cortisol   Click here for help

GtoPdb Ligand ID: 2868

Synonyms: Acticort® | Efmody® | Plenadren®
Approved drug PDB Ligand Immunopharmacology Ligand
cortisol is an approved drug (FDA (1953, prior history unavailable), EMA (2011))
Compound class: Metabolite
Comment: Cortisol is an endogenous adrenal glucocorticoid with immunosuppressant action. Approved as hydrocortisone. Hydrocortisone is a glucocorticoid receptor agonist.
Marketed formulations may contain hydrocortisone acetate (PubChem CID 5744).
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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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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 5
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 94.83
Molecular weight 362.21
XLogP 0.55
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 OCC(=O)C1(O)CCC2C1(C)CC(O)C1C2CCC2=CC(=O)CCC12C
Isomeric SMILES OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
InChI InChI=1S/C21H30O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-16,18,22,24,26H,3-8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1
InChI Key JYGXADMDTFJGBT-VWUMJDOOSA-N
Classification Click here for help
Compound class Metabolite
Approved drug? Yes (FDA (1953, prior history unavailable), EMA (2011))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
International Nonproprietary Names Click here for help
INN number INN
38 hydrocortisone
Synonyms Click here for help
Acticort® | Efmody® | Plenadren®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9678963
Reactome Reaction Reactome logo R-HSA-9678925
Other databases
BindingDB Ligand 22476
BitterDB Ligand 129
CAS Registry No. 50-23-7 (source: Scifinder)
ChEBI CHEBI:17650
ChEMBL Ligand CHEMBL389621
DrugBank Ligand DB00741
DrugCentral Ligand 1388
GtoPdb PubChem SID 53801089
LIPID MAPS LMST02030001
PubChem CID 5754
RCSB PDB Ligand HCY
Search Google for chemical match using the InChIKey JYGXADMDTFJGBT-VWUMJDOOSA-N
Search Google for chemicals with the same backbone JYGXADMDTFJGBT
Search PubMed clinical trials hydrocortisone
Search PubMed titles hydrocortisone
Search PubMed titles/abstracts hydrocortisone
SynPHARM 6573 (in complex with Glucocorticoid receptor)
UniChem Compound Search for chemical match using the InChIKey JYGXADMDTFJGBT-VWUMJDOOSA-N
UniChem Connectivity Search for chemical match using the InChIKey JYGXADMDTFJGBT-VWUMJDOOSA-N
Wikipedia Cortisol

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Tocris
Hydrocortisone (links to external site)
Cat. No. 4093