progesterone   Click here for help

GtoPdb Ligand ID: 2377

Synonyms: Prometrium® | Utrogestan®
Approved drug PDB Ligand
progesterone is an approved drug (FDA (1959))
Compound class: Metabolite
Comment: Progesterone is an endogenous steroid and progestogen sex hormone. It is the major progestogen and is required for the production of other endogenous steroids, including the sex hormones and corticosteroids.
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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

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View more information in the IUPHAR Pharmacology Education Project: progesterone

progesterone is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 2
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 34.14
Molecular weight 314.22
XLogP 4.83
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES O=C1CCC2(C(=C1)CCC1C2CCC2(C1CCC2C(=O)C)C)C
Isomeric SMILES O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C
InChI InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1
InChI Key RJKFOVLPORLFTN-LEKSSAKUSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Natural/Endogenous Targets
Target
Mineralocorticoid receptor
Progesterone receptor
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Glycine Receptor (All subtypes) N/A Subunit-specific Inhibition - - < 1x10-6 4
⤷ Conc range: < 1x10-6 M α2 > α1, α1β [4]
CatSper2 Ligand is endogenous in the given species Hs Activator Full agonist 8.1 pEC50 - 2,6
⤷ pEC50 8.1 (EC50 7.7x10-9 M) [2,6]
Voltage: -60.0 mV
Description: Patch clamp electrophysiology, kinetic rapid mixing fluorometry; 2-3 µM shows the saturating efficacy.
CatSper3 Ligand is endogenous in the given species Hs Activator Full agonist 8.1 pEC50 - 2,6
⤷ pEC50 8.1 (EC50 7.7x10-9 M) [2,6]
Voltage: -60.0 mV
Description: Patch clamp electrophysiology, kinetic rapid mixing fluorometry, 2-3µM shows the saturating efficacy.
CatSper4 Ligand is endogenous in the given species Hs Activator Full agonist 8.1 pEC50 - 2,6
⤷ pEC50 8.1 (EC50 7.7x10-9 M) [2,6]
Voltage: -60.0 mV
Description: Patch clamp electrophysiology, kinetic rapid mixing fluorometry, 2-3µM shows the saturating efficacy.
CatSper1 Ligand is endogenous in the given species Hs Activator Full agonist 8.0 – 8.1 pEC50 - 2,6
⤷ pEC50 8.0 – 8.1 (EC50 1x10-8 – 7.7x10-9 M) [2,6]
Voltage: -60.0 mV
Description: Patch clamp electrophysiology, kinetic rapid mixing fluorometry, 2-3 µM shows the saturating efficacy.
TRPC5 Hs Channel blocker Inhibition 5.3 pIC50 - 3
⤷ pIC50 5.3 [3]
Selectivity at nuclear hormone receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Progesterone receptor Primary target of this compound Hs Agonist Agonist 8.5 pKi - 7
⤷ pKi 8.5 (Ki 3.5x10-9 M) Affinity at human PR-A [7]
Progesterone receptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Agonist 8.8 pEC50 - 1
⤷ pEC50 8.8 (EC50 1.5x10-9 M) [1]
Mineralocorticoid receptor Ligand is endogenous in the given species Hs Antagonist Antagonist 11.0 pIC50 - 5
⤷ pIC50 11.0 [5]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Rank order of potency at Progesterone receptor progesterone
Rank order of potency at Mineralocorticoid receptor corticosterone, cortisol, aldosterone, progesterone 5
Targets where the ligand is described in the comment field
Target Comment
CYP21A2 Converts progesterone and 17α-hydroxyprogesterone to deoxycortisone and 11-deoxycortisol, respectively
CYP17A1 Converts pregnenolone and progesterone to 17α-hydroxypregnenolone and 17α-hydroxyprogesterone, respectively. Converts 17α-hydroxypregnenolone and 17α-hydroxyprogesterone to dehydroepiandrosterone and androstenedione, respectively. Converts corticosterone to cortisol.
Ligand mentioned in the following text fields
3C. 3-Ketosteroid receptors overview
Steroid hormone receptors overview