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
Molecular FormulaC21H28O4
Average Mass344.44460
Monoisotopic Mass344.19876
IUPAC Name(1S,2R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,17-dione
Traditional Name11-dehydrocorticosterone
CAS Registry Number72-23-1
SMILESC[C@]12CC(=O)[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2C(=O)CO
InChI IdentifierInChI=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 KeyFUFLCEKSBBHCMO-IWBQTIMDSA-N
CHEBI IDCHEBI:78600
HMDB IDHMDB0004029
Pathways
NameSMPDB/PathBank
Steroidogenesis
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency
17-alpha-hydroxylase deficiency (CYP17)
11-beta-hydroxylase deficiency (CYP11B1)
21-hydroxylase deficiency (CYP21)
Corticosterone methyl oxidase I deficiency (CMO I)
Corticosterone methyl oxidase II deficiency - CMO II
Apparent mineralocorticoid excess syndrome
3-Beta-Hydroxysteroid Dehydrogenase Deficiency
StateNot Available
Water Solubility4.79e-02 g/l
logP2.44
logS-3.86
pKa (Strongest Acidic)13.86
pKa (Strongest Basic)-3.30
Hydrogen Acceptor Count4
Hydrogen Donor Count1
Polar Surface Area71.44 Ų
Rotatable Bond Count2
Physiological Charge0
Formal Charge0
Refractivity95.07 m³·mol⁻¹
Polarizability37.88

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