Diethylstilbestrol diphosphate (CHEM019343)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:02:19 UTC
Update Date2016-11-09 01:15:58 UTC
Accession NumberCHEM019343
Identification
Common NameDiethylstilbestrol diphosphate
ClassSmall Molecule
DescriptionFosfestrol, sold under the brand name Honvan and also known as diethylstilbestrol diphosphate (DESDP), is an estrogen medication which is used in the treatment of prostate cancer in men. It is given by slow intravenous infusion once per day to once per week or by mouth once per day.Side effects of fosfestrol include nausea and vomiting, cardiovascular complications, blood clots, edema, and genital skin reactions, among others. Fosfestrol is an estrogen, and hence is an agonist of the estrogen receptor, the biological target of estrogens like estradiol. It acts as a prodrug of diethylstilbestrol.Fosfestrol was patented in 1941 and was introduced for medical use in 1955. It was previously marketed widely throughout the world, but now remains available in only a few countries.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Diethylstilbestrol bisphosphateKegg
StilphostrolKegg
Diethylstilbestrol bisphosphoric acidGenerator
Fosfestrol, tetrasodium salt, (e)-isomerMeSH
Diethyldioxystilbene diphosphateMeSH
Diethylstilbestrol diphosphateMeSH
DifostilbenMeSH
Fosfestrol, sodium salt, (e)-isomerMeSH
KyorinMeSH
Fosfestrol, 99TC-labeled CPDMeSH
FosfesterolMeSH
Fosfestrol, disodium salt, (e)-isomerMeSH
HonvanMeSH
ST-52MeSH
FostrolinMeSH
Stilbestrol diphosphateMeSH
Fosfestrol, (e)-isomerMeSH
FostestrolumMeSH
FosfestrolKEGG
Diethylstilbestrol diphosphoric acidGenerator
[4-[(e)-4-(4-Phosphonooxyphenyl)hex-3-en-3-yl]phenyl] dihydrogen phosphoric acidGenerator
{4-[(3E)-4-[4-(phosphonooxy)phenyl]hex-3-en-3-yl]phenoxy}phosphonateGenerator
Chemical FormulaC18H22O8P2
Average Molecular Mass428.314 g/mol
Monoisotopic Mass428.079 g/mol
CAS Registry Number522-40-7
IUPAC Name{4-[(3E)-4-[4-(phosphonooxy)phenyl]hex-3-en-3-yl]phenoxy}phosphonic acid
Traditional Namefosfestrol
SMILESCC\C(=C(\CC)C1=CC=C(OP(O)(O)=O)C=C1)C1=CC=C(OP(O)(O)=O)C=C1
InChI IdentifierInChI=1S/C18H22O8P2/c1-3-17(13-5-9-15(10-6-13)25-27(19,20)21)18(4-2)14-7-11-16(12-8-14)26-28(22,23)24/h5-12H,3-4H2,1-2H3,(H2,19,20,21)(H2,22,23,24)/b18-17+
InChI KeyNLORYLAYLIXTID-ISLYRVAYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Phenyl phosphate
  • Aryl phosphate
  • Aryl phosphomonoester
  • Phenylpropane
  • Phenoxy compound
  • Benzenoid
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility0.02 g/LALOGPS
logP2.86ALOGPS
logP3.89ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)1.49ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity104.99 m³·mol⁻¹ChemAxon
Polarizability39.93 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-3022900000-f0dd3283b1f6ee0ddc93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-2159500000-331fdc9897892806bfd0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-2193000000-9208d58eb1e03a31ada6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000300000-5cf1f4af7dbf70bfe431Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-88661bed129cf6fbcb59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9708862e1e7bf6faf85eSpectrum
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 IDDBSALT001389
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 LinkFosfestrol
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID3032325
Kegg Compound IDC08145
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available