2-Fluoroadenosine

Identification

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Name
2-Fluoroadenosine
Accession Number
DB04441  (EXPT00114)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 2-(6-amino-2-fluoro-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol
  • 6-amino-2-fluoro-9-β-D-ribofuranosylpurine
External IDs
NSC-30605
Categories
UNII
0S67290CRJ
CAS number
146-78-1
Weight
Average: 285.2318
Monoisotopic: 285.087332102
Chemical Formula
C10H12FN5O4
InChI Key
HBUBKKRHXORPQB-UUOKFMHZSA-N
InChI
InChI=1S/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6-,9-/m1/s1
IUPAC Name
(2R,3R,4S,5R)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
SMILES
[H][C@]1(CO)O[C@@]([H])(N2C=NC3=C(N)N=C(F)N=C23)[C@]([H])(O)[C@]1([H])O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPurine nucleoside phosphorylase DeoD-typeNot AvailableEscherichia coli (strain K12)
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
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

References

General References
Not Available
External Links
PubChem Compound
8975
PubChem Substance
46507053
ChemSpider
8628
BindingDB
50118807
ChEBI
39740
ChEMBL
CHEMBL290077
HET
2FA
PDB Entries
1pk9 / 1z35 / 2pkk / 2zj0 / 4dan / 4dc3 / 4ube

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 Solubility12.1 mg/mLALOGPS
logP-0.62ALOGPS
logP-1.5ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)0.71ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area139.54 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.06 m3·mol-1ChemAxon
Polarizability25.21 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9768
Blood Brain Barrier+0.9449
Caco-2 permeable-0.8367
P-glycoprotein substrateNon-substrate0.6983
P-glycoprotein inhibitor INon-inhibitor0.9458
P-glycoprotein inhibitor IINon-inhibitor0.9346
Renal organic cation transporterNon-inhibitor0.9451
CYP450 2C9 substrateNon-substrate0.901
CYP450 2D6 substrateNon-substrate0.8309
CYP450 3A4 substrateNon-substrate0.5708
CYP450 1A2 substrateNon-inhibitor0.8764
CYP450 2C9 inhibitorNon-inhibitor0.9273
CYP450 2D6 inhibitorNon-inhibitor0.9297
CYP450 2C19 inhibitorNon-inhibitor0.9268
CYP450 3A4 inhibitorNon-inhibitor0.8908
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.966
Ames testNon AMES toxic0.8369
CarcinogenicityNon-carcinogens0.8763
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.2152 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9765
hERG inhibition (predictor II)Non-inhibitor0.843
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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0ue9-2900000000-e5d92537d99a5fc862da

Taxonomy

Description
This compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleosides
Sub Class
Not Available
Direct Parent
Purine nucleosides
Alternative Parents
Glycosylamines / 6-aminopurines / Pentoses / 2-halopyrimidines / Aminopyrimidines and derivatives / Aryl fluorides / Imidolactams / N-substituted imidazoles / Heteroaromatic compounds / Tetrahydrofurans
show 8 more
Substituents
Purine nucleoside / Glycosyl compound / N-glycosyl compound / 6-aminopurine / Pentose monosaccharide / Imidazopyrimidine / Purine / Aminopyrimidine / 2-halopyrimidine / Halopyrimidine
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, adenosines (CHEBI:39740)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Purine-nucleoside phosphorylase activity
Specific Function
Cleavage of guanosine or inosine to respective bases and sugar-1-phosphate molecules.
Gene Name
deoD
Uniprot ID
P0ABP8
Uniprot Name
Purine nucleoside phosphorylase DeoD-type
Molecular Weight
25949.68 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 September 02, 2019 17:58