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Structure Database (LMSD)

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Common Name

Cortisol

Systematic Name

11β,17,21-trihydroxypregn-4-ene-3,20-dione

Synonyms

Cortisol

LM ID

LMST02030001

Formula

C₂₁H₃₀O₅

Exact Mass

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362.209325

Sum Composition

ST 21:3;O5

Status

Curated

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Classification

Biological Context

Cortisol, known as hydrocortisone when used as a therapeutic, is a glucocorticoid produced by the adrenal cortex in response to adrenocorticotropic hormone (ACTH).^1,2 It is an agonist at the mineralocorticoid receptor (MR) and the glucocorticoid receptor, with an approximately 6- to 10-fold greater affinity for MR. Cortisol production is increased during periods of stress, and it is a major effector molecule in the hypothalamic-pituitary-adrenal axis (HPA) stress response.² Cortisol levels increase with age and are often elevated in major depressive disorder, certain forms of hypertension, and Parkinson’s disease.^3,4,5

This information has been provided by Cayman Chemical

References

1. Quinkler, M., and Stewart, P.M. Hypertension and the cortisol-cortisone shuttle. J. Clin. Endocrinol. Metab. 88(6), 2384-2392 (2003).

2. Krieger, D.T. Rhythms of ACTH and corticosteroid secretion in health and disease, and their experimental modification. J. Steroid Biochem. 6(5), 785-791 (1975).

3. Varghese, F.P., and Brown, E.S. The hypothalamic-pituitary-adrenal axis in major depressive disorder: A brief primer for primary care physicians. Prim. Care Companion J. Clin. Psychiatry 3(4), 151-155 (2001).

4. Dunlop, B.W., and Wong, A. The hypothalamic-pituitary-adrenal axis in PTSD: Pathophysiology and treatment interventions. Prog. Neuropsychopharmacol. Biol. Psychiatry 89, 361-379 (2019).

5. Soares, N.M., Pereira, G.M., Altmann, V., et al. Cortisol levels, motor, cognitive and behavioral symptoms in Parkinson’s disease: A systematic review. J. Neural Transm. (Vienna) (2018).

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String Representations

InChiKey (Click to copy)

JYGXADMDTFJGBT-VWUMJDOOSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

[C@]12(CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])[C@@H](O)C[C@]1(C)[C@](C(=O)CO)(O)CC[C@@]21[H])[H]