3-Deoxyguanosine

Identification

Name
3-Deoxyguanosine
Accession Number
DB03609  (EXPT00167)
Type
Small Molecule
Groups
Experimental
Description

3-deoxyguanosine is a solid. This compound belongs to the purine nucleosides and analogues. These are compounds comprising a purine base attached to a sugar. This medication targets the protein purine nucleoside phosphorylase.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 267.2413
Monoisotopic: 267.096753929
Chemical Formula
C10H13N5O4
InChI Key
OROIAVZITJBGSM-OBXARNEKSA-N
InChI
InChI=1S/C10H13N5O4/c11-10-13-7-6(8(18)14-10)12-3-15(7)9-5(17)1-4(2-16)19-9/h3-5,9,16-17H,1-2H2,(H3,11,13,14,18)/t4-,5+,9+/m0/s1
IUPAC Name
9-[(2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-imino-3,9-dihydro-2H-purin-6-ol
SMILES
[H][[email protected]@]1(CO)C[[email protected]@]([H])(O)[[email protected]@]([H])(O1)N1C=NC2=C1NC(=N)N=C2O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPurine nucleoside phosphorylaseNot 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

Synthesis Reference

Tetsuro Fujishima, "Process for producing 3-deoxyguanosine." U.S. Patent US4594320, issued April, 1983.

US4594320
General References
Not Available
External Links
PubChem Compound
165138
PubChem Substance
46508922
ChemSpider
144776
BindingDB
50144937
ChEMBL
CHEMBL73502
HET
3DG
PDB Entries
1v45

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 Solubility9.05 mg/mLALOGPS
logP-1.5ALOGPS
logP-1.7ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)6.09ChemAxon
pKa (Strongest Basic)4.93ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area135.98 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity74.11 m3·mol-1ChemAxon
Polarizability25.13 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9974
Blood Brain Barrier+0.9621
Caco-2 permeable-0.8757
P-glycoprotein substrateNon-substrate0.6331
P-glycoprotein inhibitor INon-inhibitor0.9637
P-glycoprotein inhibitor IINon-inhibitor0.9353
Renal organic cation transporterNon-inhibitor0.9336
CYP450 2C9 substrateNon-substrate0.8606
CYP450 2D6 substrateNon-substrate0.8345
CYP450 3A4 substrateNon-substrate0.5919
CYP450 1A2 substrateNon-inhibitor0.8165
CYP450 2C9 inhibitorNon-inhibitor0.9408
CYP450 2D6 inhibitorNon-inhibitor0.9559
CYP450 2C19 inhibitorNon-inhibitor0.9594
CYP450 3A4 inhibitorNon-inhibitor0.9725
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9879
Ames testNon AMES toxic0.6292
CarcinogenicityNon-carcinogens0.8629
BiodegradationNot ready biodegradable0.9496
Rat acute toxicity1.9353 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9852
hERG inhibition (predictor II)Non-inhibitor0.9622
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as purine 3'-deoxyribonucleosides. These are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 3.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleosides
Sub Class
Purine 3'-deoxyribonucleosides
Direct Parent
Purine 3'-deoxyribonucleosides
Alternative Parents
6-oxopurines / Hypoxanthines / Pyrimidones / Aminopyrimidines and derivatives / N-substituted imidazoles / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Oxacyclic compounds
show 6 more
Substituents
Purine 3'-deoxyribonucleoside / 6-oxopurine / Hypoxanthine / Purinone / Imidazopyrimidine / Purine / Aminopyrimidine / Pyrimidone / N-substituted imidazole / Pyrimidine
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
guanosines, 3'-deoxyribonucleoside (CHEBI:39874)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Purine-nucleoside phosphorylase activity
Specific Function
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine ...
Gene Name
PNP
Uniprot ID
P00491
Uniprot Name
Purine nucleoside phosphorylase
Molecular Weight
32117.69 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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:16