estrone-3-sulphate   Click here for help

GtoPdb Ligand ID: 4749

Synonyms: estrone hydrogen sulfate | estrone hydrogen sulphate | estrone-3-sulfate | Ogen®
Approved drug
estrone-3-sulphate is an approved drug (FDA (1977))
Compound class: Metabolite or derivative
Comment: A component of the approved drug estropipate (a salt of estrone sulfate and piperazine).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 89.05
Molecular weight 350.12
XLogP 1.78
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES O=C1CCC2C1(C)CCC1C2CCc2c1ccc(c2)OS(=O)(=O)O
Isomeric SMILES O=C1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)OS(=O)(=O)O
InChI InChI=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 Key JKKFKPJIXZFSSB-CBZIJGRNSA-N
Bioactivity Comments
We have been unable to find publicly available affinity data for this drug at its proposed molecular target(s) to substantiate its MMOA, and have therefore not tagged a primary drug target.
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Sodium/bile acid and sulphated solute cotransporter 1
Sodium/bile acid and sulphated solute cotransporter 6
Organic anion transporter 3 3
Organic anion transporter 4 1
SLC22A24 4
OATP2B1
Selectivity at transporters
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
OATP1B1 Hs Inhibitor Inhibition 7.2 pIC50 - 2
⤷ pIC50 7.2 (IC50 6x10-8 M) [2]
Description: Measured using estropipate, which is estrone-3-sulfate stabilized with piperazine.
Targets where the ligand is described in the comment field
Target Comment
OATP1B1 Other inhibitors include, fibrates, flavonoids, glitazones and macrolide antibacterials. Estrone-3-sulphate or the drug substrates atorvastatin, pravastatin and rosuvastatin are used as a probe.