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Record Information
Version3.6
Creation Date2013-07-09 16:16:21 UTC
Update Date2016-02-11 08:17:56 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=1/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-/s2
InChI KeyInChIKey=JEPAHPFDUXQBAO-CBQAOLGZNA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassNot Available
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine ribonucleoside
  • N-glycosyl compound
  • Glycosyl compound
  • Imidazopyrimidine
  • Hydroxypyrimidine
  • Pyrimidine
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Tertiary amine
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • 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 QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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