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Structure Database (LMSD)

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Common Name

Cortisone

Systematic Name

17α,21-dihydroxypregn-4-ene-3,11,20-trione

Synonyms

LM ID

LMST02030090

Formula

C₂₁H₂₈O₅

Exact Mass

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360.193675

Sum Composition

ST 21:4;O5

Status

Curated

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Classification

Biological Context

Cortisone is a glucocorticoid receptor-inert precursor and metabolite of the glucocorticoid cortisol (hydrocortisone).^1,2 Cortisone is converted to glucocorticoid receptor-active cortisol by 11β-hydroxysteroid dehydrogenase (11β-HSD1) and is regenerated by metabolism of cortisol by 11β-HSD2 in vivo.

This information has been provided by Cayman Chemical

References

1. Dammann, C., Stapelfeld, C., and Maser, E. Expression and activity of the cortisol-activating enzyme 11β-hydroxysteroid dehydrogenase type 1 is tissue and species-specific. Chem. Biol. Interact. 303, 57-61 (2019).

2. Viglietti, A.I.P., Giambartolomei, G.H., and Delpino, M.V. Endocrine modulation of Brucella abortus-infected osteocytes function and osteoclastogenesis via modulation of RANKL/OPG. Microbes Infect. 21(7), 287-295 (2019).

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String Representations

InChiKey (Click to copy)

MFYSYFVPBJMHGN-ZPOLXVRWSA-N

InChi (Click to copy)

InChI=1S/C21H28O5/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/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1

SMILES (Click to copy)

[C@@]12([H])CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@]1([H])[C@@]3(C)CCC(=O)C=C3CC[C@@]21[H]