(5Z)-5-(3-BROMOCYCLOHEXA-2,5-DIEN-1-YLIDENE)-N-(PYRIDIN-4-YLMETHYL)-1,5-DIHYDROPYRAZOLO[1,5-A]PYRIMIDIN-7-AMINE

Identification

Name
(5Z)-5-(3-BROMOCYCLOHEXA-2,5-DIEN-1-YLIDENE)-N-(PYRIDIN-4-YLMETHYL)-1,5-DIHYDROPYRAZOLO[1,5-A]PYRIMIDIN-7-AMINE
Accession Number
DB07595
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: 381.249
Monoisotopic: 380.051083152
Chemical Formula
C18H15BrN5
InChI Key
WSIQKQLAGWVKSL-UHFFFAOYSA-O
InChI
InChI=1S/C18H14BrN5/c19-15-3-1-2-14(10-15)16-11-18(24-17(23-16)6-9-22-24)21-12-13-4-7-20-8-5-13/h1-11H,12H2,(H,21,22,23)/p+1
IUPAC Name
5-(3-bromophenyl)-7-[(pyridin-4-ylmethyl)amino]-1H-8λ⁵-pyrazolo[1,5-a]pyrimidin-8-ylium
SMILES
BrC1=CC=CC(=C1)C1=NC2=[N+](NC=C2)C(NCC2=CC=NC=C2)=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCyclin-dependent kinase 2Not 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
5327130
PubChem Substance
99444066
ChemSpider
4484380
HET
CT6
PDB Entries
2c68

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 Solubility0.00151 mg/mLALOGPS
logP1.06ALOGPS
logP0.65ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)11.65ChemAxon
pKa (Strongest Basic)5.02ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.7 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity118.71 m3·mol-1ChemAxon
Polarizability36.91 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8703
Blood Brain Barrier+0.9573
Caco-2 permeable-0.521
P-glycoprotein substrateNon-substrate0.6143
P-glycoprotein inhibitor INon-inhibitor0.9047
P-glycoprotein inhibitor IINon-inhibitor0.5154
Renal organic cation transporterNon-inhibitor0.6488
CYP450 2C9 substrateNon-substrate0.8722
CYP450 2D6 substrateNon-substrate0.8399
CYP450 3A4 substrateNon-substrate0.5624
CYP450 1A2 substrateInhibitor0.8443
CYP450 2C9 inhibitorNon-inhibitor0.6874
CYP450 2D6 inhibitorNon-inhibitor0.8183
CYP450 2C19 inhibitorInhibitor0.5676
CYP450 3A4 inhibitorNon-inhibitor0.5713
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9138
Ames testNon AMES toxic0.6243
CarcinogenicityNon-carcinogens0.7606
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5240 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8597
hERG inhibition (predictor II)Non-inhibitor0.5247
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
Pyrazolo[1,5-a]pyrimidines / Secondary alkylarylamines / Bromobenzenes / Aminopyrimidines and derivatives / Pyridines and derivatives / Aryl bromides / Pyrazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds
show 3 more
Substituents
4-phenylpyrimidine / 5-phenylpyrimidine / Pyrazolo[1,5-a]pyrimidine / Pyrazolopyrimidine / Aminopyrimidine / Bromobenzene / Halobenzene / Secondary aliphatic/aromatic amine / Aryl bromide / Aryl halide
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organobromine compound, aminoalkylpyridine, pyrazolopyrimidine (CHEBI:47354)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Serine/threonine-protein kinase involved in the control of the cell cycle; essential for meiosis, but dispensable for mitosis. Phosphorylates CTNNB1, USP37, p53/TP53, NPM1, CDK7, RB1, BRCA2, MYC, N...
Gene Name
CDK2
Uniprot ID
P24941
Uniprot Name
Cyclin-dependent kinase 2
Molecular Weight
33929.215 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 15:23 / Updated on December 01, 2017 15:53