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
Version4.0
Creation Date2013-07-04 18:55:29 UTC
Update Date2017-09-27 08:43:53 UTC
HMDB IDHMDB0060728
Secondary Accession Numbers
  • HMDB60728
Metabolite Identification
Common Name2',3'-Dideoxyadenosine-5-triphosphate
Description2',3'-Dideoxyadenosine-5-triphosphate is a metabolite of didanosine. Didanosine (2',3'-dideoxyinosine, ddI, DDI) is sold under the trade names Videx and Videx EC. It is a reverse transcriptase inhibitor, effective against HIV and used in combination with other antiretroviral drug therapy as part of highly active antiretroviral therapy (HAART). (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
DDATPChEMBL
2',3'-Dideoxyadenosine-5-triphosphoric acidGenerator
2',3'-Dideoxy-ATPMeSH
2',3'-Dideoxyadenosine triphosphateMeSH
Chemical FormulaC10H16N5O11P3
Average Molecular Weight475.1822
Monoisotopic Molecular Weight475.005915915
IUPAC Name({[({[(2S,5R)-5-(6-amino-9H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional Name({[(2S,5R)-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
NC1=NC=NC2=C1N=CN2[C@H]1CC[C@@H](CO[P@@](O)(=O)O[P@](O)(=O)OP(O)(O)=O)O1
InChI Identifier
InChI=1S/C10H16N5O11P3/c11-9-8-10(13-4-12-9)15(5-14-8)7-2-1-6(24-7)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h4-7H,1-3H2,(H,19,20)(H,21,22)(H2,11,12,13)(H2,16,17,18)/t6-,7+/m0/s1
InChI KeyOAKPWEUQDVLTCN-NKWVEPMBSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as purine 2',3'-dideoxyribonucleoside triphosphates. These are purine nucleotides with triphosphate group linked to the ribose moiety lacking a hydroxyl group at positions 2 and 3.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct ParentPurine 2',3'-dideoxyribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine 2',3'-dideoxyribonucleoside triphosphate
  • Purine 2',3'-dideoxyribonucleoside
  • Purine nucleoside
  • 6-aminopurine
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Primary aromatic amine
  • Pyrimidine
  • Alkyl phosphate
  • Imidolactam
  • Imidazole
  • Azole
  • Oxolane
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Primary amine
  • Organic oxide
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 Solubility3.05 g/LALOGPS
logP-0.44ALOGPS
logP-4.6ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.9ChemAxon
pKa (Strongest Basic)5.01ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area238.67 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity93.51 m³·mol⁻¹ChemAxon
Polarizability36.83 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
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, Positivesplash10-054k-9575100000-42be4427da05e26483edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0911100000-d76b4a94b9c69db119ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-e2799f4a40f49f84b423View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-9a5ab86eeb22480831fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0120900000-18b657b7a04d8a549b32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0569-9880100000-a205f6cf9355582bfe47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-bfa06fc50b2d3a56d934View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Didanosine Action PathwayPw000716Pw000716 greyscalePw000716 simpleNot Available
Displaying 1 entry
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 IDDBMET00689
      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
      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