Structure Database (LMSD)

Common Name
Cortisol
Systematic Name
11β,17,21-trihydroxypregn-4-ene-3,20-dione
Synonyms
  • Cortisol
LM ID
LMST02030001
Formula
Exact Mass
Calculate m/z
362.209325
Sum Composition
Status
Curated




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).
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).

Reactions

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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]

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
SST0244
PubChem CID
SwissLipids ID
Cayman ID
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 26
Rings 4
Aromatic Rings 0
Rotatable Bonds 2
Van der Waals Molecular Volume 358.45
Topological Polar Surface Area 94.83
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 5
logP 2.64
Molar Refractivity 96.66

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Updated at
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