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Human Metabolome Database Version 3.5

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Showing metabocard for Corticosterone (HMDB01547)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:45 -0700
HMDB ID HMDB01547
Secondary Accession Numbers None
Metabolite Identification
Common Name Corticosterone
Description Corticosterone 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C21H30O4
Average Molecular Weight 346.4605
Monoisotopic Molecular Weight 346.214409448
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 Name corticosterone
CAS Registry Number 50-22-6
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 Key OMFXVFTZEKFJBZ-HJTSIMOOSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Gluco/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 Parent Gluco/mineralocorticoids, Progestogins and Derivatives
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point 179 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.199 mg/mL Not Available
LogP 1.94 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.046 g/L ALOGPS
LogP 2.09 ALOGPS
LogP 2.02 ChemAxon
LogS -3.88 ALOGPS
pKa (strongest acidic) 13.86 ChemAxon
pKa (strongest basic) -0.26 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 74.6 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 96 ChemAxon
Polarizability 38.67 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI M-80)
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
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
Name SMPDB Link KEGG Link
Steroidogenesis SMP00130 map00140 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.027 +/- 0.005 uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.023 +/- 0.0034 uM Adult (>18 years old) Both Depersonalization syndrome Not Available
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 Link_out
    Associated OMIM IDs None
    DrugBank ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB022684
    KNApSAcK ID Not Available
    Chemspider ID 5550 Link_out
    KEGG Compound ID C02140 Link_out
    BioCyc ID Not Available
    BiGG ID 39187 Link_out
    Wikipedia Link Corticosterone Link_out
    NuGOwiki Link HMDB01547 Link_out
    Metagene Link HMDB01547 Link_out
    METLIN ID 6314 Link_out
    PubChem Compound 5753 Link_out
    PDB ID C0R Link_out
    ChEBI ID 16827 Link_out
    References
    Synthesis Reference Oliveto, 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) Download (PDF)
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    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 Link_out
    Enzymes
    Name: Cytochrome P450 11B1, mitochondrial
    Reactions:
    • a steroid + reduced adrenal ferredoxin + O2 = an 11beta-hydroxysteroid + oxidized adrenal ferredoxin + H2O [RN:R02726]
    Gene Name: CYP11B1
    Uniprot ID: P15538 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: 3-oxo-5-beta-steroid 4-dehydrogenase
    Reactions:
    • (1) 5beta-cholestan-3-one + NADP+ = cholest-4-en-3-one + NADPH + H+ [RN:R02609]
    • (2) 17,21-dihydroxy-5beta-pregnane-3,11,20-trione + NADP+ = cortisone + NADPH + H+ [RN:R02893]
    Gene Name: AKR1D1
    Uniprot ID: P51857 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Corticosteroid 11-beta-dehydrogenase isozyme 2
    Reactions:
    • --- []
    Gene Name: HSD11B2
    Uniprot ID: P80365 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Corticosteroid 11-beta-dehydrogenase isozyme 1
    Reactions:
    • an 11beta-hydroxysteroid + NADP+ = an 11-oxosteroid + NADPH + H+ [RN:R03203]
    Gene Name: HSD11B1
    Uniprot ID: P28845 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Mineralocorticoid receptor
    Reactions:
      Gene Name: NR3C2
      Uniprot ID: P08235 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cytochrome P450 21-hydroxylase
      Reactions:
        Gene Name: P450-CYP21B
        Uniprot ID: Q16874 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Cytochrome P450, family 21, subfamily A, polypeptide 2
        Reactions:
          Gene Name: CYP21A2
          Uniprot ID: Q08AG9 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Neutrophil defensin 4
          Reactions:
            Gene Name: DEFA4
            Uniprot ID: P12838 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA