Record Information
Version1.0
Creation date2011-09-21 00:24:06 UTC
Update date2015-10-09 22:33:10 UTC
Primary IDFDB023065
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCortisone
DescriptionA 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 to the active metabolite hydrocortisone. (From Martindale, The Extra Pharmacopoeia, 30th ed, p726) -- Pubchem; Cortisone is a hormone. Chemically it is a corticosteroid with formula C21H28O5 and IUPAC name 17-hydroxy-11-dehydrocorticosterone. It is closely related to corticosterone. -- Wikipedia; 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. -- Wikipedia [HMDB]
CAS Number53-06-5
Structure
Thumb
Synonyms
SynonymSource
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
11-dehydro-17-HydroxycorticosteroneChEBI
17α,21-dihydroxy-4-pregnene-3,11,20-trioneGenerator
Balneol-Hchmdb
Beta-Hchmdb
Compound Ehmdb
Cortef Acetatehmdb
Cortisone Acetatehmdb
Fludrocortisone Acetatehmdb
Hemsol-Hchmdb
Hi-Corhmdb
Kendall's compoundhmdb
Kendall's Compound Ehmdb
Locoid Lipocreamhmdb
Micort-Hchmdb
Orabase HCAhmdb
Reichstein Fahmdb
Reichstein's Substance FAhmdb
Solu-Cortefhmdb
Stie-Corthmdb
δ(4)-pregnene-17a,21-diol-3,11,20-trioneGenerator
δ(4)-pregnene-17α,21-diol-3,11,20-trioneGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H28O5
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
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
Isomeric 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
Average Molecular Weight360.444
Monoisotopic Molecular Weight360.193674006
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSCortisone, non-derivatized, GC-MS Spectrumsplash10-00kf-2910000000-da435cee921dd7b9f8e6Spectrum
GC-MSCortisone, non-derivatized, GC-MS Spectrumsplash10-00kf-2910000000-da435cee921dd7b9f8e6Spectrum
Predicted GC-MSCortisone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05ai-5879000000-d8ce750671bf51b487e2Spectrum
Predicted GC-MSCortisone, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f79-2918800000-ab308a6a5023c34bc22fSpectrum
Predicted GC-MSCortisone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCortisone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0009000000-5d34de066e82cc9f0a412012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0900000000-24ec04976da03c3f9c772012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fdo-4900000000-d0880bfc6f3d80e4aa722012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-3940000000-16be8720b1c49cea9b062017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0009000000-6c22c083c2dfab97a2992017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0109000000-48c96b3d1471c5cd61712017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-002r-0914000000-2466a9146383b4265e422017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0900000000-214430a00501054cc7742017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-059j-1900000000-0e23516e07f0baf74c792017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0abj-1900000000-ad0282ab7188d9ec3dc12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0aba-3900000000-e36e464b157b3e6159f12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4j-5900000000-fe9092d76099e1e70a4e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0aou-6900000000-1b218b97a890ac7e8f452017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03fr-0049000000-3bd424d473bdadd2b9b42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0039000000-fd181dfb87e1cbb8ab6f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0049000000-7633496a1a53bda217072017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0009000000-59db5e627634e4be39072017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0009000000-9781e204df305d722d2d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0009000000-0b5e40226163a1a334db2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0009000000-946472abc72d41b1633c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003u-0149000000-efb3f94efcbdfc4688592017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5j-2392000000-d014016e46f2ae8b1bd12017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-1c4a8c3698ff1bfa2bd92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-2029000000-82b546174619108311f82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-8093000000-47f7996c84edb1324aad2017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
ChemSpider ID193441
ChEMBL IDCHEMBL1499
KEGG Compound IDC00762
Pubchem Compound ID222786
Pubchem Substance IDNot Available
ChEBI ID16962
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02802
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID35911
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCortisone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
3-oxo-5-beta-steroid 4-dehydrogenaseAKR1D1P51857
Corticosteroid 11-beta-dehydrogenase isozyme 1HSD11B1P28845
Dehydrogenase/reductase SDR family member 2DHRS2Q13268
Pathways
NameSMPDB LinkKEGG Link
SteroidogenesisSMP00130 map00140
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference