NAV

[(2R,3R,4S,5S)-3,4-Dihydroxy-5-(4-oxo-4,5-dihydro-1H-pyrrolo[3,2-d]pyrimidin-7-yl)-2-pyrrolidinyl]methyl dihydrogen phosphate

Identification

Generic Name
[(2R,3R,4S,5S)-3,4-Dihydroxy-5-(4-oxo-4,5-dihydro-1H-pyrrolo[3,2-d]pyrimidin-7-yl)-2-pyrrolidinyl]methyl dihydrogen phosphate
DrugBank Accession Number
DB02075
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 346.2332
Monoisotopic: 346.067835366
Chemical Formula
C11H15N4O7P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHypoxanthine-guanine-xanthine phosphoribosyltransferaseNot AvailablePlasmodium falciparum (isolate FCR-3 / Gambia)
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 / Monoalkyl phosphates / Aralkylamines / Substituted pyrroles / Vinylogous amides / Pyrrolidines / Heteroaromatic compounds / Secondary alcohols / 1,2-diols / 1,2-aminoalcohols
show 5 more
Substituents
1,2-aminoalcohol / 1,2-diol / Alcohol / Alkyl phosphate / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
ribitol phosphate, dihydroxypyrrolidine, pyrrolopyrimidine (CHEBI:43395)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
VJTAXXUIRYOXBT-KUBHLMPHSA-N
InChI
InChI=1S/C11H15N4O7P/c16-9-5(2-22-23(19,20)21)15-7(10(9)17)4-1-12-8-6(4)13-3-14-11(8)18/h1,3,5,7,9-10,12,15-17H,2H2,(H,13,14,18)(H2,19,20,21)/t5-,7+,9-,10+/m1/s1
IUPAC Name
{[(2R,3R,4S,5S)-3,4-dihydroxy-5-{4-oxo-1H,4H,5H-pyrrolo[3,2-d]pyrimidin-7-yl}pyrrolidin-2-yl]methoxy}phosphonic acid
SMILES
[H]N1C=C([C@@H]2N([H])[C@H](COP(O)(O)=O)[C@@H](O)[C@H]2O)C2=C1C(=O)N=CN2[H]

References

General References
Not Available
PubChem Compound
444833
PubChem Substance
46507599
ChemSpider
392646
ZINC
ZINC000015479974
PDBe Ligand
IRP
PDB Entries
1cjb / 8fx2

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 Solubility3.77 mg/mLALOGPS
logP-1.3ALOGPS
logP-3.5Chemaxon
logS-2ALOGPS
pKa (Strongest Acidic)1.5Chemaxon
pKa (Strongest Basic)8.62Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count7Chemaxon
Polar Surface Area176.5 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity76.81 m3·mol-1Chemaxon
Polarizability29.26 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6272
Blood Brain Barrier-0.6851
Caco-2 permeable-0.733
P-glycoprotein substrateSubstrate0.5246
P-glycoprotein inhibitor INon-inhibitor0.9428
P-glycoprotein inhibitor IINon-inhibitor0.9709
Renal organic cation transporterNon-inhibitor0.9286
CYP450 2C9 substrateNon-substrate0.7786
CYP450 2D6 substrateNon-substrate0.8141
CYP450 3A4 substrateNon-substrate0.5239
CYP450 1A2 substrateNon-inhibitor0.8235
CYP450 2C9 inhibitorNon-inhibitor0.8997
CYP450 2D6 inhibitorNon-inhibitor0.8794
CYP450 2C19 inhibitorNon-inhibitor0.8915
CYP450 3A4 inhibitorNon-inhibitor0.8687
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9252
Ames testNon AMES toxic0.7568
CarcinogenicityNon-carcinogens0.8876
BiodegradationNot ready biodegradable0.9194
Rat acute toxicity2.3575 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9801
hERG inhibition (predictor II)Non-inhibitor0.8225
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/MSsplash10-0002-0091000000-cc01ac142f0e4c4117c2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004j-9003000000-aec074e706cca1e14497
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001s-0490000000-ab0bcc8be687c1f2cbea
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-9bbc041a48805948beff
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000b-0950000000-bd2cb3fca007618b6c49
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-5b9c2629eda64da62458
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]-160.68983
predicted
DeepCCS 1.0 (2019)
[M+H]+163.08542
predicted
DeepCCS 1.0 (2019)
[M+Na]+168.99794
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Hypoxanthine-guanine-xanthine phosphoribosyltransferase
Kind
Protein
Organism
Plasmodium falciparum (isolate FCR-3 / Gambia)
Pharmacological action
Unknown
General Function
Xanthine phosphoribosyltransferase activity
Specific Function
Converts guanine to guanosine monophosphate, and hypoxanthine to inosine monophosphate. Transfers the 5-phosphoribosyl group from 5-phosphoribosylpyrophosphate onto the purine. Works with guanine, ...
Gene Name
LACZ
Uniprot ID
P20035
Uniprot Name
Hypoxanthine-guanine-xanthine phosphoribosyltransferase
Molecular Weight
26348.18 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52