You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2013-07-09 16:16:21 UTC
Update Date2017-03-02 22:05:42 UTC
HMDB IDHMDB61067
Secondary Accession NumbersNone
Metabolite Identification
Common Namearabinofuranosylguanine
Descriptionarabinofuranosylguanine is a metabolite of nelarabine. Nelarabine is a chemotherapy drug used in T-cell acute lymphoblastic leukemia. It was previously known as 506U78. Nelarabine is a purine nucleoside analog converted to its corresponding arabinosylguanine nucleotide triphosphate (araGTP), resulting in inhibition of DNA synthesis and cytotoxicity. Pre-clinical studies suggest that T-cells are particularly sensitive to nelarabine. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC10H14N5O5
Average Molecular Weight284.2487
Monoisotopic Molecular Weight284.099493583
IUPAC Name(2R,3S,4S,5R)-2-(6-hydroxy-2-imino-3,7,8,9-tetrahydro-2H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Traditional Name(2R,3S,4S,5R)-2-(6-hydroxy-2-imino-7,8-dihydro-3H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@H]([C@@H](O)[C@@H]1O)N1[CH]NC2=C1NC(=N)N=C2O
InChI Identifier
InChI=1S/C10H14N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,12,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6+,9-/m1/s1
InChI KeyJEPAHPFDUXQBAO-FJFJXFQQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleosides
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Hydroxypyrimidine
  • Monosaccharide
  • Pyrimidine
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Primary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.81 mg/mLALOGPS
logP-2.1ALOGPS
logP-4ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)-3.2ChemAxon
pKa (Strongest Basic)15.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area153.66 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity85.11 m3·mol-1ChemAxon
Polarizability25.87 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00412
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB61067
      Metagene LinkHMDB61067
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available