NAV

R-9-(2-hydroxypropyl)adenine

Identification

Generic Name
R-9-(2-hydroxypropyl)adenine
DrugBank Accession Number
DB02765
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 193.2058
Monoisotopic: 193.096359999
Chemical Formula
C8H11N5O
Synonyms
  • 9-Hydroxypropyladenine, R-Isomer

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
NThymidine kinase
ligand
HHV-1
NThymidine kinase
ligand
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 6-aminopurines. These are purines that carry an amino group at position 6. 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
6-aminopurines
Alternative Parents
Aminopyrimidines and derivatives / N-substituted imidazoles / Imidolactams / Heteroaromatic compounds / Secondary alcohols / Azacyclic compounds / Primary amines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
6-aminopurine / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
43H6SBP55W
CAS number
14047-28-0
InChI Key
MJZYTEBKXLVLMY-RXMQYKEDSA-N
InChI
InChI=1S/C8H11N5O/c1-5(14)2-13-4-12-6-7(9)10-3-11-8(6)13/h3-5,14H,2H2,1H3,(H2,9,10,11)/t5-/m1/s1
IUPAC Name
(2R)-1-(6-amino-9H-purin-9-yl)propan-2-ol
SMILES
C[C@@H](O)CN1C=NC2=C1N=CN=C2N

References

General References
Not Available
PubChem Compound
445211
PubChem Substance
46508231
ChemSpider
392914
ZINC
ZINC000002046906
PDBe Ligand
ARP
PDB Entries
1e2i

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 Solubility5.45 mg/mLALOGPS
logP-0.29ALOGPS
logP-0.58Chemaxon
logS-1.6ALOGPS
pKa (Strongest Acidic)15.15Chemaxon
pKa (Strongest Basic)3.74Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area89.85 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity52.21 m3·mol-1Chemaxon
Polarizability19.18 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9944
Blood Brain Barrier+0.9221
Caco-2 permeable-0.5142
P-glycoprotein substrateSubstrate0.5358
P-glycoprotein inhibitor INon-inhibitor0.9586
P-glycoprotein inhibitor IINon-inhibitor0.5412
Renal organic cation transporterNon-inhibitor0.8308
CYP450 2C9 substrateNon-substrate0.8562
CYP450 2D6 substrateNon-substrate0.8352
CYP450 3A4 substrateNon-substrate0.6618
CYP450 1A2 substrateNon-inhibitor0.7767
CYP450 2C9 inhibitorNon-inhibitor0.9297
CYP450 2D6 inhibitorNon-inhibitor0.7355
CYP450 2C19 inhibitorNon-inhibitor0.9147
CYP450 3A4 inhibitorNon-inhibitor0.8764
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7937
Ames testAMES toxic0.7817
CarcinogenicityNon-carcinogens0.781
BiodegradationNot ready biodegradable0.9875
Rat acute toxicity2.5125 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8883
hERG inhibition (predictor II)Non-inhibitor0.825
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Targets

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Details1. Thymidine kinase
Kind
Protein
Organism
HHV-1
Pharmacological action
No
Actions
Ligand
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. Sharmila Tagore S, Swaminathan J, Manikandan D, Gomathi S, Sabarinathan N, Ramalingam M, Sethuraman V: Crystallographic investigation, Hirshfeld surface analysis, NLO characterization and experimental spectral (UV and NMR) studies with DFT probe on(R)-9-(2-hydroxy propyl)adenine. Heliyon. 2021 Apr 29;7(4):e06593. doi: 10.1016/j.heliyon.2021.e06593. eCollection 2021 Apr. [Article]
Details2. Thymidine kinase
Kind
Protein
Organism
Not Available
Pharmacological action
No
Actions
Ligand
General Function
Catalyzes the transfer of the gamma-phospho group of ATP to thymidine to generate dTMP in the salvage pathway of pyrimidine synthesis. The dTMP serves as a substrate for DNA polymerase during viral DNA replication. Allows the virus to be reactivated and to grow in non-proliferative cells lacking a high concentration of phosphorylated nucleic acid precursors.
Specific Function
Atp binding
Gene Name
TK
Uniprot ID
P09250
Uniprot Name
Thymidine kinase
Molecular Weight
37816.49 Da
References
  1. Sharmila Tagore S, Swaminathan J, Manikandan D, Gomathi S, Sabarinathan N, Ramalingam M, Sethuraman V: Crystallographic investigation, Hirshfeld surface analysis, NLO characterization and experimental spectral (UV and NMR) studies with DFT probe on(R)-9-(2-hydroxy propyl)adenine. Heliyon. 2021 Apr 29;7(4):e06593. doi: 10.1016/j.heliyon.2021.e06593. eCollection 2021 Apr. [Article]

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