NAV

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

Identification

Generic Name
1-(2-Fluorobenzyl)-3-Butyl-8-(N-Acetyl-4-Aminobenzyl)-Xanthine
DrugBank Accession Number
DB02008
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 463.504
Monoisotopic: 463.201967928
Chemical Formula
C25H26FN5O3
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
UPhosphoenolpyruvate carboxykinase, cytosolic [GTP]Not 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

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 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
6-oxopurine / Acetamide / Acetanilide / Alkaloid or derivatives / Anilide / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Azole
show 28 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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

References

General References
Not Available
PubChem Compound
447371
PubChem Substance
46504933
ChemSpider
394495
BindingDB
50133801
ChEMBL
CHEMBL120708
ZINC
ZINC000015804848
PDBe Ligand
FTB
PDB Entries
1nhx

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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/MSsplash10-03di-0000900000-930a98c7746e1ccec888
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-02mi-0000900000-705aea692f0a50a3dbf7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03k9-0004900000-53288347025825754b14
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03xr-0001900000-3fdd69287ff2585f7a6e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-8657900000-0f669acd5ae1ed05ec98
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-3129500000-b6f9ba8bc93de5211713
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]-208.65019
predicted
DeepCCS 1.0 (2019)
[M+H]+211.04576
predicted
DeepCCS 1.0 (2019)
[M+Na]+217.03139
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Phosphoenolpyruvate carboxykinase, cytosolic [GTP]
Kind
Protein
Organism
Humans
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. [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]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52