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Purine nucleoside (M2MDB003628)

Record Information
Version2.0
Creation Date2012-10-10 12:23:25 -0600
Update Date2015-08-05 16:22:04 -0600
Secondary Accession Numbers
  • ECMDB23238
Identification
Name:Purine nucleoside
DescriptionA purine ribonucleoside that is 9H-purine attached to a β-D-ribofuranosyl residue at position 9 via a glycosidic (N-glycosyl) linkage
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • N-D-Ribosylpurine
  • Purine nucleoside
  • Purine riboside
Chemical Formula:C10H12N4O4
Weight:Average: 252.2267
Monoisotopic: 252.085854892
InChI Key:MRWXACSTFXYYMV-FDDDBJFASA-N
InChI:InChI=1S/C10H12N4O4/c15-2-6-7(16)8(17)10(18-6)14-4-13-5-1-11-3-12-9(5)14/h1,3-4,6-8,10,15-17H,2H2/t6-,7-,8-,10-/m1/s1
CAS number:550-33-4
IUPAC Name:(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(9H-purin-9-yl)oxolane-3,4-diol
Traditional IUPAC Name:purine nucleoside
SMILES:[H][C@]1(CO)O[C@@]([H])(N2C=NC3=CN=CN=C23)[C@]([H])(O)[C@]1([H])O
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Primary alcohol
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:182 - 183 C
Experimental Properties:
PropertyValueSource
Water Solubility:100 mg/mLPhysProp
Predicted Properties
PropertyValueSource
Water Solubility16.8 g/LALOGPS
logP-0.99ALOGPS
logP-1.9ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)3.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.52 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.18 m³·mol⁻¹ChemAxon
Polarizability23.51 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Purine nucleoside + Inorganic phosphate > Purine + Ribose-1-phosphate
Purine nucleoside + Phosphate + Purine deoxyribonucleoside <> Purine + Ribose-1-phosphate + Deoxyribose 1-phosphate
SMPDB Pathways:
Pyrimidine metabolismPW000942 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-0960000000-02588b36be524da1fbdbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0uk9-0690000000-3132e9cf975c9d333807View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-30611d46c742b20458a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-bf687a37f1a8fdee4b9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0900000000-1ca445719eb772d826e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-2900000000-d4186191baed33ece266View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-00di-0900000000-fe942a1442dc2ba58705View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0940000000-558c13580fe37e7be7ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-c0a60904cd95924d259fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-8900000000-dece14475c7e39a2463eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uxr-0790000000-52cdec17cf806f6a8d60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-825da67e9ee8ead415d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9800000000-eeb587fff62d67752a0cView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID139743
HMDB IDHMDB29956
Pubchem Compound ID248425
Kegg IDC15586
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoPUR

Enzymes

Protein Details
1. Purine nucleoside phosphorylase deoD-type
General function:
Involved in purine-nucleoside phosphorylase activity
Specific function:
Cleavage of guanosine or inosine to respective bases and sugar-1-phosphate molecules
Gene Name:
deoD
Uniprot ID:
P0ABP8
Molecular weight:
25950
Reactions
Purine nucleoside + phosphate = purine + alpha-D-ribose 1-phosphate.