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4-[4-(1-Amino-1-Methylethyl)Phenyl]-5-Chloro-N-[4-(2-Morpholin-4-Ylethyl)Phenyl]Pyrimidin-2-Amine

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Overview

Structure
DrugBank ID
DB02491
Type
Small Molecule
US Approved
NO
Other Approved
NO
Patents
0
Indicated Conditions
0
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Identification

Generic Name
4-[4-(1-Amino-1-Methylethyl)Phenyl]-5-Chloro-N-[4-(2-Morpholin-4-Ylethyl)Phenyl]Pyrimidin-2-Amine
DrugBank Accession Number
DB02491
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 451.992
Monoisotopic: 451.213888314
Chemical Formula
C25H30ClN5O
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UFibroblast growth factor receptor 2Not 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
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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
Phenylpropanes / Phenethylamines / Aniline and substituted anilines / Aminopyrimidines and derivatives / Aralkylamines / Halopyrimidines / Aryl chlorides / Morpholines / Heteroaromatic compounds / Trialkylamines
show 8 more
Substituents
4-phenylpyrimidine / 5-phenylpyrimidine / Amine / Aminopyrimidine / Aniline or substituted anilines / Aralkylamine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle
show 24 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
CJSSYVIHFXDFFC-UHFFFAOYSA-N
InChI
InChI=1S/C25H30ClN5O/c1-25(2,27)20-7-5-19(6-8-20)23-22(26)17-28-24(30-23)29-21-9-3-18(4-10-21)11-12-31-13-15-32-16-14-31/h3-10,17H,11-16,27H2,1-2H3,(H,28,29,30)
IUPAC Name
4-[4-(2-aminopropan-2-yl)phenyl]-5-chloro-N-{4-[2-(morpholin-4-yl)ethyl]phenyl}pyrimidin-2-amine
SMILES
CC(C)(N)C1=CC=C(C=C1)C1=NC(NC2=CC=C(CCN3CCOCC3)C=C2)=NC=C1Cl

References

General References
Not Available
PubChem Compound
447622
PubChem Substance
46505042
ChemSpider
394661
BindingDB
50206280
ChEMBL
CHEMBL233209
ZINC
ZINC000012502169
PDBe Ligand
AA2
PDB Entries
1oec

Clinical Trials

Clinical Trials
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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 Solubility0.00603 mg/mLALOGPS
logP4.45ALOGPS
logP4.64Chemaxon
logS-4.9ALOGPS
pKa (Strongest Acidic)13.61Chemaxon
pKa (Strongest Basic)9.67Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area76.3 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity130.63 m3·mol-1Chemaxon
Polarizability50.04 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.997
Blood Brain Barrier+0.7675
Caco-2 permeable-0.5182
P-glycoprotein substrateSubstrate0.7099
P-glycoprotein inhibitor INon-inhibitor0.6411
P-glycoprotein inhibitor IINon-inhibitor0.5205
Renal organic cation transporterNon-inhibitor0.5181
CYP450 2C9 substrateNon-substrate0.875
CYP450 2D6 substrateNon-substrate0.7728
CYP450 3A4 substrateSubstrate0.6182
CYP450 1A2 substrateInhibitor0.5458
CYP450 2C9 inhibitorNon-inhibitor0.7049
CYP450 2D6 inhibitorNon-inhibitor0.6155
CYP450 2C19 inhibitorNon-inhibitor0.555
CYP450 3A4 inhibitorNon-inhibitor0.567
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8059
Ames testNon AMES toxic0.7207
CarcinogenicityNon-carcinogens0.8468
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6109 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5986
hERG inhibition (predictor II)Inhibitor0.8169
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/MSsplash10-000i-0000900000-61e126927649a3065479
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-1000900000-a7c96328cce648ad5ceb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000j-0009800000-71a0cd5893cdd4feb153
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9001200000-e2faa6726decede5c6f0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ldi-0009300000-e28a35a07cbec63657a2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9001200000-f74a0269320471041d17
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]-201.31712
predicted
DeepCCS 1.0 (2019)
[M+H]+203.67514
predicted
DeepCCS 1.0 (2019)
[M+Na]+209.9894
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Fibroblast growth factor receptor 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tyrosine-protein kinase that acts as a cell-surface receptor for fibroblast growth factors and plays an essential role in the regulation of cell proliferation, differentiation, migration and apoptosis, and in the regulation of embryonic development. Required for normal embryonic patterning, trophoblast function, limb bud development, lung morphogenesis, osteogenesis and skin development. Plays an essential role in the regulation of osteoblast differentiation, proliferation and apoptosis, and is required for normal skeleton development. Promotes cell proliferation in keratinocytes and immature osteoblasts, but promotes apoptosis in differentiated osteoblasts. Phosphorylates PLCG1, FRS2 and PAK4. Ligand binding leads to the activation of several signaling cascades. Activation of PLCG1 leads to the production of the cellular signaling molecules diacylglycerol and inositol 1,4,5-trisphosphate. Phosphorylation of FRS2 triggers recruitment of GRB2, GAB1, PIK3R1 and SOS1, and mediates activation of RAS, MAPK1/ERK2, MAPK3/ERK1 and the MAP kinase signaling pathway, as well as of the AKT1 signaling pathway. FGFR2 signaling is down-regulated by ubiquitination, internalization and degradation. Mutations that lead to constitutive kinase activation or impair normal FGFR2 maturation, internalization and degradation lead to aberrant signaling. Over-expressed FGFR2 promotes activation of STAT1.
Specific Function
ATP binding
Gene Name
FGFR2
Uniprot ID
P21802
Uniprot Name
Fibroblast growth factor receptor 2
Molecular Weight
92024.29 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:17