Diethylstilbestrol diphosphateProduct ingredient for Diethylstilbestrol

Name
Diethylstilbestrol diphosphate
Drug Entry
Diethylstilbestrol

A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed)

The FDA withdrew its approval for the use of all oral and parenteral drug products containing 25 milligrams or more of diethylstilbestrol per unit dose.6

Accession Number
DBSALT001389
Structure
Synonyms
Diethylstilbestrol bisphosphate / Fosfestrol / Stilphostrol
UNII
A0E0NMA80F
CAS Number
522-40-7
Weight
Average: 428.314
Monoisotopic: 428.078991664
Chemical Formula
C18H22O8P2
InChI Key
NLORYLAYLIXTID-ISLYRVAYSA-N
InChI
InChI=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+
IUPAC Name
{4-[(3E)-4-[4-(phosphonooxy)phenyl]hex-3-en-3-yl]phenoxy}phosphonic acid
SMILES
CC\C(=C(\CC)C1=CC=C(OP(O)(O)=O)C=C1)C1=CC=C(OP(O)(O)=O)C=C1
KEGG Drug
D00946
KEGG Compound
C08145
ChemSpider
2297327
ChEBI
4532
ChEMBL
CHEMBL1200598
ZINC
ZINC000001531012
Wikipedia
Fosfestrol
Predicted Properties
PropertyValueSource
Water Solubility0.0205 mg/mLALOGPS
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 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity104.99 m3·mol-1Chemaxon
Polarizability39.93 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon