Showing Metabocard for cortisone (BASm0000796)

Common NameCortisone
DescriptionCortisone is a naturally occurring glucocorticoid. It has been used in replacement therapy for adrenal insufficiency and as an anti-inflammatory agent. Cortisone itself is inactive. It is converted in the liver into the active metabolite cortisol. Cortisone is a corticosteroid hormone released by the adrenal gland in response to stress. One of cortisone's effects on the body, and a potentially harmful side effect when administered clinically, is the suppression of the immune system. This is an explanation for the apparent correlation between high stress and sickness.
Structure
Molecular FormulaC21H28O5
Average Mass360.44400
Monoisotopic Mass360.19367
IUPAC Name(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,17-dione
Traditional NameCortisone
CAS Registry Number1953-06-05
SMILESC[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO
InChI IdentifierInChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1
InChI KeyMFYSYFVPBJMHGN-ZPOLXVRWSA-N
CHEBI IDCHEBI:16962
HMDB IDHMDB0002802
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 Solubility1.36e-01 g/l
logP1.98
logS-3.42
pKa (Strongest Acidic)12.58
pKa (Strongest Basic)-3.33
Hydrogen Acceptor Count5
Hydrogen Donor Count2
Polar Surface Area91.67 Ų
Rotatable Bond Count2
Physiological Charge0
Formal Charge0
Refractivity96.47 m³·mol⁻¹
Polarizability38.78

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