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Showing Compound Cortisone (FDB023065)

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
MOLSDFPDBSMILESInChI
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-0009000000-5d34de066e82cc9f0a41Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0900000000-24ec04976da03c3f9c77Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0fdo-4900000000-d0880bfc6f3d80e4aa72Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-3940000000-16be8720b1c49cea9b06Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0009000000-6c22c083c2dfab97a299Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0109000000-48c96b3d1471c5cd6171Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-002r-0914000000-2466a9146383b4265e42Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0900000000-214430a00501054cc774Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-059j-1900000000-0e23516e07f0baf74c79Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0abj-1900000000-ad0282ab7188d9ec3dc1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0aba-3900000000-e36e464b157b3e6159f1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4j-5900000000-fe9092d76099e1e70a4eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0aou-6900000000-1b218b97a890ac7e8f45Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03fr-0049000000-3bd424d473bdadd2b9b4Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0039000000-fd181dfb87e1cbb8ab6fSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0049000000-7633496a1a53bda21707Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0009000000-59db5e627634e4be3907Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0009000000-9781e204df305d722d2dSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0009000000-0b5e40226163a1a334dbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0009000000-946472abc72d41b1633cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003u-0149000000-efb3f94efcbdfc468859Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5j-2392000000-d014016e46f2ae8b1bd1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-1c4a8c3698ff1bfa2bd9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-2029000000-82b546174619108311f8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-8093000000-47f7996c84edb1324aadSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
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