Structure Database (LMSD)

Common Name
corticosterone
Systematic Name
11β,21-dihydroxypregn-4-ene-3,20-dione
Synonyms
  • (11beta)-11,21-dihydroxypregn-4-ene-3,20-dione
  • 11beta,21-Dihydroxy-4-pregnene-3,20-dione
  • 11beta,21-dihydroxyprogesterone
  • 17-deoxycortisol
  • CORTICOSTERONE
  • Corticosterone
  • Kendall's compound B
  • Reichstein's substance H
  • corticosterone
LM ID
LMST02030186
Formula
C21H30O4
Exact Mass
Calculate m/z
346.21441
Sum Composition
ST 21:3;O4
Status
Curated
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Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroids [ST02]
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]

Biological Context

Corticosterone is a steroid hormone produced in the cortex of the adrenal glands that binds to both glucocorticoid and mineralocorticoid receptors.1 It is produced in response to ACTH (corticotropic hormone) and is the precursor to aldosterone synthesis.2 Since the production of glucocorticoids is increased by stress, it is often used as a biomarker of stress.3 Plasma corticosterone levels have a circadian variation and corticosterone may be important in the regulation of the sleep-wake cycle.4,5

This information has been provided by Cayman Chemical

References

1. Goymann, W., Möstl, E., and Gwinner, E. Corticosterone metabolites can be measured noninvasively in excreta of European stonechats (Saxicola torquata rubicola). Auk 119(4), 1167-1173 (2002).
2. Vázquez-Palacios, G., Retana-Márquez, S., Bonilla-Jaime, H., et al. Further definition of the effect of corticosterone on the sleep-wake pattern in the male rat. Pharmacol. Biochem. Behav. 70(2-3), 305-310 (2001).
3. Millspaugh, J.J., Washburn, B.E., Milanick, M.A., et al. Effects of heat and chemical treatments on fecal glucocorticoid measurements: Implications for sample transport. Wildl. Soc. Bull. 31(2), 399-406 (2003).
4. Palme, R., Rettenbacher, C., Touma, C., et al. Stress hormones in mammals and birds: Comparative aspects regarding metabolism, excretion, and noninvasive measurement in fecal samples. Ann. N. Y. Acad. Sci. 1040(21), 162-171 (2005).
5. Lu, N.Z., Wardell, S.E., Burnstein, K.L., et al. International Union of Pharmacology. LXV. The pharmacology and classification of the nuclear receptor superfamily: Glucocorticoid, mineralocorticoid, progesterone, and androgen receptors. Pharmacol. Rev. 58(4), 782-797 (2006).

Reactions

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String Representations

InChiKey (Click to copy)
OMFXVFTZEKFJBZ-HJTSIMOOSA-N
InChi (Click to copy)
InChI=1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19+,20-,21-/m0/s1
SMILES (Click to copy)
C1CC2[C@]([C@@]3([H])[C@@H](O)C[C@@]4(C)[C@@]([H])(CC[C@@]4(C(=O)CO)[H])[C@]13[H])(C)CCC(=O)C=2

Other Databases

Wikipedia
corticosterone
KEGG ID
C02140
HMDB ID
HMDB0001547
CHEBI ID
16827
PubChem CID
5753
SwissLipids ID
SLM:000485331
Cayman ID
16063
PDB ID
C0R
GuidePharm ID
2869

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 4
Aromatic Rings 0
Rotatable Bonds 2
Van der Waals Molecular Volume 349.66
Topological Polar Surface Area 74.60
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 3.24
Molar Refractivity 94.68

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Updated at
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