1-(2-Fluorobenzyl)-3-Butyl-8-(N-Acetyl-4-Aminobenzyl)-Xanthine

Identification

Name
1-(2-Fluorobenzyl)-3-Butyl-8-(N-Acetyl-4-Aminobenzyl)-Xanthine
Accession Number
DB02008  (EXPT01503)
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: 463.504
Monoisotopic: 463.201967928
Chemical Formula
C25H26FN5O3
InChI Key
JHSHXKJSPVHPCJ-UHFFFAOYSA-N
InChI
InChI=1S/C25H26FN5O3/c1-3-4-13-30-23-22(24(33)31(25(30)34)15-18-7-5-6-8-20(18)26)28-21(29-23)14-17-9-11-19(12-10-17)27-16(2)32/h5-12H,3-4,13-15H2,1-2H3,(H,27,32)(H,28,29)
IUPAC Name
N-[4-({3-butyl-1-[(2-fluorophenyl)methyl]-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl}methyl)phenyl]acetamide
SMILES
CCCCN1C2=C(NC(CC3=CC=C(NC(C)=O)C=C3)=N2)C(=O)N(CC2=CC=CC=C2F)C1=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPhosphoenolpyruvate carboxykinase, cytosolic [GTP]Not 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
447371
PubChem Substance
46504933
ChemSpider
394495
BindingDB
50133801
ChEMBL
CHEMBL120708
HET
FTB
PDB Entries
1nhx

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 Solubility0.0277 mg/mLALOGPS
logP3.63ALOGPS
logP3.62ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)7.86ChemAxon
pKa (Strongest Basic)-0.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area98.4 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity127.66 m3·mol-1ChemAxon
Polarizability48.18 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.7112
Caco-2 permeable-0.6579
P-glycoprotein substrateSubstrate0.7991
P-glycoprotein inhibitor IInhibitor0.5948
P-glycoprotein inhibitor IINon-inhibitor0.7409
Renal organic cation transporterNon-inhibitor0.7559
CYP450 2C9 substrateNon-substrate0.803
CYP450 2D6 substrateNon-substrate0.8281
CYP450 3A4 substrateSubstrate0.536
CYP450 1A2 substrateNon-inhibitor0.8061
CYP450 2C9 inhibitorInhibitor0.5662
CYP450 2D6 inhibitorNon-inhibitor0.8806
CYP450 2C19 inhibitorInhibitor0.5739
CYP450 3A4 inhibitorInhibitor0.638
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.724
Ames testAMES toxic0.5351
CarcinogenicityNon-carcinogens0.8247
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7661 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7485
hERG inhibition (predictor II)Inhibitor0.5
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 xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
Xanthines
Alternative Parents
6-oxopurines / Acetanilides / N-acetylarylamines / Alkaloids and derivatives / Pyrimidones / Fluorobenzenes / Aryl fluorides / Vinylogous amides / Acetamides / Imidazoles
show 10 more
Substituents
Xanthine / 6-oxopurine / Acetanilide / Purinone / N-acetylarylamine / Alkaloid or derivatives / Anilide / N-arylamide / Fluorobenzene / Halobenzene
show 28 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Phosphoenolpyruvate carboxykinase (gtp) activity
Specific Function
Catalyzes the conversion of oxaloacetate (OAA) to phosphoenolpyruvate (PEP), the rate-limiting step in the metabolic pathway that produces glucose from lactate and other precursors derived from the...
Gene Name
PCK1
Uniprot ID
P35558
Uniprot Name
Phosphoenolpyruvate carboxykinase, cytosolic [GTP]
Molecular Weight
69193.975 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. [PubMed:17139284]
  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. [PubMed:17016423]
  3. 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 June 13, 2005 07:24 / Updated on December 01, 2017 14:51