NAV

7-(5-DEOXY-BETA-D-RIBOFURANOSYL)-5-IODO-7H-PYRROLO[2,3-D]PYRIMIDIN-4-AMINE

Identification

Generic Name
7-(5-DEOXY-BETA-D-RIBOFURANOSYL)-5-IODO-7H-PYRROLO[2,3-D]PYRIMIDIN-4-AMINE
DrugBank Accession Number
DB07173
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 376.1504
Monoisotopic: 376.003233722
Chemical Formula
C11H13IN4O3
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAdenosine kinaseNot AvailableHumans
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 glycosylamines. These are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Glycosylamines
Alternative Parents
Pyrrolo[2,3-d]pyrimidines / Aminopyrimidines and derivatives / Substituted pyrroles / Imidolactams / Aryl iodides / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / 1,2-diols / Oxacyclic compounds
show 5 more
Substituents
1,2-diol / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Aryl halide / Aryl iodide / Azacycle / Heteroaromatic compound / Hydrocarbon derivative
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organoiodine compound, N-glycosylpyrrolopyrimidine (CHEBI:40125)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
NTXUAWGNGBSCRS-TZQXKBMNSA-N
InChI
InChI=1S/C11H13IN4O3/c1-4-7(17)8(18)11(19-4)16-2-5(12)6-9(13)14-3-15-10(6)16/h2-4,7-8,11,17-18H,1H3,(H2,13,14,15)/t4-,7-,8-,11-/m1/s1
IUPAC Name
(2R,3R,4S,5R)-2-{4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-5-methyloxolane-3,4-diol
SMILES
[H][C@]1(C)O[C@@]([H])(N2C=C(I)C3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O

References

General References
Not Available
PubChem Compound
9842606
PubChem Substance
99443644
ChemSpider
8018321
BindingDB
14486
ChEMBL
CHEMBL66280
PDBe Ligand
5I5
PDB Entries
2i6a

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 Solubility2.55 mg/mLALOGPS
logP0.42ALOGPS
logP0.7Chemaxon
logS-2.2ALOGPS
pKa (Strongest Acidic)12.48Chemaxon
pKa (Strongest Basic)5.79Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area106.42 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity77.19 m3·mol-1Chemaxon
Polarizability30.27 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9849
Blood Brain Barrier+0.8719
Caco-2 permeable-0.6029
P-glycoprotein substrateNon-substrate0.7492
P-glycoprotein inhibitor INon-inhibitor0.9408
P-glycoprotein inhibitor IINon-inhibitor0.8562
Renal organic cation transporterNon-inhibitor0.9579
CYP450 2C9 substrateNon-substrate0.8291
CYP450 2D6 substrateNon-substrate0.8382
CYP450 3A4 substrateNon-substrate0.5747
CYP450 1A2 substrateNon-inhibitor0.8167
CYP450 2C9 inhibitorNon-inhibitor0.8455
CYP450 2D6 inhibitorNon-inhibitor0.8973
CYP450 2C19 inhibitorNon-inhibitor0.7416
CYP450 3A4 inhibitorNon-inhibitor0.943
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8678
Ames testNon AMES toxic0.6353
CarcinogenicityNon-carcinogens0.855
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4812 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9905
hERG inhibition (predictor II)Non-inhibitor0.8489
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. Adenosine kinase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Poly(a) rna binding
Specific Function
ATP dependent phosphorylation of adenosine and other related nucleoside analogs to monophosphate derivatives. Serves as a potential regulator of concentrations of extracellular adenosine and intrac...
Gene Name
ADK
Uniprot ID
P55263
Uniprot Name
Adenosine kinase
Molecular Weight
40545.075 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