYP450 3A4 substrateSubstrate0.6702
CYP450 1A2 substrateInhibitor0.6687
CYP450 2C9 inhibitorInhibitor0.602
CYP450 2D6 inhibitorNon-inhibitor0.6677
CYP450 2C19 inhibitorInhibitor0.5669
CYP450 3A4 inhibitorNon-inhibitor0.7215
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.874
Ames testNon AMES toxic0.6081
CarcinogenicityNon-carcinogens0.8179
BiodegradationNot ready biodegradable0.9841
Rat acute toxicity2.5571 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7218
hERG inhibition (predictor II)Inhibitor0.8716
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 phenylpyrimidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrimidine ring through a CC or CN bond. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Phenylpyrimidines
Alternative Parents
Pyrimidinecarboxamides / Thienopyrimidines / Dichlorobenzenes / 2-heteroaryl carboxamides / Phenol ethers / Phenoxy compounds / 2,3,5-trisubstituted thiophenes / Thiophene carboxamides / Alkyl aryl ethers / Aminopyrimidines and derivatives
show 12 more
Substituents
4-phenylpyrimidine / 5-phenylpyrimidine / Pyrimidinecarboxamide / Thienopyrimidine / 2-heteroaryl carboxamide / Phenoxy compound / 1,3-dichlorobenzene / Phenol ether / 2,3,5-trisubstituted thiophene / Thiophene carboxamide
show 33 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Tpr domain binding
Specific Function
Molecular chaperone that promotes the maturation, structural maintenance and proper regulation of specific target proteins involved for instance in cell cycle control and signal transduction. Under...
Gene Name
HSP90AA1
Uniprot ID
P07900
Uniprot Name
Heat shock protein HSP 90-alpha
Molecular Weight
84659.015 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