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Showing metabocard for Corticosterone (HMDB0001547)

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enzymes (10) Show 10 proteins
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:29 UTC
HMDB IDHMDB0001547
Secondary Accession Numbers
  • HMDB01547
Metabolite Identification
Common NameCorticosterone
DescriptionCorticosterone, also known as 17-deoxycortisol, belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Thus, corticosterone is considered to be a steroid lipid molecule. Corticosterone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Corticosterone is a potentially toxic compound.
Structure
Data?1582752209
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(11beta)-11,21-Dihydroxypregn-4-ene-3,20-dioneChEBI
11beta,21-Dihydroxy-4-pregnene-3,20-dioneChEBI
11beta,21-DihydroxyprogesteroneChEBI
17-DeoxycortisolChEBI
Kendall's compound bChEBI
Reichstein's substance HChEBI
(11b)-11,21-Dihydroxypregn-4-ene-3,20-dioneGenerator
(11Β)-11,21-dihydroxypregn-4-ene-3,20-dioneGenerator
11b,21-Dihydroxy-4-pregnene-3,20-dioneGenerator
11Β,21-dihydroxy-4-pregnene-3,20-dioneGenerator
11b,21-DihydroxyprogesteroneGenerator
11Β,21-dihydroxyprogesteroneGenerator
11,21-Dihydroxypregn-4-ene-3,20-dioneHMDB
11,21-DihydroxyprogesteroneHMDB
11-HydroxycorticoaldosteroneHMDB
4-Pregnene-11 corticosteronHMDB
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 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
CAS Registry Number50-22-6
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])[C@@]([H])(O)C[C@]12C)C(=O)CO
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
Description belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 21-hydroxysteroid
  • Pregnane-skeleton
  • 20-oxosteroid
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Primary alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point179 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.2 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 Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96 m³·mol⁻¹ChemAxon
Polarizability38.83 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 2 TMS)splash10-0f9l-4920000000-13c56138ef34befd6786Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 2 TMS)splash10-0f7c-4921100000-1d2ace868fd94080c88eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-1798000000-b39fe3c8aaf8f09d7cdeSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f9l-4920000000-13c56138ef34befd6786Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f7c-4921100000-1d2ace868fd94080c88eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1968000000-377b49ad20a23591ce73Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-2640900000-6a05b10a0e80ea76b38aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0009000000-81d0a5e41401c962645eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05fs-2910000000-7a585bd042169de23cfeSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0597-6900000000-4c9bb40342921d7ff55eSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-014i-1798000000-e8ef26b439701fc96537Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-0759000000-8c04fadb6bd7d3e86c28Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05gi-3920000000-db0dc9413f5ca5cb69e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0009000000-362accabc0136898e549Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0459000000-e31660ef75e29d9d9d78Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00fr-0941000000-1453953f7526fa9b8de6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00e9-0920000000-da03f39d4590a6248157Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00gi-0900000000-2ec9e62e392a282f6de4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0009000000-1db6d72ffc02b6efa63dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00ba-1964000000-d35661aaf929a1609854Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00dj-2920000000-b29d21507e63bc379164Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05fv-3900000000-8cd56447e4fa2da8c30bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0596-4900000000-0fdf5a6f27425f6540baSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052f-6900000000-d6cd49302b0991f7a681Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00mo-9800000000-fcf363e8a5a69914ad88Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00mp-9600000000-493d479336ae32a15124Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0029000000-7c715165a4b71930bea5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02dj-0349000000-ccef7282ed548096a4d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06dj-4391000000-c5bd1940f400fd8a11f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-e0a478591970f0721633Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00mk-2049000000-d03aea1301697772cf2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abi-3092000000-80dac4c435cb4f3567a6Spectrum
MSMass Spectrum (Electron Ionization)splash10-014i-8953000000-cdd7d53a6012a6eb3f28Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
Tissue Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Brain
  • Epidermis
  • Fibroblasts
  • Gonads
  • Hypothalamus
  • Intestine
  • Kidney
  • Liver
  • Nerve Cells
  • Neuron
  • Placenta
  • Platelet
  • Spleen
  • Stratum Corneum
  • Testes
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.027 +/- 0.005 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.023 +/- 0.0034 uMAdult (>18 years old)BothDepersonalization syndrome details
Associated Disorders and Diseases
Disease References
Depersonalization disorder
  1. 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 IDDB04652
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022684
KNApSAcK IDNot Available
Chemspider ID5550
KEGG Compound IDC02140
BioCyc IDCORTICOSTERONE
BiGG ID39187
Wikipedia LinkCorticosterone
METLIN ID6314
PubChem Compound5753
PDB IDNot Available
ChEBI ID16827
Food Biomarker OntologyNot Available
VMH IDCRTSTRN
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)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 ]
  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

Enzyme Details
1. Cytochrome P450 11B1, mitochondrial
General function:
Involved in monooxygenase activity
Specific function:
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:
CYP11B1
Uniprot ID:
P15538
Molecular weight:
57572.44
Reactions
Deoxycorticosterone + Reduced ferredoxin + Oxygen → Corticosterone + Oxidized ferredoxin + Waterdetails
Enzyme Details
2. 3-oxo-5-beta-steroid 4-dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38
Enzyme Details
3. Corticosteroid 11-beta-dehydrogenase isozyme 2
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of cortisol to the inactive metabolite cortisone. Modulates intracellular glucocorticoid levels, thus protecting the nonselective mineralocorticoid receptor from occupation by glucocorticoids.
Gene Name:
HSD11B2
Uniprot ID:
P80365
Molecular weight:
44126.06
Enzyme Details
4. Corticosteroid 11-beta-dehydrogenase isozyme 1
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the reaction runs only in one direction, from 7-ketocholesterol to 7-beta-hydroxycholesterol (By similarity).
Gene Name:
HSD11B1
Uniprot ID:
P28845
Molecular weight:
32400.665
Reactions
Corticosterone + NADP → 11-Dehydrocorticosterone + NADPH + Hydrogen Iondetails
Enzyme Details
5. Mineralocorticoid receptor
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates target genes. The effect of MC is to increase ion and water transport and thus raise extracellular fluid volume and blood pressure and lower potassium levels
Gene Name:
NR3C2
Uniprot ID:
P08235
Molecular weight:
107066.6
Enzyme Details
6. Cytochrome P450 11B2, mitochondrial
General function:
Involved in monooxygenase activity
Specific function:
Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
Gene Name:
CYP11B2
Uniprot ID:
P19099
Molecular weight:
57559.62
Reactions
Corticosterone + reduced adrenal ferredoxin + Oxygen → 18-Hydroxycorticosterone + oxidized adrenal ferredoxin + Waterdetails
Corticosterone + Reduced adrenal ferredoxin + Oxygen → 18-Hydroxycorticosterone + Oxidized adrenal ferredoxin + Waterdetails
Deoxycorticosterone + Reduced ferredoxin + Oxygen → Corticosterone + Oxidized ferredoxin + Waterdetails
Enzyme Details
7. Cytochrome P450 21-hydroxylase
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
P450-CYP21B
Uniprot ID:
Q16874
Molecular weight:
56000.9
Enzyme Details
8. Cytochrome P450, family 21, subfamily A, polypeptide 2
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP21A2
Uniprot ID:
Q08AG9
Molecular weight:
55972.9
Enzyme Details
9. Neutrophil defensin 4
General function:
Involved in defense response
Specific function:
Has antimicrobial activity against Gram-negative bacteria, and to a lesser extent also against Gram-positive bacteria and fungi. Protects blood cells against infection with HIV-1 (in vitro). Inhibits corticotropin (ACTH)-stimulated corticosterone production
Gene Name:
DEFA4
Uniprot ID:
P12838
Molecular weight:
10504.0
Enzyme Details
10. Steroid 21-hydroxylase
General function:
Not Available
Specific function:
Specifically catalyzes the 21-hydroxylation of steroids. Required for the adrenal synthesis of mineralocorticoids and glucocorticoids.
Gene Name:
CYP21A2
Uniprot ID:
P08686
Molecular weight:
56000.94
Reactions
11b-Hydroxyprogesterone + Reduced acceptor + Oxygen → Corticosterone + Acceptor + Waterdetails