NAV

9-DEAZAINOSINE-2',3'-O-ETHYLIDENEPHOSPHONATE

Identification

Generic Name
9-DEAZAINOSINE-2',3'-O-ETHYLIDENEPHOSPHONATE
DrugBank Accession Number
DB04753
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 373.2552
Monoisotopic: 373.067501015
Chemical Formula
C13H16N3O8P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPurine nucleoside phosphorylaseNot 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 pyrrolopyrimidines. These are compounds containing a pyrrolopyrimidine moiety, which consists of a pyrrole ring fused to a pyrimidine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrrolopyrimidines
Sub Class
Not Available
Direct Parent
Pyrrolopyrimidines
Alternative Parents
Pyrimidones / Substituted pyrroles / Monosaccharides / Vinylogous amides / Tetrahydrofurans / 1,3-dioxolanes / Organic phosphonic acids / Heteroaromatic compounds / Oxacyclic compounds / Acetals
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Substituents
Acetal / Alcohol / Aromatic heteropolycyclic compound / Azacycle / Dialkyl ether / Ether / Heteroaromatic compound / Hydrocarbon derivative / Meta-dioxolane / Monosaccharide
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
pyrrolopyrimidine, furodioxole (CHEBI:44755)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
ZOEDLCUBOBTIHG-USQSKNHBSA-N
InChI
InChI=1S/C13H16N3O8P/c17-2-6-11-12(24-7(23-11)3-25(19,20)21)10(22-6)5-1-14-9-8(5)15-4-16-13(9)18/h1,4,6-7,10-12,14,17H,2-3H2,(H,15,16,18)(H2,19,20,21)/t6-,7-,10+,11-,12+/m1/s1
IUPAC Name
{[(2S,3aR,4R,6S,6aS)-4-(hydroxymethyl)-6-{4-oxo-1H,4H,5H-pyrrolo[3,2-d]pyrimidin-7-yl}-tetrahydro-2H-furo[3,4-d][1,3]dioxol-2-yl]methyl}phosphonic acid
SMILES
OC[C@H]1O[C@H]([C@@H]2O[C@H](CP(O)(O)=O)O[C@H]12)C1=CNC2=C1NC=NC2=O

References

General References
Not Available
PubChem Compound
5327013
PubChem Substance
46508981
ChemSpider
4484281
ZINC
ZINC000012504494
PDBe Ligand
P1D
PDB Entries
2ai2

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 Solubility12.6 mg/mLALOGPS
logP-1ALOGPS
logP-2Chemaxon
logS-1.5ALOGPS
pKa (Strongest Acidic)1.73Chemaxon
pKa (Strongest Basic)-0.31Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area162.7 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity81.86 m3·mol-1Chemaxon
Polarizability32.83 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.7963
Blood Brain Barrier+0.5293
Caco-2 permeable-0.7244
P-glycoprotein substrateNon-substrate0.5971
P-glycoprotein inhibitor INon-inhibitor0.9697
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9673
CYP450 2C9 substrateNon-substrate0.7965
CYP450 2D6 substrateNon-substrate0.8105
CYP450 3A4 substrateNon-substrate0.6108
CYP450 1A2 substrateNon-inhibitor0.78
CYP450 2C9 inhibitorNon-inhibitor0.8738
CYP450 2D6 inhibitorNon-inhibitor0.8732
CYP450 2C19 inhibitorNon-inhibitor0.8633
CYP450 3A4 inhibitorNon-inhibitor0.8503
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9556
Ames testNon AMES toxic0.6845
CarcinogenicityNon-carcinogens0.8469
BiodegradationNot ready biodegradable0.7107
Rat acute toxicity2.5358 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9776
hERG inhibition (predictor II)Non-inhibitor0.885
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-67b4231b035d722d5adf
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-2029000000-358ca551349517c7b017
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-006x-0296000000-13e071381a0129116acf
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01t9-9100000000-ae3419cafa96878d3b68
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kai-0193000000-01b3f44fc75d5eb5bd6c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004l-7923000000-9d68f68a2bfcd64d7e03
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]-169.52312
predicted
DeepCCS 1.0 (2019)
[M+H]+171.91869
predicted
DeepCCS 1.0 (2019)
[M+Na]+177.83598
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Purine nucleoside phosphorylase
Kind
Protein
Organism
Humans
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. 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 11, 2007 17:49 / Updated at June 12, 2020 16:52