Cortisone (CHEM016643)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:39:15 UTC
Update Date2016-11-09 01:15:26 UTC
Accession NumberCHEM016643
Identification
Common NameCortisone
ClassSmall Molecule
DescriptionCortisonee, also known as cortisone or cortisone, 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, cortisonee is considered to be a steroid lipid molecule. Cortisonee exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Cortisonee participates in a number of enzymatic reactions, within cattle. In particular, Cortisonee can be biosynthesized from 17a,21-dihydroxy-5b-pregnane-3,11,20-trione; which is mediated by the enzyme 3-oxo-5-beta-steroid 4-dehydrogenase. In addition, Cortisonee, nadph, and hydrogen ion can be biosynthesized from cortisol and nadp through its interaction with the enzyme corticosteroid 11-beta-dehydrogenase isozyme 2. In cattle, cortisonee is involved in the metabolic pathway called the steroidogenesis pathway.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
11-Dehydro-17-hydroxycorticosteroneChEBI
17-Hydroxy-11-dehydrocorticosteroneChEBI
17alpha,21-Dihydroxy-4-pregnene-3,11,20-trioneChEBI
4-Pregnene-17alpha,21-diol-3,11,20-trioneChEBI
CortisonChEBI
Delta(4)-Pregnene-17alpha,21-diol-3,11,20-trioneChEBI
Kendall's compound eChEBI
KortisonChEBI
Pregn-4-en-17alpha,21-diol-3,11,20-trioneChEBI
Reichstein's substance faChEBI
Wintersteiner's compound FChEBI
17a,21-Dihydroxy-4-pregnene-3,11,20-trioneGenerator
17Α,21-dihydroxy-4-pregnene-3,11,20-trioneGenerator
4-Pregnene-17a,21-diol-3,11,20-trioneGenerator
4-Pregnene-17α,21-diol-3,11,20-trioneGenerator
delta(4)-Pregnene-17a,21-diol-3,11,20-trioneGenerator
Δ(4)-pregnene-17α,21-diol-3,11,20-trioneGenerator
Pregn-4-en-17a,21-diol-3,11,20-trioneGenerator
Pregn-4-en-17α,21-diol-3,11,20-trioneGenerator
Δ(4)-pregnene-17a,21-diol-3,11,20-trioneHMDB
AndresonHMDB
Anusol HCHMDB
Balneol-HCHMDB
beta-HCHMDB
ColocortHMDB
Compound eHMDB
CorlinHMDB
CortadrenHMDB
CortandrenHMDB
CortefHMDB
Cortef acetateHMDB
CortisalHMDB
CortisateHMDB
Cortisone acetateHMDB
CortistalHMDB
CortiviteHMDB
CortogenHMDB
CortoneHMDB
CortrilHMDB
DermacortHMDB
DricortHMDB
FlexicortHMDB
FlorinefHMDB
Fludrocortisone acetateHMDB
GlycortHMDB
Hemsol-HCHMDB
Hi-corHMDB
IncortinHMDB
Kendall'S compoundHMDB
LocoidHMDB
Locoid lipocreamHMDB
Micort-HCHMDB
Nogenic HCHMDB
Orabase hcaHMDB
PandelHMDB
Prestwick_132HMDB
Reichstein faHMDB
ScherosonHMDB
Solu-cortefHMDB
Stie-cortHMDB
TexacortHMDB
WestcortHMDB
AdresonHMDB
Cortone acetateHMDB
17-Hydroxy-3,11,20-trioxopregn-4-en-21-yl acetateHMDB
Chemical FormulaC21H28O5
Average Molecular Mass360.444 g/mol
Monoisotopic Mass360.194 g/mol
CAS Registry Number53-06-5
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 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
SMILES[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
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
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
  • 17-hydroxysteroid
  • Oxosteroid
  • 11-oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Tertiary alcohol
  • Cyclic ketone
  • Ketone
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP1.98ALOGPS
logP1.66ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)12.58ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96.47 m³·mol⁻¹ChemAxon
Polarizability38.95 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kf-2910000000-da435cee921dd7b9f8e6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kf-2910000000-da435cee921dd7b9f8e6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05ai-5879000000-d8ce750671bf51b487e2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0f79-2918800000-ab308a6a5023c34bc22fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0009000000-5d34de066e82cc9f0a41Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0900000000-24ec04976da03c3f9c77Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fdo-4900000000-d0880bfc6f3d80e4aa72Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-3940000000-16be8720b1c49cea9b06Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0009000000-6c22c083c2dfab97a299Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0109000000-48c96b3d1471c5cd6171Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-002r-0914000000-2466a9146383b4265e42Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0900000000-214430a00501054cc774Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-059j-1900000000-0e23516e07f0baf74c79Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0abj-1900000000-ad0282ab7188d9ec3dc1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0aba-3900000000-e36e464b157b3e6159f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4j-5900000000-fe9092d76099e1e70a4eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0aou-6900000000-1b218b97a890ac7e8f45Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03fr-0049000000-3bd424d473bdadd2b9b4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0039000000-fd181dfb87e1cbb8ab6fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0049000000-7633496a1a53bda21707Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0009000000-59db5e627634e4be3907Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0009000000-9781e204df305d722d2dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0009000000-0b5e40226163a1a334dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0009000000-946472abc72d41b1633cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003u-0149000000-efb3f94efcbdfc468859Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5j-2392000000-d014016e46f2ae8b1bd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-1c4a8c3698ff1bfa2bd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-2029000000-82b546174619108311f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-8093000000-47f7996c84edb1324aadSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002802
FooDB IDFDB023065
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID35911
BioCyc IDCORTISONE
METLIN ID271
PDB IDNot Available
Wikipedia LinkCortisone
Chemspider ID193441
ChEBI ID16962
PubChem Compound ID222786
Kegg Compound IDC00762
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Ganis, Frank M.; Axelrod, Leonard R.; Miller, Leon L. The metabolism of hydrocortisone by kidney tissue in vitro. Journal of Biological Chemistry (1956), 218 841-8.
2. Ganis, Frank M.; Axelrod, Leonard R.; Miller, Leon L. The metabolism of hydrocortisone by kidney tissue in vitro. Journal of Biological Chemistry (1956), 218 841-8.
3. Zuber M, Miesel R, Brandl B: A patient with a high titer of antinuclear antibody and a functioning adrenal tumour. Clin Rheumatol. 1995 Jan;14(1):100-3.
4. Edwin B, Raeder I, Trondsen E, Kaaresen R, Buanes T: Outpatient laparoscopic adrenalectomy in patients with Conn's syndrome. Surg Endosc. 2001 Jun;15(6):589-91. Epub 2001 Mar 13.
5. Onyimba CU, Vijapurapu N, Curnow SJ, Khosla P, Stewart PM, Murray PI, Walker EA, Rauz S: Characterisation of the prereceptor regulation of glucocorticoids in the anterior segment of the rabbit eye. J Endocrinol. 2006 Aug;190(2):483-93.
6. Weigand A, Hinzpeter B, Schicha H: [Deterioration of endocrine ophthalmology after radioiodine therapy in Graves' disease?]. Nuklearmedizin. 1998;37(7):234-8.
7. Mark PJ, Waddell BJ: P-glycoprotein restricts access of cortisol and dexamethasone to the glucocorticoid receptor in placental BeWo cells. Endocrinology. 2006 Nov;147(11):5147-52. Epub 2006 Jul 27.
8. Sandeep TC, Andrew R, Homer NZ, Andrews RC, Smith K, Walker BR: Increased in vivo regeneration of cortisol in adipose tissue in human obesity and effects of the 11beta-hydroxysteroid dehydrogenase type 1 inhibitor carbenoxolone. Diabetes. 2005 Mar;54(3):872-9.
9. Pepe GJ, Albrecht ED: Regulation of the primate fetal adrenal cortex. Endocr Rev. 1990 Feb;11(1):151-76.
10. Boman HG: Innate immunity and the normal microflora. Immunol Rev. 2000 Feb;173:5-16.
11. Andrew R, Westerbacka J, Wahren J, Yki-Jarvinen H, Walker BR: The contribution of visceral adipose tissue to splanchnic cortisol production in healthy humans. Diabetes. 2005 May;54(5):1364-70.
12. Sharma KK, Lindqvist A, Zhou XJ, Auchus RJ, Penning TM, Andersson S: Deoxycorticosterone inactivation by AKR1C3 in human mineralocorticoid target tissues. Mol Cell Endocrinol. 2006 Mar 27;248(1-2):79-86. Epub 2005 Dec 5.
13. Draper N, Stewart PM: 11beta-hydroxysteroid dehydrogenase and the pre-receptor regulation of corticosteroid hormone action. J Endocrinol. 2005 Aug;186(2):251-71.
14. AvRuskin TW, Krishnan N, Juan CS: Congenital adrenal hypoplasia and male pseudohermaphroditism due to DAX1 mutation, SF1 mutation or neither: a patient report. J Pediatr Endocrinol Metab. 2004 Aug;17(8):1125-32.
15. Ferrari P, Bianchetti M, Frey FJ: Juvenile hypertension, the role of genetically altered steroid metabolism. Horm Res. 2001;55(5):213-23.
16. Stormer FC, Reistad R, Alexander J: Glycyrrhizic acid in liquorice--evaluation of health hazard. Food Chem Toxicol. 1993 Apr;31(4):303-12.
17. Bolt RJ, Van Weissenbruch MM, Popp-Snijders C, Sweep FG, Lafeber HN, Delemarre-van de Waal HA: Maturity of the adrenal cortex in very preterm infants is related to gestational age. Pediatr Res. 2002 Sep;52(3):405-10.
18. Jiang JQ, Wang DS, Senthilkumaran B, Kobayashi T, Kobayashi HK, Yamaguchi A, Ge W, Young G, Nagahama Y: Isolation, characterization and expression of 11beta-hydroxysteroid dehydrogenase type 2 cDNAs from the testes of Japanese eel (Anguilla japonica) and Nile tilapia (Oreochromis niloticus). J Mol Endocrinol. 2003 Oct;31(2):305-15.
19. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=11710540
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=14874924
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=2268561
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=24391193
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=8989250