Adefovir (CHEM018835)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:34:37 UTC
Update Date2016-11-09 01:15:52 UTC
Accession NumberCHEM018835
Identification
Common NameAdefovir
ClassSmall Molecule
DescriptionA member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
9-(2-(Phosphonomethoxy)ethyl)adenineChEBI
9-(2-Phosphonylmethoxyethyl)adenineChEBI
DRG-0156ChEBI
GS 0393ChEBI
GS 393ChEBI
GS-0393ChEBI
HSDB 8079ChEBI
N-(2-Phosphonylmethoxyethyl)adenineChEBI
PMEAChEBI
9-(2-Phosphonomethoxyethyl)adenineMeSH
9-PMEAMeSH
Chemical FormulaC8H12N5O4P
Average Molecular Mass273.186 g/mol
Monoisotopic Mass273.063 g/mol
CAS Registry Number106941-25-7
IUPAC Name{[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}phosphonic acid
Traditional Nameadefovir
SMILESNC1=C2N=CN(CCOCP(O)(O)=O)C2=NC=N1
InChI IdentifierInChI=1S/C8H12N5O4P/c9-7-6-8(11-3-10-7)13(4-12-6)1-2-17-5-18(14,15)16/h3-4H,1-2,5H2,(H2,9,10,11)(H2,14,15,16)
InChI KeySUPKOOSCJHTBAH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-aminopurines
Alternative Parents
Substituents
  • 6-aminopurine
  • Aminopyrimidine
  • N-substituted imidazole
  • Pyrimidine
  • Imidolactam
  • Azole
  • Imidazole
  • Organophosphonic acid
  • Organophosphonic acid derivative
  • Heteroaromatic compound
  • Azacycle
  • Organophosphorus compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Amine
  • Primary amine
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.02 g/LALOGPS
logP-1.8ALOGPS
logP-4.5ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.35ChemAxon
pKa (Strongest Basic)5.12ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area136.38 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity63.12 m³·mol⁻¹ChemAxon
Polarizability23.56 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007k-5910000000-b080ba968f1869c600c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0490000000-5d3a0dcefb9dae3bc851Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9830000000-fbccf71652a06f9f4cbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-e4e8a5512909b00d6b87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2490000000-a694dfaa16b951ffcf1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-9730000000-695eec81f6ffc3fff6cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9810000000-5c5fd9cbacd414cbef52Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB13868
HMDB IDHMDB0060695
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAdefovir
Chemspider IDNot Available
ChEBI ID2469
PubChem Compound ID60172
Kegg Compound IDC11277
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10676990
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11796353
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=14647052
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=14978283
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15866657
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22976988
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24338503
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=27079793
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=27381944
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=27649318
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=27664568
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=27698751
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=27729626
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=27746441
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=27806120
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=27858892
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=27880997
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=27977591
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=28011962
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=28079295
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=28081595
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=28123560
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=28322924
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=28397817
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=28436380