cortisol   Click here for help

GtoPdb Ligand ID: 2868

Synonyms: Acticort® | Plenadren®
Approved drug PDB Ligand Immunopharmacology Ligand
cortisol is an approved drug (FDA (1953, prior history unavailable), EMA (2011))
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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2D Structure
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Physico-chemical Properties
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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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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 or derivative
Approved drug? Yes (FDA (1953, prior history unavailable), EMA (2011))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
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® | 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
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
Search UniChem for chemical match using the InChIKey JYGXADMDTFJGBT-VWUMJDOOSA-N
Search UniChem for chemicals with the same backbone JYGXADMDTFJGBT
SynPHARM 6573 (in complex with Glucocorticoid receptor)
Wikipedia Cortisol

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Tocris
Hydrocortisone
Cat. No. 4093