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

Identification

Generic Name
2-amino-4-[2,4-dichloro-5-(2-pyrrolidin-1-ylethoxy)phenyl]-N-ethylthieno[2,3-d]pyrimidine-6-carboxamide
DrugBank Accession Number
DB06969
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 480.411
Monoisotopic: 479.094951109
Chemical Formula
C21H23Cl2N5O2S
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHeat shock protein HSP 90-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 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
1,3-dichlorobenzene / 2,3,5-trisubstituted thiophene / 2-heteroaryl carboxamide / 4-phenylpyrimidine / 5-phenylpyrimidine / Alkyl aryl ether / Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound
show 33 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
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

References

General References
Not Available
PubChem Compound
25210273
PubChem Substance
99443440
ChemSpider
24629112
BindingDB
33237
ChEMBL
CHEMBL563327
ZINC
ZINC000036966109
PDBe Ligand
2KL
PDB Entries
2wi7

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 Solubility0.00249 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/MSsplash10-001i-0000900000-d1a51768b0cc5f57e986
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-003r-0002900000-24f5af3c580be29e3aa1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0079-6000900000-8ee357afdc0dbcfe4f73
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01qi-0009000000-801ca5d6c62f0bbd1a31
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001j-9103400000-1e7927a4a6c15837a90a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bta-0109100000-c31f16d19cf7a3c98a80
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-197.51653
predicted
DeepCCS 1.0 (2019)
[M+H]+199.9121
predicted
DeepCCS 1.0 (2019)
[M+Na]+206.0895
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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. [Article]

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