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 Date2013-07-04 18:57:12 UTC
Update Date2017-03-02 22:05:23 UTC
HMDB IDHMDB60752
Secondary Accession NumbersNone
Metabolite Identification
Common Name3'-Azido-3'-deoxy-5'- O-beta-D-glucopyranuronosylthymidine
Description3'-Azido-3'-deoxy-5'- O-beta-D-glucopyranuronosylthymidine is a metabolite of zidovudine. Zidovudine or azidothymidine (AZT) (also called ZDV) is a nucleoside analog reverse-transcriptase inhibitor (NRTI), a type of antiretroviral drug used for the successful treatment of HIV/AIDS infectiousness. It is a therapeutic analog of thymidine. AZT is the first U.S. government-approved treatment for HIV therapy, prescribed under the names Retrovir and Retrovis. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
AZT glucuronideMeSH
3'-azido-3'-Deoxy-5'-O-beta-glucopyranuronosylthymidineMeSH
GAZTMeSH
Chemical FormulaC16H21N5O10
Average Molecular Weight443.3654
Monoisotopic Molecular Weight443.128841917
IUPAC Name(2S,3S,4S,5R)-6-{[(2S)-3-azido-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R)-6-{[(2S)-3-azido-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC1=CN(C2CC(N=[N+]=[N-])[C@@H](COC3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)O2)C(=O)N=C1O
InChI Identifier
InChI=1S/C16H21N5O10/c1-5-3-21(16(28)18-13(5)25)8-2-6(19-20-17)7(30-8)4-29-15-11(24)9(22)10(23)12(31-15)14(26)27/h3,6-12,15,22-24H,2,4H2,1H3,(H,26,27)(H,18,25,28)/t6?,7-,8?,9+,10+,11-,12+,15?/m1/s1
InChI KeyNFXAJWJJNLWLOV-OTQDERTISA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as pyrimidine 2',3'-dideoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at positions 2 and 3.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPyrimidine nucleosides
Direct ParentPyrimidine 2',3'-dideoxyribonucleosides
Alternative Parents
Substituents
  • Pyrimidine 2',3'-dideoxyribonucleoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Beta-hydroxy acid
  • Hydroxypyrimidine
  • Pyrimidone
  • Monosaccharide
  • Hydropyrimidine
  • Hydroxy acid
  • Oxane
  • Pyran
  • Pyrimidine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Azo imide
  • Azo compound
  • Secondary alcohol
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Azacycle
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic zwitterion
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility27.5 mg/mLALOGPS
logP-0.36ALOGPS
logP-1.4ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)3.24ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area208.01 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity94.31 m3·mol-1ChemAxon
Polarizability40.98 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
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 IDDBMET00718
      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 LinkHMDB60752
      Metagene LinkHMDB60752
      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