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GUANOSINE-2',3'-O-ETHYLIDENEPHOSPHONATE

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Identification

Generic Name
GUANOSINE-2',3'-O-ETHYLIDENEPHOSPHONATE
DrugBank Accession Number
DB04754
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 389.2579
Monoisotopic: 389.073649025
Chemical Formula
C12H16N5O8P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
APurine nucleoside phosphorylase
inhibitor
Humans
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 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
6-oxopurines / Hypoxanthines / Pyrimidones / Aminopyrimidines and derivatives / N-substituted imidazoles / Monosaccharides / Vinylogous amides / Tetrahydrofurans / 1,3-dioxolanes / Organic phosphonic acids
show 10 more
Substituents
6-oxopurine / Acetal / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
HYAPEMYRVFIHDJ-QWEIRQIHSA-N
InChI
InChI=1S/C12H16N5O8P/c13-12-15-9-6(10(19)16-12)14-3-17(9)11-8-7(4(1-18)23-11)24-5(25-8)2-26(20,21)22/h3-5,7-8,11,18H,1-2H2,(H2,20,21,22)(H3,13,15,16,19)/t4-,5-,7-,8-,11-/m1/s1
IUPAC Name
{[(2R,3aR,4R,6R,6aR)-4-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-6-(hydroxymethyl)-tetrahydro-2H-furo[3,4-d][1,3]dioxol-2-yl]methyl}phosphonic acid
SMILES
NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@H]2O[C@@H](CP(O)(O)=O)O[C@@H]12

References

General References
Not Available
PubChem Compound
5327012
PubChem Substance
46506626
ChemSpider
4484280
ZINC
ZINC000012504495
PDBe Ligand
P1G
PDB Entries
2ai1

Clinical Trials

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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 Solubility3.45 mg/mLALOGPS
logP-2ALOGPS
logP-2.9Chemaxon
logS-2ALOGPS
pKa (Strongest Acidic)1.69Chemaxon
pKa (Strongest Basic)2.86Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area190.75 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity81.79 m3·mol-1Chemaxon
Polarizability33.73 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5918
Blood Brain Barrier+0.9136
Caco-2 permeable-0.7365
P-glycoprotein substrateNon-substrate0.6944
P-glycoprotein inhibitor INon-inhibitor0.9704
P-glycoprotein inhibitor IINon-inhibitor0.9918
Renal organic cation transporterNon-inhibitor0.9604
CYP450 2C9 substrateNon-substrate0.8566
CYP450 2D6 substrateNon-substrate0.8329
CYP450 3A4 substrateNon-substrate0.6374
CYP450 1A2 substrateNon-inhibitor0.852
CYP450 2C9 inhibitorNon-inhibitor0.8834
CYP450 2D6 inhibitorNon-inhibitor0.8812
CYP450 2C19 inhibitorNon-inhibitor0.89
CYP450 3A4 inhibitorNon-inhibitor0.8673
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9741
Ames testNon AMES toxic0.6822
CarcinogenicityNon-carcinogens0.7997
BiodegradationNot ready biodegradable0.9053
Rat acute toxicity2.5422 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9783
hERG inhibition (predictor II)Non-inhibitor0.9138
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/MSsplash10-0006-0009000000-c11496736e25472ab184
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0903000000-7d3bd6a7273188b822ec
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-2019000000-fd9d49e9c6085b846d19
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0907000000-4f4d843df03637b96795
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03fr-9105000000-934e66a18f93e44b0298
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4j-4903000000-8479b17acb913cdeb07f
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]-175.2672
predicted
DeepCCS 1.0 (2019)
[M+H]+177.5713
predicted
DeepCCS 1.0 (2019)
[M+Na]+183.42067
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Purine nucleoside phosphorylase
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Catalyzes the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate (PubMed:23438750, PubMed:9305964). Preferentially acts on 6-oxopurine nucleosides including inosine and guanosine (PubMed:9305964).
Specific Function
guanosine phosphorylase activity
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]
  2. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at September 11, 2007 17:49 / Updated at August 26, 2024 19:22