Corticosterone

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[http://crdd.osdd.net/raghava/hmrbase/test_extract.php?db=arun&table=nphormonet&id=1032&show=SHOW-3D Show 3-D Structure]
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{{Drugbox
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| IUPAC_name        = (8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
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| CAS_number        = 50-22-6
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| CAS_supplemental  =
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| ATC_suffix =
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| ATC_supplemental  =
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| PubChem          = 5753
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| ChemSpiderID      =
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| chemical_formula  =C<sub>21</sub>H<sub>30</sub>O<sub>4</sub>
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| molecular_weight  = 346.46
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| smiles            =CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4C(=O)CO)C)O
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| synonyms          = 17-Deoxycortisol
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| density          =
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| melting_point    = 181
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| boiling_point    =
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| solubility        = 199 mg/L at 25<sup>o</sup>C EXP
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| specific_rotation =
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| sec_combustion    =
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| bioavailability  =
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| protein_bound    =
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| metabolism        =
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| elimination_half-life =
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| excretion        =
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| pregnancy_category=
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| dependency_liability =
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| routes_of_administration =
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}}
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An adrenocortical steroid that has modest but significant activities as a mineralocorticoid and a glucocorticoid. (From Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p1437).Corticosterone is a 21 carbon [[steroid hormone]] of the [[corticosteroid]] type produced in the cortex of the [[adrenal gland]]s.
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==Physiochemical Properties==
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===Melting Point===
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181 deg C EXP
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===log P===
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1.94
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===Water Solubility====
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199 mg/L 25 EXP
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===Vapor Pressure===
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4.74E-12 mm Hg 25 EST
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===Henry's Law Constant===
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3.70E-10 atm-m3/mole 25 EST
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===Atmospheric OH Rate Constant===
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1.16E-10 cm3/molecule-sec 25 EST
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==Roles==
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In many species, including [[rodent]]s, corticosterone is the principal [[glucocorticoid]], involved in regulation of fuel [[metabolism]], [[immune]] reactions, and [[stress (medicine)|stress]] responses.
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<table align='right' border=1>
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However, in [[humans]], corticosterone is produced primarily in the [[zona fasciculata]] of the [[adrenal cortex]]. It has only weak [[glucocorticoid]] and [[mineralocorticoid]] potencies in humans and is important mainly as an intermediate in the [[steroidogenic pathway]] from [[pregnenolone]] to [[aldosterone]]. Corticosterone is converted to aldosterone by aldosterone synthase, found only in the mitochondria of glomerulosa cells.  Glomerulosa cells are found in the [[Zona glomerulosa]], which is the most superficial region of endocrine cells in the [[adrenal cortex]].
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<script>spin on;color atoms amino;</script>
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<uploadedFileContents>NPH132.SDF</uploadedFileContents>
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==Description==
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An adrenocortical steroid that has modest but significant activities  as a mineralocorticoid and a glucocorticoid. (From Goodman and  Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p1437)
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==General Properties==
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<b>*Molecular Weight</b>
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==Release or generation mechanisms==
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One example of a release pathway relates to [[UV-B]] stimulation on the skins of certain [[amphibian]]s such as the [[Rough-skinned Newt]], ''[[Taricha granulosa]]''; this trigger seems to cause the internal generation of corticosterone in that species.<ref>C.M. Hogan, 2008</ref>
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346.46
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==References==
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* C. Michael Hogan (2008) ''Rough-skinned Newt (Taricha granulosa)'', Globaltwitcher, ed. Nicklas Stromberg [http://www.globaltwitcher.com/artspec_information.asp?thingid=43182]
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* Etienne-Emile Baulieu and Paul A. Kelly (1990) ''Hormones: From Molecules to Disease'', Published by Springer Science & Business, 697 pages, ISBN 2705660305, 9782705660307
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<b>*Molecular Formula</b>
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[[Category:Corticosteroids]]
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[[Category:Hormones]]
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C<sub>2</sub><sub>1</sub>H<sub>3</sub><sub>0</sub>O<sub>4</sub>
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<b>*IUPAC NAME</b>
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(8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
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<b>*Canonical Smiles</b>
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CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4C(=O)CO)C)O
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<b>*Isomeric Smiles</b>
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C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@H]4C(=O)CO)C)O
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==PhysioChemical Properties==
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<b>*Melting Point</b>
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181(EXP)
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<b>*LogP</b>
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1.94(EXP)
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<b>*Water Solubility</b>
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199(EXP) at 25C
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==External Links==
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*[http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5753]Pubchem
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*[http://www.rcsb.org/pdb/cgi/explore.cgi?pdbId=1Y5R]]1Y5R,
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*[http://www.genome.jp/dbget-bin/www_bget?compound+C02140]]KEGG Compound
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*[http://www.hmdb.ca/metabolites/HMDB01547]Human Metabolome DataBase
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[[Categories:Hormones]]
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Current revision

Show 3-D Structure

Corticosterone
Systematic (IUPAC) name
(8S,9S,10R,11S,13S,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Identifiers
CAS number 50-22-6
ATC code  ?
PubChem 5753
Chemical data
Formula C21H30O4
Mol. mass 346.46
SMILES eMolecules & PubChem
Synonyms 17-Deoxycortisol
Physical data
Melt. point 181 °C
Solubility in water 199 mg/L at 25oC EXP mg/mL
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?

Legal status
Routes  ?

An adrenocortical steroid that has modest but significant activities as a mineralocorticoid and a glucocorticoid. (From Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p1437).Corticosterone is a 21 carbon steroid hormone of the corticosteroid type produced in the cortex of the adrenal glands.

Contents

[edit] Physiochemical Properties

[edit] Melting Point

181 deg C EXP

[edit] log P

1.94

[edit] Water Solubility=

199 mg/L 25 EXP

[edit] Vapor Pressure

4.74E-12 mm Hg 25 EST

[edit] Henry's Law Constant

3.70E-10 atm-m3/mole 25 EST

[edit] Atmospheric OH Rate Constant

1.16E-10 cm3/molecule-sec 25 EST

[edit] Roles

In many species, including rodents, corticosterone is the principal glucocorticoid, involved in regulation of fuel metabolism, immune reactions, and stress responses.

However, in humans, corticosterone is produced primarily in the zona fasciculata of the adrenal cortex. It has only weak glucocorticoid and mineralocorticoid potencies in humans and is important mainly as an intermediate in the steroidogenic pathway from pregnenolone to aldosterone. Corticosterone is converted to aldosterone by aldosterone synthase, found only in the mitochondria of glomerulosa cells. Glomerulosa cells are found in the Zona glomerulosa, which is the most superficial region of endocrine cells in the adrenal cortex.

[edit] Release or generation mechanisms

One example of a release pathway relates to UV-B stimulation on the skins of certain amphibians such as the Rough-skinned Newt, Taricha granulosa; this trigger seems to cause the internal generation of corticosterone in that species.<ref>C.M. Hogan, 2008</ref>

[edit] References

  • C. Michael Hogan (2008) Rough-skinned Newt (Taricha granulosa), Globaltwitcher, ed. Nicklas Stromberg [1]
  • Etienne-Emile Baulieu and Paul A. Kelly (1990) Hormones: From Molecules to Disease, Published by Springer Science & Business, 697 pages, ISBN 2705660305, 9782705660307
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