NAV

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

Identification

Generic Name
(2S,3R,4S,5S)-3,4-Dihydroxy-2-[(methylsulfanyl)methyl]-5-(4-oxo-4,5-dihydro-1H-pyrrolo[3,2-d]pyrimidin-7-yl)pyrrolidinium
DrugBank Accession Number
DB03881
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 297.353
Monoisotopic: 297.10213612
Chemical Formula
C12H17N4O3S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPurine nucleotide phosphorylase, putativeNot AvailablePlasmodium falciparum (isolate 3D7)
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 / Aralkylamines / Substituted pyrroles / Vinylogous amides / Quaternary ammonium salts / Pyrrolidines / Heteroaromatic compounds / 1,2-aminoalcohols / Secondary alcohols / 1,2-diols
show 7 more
Substituents
1,2-aminoalcohol / 1,2-diol / Alcohol / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Dialkylthioether / Heteroaromatic compound / Hydrocarbon derivative
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dihydroxypyrrolidine, pyrrolopyrimidine (CHEBI:44290)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
CEGIKIXYDFDYDN-RXDXJJGDSA-O
InChI
InChI=1S/C12H16N4O3S/c1-20-3-6-10(17)11(18)8(16-6)5-2-13-9-7(5)14-4-15-12(9)19/h2,4,6,8,10-11,13,16-18H,3H2,1H3,(H,14,15,19)/p+1/t6-,8+,10-,11+/m1/s1
IUPAC Name
(2S,3R,4S,5S)-3,4-dihydroxy-2-[(methylsulfanyl)methyl]-5-{4-oxo-1H,4H,5H-pyrrolo[3,2-d]pyrimidin-7-yl}pyrrolidin-1-ium
SMILES
[H]N1C=C([C@H]2[C@H](O)[C@H](O)[C@@H](CSC)[N+]2([H])[H])C2=C1C(=O)N=CN2[H]

References

General References
Not Available
PubChem Compound
131704261
PubChem Substance
46506174
ChemSpider
4883415
PDBe Ligand
MTI
PDB Entries
1q1g

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
logP-0.72Chemaxon
pKa (Strongest Acidic)12.5Chemaxon
pKa (Strongest Basic)8.45Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area114.32 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity88.19 m3·mol-1Chemaxon
Polarizability29.18 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9838
Blood Brain Barrier-0.835
Caco-2 permeable-0.7163
P-glycoprotein substrateSubstrate0.6708
P-glycoprotein inhibitor INon-inhibitor0.9827
P-glycoprotein inhibitor IINon-inhibitor0.979
Renal organic cation transporterNon-inhibitor0.9203
CYP450 2C9 substrateNon-substrate0.8061
CYP450 2D6 substrateNon-substrate0.7812
CYP450 3A4 substrateSubstrate0.5428
CYP450 1A2 substrateNon-inhibitor0.7826
CYP450 2C9 inhibitorNon-inhibitor0.8315
CYP450 2D6 inhibitorNon-inhibitor0.8693
CYP450 2C19 inhibitorNon-inhibitor0.81
CYP450 3A4 inhibitorNon-inhibitor0.9584
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8782
Ames testNon AMES toxic0.7057
CarcinogenicityNon-carcinogens0.9506
BiodegradationNot ready biodegradable0.9794
Rat acute toxicity2.4136 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9915
hERG inhibition (predictor II)Non-inhibitor0.7918
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 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-159.62257
predicted
DeepCCS 1.0 (2019)
[M+H]+162.01813
predicted
DeepCCS 1.0 (2019)
[M+Na]+168.25238
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Purine nucleotide phosphorylase, putative
Kind
Protein
Organism
Plasmodium falciparum (isolate 3D7)
Pharmacological action
Unknown
General Function
Uridine phosphorylase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q8I3X4
Uniprot Name
Purine nucleotide phosphorylase, putative
Molecular Weight
26857.88 Da
Details2. 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. Shi W, Ting LM, Kicska GA, Lewandowicz A, Tyler PC, Evans GB, Furneaux RH, Kim K, Almo SC, Schramm VL: Plasmodium falciparum purine nucleoside phosphorylase: crystal structures, immucillin inhibitors, and dual catalytic function. J Biol Chem. 2004 Apr 30;279(18):18103-6. Epub 2004 Feb 23. [Article]

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