4-[(5-{[4-(3-CHLOROPHENYL)-3-OXOPIPERAZIN-1-YL]METHYL}-1H-IMIDAZOL-1-YL)METHYL]BENZONITRILE

Identification

Name
4-[(5-{[4-(3-CHLOROPHENYL)-3-OXOPIPERAZIN-1-YL]METHYL}-1H-IMIDAZOL-1-YL)METHYL]BENZONITRILE
Accession Number
DB07227
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
31ZXM8ZKQ3
CAS number
Not Available
Weight
Average: 405.88
Monoisotopic: 405.135637994
Chemical Formula
C22H20ClN5O
InChI Key
JNUGFGAVPBYSHF-UHFFFAOYSA-N
InChI
InChI=1S/C22H20ClN5O/c23-19-2-1-3-20(10-19)28-9-8-26(15-22(28)29)14-21-12-25-16-27(21)13-18-6-4-17(11-24)5-7-18/h1-7,10,12,16H,8-9,13-15H2
IUPAC Name
4-[(5-{[4-(3-chlorophenyl)-3-oxopiperazin-1-yl]methyl}-1H-imidazol-1-yl)methyl]benzonitrile
SMILES
ClC1=CC=CC(=C1)N1CCN(CC2=CN=CN2CC2=CC=C(C=C2)C#N)CC1=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaNot AvailableHuman
UProtein farnesyltransferase subunit betaNot AvailableHuman
UGeranylgeranyl transferase type-1 subunit betaNot 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
216454
PubChem Substance
99443698
ChemSpider
187601
BindingDB
50097071
ChEMBL
CHEMBL279433
HET
778
PDB Entries
1s63 / 1s64 / 3q7a

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 Solubility0.17 mg/mLALOGPS
logP2.96ALOGPS
logP2.73ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)17.53ChemAxon
pKa (Strongest Basic)6.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area65.16 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity112.98 m3·mol-1ChemAxon
Polarizability42.35 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9849
Blood Brain Barrier+0.9204
Caco-2 permeable+0.5164
P-glycoprotein substrateNon-substrate0.5353
P-glycoprotein inhibitor IInhibitor0.862
P-glycoprotein inhibitor IIInhibitor0.8472
Renal organic cation transporterInhibitor0.7014
CYP450 2C9 substrateNon-substrate0.7747
CYP450 2D6 substrateNon-substrate0.7064
CYP450 3A4 substrateSubstrate0.7504
CYP450 1A2 substrateInhibitor0.9074
CYP450 2C9 inhibitorNon-inhibitor0.6902
CYP450 2D6 inhibitorInhibitor0.6086
CYP450 2C19 inhibitorInhibitor0.9066
CYP450 3A4 inhibitorInhibitor0.5809
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9002
Ames testNon AMES toxic0.8076
CarcinogenicityNon-carcinogens0.9107
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7985 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6439
hERG inhibition (predictor II)Inhibitor0.849
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 phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazinanes
Sub Class
Piperazines
Direct Parent
Phenylpiperazines
Alternative Parents
N-arylpiperazines / Alpha amino acids and derivatives / Benzonitriles / Aralkylamines / Chlorobenzenes / N-alkylpiperazines / Aryl chlorides / N-substituted imidazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds
show 9 more
Substituents
Phenylpiperazine / N-arylpiperazine / Alpha-amino acid or derivatives / Benzonitrile / Halobenzene / N-alkylpiperazine / Aralkylamine / Chlorobenzene / Benzenoid / Aryl halide
show 28 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Rab geranylgeranyltransferase activity
Specific Function
Essential subunit of both the farnesyltransferase and the geranylgeranyltransferase complex. Contributes to the transfer of a farnesyl or geranylgeranyl moiety from farnesyl or geranylgeranyl dipho...
Gene Name
FNTA
Uniprot ID
P49354
Uniprot Name
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha
Molecular Weight
44408.32 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
Zinc ion binding
Specific Function
Essential subunit of the farnesyltransferase complex. Catalyzes the transfer of a farnesyl moiety from farnesyl diphosphate to a cysteine at the fourth position from the C-terminus of several prote...
Gene Name
FNTB
Uniprot ID
P49356
Uniprot Name
Protein farnesyltransferase subunit beta
Molecular Weight
48773.2 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
Zinc ion binding
Specific Function
Catalyzes the transfer of a geranyl-geranyl moiety from geranyl-geranyl pyrophosphate to a cysteine at the fourth position from the C-terminus of proteins having the C-terminal sequence Cys-aliphat...
Gene Name
PGGT1B
Uniprot ID
P53609
Uniprot Name
Geranylgeranyl transferase type-1 subunit beta
Molecular Weight
42367.81 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 15:19 / Updated on December 01, 2017 15:48