Estrone sulfate

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Estrone sulfate are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Estrone sulfate?

The molecule Estrone sulfate presents a molecular formula of C18H22O5S and its IUPAC name is [(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate.

Estrone sulfate (abbreviated E1S) is a synthetic, steroidal estrogen and a prodrug of estrone. It is used as an estrogen in hormone therapy for menopausal symptoms and low estrogen levels. It is also used in combination with a progestin in menopausal hormone therapy to reduce the risk of endometrial cancer. Estrone sulfate was first synthesized in 1935..

Estrone sulfate is a white to off-white, crystalline powder that is insoluble in water. Each mL of sterile, aqueous solution contains estrone sulfate USP 0.5 mg, polysorbate 80 USP 0.5 mg, and sodium chloride USP 9 mg. The pH is adjusted to 4.0-5.5 with hydrochloric acid and/or sodium hydroxide..

Estrone sulfate is a prodrug of estrone, and is converted to estrone in the body. Estrone is a natural, weak estrogen that is produced by the ovaries, placenta, and adrenal glands. In the body, estrone is converted to other, more potent estrogens, such as estradiol..

Estrone sulfate is used as an estrogen in hormone therapy for menopausal symptoms and low estrogen levels. It is also used in combination with a progestin in menopausal hormone therapy to reduce the risk of endometrial cancer..

Estrone sulfate is a synthetic, steroidal estrogen, and is not approved for use in the United States. It exists in other countries, however, such as Canada and the United Kingdom..

3D structure

Cartesian coordinates

Geometry of Estrone sulfate in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Estrone sulfate JKKFKPJIXZFSSB-CBZIJGRNSA-N chemical compound 2D structure molecule svg
Estrone sulfate

 

Molecule descriptors

 
IUPAC name[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
InChI codeInChI=1S/C18H22O5S/c1-18-9-8-14-13-5-3-12(23-24(20,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)19/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,18+/m1/s1
InChI KeyJKKFKPJIXZFSSB-CBZIJGRNSA-N
SMILESC[C@]12CC[C@@H]3c4ccc(OS(=O)(=O)O)cc4CC[C@H]3[C@@H]1CCC2=O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 17-oxoestra-1,3,5(10)-trien-3-yl hydrogen sulfate
  • 3-Hydroxyestra-1,3,5(10)-trien-17-one hydrogen sulphate
  • 438-67-5
  • 481-97-0
  • AB00514744
  • BDBM50366524
  • BPBio1_000897
  • BSPBio_000815
  • C02538
  • CCRIS 9319
  • CONJUGOL
  • Conestoral
  • DB04574
  • ESTRADIOL METABOLITE (E1S)
  • ESTRONE 3 SULFATE
  • Estra-1(10),2,4-trien-17-one, 3-(sulfooxy)-
  • Estra-1,3,5 (10)-triene-17-one-3-yl-sulfate
  • Estra-1,3,5(10)-trien-17-one, 3-(sulfooxy)-
  • Estrogenic substances
  • Estrone hydrogen sulfate
  • Estrone hydrogen sulphate
  • Estrone 3-sulfate
  • Estrone 3-sulphate
  • Estrone bisulfate
  • Estrone hemisulfate
  • Estrone hydrogen sulfate
  • Estrone sulfate
  • Estrone sulfate sodium
  • Estrone sulphate
  • Estrone sulphate sodium
  • Estrone, hydrogen sulfate
  • GTPL4748
  • GTPL4749
  • Hyhorin
  • LMST02010043
  • Morestin
  • NCGC00179418-01
  • PRICE
  • Par Estro
  • Premarin
  • Prestwick0_000688
  • Prestwick1_000688
  • Prestwick2_000688
  • Prestwick3_000688
  • Q5401864
  • QTL48N278K
  • Sodium estrone 3-monosulfate
  • Sodium estrone 3-monosulphate
  • Sodium estrone 3-sulfate
  • Sodium estrone 3-sulphate
  • US-2917522
  • [(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-5-yl]oxidanesulfonic acid
  • [(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
  • [3H]-estrone hydrogen sulfate
  • [3H]-estrone-3-sulphate
  • [3H]estrone-3-sulfate
  • [3H]estrone-3-sulphate
  • estron-3-sulfate
  • estrone hydrogen sulphate
  • estrone-3-sulfate
  • estrone-3-sulphate
  • evex

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3876186
  • UNII-QTL48N278K
  • BRD-K51095933-231-03-2
  • DTXSID50891501
  • CHEMBL494753
  • CHEBI:17474
  • EINECS 207-575-9
  • SPBio_002736
  • SCHEMBL22846

Physico-Chemical properties

IUPAC name[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
Molecular formulaC18H22O5S
Molecular weight350.429
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity90.26
LogP4.4
Topological polar surface area89.1

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.