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Record Information
Version4.0
Creation Date2006-05-22 15:12:28 UTC
Update Date2017-09-27 08:24:19 UTC
HMDB IDHMDB0003040
Secondary Accession Numbers
  • HMDB03040
Metabolite Identification
Common NameArabinosylhypoxanthine
DescriptionArabinosylhypoxanthine is found to have a potent antiviral activity for herpes simplex infected cells. The final metabolite in the conversion of Arabinosyladenine-5'-monophosphate to arabinosyladenine then to Arabinosylhypoxanthine.
Structure
Thumb
Synonyms
ValueSource
Ara-HXHMDB
9 beta-D-Arabinofuranosyl-1,9-dihydro-6H-purin-6-oneMeSH
Hypoxanthine arabinosideMeSH
9 beta-D-ArabinofuranosylhypoxanthineMeSH
AraHxMeSH
Ara-HMeSH
Chemical FormulaC10H12N4O5
Average Molecular Weight268.2261
Monoisotopic Molecular Weight268.080769514
IUPAC Name9-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one
Traditional Name9-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
CAS Registry Number7013-16-3
SMILES
OC[C@H]1OC([C@@H](O)[C@@H]1O)N1C=NC2=C1NC=NC2=O
InChI Identifier
InChI=1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7+,10?/m1/s1
InChI KeyUGQMRVRMYYASKQ-KBNQYOMWSA-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
  • 6-oxopurine
  • Hypoxanthine
  • Pentose monosaccharide
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Pyrimidone
  • Pyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Vinylogous amide
  • Heteroaromatic compound
  • Azole
  • Oxolane
  • Imidazole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

  Health condition:

    Infections and infestations:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility14.3 g/LALOGPS
logP-1.7ALOGPS
logP-2ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)6.94ChemAxon
pKa (Strongest Basic)2.74ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.2 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity60.9 m³·mol⁻¹ChemAxon
Polarizability24.68 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adl-9250000000-d6ee10ae0804bda3e4ceView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0gc0-3392100000-105fd86588f87bbc7682View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0940000000-1edfa7642cf5a4fed66dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-c4a771b28fab50986335View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06ri-1900000000-bad238ac23d41426077aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-0590000000-987a2099b121adf31362View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-1f1240b42ef89dc97aaeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-3900000000-ffc6c0f2b3a8bd03b941View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified10.63 (1.60 - 78.33) uMAdult (>18 years old)Both
Herpes zoster infections
details
Associated Disorders and Diseases
Disease References
Herpes zoster
  1. McCann WP, Hall LM, Siler W, Barton N, Whitley RJ: High-pressure liquid chromatographic methods for determining arabinosyladenine-5'-monophosphate, arabinosyladenine, and arabinosylhypoxanthine in plasma and urine. Antimicrob Agents Chemother. 1985 Aug;28(2):265-73. [PubMed:2423028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023100
KNApSAcK IDNot Available
Chemspider ID24654354
KEGG Compound IDNot Available
BioCyc IDINOSINE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3022
PubChem Compound46874582
PDB IDNot Available
ChEBI ID705435
References
Synthesis ReferenceReist, Elmer J.; Benitez, Allen; Goodman, Leon; Baker, B. R.; Lee, William W. Potential anticancer agents. LXXVI. Synthesis of purine nucleosides of b-D-arabinofuranose. Journal of Organic Chemistry (1962), 27 3274-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Schwartz PM, Shipman C Jr, Drach JC: Antiviral activity of arabinosyladenine and arabinosylhypoxanthine in herpes simplex virus-infected KB cells: selective inhibition of viral deoxyribonucleic acid synthesis in the presence of an adenosine deaminase inhibitor. Antimicrob Agents Chemother. 1976 Jul;10(1):64-74. [PubMed:185947 ]
  2. Buchanan RA, Kinkel AW, Alford CA Jr, Whitley RJ: Plasma levels and urinary excretion of vidarabine after repeated dosing. Clin Pharmacol Ther. 1980 May;27(5):690-6. [PubMed:7371366 ]
  3. Chang T, Glazko AJ: Effect of an adenosine deaminase inhibitor on the uptake and metabolism of arabinosyl adenine (Vidarabine) by intact human erythrocytes. Res Commun Chem Pathol Pharmacol. 1976 May;14(1):127-40. [PubMed:935646 ]
  4. McCann WP, Hall LM, Siler W, Barton N, Whitley RJ: High-pressure liquid chromatographic methods for determining arabinosyladenine-5'-monophosphate, arabinosyladenine, and arabinosylhypoxanthine in plasma and urine. Antimicrob Agents Chemother. 1985 Aug;28(2):265-73. [PubMed:2423028 ]