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Record Information
Version3.6
Creation Date2006-08-13 09:21:39 UTC
Update Date2016-02-11 01:06:32 UTC
HMDB IDHMDB04029
Secondary Accession NumbersNone
Metabolite Identification
Common Name11-Dehydrocorticosterone
Description11-Dehydrocorticosterone is a mineral corticosteroid. The conversion of inactive 11-ketoglucocorticoids such as 11-dehydrocorticosterone) into active 11b-hydroxyglucocorticoids (such as corticosterone) is catalyzed by 11beta-hydroxysteroid dehydrogenase (11b-HSD1, EC 1.1.1.146), which is expressed in many tissues and plays an important role in metabolically relevant tissues such as the liver, adipose tissue, skeletal muscles and possibly kidney. Chronically elevated local glucocorticoid action as a result of increased 11beta-HSD1 activity rather than elevated systemic glucocorticoid levels has been associated with metabolic syndrome, which is characterized by obesity, insulin resistance, type 2 diabetes and cardiovascular complications. Recent studies indicate that compounds inhibiting 11beta-HSD1 activity ameliorate the adverse effects of excessive glucocorticoid concentrations on metabolic processes, providing promising opportunities for the development of therapeutic interventions. 11-dehydrocorticosterone and corticosterone display antinatriuretic activity, although 11-dehydrocorticosterone is generally a more potent sodium retainer than corticosterone. (PMID: 17584152 , Endocr Metab Immune Disord Drug Targets. 2007 Jun;7(2):125-40.).
Structure
Thumb
Synonyms
ValueSource
11-dehydro-CorticosteroneHMDB
11-DehydrocorticosteronHMDB
11-oxo-11-DeoxycorticosteroneHMDB
11-OxocorticosteroneHMDB
17-(1-keto-2-Hydroxyethyl)-D4-androsten-3,11-dioneHMDB
17-DeoxycortisoneHMDB
21-Hydroxypregn-4-ene-3,11,20-trioneHMDB
21-Hydroxypregn-4-ene-3,11-20-trioneHMDB
4-Pregnen-21-ol-3,11,20-trioneHMDB
D4-Pregnen-21-ol-3,11,20-trioneHMDB
D4-Pregnene-21-ol-3,11,20-trioneHMDB
DehydrocorticosteroneHMDB
DehydrocortocicosteroneHMDB
Kendall'S compound aHMDB
Chemical FormulaC21H28O4
Average Molecular Weight344.4446
Monoisotopic Molecular Weight344.198759384
IUPAC Name(1S,2R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,17-dione
Traditional Name11-dehydrocorticosterone
CAS Registry Number72-23-1
SMILES
[H][C@@]12CCC(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C21H28O4/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/h9,14-16,19,22H,3-8,10-11H2,1-2H3/t14-,15-,16?,19+,20-,21-/m0/s1
InChI KeyInChIKey=FUFLCEKSBBHCMO-IWBQTIMDSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • Pregnane-skeleton
  • 20-oxosteroid
  • Oxosteroid
  • 11-oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclohexanone
  • Alpha-hydroxy ketone
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030192 )
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point183.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.048 mg/mLALOGPS
logP2.44ALOGPS
logP2.41ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.44 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity95.07 m3·mol-1ChemAxon
Polarizability37.88 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • Adipose Tissue
  • Kidney
  • Liver
  • Placenta
Pathways
NameSMPDB LinkKEGG Link
11-beta-hydroxylase deficiency (CYP11B1)SMP00575Not Available
17-alpha-hydroxylase deficiency (CYP17)SMP00566Not Available
21-hydroxylase deficiency (CYP21)SMP00576Not Available
3-Beta-Hydroxysteroid Dehydrogenase DeficiencySMP00718Not Available
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase DeficiencySMP00373Not Available
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase DeficiencySMP00372Not Available
Apparent mineralocorticoid excess syndromeSMP00717Not Available
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAHSMP00371Not Available
Corticosterone methyl oxidase I deficiency (CMO I)SMP00577Not Available
Corticosterone methyl oxidase II deficiency - CMO IISMP00578Not Available
SteroidogenesisSMP00130map00140
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0278 +/- 0.0060 uMElderly (>65 years old)Male
Kidney cancer
details
BloodDetected and Quantified0.0142 +/- 0.0039 uMElderly (>65 years old)Male
Kidney Cancer
details
BloodDetected and Quantified0.0336 +/- 0.0054 uMElderly (>65 years old)Female
Kidney Cancer
details
BloodDetected and Quantified0.0204 +/- 0.0034 uMElderly (>65 years old)Female
Kidney Cancer
details
Associated Disorders and Diseases
Disease References
Kidney cancer
  1. Tortorella C, Aragona F, Nussdorfer GG: In vivo evidence that human adrenal glands possess 11 beta-hydroxysteroid dehydrogenase activity. Life Sci. 1999;65(26):2823-7. [10622271 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023282
KNApSAcK IDNot Available
Chemspider ID24850107
KEGG Compound IDC05490
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB04029
Metagene LinkHMDB04029
METLIN ID7003
PubChem Compound13783449
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNikiforova, O. K.; Suvorov, N. N. Steroids. IV. Synthesis of 11-dehydrocorticosterone from 11-oxopregesterone. Zhurnal Obshchei Khimii (1959), 29 2428-31.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ronquist-Nii Y, Edlund PO: Determination of corticosteroids in tissue samples by liquid chromatography-tandem mass spectrometry. J Pharm Biomed Anal. 2005 Feb 23;37(2):341-50. [15708676 ]
  2. Walker BR, Rodin A, Taylor NF, Clayton RN: Endogenous inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 do not explain abnormal cortisol metabolism in polycystic ovary syndrome. Clin Endocrinol (Oxf). 2000 Jan;52(1):77-80. [10651756 ]
  3. Edwards CR, Benediktsson R, Lindsay RS, Seckl JR: 11 beta-Hydroxysteroid dehydrogenases: key enzymes in determining tissue-specific glucocorticoid effects. Steroids. 1996 Apr;61(4):263-9. [8733012 ]
  4. Livingstone DE, Jones GC, Smith K, Jamieson PM, Andrew R, Kenyon CJ, Walker BR: Understanding the role of glucocorticoids in obesity: tissue-specific alterations of corticosterone metabolism in obese Zucker rats. Endocrinology. 2000 Feb;141(2):560-3. [10650936 ]
  5. Atanasov AG, Odermatt A: Readjusting the glucocorticoid balance: an opportunity for modulators of 11beta-hydroxysteroid dehydrogenase type 1 activity? Endocr Metab Immune Disord Drug Targets. 2007 Jun;7(2):125-40. [17584152 ]

Enzymes

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
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
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