9-(4-hydroxybutyl)-N2-phenylguanine

Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Name
9-(4-hydroxybutyl)-N2-phenylguanine
Accession Number
DB02495  (EXPT00745)
Type
Small Molecule
Groups
Experimental
Description

9-(4-hydroxybutyl)-N2-phenylguanine is a solid. This compound belongs to the hypoxanthines. These are compounds containing the purine derivative 1H-purin-6(9H)-one. 9-(4-hydroxybutyl)-n2-phenylguanine is known to target thymidine kinase.

Structure
Thumb
Synonyms
  • HBPG
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 299.3278
Monoisotopic: 299.138224813
Chemical Formula
C15H17N5O2
InChI Key
JHBXNPBKSPYOFT-UHFFFAOYSA-N
InChI
InChI=1S/C15H17N5O2/c21-9-5-4-8-20-10-16-12-13(20)18-15(19-14(12)22)17-11-6-2-1-3-7-11/h1-3,6-7,10,21H,4-5,8-9H2,(H2,17,18,19,22)
IUPAC Name
9-(4-hydroxybutyl)-2-(phenylamino)-6,9-dihydro-1H-purin-6-one
SMILES
OCCCCN1C=NC2=C1N=C(NC1=CC=CC=C1)NC2=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UThymidine kinaseNot Available
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
  1. Kaufman HE, Varnell ED, Wright GE, Xu H, Gebhardt BM, Thompson HW: Effect of 9-(4-hydroxybutyl)-N2-phenylguanine (HBPG), a thymidine kinase inhibitor, on clinical recurrences of ocular herpetic keratitis in squirrel monkeys. Antiviral Res. 1996 Dec;33(1):65-72. [PubMed:8955854]
  2. Gebhardt BM, Focher F, Eberle R, Manikowski A, Wright GE: Effect of combinations of antiviral drugs on herpes simplex encephalitis. Drug Des Devel Ther. 2009 Dec 29;3:289-94. [PubMed:20054446]
External Links
PubChem Compound
448110
PubChem Substance
46507186
ChemSpider
395019
BindingDB
21866
ChEMBL
CHEMBL406254
HET
BPG
PDB Entries
1qhi

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 Solubility0.775 mg/mLALOGPS
logP1.44ALOGPS
logP1.15ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)9.43ChemAxon
pKa (Strongest Basic)0.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area91.54 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity85.06 m3·mol-1ChemAxon
Polarizability31.23 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9928
Blood Brain Barrier+0.9145
Caco-2 permeable-0.8142
P-glycoprotein substrateSubstrate0.6717
P-glycoprotein inhibitor INon-inhibitor0.7652
P-glycoprotein inhibitor IINon-inhibitor0.7262
Renal organic cation transporterNon-inhibitor0.5997
CYP450 2C9 substrateNon-substrate0.748
CYP450 2D6 substrateNon-substrate0.7243
CYP450 3A4 substrateNon-substrate0.5204
CYP450 1A2 substrateNon-inhibitor0.6718
CYP450 2C9 inhibitorNon-inhibitor0.7567
CYP450 2D6 inhibitorNon-inhibitor0.9194
CYP450 2C19 inhibitorNon-inhibitor0.8972
CYP450 3A4 inhibitorNon-inhibitor0.9169
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7985
Ames testNon AMES toxic0.5413
CarcinogenicityNon-carcinogens0.9133
BiodegradationNot ready biodegradable0.9389
Rat acute toxicity2.1388 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.746
hERG inhibition (predictor II)Non-inhibitor0.6504
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 hypoxanthines. These are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
Hypoxanthines
Alternative Parents
6-oxopurines / Aniline and substituted anilines / Pyrimidones / Aminopyrimidines and derivatives / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds / Secondary amines / Azacyclic compounds / Alkanolamines
show 4 more
Substituents
6-oxopurine / Hypoxanthine / Aniline or substituted anilines / Aminopyrimidine / Pyrimidone / Monocyclic benzene moiety / N-substituted imidazole / Pyrimidine / Benzenoid / Azole
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Not Available
Pharmacological action
Unknown
General Function
Thymidine kinase activity
Specific Function
In latent infection, may allow the virus to be reactivated and to grow in cells lacking a high concentration of phosphorylated nucleic acid precursors, such as nerve cells that do not replicate the...
Gene Name
TK
Uniprot ID
P03176
Uniprot Name
Thymidine kinase
Molecular Weight
40971.555 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 June 04, 2019 05:35