Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:45 UTC
HMDB IDHMDB01547
Secondary Accession NumbersNone
Metabolite Identification
Common NameCorticosterone
DescriptionCorticosterone is 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).
Structure
Thumb
Synonyms
  1. 11,21-Dihydroxypregn-4-ene-3,20-dione
  2. 11,21-Dihydroxyprogesterone
  3. 11-Hydroxycorticoaldosterone
  4. 17-Deoxycortisol
  5. 4-Pregnene-11 Corticosteron
  6. Corticosterone
  7. Kendall'S compound B
  8. Reichstein'S substance H
Chemical FormulaC21H30O4
Average Molecular Weight346.4605
Monoisotopic Molecular Weight346.214409448
IUPAC Name(1S,2R,10S,11S,14S,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional IUPAC Namecorticosterone
CAS Registry Number50-22-6
SMILES
[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
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
InChI KeyOMFXVFTZEKFJBZ-HJTSIMOOSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassGluco/mineralocorticoids, Progestogins and Derivatives
Other Descriptors
  • 11beta-hydroxy steroid(ChEBI)
  • 20-oxo steroid(ChEBI)
  • 21-hydroxy steroid(ChEBI)
  • 3-oxo steroid(ChEBI)
  • Aliphatic Homopolycyclic Compounds
  • C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives(KEGG)
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives(Lipidmaps)
  • C21-steroid(ChEBI)
  • Mineralocorticoids(KEGG)
  • Pregnane and derivatives [Fig](KEGG)
  • glucocorticoid(ChEBI)
Substituents
  • 11 Hydroxy Steroid
  • 20 Keto Steroid
  • 3 Keto Steroid
  • Alpha Ketoaldehyde
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Ketone
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentGluco/mineralocorticoids, Progestogins and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of C21-Steroid hormone metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point179 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.199 mg/mLNot Available
LogP1.94HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility0.046 g/LALOGPS
logP2.09ALOGPS
logP2.02ChemAxon
logS-3.9ALOGPS
pKa (strongest acidic)13.86ChemAxon
pKa (strongest basic)-0.26ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area74.6ChemAxon
rotatable bond count2ChemAxon
refractivity96ChemAxon
polarizability38.67ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Brain
  • Epidermis
  • Fibroblasts
  • Gonads
  • Hypothalamus
  • Intestine
  • Kidney
  • Liver
  • Nerve Cells
  • Neuron
  • Placenta
  • Platelet
  • Spleen
  • Stratum Corneum
  • Testes
Pathways
NameSMPDB LinkKEGG Link
SteroidogenesisSMP00130map00140
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.027 +/- 0.005 uMAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.023 +/- 0.0034 uMAdult (>18 years old)BothDepersonalization syndrome
Associated Disorders and Diseases
Disease References
Depersonalization disorder
  • Nuller YL, Morozova MG, Kushnir ON, Hamper N: Effect of naloxone therapy on depersonalization: a pilot study. J Psychopharmacol. 2001 Jun;15(2):93-5. Pubmed: 11448093
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022684
KNApSAcK IDNot Available
Chemspider ID5550
KEGG Compound IDC02140
BioCyc IDNot Available
BiGG ID39187
Wikipedia LinkCorticosterone
NuGOwiki LinkHMDB01547
Metagene LinkHMDB01547
METLIN ID6314
PubChem Compound5753
PDB IDC0R
ChEBI ID16827
References
Synthesis ReferenceOliveto, Eugene P.; Smith, Herbert Q.; Gerold, Corinne; Rausser, Richard; Hershberg, E. B. 11-Oxygenated steroids. XIV. New syntheses of corticosterone. Journal of the American Chemical Society (1956), 78 1414-16.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Oprica M, Zhu S, Goiny M, Pham TM, Mohammed AH, Winblad B, Bartfai T, Schultzberg M: Transgenic overexpression of interleukin-1 receptor antagonist in the CNS influences behaviour, serum corticosterone and brain monoamines. Brain Behav Immun. 2005 May;19(3):223-34. Pubmed: 15797311
  2. Hajdasz P: [Mineralocorticoids in cervical mucous and female blood serum: levels in the preovulatory phase of the menstrual cycle] Ginekol Pol. 2000 Sep;71(9):1007-10. Pubmed: 11082965
  3. Ghulam A, Kouach M, Racadot A, Boersma A, Vantyghem MC, Briand G: Quantitative analysis of human serum corticosterone by high-performance liquid chromatography coupled to electrospray ionization mass spectrometry. J Chromatogr B Biomed Sci Appl. 1999 Apr 30;727(1-2):227-33. Pubmed: 10360442
  4. Pravosudov VV, Omanska A: Prolonged moderate elevation of corticosterone does not affect hippocampal anatomy or cell proliferation rates in mountain chickadees (Poecile gambeli). J Neurobiol. 2005 Jan;62(1):82-91. Pubmed: 15389682
  5. Pardridge WM, Sakiyama R, Judd HL: Protein-bound corticosteroid in human serum is selectively transported into rat brain and liver in vivo. J Clin Endocrinol Metab. 1983 Jul;57(1):160-5. Pubmed: 6853674
  6. Kahri AI, Voutilainen R, Salmenpera M: Different biological action of corticosteroids, corticosterone and cortisol, as a base of zonal function of adrenal cortex. Acta Endocrinol (Copenh). 1979 Jun;91(2):329-37. Pubmed: 223358
  7. Pruett SB, Fan R, Myers LP, Wu WJ, Collier S: Quantitative analysis of the neuroendocrine-immune axis: linear modeling of the effects of exogenous corticosterone and restraint stress on lymphocyte subpopulations in the spleen and thymus in female B6C3F1 mice. Brain Behav Immun. 2000 Dec;14(4):270-87. Pubmed: 11120596
  8. Evans SB, Wilkinson CW, Bentson K, Gronbeck P, Zavosh A, Figlewicz DP: PVN activation is suppressed by repeated hypoglycemia but not antecedent corticosterone in the rat. Am J Physiol Regul Integr Comp Physiol. 2001 Nov;281(5):R1426-36. Pubmed: 11641112
  9. Lescoat G, Feliot J, Maniey J: [Evolution of plasma corticosterone concentration in basal conditions or after psychic aggression during growth in the Rat. Influence of neonatal gonadectomy (author's transl)] J Physiol (Paris). 1978 Dec;74(6):591-9. Pubmed: 570600
  10. Slominski A, Zbytek B, Semak I, Sweatman T, Wortsman J: CRH stimulates POMC activity and corticosterone production in dermal fibroblasts. J Neuroimmunol. 2005 May;162(1-2):97-102. Pubmed: 15833364
  11. Kero J, Poutanen M, Zhang FP, Rahman N, McNicol AM, Nilson JH, Keri RA, Huhtaniemi IT: Elevated luteinizing hormone induces expression of its receptor and promotes steroidogenesis in the adrenal cortex. J Clin Invest. 2000 Mar;105(5):633-41. Pubmed: 10712435

Enzymes

Gene Name:
CYP11B1
Uniprot ID:
P15538
Reactions
Deoxycorticosterone + Reduced ferredoxin + Oxygen unknown Corticosterone + Oxidized ferredoxin + Waterdetails
Gene Name:
AKR1D1
Uniprot ID:
P51857
Gene Name:
HSD11B1
Uniprot ID:
P28845
Reactions
Corticosterone + NADP unknown 11-Dehydrocorticosterone + NADPH + Hydrogen Iondetails
Gene Name:
NR3C2
Uniprot ID:
P08235
Gene Name:
CYP11B2
Uniprot ID:
P19099
Reactions
Corticosterone + reduced adrenal ferredoxin + Oxygen unknown 18-Hydroxycorticosterone + oxidized adrenal ferredoxin + Waterdetails
Corticosterone + Reduced adrenal ferredoxin + Oxygen unknown 18-Hydroxycorticosterone + Oxidized adrenal ferredoxin + Waterdetails
Deoxycorticosterone + Reduced ferredoxin + Oxygen unknown Corticosterone + Oxidized ferredoxin + Waterdetails
Gene Name:
P450-CYP21B
Uniprot ID:
Q16874
Gene Name:
DEFA4
Uniprot ID:
P12838
Gene Name:
CYP21A2
Uniprot ID:
P08686
Reactions
11b-Hydroxyprogesterone + Reduced acceptor + Oxygen unknown Corticosterone + Acceptor + Waterdetails