ChemFOnt: Showing chemical card for 17beta-Estradiol 3-sulfate (CFc000002135)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:56 UTC

Chemfont ID

CFc000002135

Molecule Identification

Common Name

17beta-Estradiol 3-sulfate

Definition

17beta-Estradiol 3-sulfate, also known as estradiol 3-sulfuric acid or estradiol-17beta 3-sulfate, belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. 17beta-Estradiol 3-sulfate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. The estrogen patch is a delivery system for estradiol used as hormone replacement therapy to treat the symptoms of menopause, such as hot flashes and vaginal dryness, and to prevent osteoporosis. Originally marketed as Vivelle(Novartis), it was discontinued in 2003 and reintroduced in a smaller form as Vivelle-Dot. Although estrogen is given transdermally rather than in the standard oral tablets, the estrogen patch carries similar risks and benefits as more conventional forms of estrogen-only hormone replacement therapy.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(17beta)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfate	ChEBI
17beta-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfate	ChEBI
Estradiol 3-sulphate	ChEBI
Estradiol-17beta 3-sulfate	ChEBI
Estradiol-3-sulfate	ChEBI
(17b)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfate	Generator
(17b)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfuric acid	Generator
(17b)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphate	Generator
(17b)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphuric acid	Generator
(17beta)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfuric acid	Generator
(17beta)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphate	Generator
(17beta)-17-Hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphuric acid	Generator
(17Β)-17-hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfate	Generator
(17Β)-17-hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulfuric acid	Generator
(17Β)-17-hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphate	Generator
(17Β)-17-hydroxyestra-1(10),2,4-trien-3-yl hydrogen sulphuric acid	Generator
17b-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfate	Generator
17b-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfuric acid	Generator
17b-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphate	Generator
17b-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphuric acid	Generator
17beta-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfuric acid	Generator
17beta-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphate	Generator
17beta-Hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphuric acid	Generator
17Β-hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfate	Generator
17Β-hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulfuric acid	Generator
17Β-hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphate	Generator
17Β-hydroxyestra-1,3,5(10)-trien-3-yl hydrogen sulphuric acid	Generator
Estradiol 3-sulfate	Generator
Estradiol 3-sulfuric acid	Generator
Estradiol 3-sulphuric acid	Generator
Estradiol-17b 3-sulfate	Generator
Estradiol-17b 3-sulfuric acid	Generator
Estradiol-17b 3-sulphate	Generator
Estradiol-17b 3-sulphuric acid	Generator
Estradiol-17beta 3-sulfuric acid	Generator
Estradiol-17beta 3-sulphate	Generator
Estradiol-17beta 3-sulphuric acid	Generator
Estradiol-17β 3-sulfate	Generator
Estradiol-17β 3-sulfuric acid	Generator
Estradiol-17β 3-sulphate	Generator
Estradiol-17β 3-sulphuric acid	Generator
Estradiol-3-sulfuric acid	Generator
Estradiol-3-sulphate	Generator
Estradiol-3-sulphuric acid	Generator
17b-Estradiol 3-sulfate	Generator
17b-Estradiol 3-sulfuric acid	Generator
17b-Estradiol 3-sulphate	Generator
17b-Estradiol 3-sulphuric acid	Generator
17beta-Estradiol 3-sulfuric acid	Generator
17beta-Estradiol 3-sulphate	Generator
17beta-Estradiol 3-sulphuric acid	Generator
17Β-estradiol 3-sulfate	Generator
17Β-estradiol 3-sulfuric acid	Generator
17Β-estradiol 3-sulphate	Generator
17Β-estradiol 3-sulphuric acid	Generator
17beta-Estradiol sulfate	HMDB
17beta-Estradiol sulphate	HMDB
17Β-estradiol sulfate	HMDB
17Β-estradiol sulphate	HMDB
17beta-Estradiol 3-sulfate	HMDB

Chemical Formula

C₁₈H₂₄O₅S

Average Molecular Weight

352.45

Monoisotopic Molecular Weight

352.134445047

IUPAC Name

[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-5-yl]oxidanesulfonic acid

Traditional Name

[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-5-yl]oxidanesulfonic acid

CAS Registry Number

481-96-9

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(OS(O)(=O)=O)C=C3CC[C@@]21[H]

InChI Identifier

InChI=1S/C18H24O5S/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/h3,5,10,14-17,19H,2,4,6-9H2,1H3,(H,20,21,22)/t14-,15-,16+,17+,18+/m1/s1

InChI Key

QZIGLSSUDXBTLJ-ZBRFXRBCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Sulfated steroids

Direct Parent

Sulfated steroids

Alternative Parents

Substituents

Sulfated steroid skeleton
Estrane-skeleton
Hydroxysteroid
17-hydroxysteroid
Phenanthrene
Arylsulfate
Tetralin
Benzenoid
Sulfuric acid monoester
Sulfate-ester
Sulfuric acid ester
Organic sulfuric acid or derivatives
Cyclic alcohol
Secondary alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Alcohol
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

steroid sulfate (CHEBI:4866 )
17beta-hydroxy steroid (CHEBI:4866 )
sulfates (C08357 )
C18 steroids (estrogens) and derivatives (C08357 )
Sulfates (LMST05020005 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Organ

Liver (HMDB: HMDB0004448)
Kidney (HMDB: HMDB0004448)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0004448)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	0.16	ALOGPS
logP	1.57	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	-1.8	ChemAxon
pKa (Strongest Basic)	-0.83	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.9 m³·mol⁻¹	ChemAxon
Polarizability	37.68 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0004448

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112363

KNApSAcK ID

Not Available

Chemspider ID

59790

KEGG Compound ID

C08357

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

66416

PDB ID

Not Available

ChEBI ID

4866

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 17beta-Estradiol 3-sulfate (CFc000002135)

MOL for CFc000002135 (17beta-Estradiol 3-sulfate)

3D MOL for CFc000002135 (17beta-Estradiol 3-sulfate)

3D SDF for CFc000002135 (17beta-Estradiol 3-sulfate)

3D-SDF for CFc000002135 (17beta-Estradiol 3-sulfate)

PDB for CFc000002135 (17beta-Estradiol 3-sulfate)

3D PDB for CFc000002135 (17beta-Estradiol 3-sulfate)

SMILES for CFc000002135 (17beta-Estradiol 3-sulfate)

INCHI for CFc000002135 (17beta-Estradiol 3-sulfate)

Structure for CFc000002135 (17beta-Estradiol 3-sulfate)

3D Structure for CFc000002135 (17beta-Estradiol 3-sulfate)