1-[4-(4-chlorobenzyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-yl]methanamine

Identification

Name
1-[4-(4-chlorobenzyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-yl]methanamine
Accession Number
DB08149
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: 355.864
Monoisotopic: 355.156373436
Chemical Formula
C19H22ClN5
InChI Key
KCWPSUKJCKZEAO-UHFFFAOYSA-N
InChI
InChI=1S/C19H22ClN5/c20-15-3-1-14(2-4-15)11-19(12-21)6-9-25(10-7-19)18-16-5-8-22-17(16)23-13-24-18/h1-5,8,13H,6-7,9-12,21H2,(H,22,23,24)
IUPAC Name
{4-[(4-chlorophenyl)methyl]-1-{7H-pyrrolo[2,3-d]pyrimidin-4-yl}piperidin-4-yl}methanamine
SMILES
NCC1(CC2=CC=C(Cl)C=C2)CCN(CC1)C1=C2C=CNC2=NC=N1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UcAMP-dependent protein kinase catalytic subunit alphaNot AvailableHuman
UcAMP-dependent protein kinase inhibitor 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
11696113
PubChem Substance
99444620
ChemSpider
9870838
BindingDB
50376067
ChEMBL
CHEMBL260000
HET
M04
PDB Entries
2vo3

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 Solubility0.0263 mg/mLALOGPS
logP2.8ALOGPS
logP3.45ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)13.58ChemAxon
pKa (Strongest Basic)9.72ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.83 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity102.6 m3·mol-1ChemAxon
Polarizability38.49 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9974
Blood Brain Barrier+0.9595
Caco-2 permeable-0.6428
P-glycoprotein substrateSubstrate0.6659
P-glycoprotein inhibitor INon-inhibitor0.6782
P-glycoprotein inhibitor IIInhibitor0.9291
Renal organic cation transporterInhibitor0.7364
CYP450 2C9 substrateNon-substrate0.8684
CYP450 2D6 substrateNon-substrate0.7267
CYP450 3A4 substrateNon-substrate0.5064
CYP450 1A2 substrateInhibitor0.7683
CYP450 2C9 inhibitorNon-inhibitor0.9295
CYP450 2D6 inhibitorInhibitor0.8196
CYP450 2C19 inhibitorNon-inhibitor0.8585
CYP450 3A4 inhibitorNon-inhibitor0.6173
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6622
Ames testNon AMES toxic0.6258
CarcinogenicityNon-carcinogens0.908
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.9019 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7924
hERG inhibition (predictor II)Inhibitor0.9198
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 4-benzylpiperidines. These are organic compounds containing a benzyl group attached to the 4-position of a piperidine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Benzylpiperidines
Direct Parent
4-benzylpiperidines
Alternative Parents
Pyrrolo[2,3-d]pyrimidines / Dialkylarylamines / Chlorobenzenes / Aralkylamines / Aminopyrimidines and derivatives / Imidolactams / Aryl chlorides / Pyrroles / Heteroaromatic compounds / Azacyclic compounds
show 4 more
Substituents
4-benzylpiperidine / Pyrrolopyrimidine / Pyrrolo[2,3-d]pyrimidine / Dialkylarylamine / Aminopyrimidine / Chlorobenzene / Halobenzene / Aralkylamine / Aryl chloride / Aryl halide
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquitin protein ligase binding
Specific Function
Phosphorylates a large number of substrates in the cytoplasm and the nucleus. Regulates the abundance of compartmentalized pools of its regulatory subunits through phosphorylation of PJA2 which bin...
Gene Name
PRKACA
Uniprot ID
P17612
Uniprot Name
cAMP-dependent protein kinase catalytic subunit alpha
Molecular Weight
40589.38 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
Protein kinase a catalytic subunit binding
Specific Function
Extremely potent competitive inhibitor of cAMP-dependent protein kinase activity, this protein interacts with the catalytic subunit of the enzyme after the cAMP-induced dissociation of its regulato...
Gene Name
PKIA
Uniprot ID
P61925
Uniprot Name
cAMP-dependent protein kinase inhibitor alpha
Molecular Weight
7988.435 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 15:28 / Updated on December 01, 2017 16:00