5'-Fluoro-5'-Deoxyadenosine

Identification

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Name
5'-Fluoro-5'-Deoxyadenosine
Accession Number
DB03716  (EXPT00245)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 269.236
Monoisotopic: 269.092417429
Chemical Formula
C10H12FN5O3
InChI Key
QPVLKMICBYRPSX-KQYNXXCUSA-N
InChI
InChI=1S/C10H12FN5O3/c11-1-4-6(17)7(18)10(19-4)16-3-15-5-8(12)13-2-14-9(5)16/h2-4,6-7,10,17-18H,1H2,(H2,12,13,14)/t4-,6-,7-,10-/m1/s1
IUPAC Name
(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-(fluoromethyl)oxolane-3,4-diol
SMILES
NC1=C2N=CN([C@@H]3O[C@H](CF)[C@@H](O)[C@H]3O)C2=NC=N1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U5'-fluoro-5'-deoxy-adenosine synthaseNot AvailableStreptomyces cattleya
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
448403
PubChem Substance
46507287
ChemSpider
395211
ChEBI
12060
ChEMBL
CHEMBL1212979
HET
5FD

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 Solubility9.47 mg/mLALOGPS
logP-0.5ALOGPS
logP-1.2ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)3.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area119.31 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.5 m3·mol-1ChemAxon
Polarizability24.28 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.983
Blood Brain Barrier+0.9315
Caco-2 permeable-0.7144
P-glycoprotein substrateNon-substrate0.6701
P-glycoprotein inhibitor INon-inhibitor0.8727
P-glycoprotein inhibitor IINon-inhibitor0.7737
Renal organic cation transporterNon-inhibitor0.89
CYP450 2C9 substrateNon-substrate0.8233
CYP450 2D6 substrateNon-substrate0.8165
CYP450 3A4 substrateNon-substrate0.5254
CYP450 1A2 substrateNon-inhibitor0.7801
CYP450 2C9 inhibitorNon-inhibitor0.8576
CYP450 2D6 inhibitorNon-inhibitor0.9063
CYP450 2C19 inhibitorNon-inhibitor0.8146
CYP450 3A4 inhibitorNon-inhibitor0.9676
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9536
Ames testNon AMES toxic0.6055
CarcinogenicityNon-carcinogens0.8872
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4015 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.992
hERG inhibition (predictor II)Non-inhibitor0.8705
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 5'-deoxyribonucleosides. These are nucleosides in which the oxygen atom at the 5'position of the ribose moiety has been replaced by another atom. The nucleobases here are limited to purine, pyrimidine, and pyridine derivatives.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
5'-deoxyribonucleosides
Sub Class
Not Available
Direct Parent
5'-deoxyribonucleosides
Alternative Parents
Glycosylamines / Pentoses / 6-aminopurines / Aminopyrimidines and derivatives / N-substituted imidazoles / Imidolactams / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / 1,2-diols
show 7 more
Substituents
5'-deoxyribonucleoside / Glycosyl compound / N-glycosyl compound / 6-aminopurine / Pentose monosaccharide / Imidazopyrimidine / Purine / Aminopyrimidine / Monosaccharide / N-substituted imidazole
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, adenosines (CHEBI:12060)

Targets

Kind
Protein
Organism
Streptomyces cattleya
Pharmacological action
Unknown
General Function
Adenosyl-fluoride synthase activity
Specific Function
Involved in the biosynthesis of fluorometabolites. Catalyzes the formation of a C-F bond by combining S-adenosyl-L-methionine (SAM) and fluoride to generate 5'-fluoro-5'-deoxyadenosine (5'-FDA) and...
Gene Name
flA
Uniprot ID
Q70GK9
Uniprot Name
5'-fluoro-5'-deoxy-adenosine synthase
Molecular Weight
32369.26 Da

Drug created on June 13, 2005 07:24 / Updated on September 02, 2019 17:45