NAV

9-(4-hydroxybutyl)-N2-phenylguanine

Identification

Generic Name
9-(4-hydroxybutyl)-N2-phenylguanine
DrugBank Accession Number
DB02495
Background

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.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 299.3278
Monoisotopic: 299.138224813
Chemical Formula
C15H17N5O2
Synonyms
  • HBPG
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UThymidine kinase
inhibitor
HHV-1
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 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 / Alcohol / Alkanolamine / Amine / Aminopyrimidine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid
show 17 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
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

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. [Article]
  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. [Article]
PubChem Compound
448110
PubChem Substance
46507186
ChemSpider
395019
BindingDB
21866
ChEMBL
CHEMBL406254
PDBe Ligand
BPG
PDB Entries
1qhi

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 Solubility0.775 mg/mLALOGPS
logP1.44ALOGPS
logP1.15Chemaxon
logS-2.6ALOGPS
pKa (Strongest Acidic)9.43Chemaxon
pKa (Strongest Basic)0.48Chemaxon
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/MSsplash10-0udi-0009000000-daf0a3100ef284259045
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-592889295476f262bcb5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0059-0090000000-004bdbbd3a357c895ac3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0059-0390000000-66195bb441b4f9b61fe5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-1191000000-32c9d13a2ed064da43b7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05mw-1920000000-e41349e156cf2d9c3a18
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]-186.0849893
predicted
DarkChem Lite v0.1.0
[M-H]-160.25926
predicted
DeepCCS 1.0 (2019)
[M+H]+187.7510893
predicted
DarkChem Lite v0.1.0
[M+H]+162.61726
predicted
DeepCCS 1.0 (2019)
[M+Na]+186.3795893
predicted
DarkChem Lite v0.1.0
[M+Na]+168.71043
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Thymidine kinase
Kind
Protein
Organism
HHV-1
Pharmacological action
Unknown
Actions
Inhibitor
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
Q9QNF7
Uniprot Name
Thymidine kinase
Molecular Weight
40896.475 Da
References
  1. Gebhardt BM, Wright GE, Xu H, Focher F, Spadari S, Kaufman HE: 9-(4-Hydroxybutyl)-N2-phenylguanine (HBPG), a thymidine kinase inhibitor, suppresses herpes virus reactivation in mice. Antiviral Res. 1996 May;30(2-3):87-94. doi: 10.1016/0166-3542(95)00900-0. [Article]

Drug created at June 13, 2005 13:24 / Updated at April 30, 2023 10:33