bis(POC)PMPA, bis(POC)PMPA, bis(POC)PMPA, bis(POC)PMPA, bis(POC)PMPA (CHEM042618)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 10:01:40 UTC
Update Date2016-11-09 01:22:43 UTC
Accession NumberCHEM042618
Identification
Common Namebis(POC)PMPA, bis(POC)PMPA, bis(POC)PMPA, bis(POC)PMPA, bis(POC)PMPA
ClassSmall Molecule
DescriptionAn organic phosphonate that is the disoproxil ester of tenofovir. A prodrug for tenofovir, an HIV-1 reverse transcriptase inhibitor, tenofovir disoproxil is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
9-((R)-2-((Bis(((isopropoxycarbonyl)oxy)methoxy)phosphinyl)methoxy)propyl)adenineChEBI
Bis(POC)pmpaChEBI
PMPA prodrugChEBI
Tenofovir bis(isopropyloxycarbonyloxymethyl) esterChEBI
Fumarate, tenofovir disoproxilMeSH
9-(2-Phosphonylmethoxypropyl)adenine, (+-)-isomerMeSH
TenofovirMeSH
9-(2-Phosphonylmethoxypropyl)adenine, (S)-isomerMeSH
9-(2-Phosphonylmethoxypropyl)adenineMeSH
VireadMeSH
9-PMPA (tenofovir)MeSH
9-(2-Phosphonylmethoxypropyl)adenine, (R)-isomer - T357098MeSH
Disoproxil fumarate, tenofovirMeSH
(R)-9-(2-Phosphonylmethoxypropyl)adenineMeSH
9-(2-Phosphonomethoxypropyl)adenineMeSH
Disoproxil, tenofovirMeSH
Tenofovir disoproxil fumarateMeSH
Bis({[(propan-2-yloxy)carbonyl]oxy}methyl) {[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methanephosphonic acidGenerator
Chemical FormulaC19H30N5O10P
Average Molecular Mass519.448 g/mol
Monoisotopic Mass519.173 g/mol
CAS Registry Number201341-05-1
IUPAC Namebis({[(propan-2-yloxy)carbonyl]oxy}methyl) {[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methanephosphonate
Traditional Namepmpa prodrug
SMILES[H][C@@](C)(CN1C=NC2=C(N)N=CN=C12)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C
InChI IdentifierInChI=1S/C19H30N5O10P/c1-12(2)33-18(25)28-9-31-35(27,32-10-29-19(26)34-13(3)4)11-30-14(5)6-24-8-23-15-16(20)21-7-22-17(15)24/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22)/t14-/m1/s1
InChI KeyJFVZFKDSXNQEJW-CQSZACIVSA-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
  • Dialkyl alkylphosphonate
  • Phosphonic acid diester
  • Carbonic acid diester
  • Imidolactam
  • Pyrimidine
  • N-substituted imidazole
  • Phosphonic acid ester
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Organophosphonic acid derivative
  • Carbonic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organophosphorus compound
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility0.71 g/LALOGPS
logP-0.02ALOGPS
logP2.65ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)18.59ChemAxon
pKa (Strongest Basic)4.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area185.44 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity118.59 m³·mol⁻¹ChemAxon
Polarizability49.18 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zi9-1923410000-5f1cd970edf5f04f33a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ti-6935400000-aa42e62ec1896201d6a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-7913000000-545bd583eab18a2ac9bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1535920000-7d0f7a9518484f92d296Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1911000000-91af4bd4b9fc5980fe6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1900000000-436151173cf8dcae5801Spectrum
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 IDDB00300
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTenofovir disoproxil
Chemspider IDNot Available
ChEBI ID63717
PubChem Compound ID5481350
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available