NAV

5'-FLUORO-2',5'-DIDEOXYADENOSINE

Identification

Generic Name
5'-FLUORO-2',5'-DIDEOXYADENOSINE
DrugBank Accession Number
DB07170
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 253.233
Monoisotopic: 253.097502858
Chemical Formula
C10H12FN5O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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

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 2',5'-dideoxyribonucleosides. These are nucleosides characterized by a purine or pyrimidine base, which is N-linked to a 2',5'-dideoxyribose moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
2',5'-dideoxyribonucleosides
Sub Class
Not Available
Direct Parent
2',5'-dideoxyribonucleosides
Alternative Parents
6-aminopurines / Aminopyrimidines and derivatives / N-substituted imidazoles / Imidolactams / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Oxacyclic compounds / Azacyclic compounds / Primary amines
show 4 more
Substituents
2',5'-dideoxyribonucleoside / 6-aminopurine / Alcohol / Alkyl fluoride / Alkyl halide / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organofluorine compound, adenosines (CHEBI:40179)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
QKUCDAPGYBWICH-RRKCRQDMSA-N
InChI
InChI=1S/C10H12FN5O2/c11-2-6-5(17)1-7(18-6)16-4-15-8-9(12)13-3-14-10(8)16/h3-7,17H,1-2H2,(H2,12,13,14)/t5-,6+,7+/m0/s1
IUPAC Name
(2S,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(fluoromethyl)oxolan-3-ol
SMILES
[H][C@]1(O)C[C@@]([H])(O[C@]1([H])CF)N1C=NC2=C1N=CN=C2N

References

General References
Not Available
PubChem Compound
15991535
PubChem Substance
99443641
ChemSpider
13122470
ZINC
ZINC000016051853
PDBe Ligand
5F1
PDB Entries
2c5b

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 Solubility6.99 mg/mLALOGPS
logP-0.28ALOGPS
logP-0.3Chemaxon
logS-1.6ALOGPS
pKa (Strongest Acidic)13.97Chemaxon
pKa (Strongest Basic)3.96Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area99.08 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity59.99 m3·mol-1Chemaxon
Polarizability23.62 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9751
Caco-2 permeable-0.6531
P-glycoprotein substrateNon-substrate0.6985
P-glycoprotein inhibitor INon-inhibitor0.886
P-glycoprotein inhibitor IINon-inhibitor0.8691
Renal organic cation transporterNon-inhibitor0.8688
CYP450 2C9 substrateNon-substrate0.9117
CYP450 2D6 substrateNon-substrate0.7767
CYP450 3A4 substrateSubstrate0.5126
CYP450 1A2 substrateNon-inhibitor0.8751
CYP450 2C9 inhibitorNon-inhibitor0.8587
CYP450 2D6 inhibitorNon-inhibitor0.8789
CYP450 2C19 inhibitorNon-inhibitor0.8317
CYP450 3A4 inhibitorNon-inhibitor0.9105
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.844
Ames testNon AMES toxic0.5874
CarcinogenicityNon-carcinogens0.7773
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3592 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9784
hERG inhibition (predictor II)Non-inhibitor0.8218
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-MSsplash10-0006-9610000000-f479851e6ca073f7c67a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0090000000-486a3a4ae3f12e7f832d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ue9-0090000000-e117ccff72b662e0026b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0920000000-b6eb9b14b7b136f14af0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f89-2970000000-75af40a83d70d04ee0e3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-1900000000-d7a22d65166917d9a793
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0api-0900000000-84b326ae0a624bdeda78
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]-144.13573
predicted
DeepCCS 1.0 (2019)
[M+H]+146.5313
predicted
DeepCCS 1.0 (2019)
[M+Na]+152.84233
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 5'-fluoro-5'-deoxy-adenosine synthase
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
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:19 / Updated at June 12, 2020 16:52