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Record Information
Version1.0
Creation Date2016-07-13 19:40:47 UTC
Update Date2016-07-19 23:08:56 UTC
LmdbLMDB00028
Secondary Accession NumbersNone
Metabolite Identification
Common NameCortisol
DescriptionCortisol is a corticosteroid hormone produced by the adrenal cortex that is involved in the response to stress; The main glucocorticoid secreted by the adrenal cortex. Its synthetic counterpart is used, either as an injection or topically, in the treatment of inflammation, allergy, collagen diseases, asthma, adrenocortical deficiency, shock, and some neoplastic conditions. As an oral or injectable drug, cortisol is also known as hydrocortisone. It is used as an immunosuppressive drug, given by injection in the treatment of severe allergic reactions such as anaphylaxis and angioedema, in place of prednisolone in patients who need steroid treatment but cannot take oral medication, and peri-operatively in patients on long-term steroid treatment to prevent an Addisonian crisis. Cortisol or Hydrocortisone is a corticosteroid hormone produced by the adrenal cortex that is involved in the response to stress. It increases blood pressure, blood sugar levels, may cause infertility in women, and suppresses the immune system. Its synthetic counterpart (hydrocortisone) is used, either as an injection or topically, in the treatment of inflammation, allergy, collagen diseases, asthma, adrenocortical deficiency, shock, and some neoplastic conditions. Cortisol is synthesized from pregnenolone. The amount of cortisol present in the serum undergoes diurnal variation, with the highest levels present in the early morning, and lower levels in the evening, several hours after the onset of sleep. Cortisol is a corticosteroid hormone produced by the adrenal cortex that is involved in the response to stress; it increases blood pressure, blood sugar levels, may cause infertility in women, and suppresses the immune system. Synthetic cortisol, also known as hydrocortisone, is used as a drug mainly to fight allergies and inflammation; it increases blood pressure, blood sugar levels, may cause infertility in women, and suppresses the immune system. Synthetic cortisol, also known as hydrocortisone, is used as a drug mainly to fight allergies and inflammation.
Structure
Thumb
Synonyms
ValueSource
(11beta)-11,17,21-Trihydroxypregn-4-ene-3,20-dioneChEBI
11beta,17alpha,21-Trihydroxy-4-pregnene-3,20-dioneChEBI
11beta-HydrocortisoneChEBI
17-HydroxycorticosteroneChEBI
4-Pregnen-11beta,17alpha,21-triol-3,20-dioneChEBI
HidrocortisonaChEBI
HydrocortisoneChEBI
HydrocortisonumChEBI
Kendall's compound FChEBI
Reichstein's substance mChEBI
HCKegg
ActicortKegg
Anusol HCKegg
ColocortKegg
CortefKegg
HytoneKegg
PlenadrenKegg
Balneol-HCChEMBL
CORTRILChEMBL
CetacortChEMBL
Cort-domeChEMBL
FlexicortChEMBL
Hi-corChEMBL
Hydrocortisone in absorbaseChEMBL
Nogenic HCChEMBL
Aeroseb-HCChEMBL
Ala-cortChEMBL
Ala-scalpChEMBL
PenecortChEMBL
TexacortChEMBL
H-CortChEMBL
HYDROCORTONEChEMBL
OphthocortChEMBL
Terra-cortrilChEMBL
Cor-oticinChEMBL
NutracortChEMBL
CortifoamChEMBL
GlycortChEMBL
HC #1ChEMBL
HC #4ChEMBL
ProctocortChEMBL
Anucort-HCChEMBL
CortenemaChEMBL
DermacortChEMBL
Micort-HCChEMBL
SynacortChEMBL
U-cortChEMBL
EldecortChEMBL
EpicortChEMBL
neo-CortefChEMBL
Stie-cortChEMBL
Anusol-HCChEMBL
Beta-HCChEMBL
hydro-RXChEMBL
LocoidChEMBL
(11b)-11,17,21-Trihydroxypregn-4-ene-3,20-dioneGenerator
(11β)-11,17,21-trihydroxypregn-4-ene-3,20-dioneGenerator
11b,17a,21-Trihydroxy-4-pregnene-3,20-dioneGenerator
11β,17α,21-trihydroxy-4-pregnene-3,20-dioneGenerator
11b-HydrocortisoneGenerator
11β-hydrocortisoneGenerator
4-Pregnen-11b,17a,21-triol-3,20-dioneGenerator
4-Pregnen-11β,17α,21-triol-3,20-dioneGenerator
b-HCGenerator
β-HCGenerator
11-beta-HydrocortisoneHMDB
11-beta-HydroxycortisoneHMDB
11-HydrocortisoneHMDB
11a-HydroxycorticosteroneHMDB
11alpha-HydroxycorticosteroneHMDB
11b,17,21-TrihydroxyprogesteroneHMDB
11b-HydroxycortisoneHMDB
11beta,17,21-TrihydroxyprogesteroneHMDB
11beta-HydroxycortisoneHMDB
17a-HydroxycorticosteroneHMDB
17alpha-HydroxycorticosteroneHMDB
4-Pregnene-11alpha,21-triol 3,20-dioneHMDB
4-Pregnene-11b,17a,21-triol-3,20-dioneHMDB
Aeroseb HCHMDB
AlacortHMDB
AlgicirtisHMDB
AlphadermHMDB
AmberinHMDB
AnflamHMDB
Anti-inflammatory hormoneHMDB
AquacortHMDB
Aquanil HCHMDB
Barseb HCHMDB
Basan-cortiHMDB
CaldeCORT sprayHMDB
ChronocortHMDB
Clear aidHMDB
CleitonHMDB
CobadexHMDB
Compound FHMDB
Cor-tar-quinHMDB
Cort-quinHMDB
CortanalHMDB
CortesalHMDB
CorticremeHMDB
CortifanHMDB
CortimentHMDB
Cortisol alcoholHMDB
CortisolonumHMDB
CortisporinHMDB
Cortisporin oticoHMDB
CortisprayHMDB
CortizolHMDB
CortolotionHMDB
CortonemaHMDB
CortoxideHMDB
CremesoneHMDB
Cremicort-HHMDB
CutisolHMDB
DelacortHMDB
Derm-aidHMDB
DermilHMDB
DermolateHMDB
DihydrocostisoneHMDB
DiodermHMDB
Dome-cortHMDB
Domolene-HCHMDB
DroticHMDB
Ef corlinHMDB
EfcorbinHMDB
EfcortelanHMDB
EfcortelinHMDB
EldercortHMDB
Epiderm HHMDB
Esiderm HHMDB
EvacortHMDB
FicortrilHMDB
FiocortrilHMDB
Foille insettiHMDB
GenacortHMDB
gyno-CortisoneHMDB
Heb cortHMDB
Heb-cortHMDB
HidaloneHMDB
hidro-ColisonaHMDB
HycortHMDB
HycortolHMDB
HycortoleHMDB
HydracortHMDB
HydrassonHMDB
hydro-AdresonHMDB
hydro-ColisonaHMDB
HydrocortHMDB
HydrocortalHMDB
HydrocorticosteroneHMDB
Hydrocortisone alcoholHMDB
Hydrocortisone baseHMDB
Hydrocortisone free alcoholHMDB
HydrocortistabHMDB
HydrocortisylHMDB
HydroskinHMDB
HydroxycortisoneHMDB
HysoneHMDB
HytisoneHMDB
Hytone lotionHMDB
IdrocortisoneHMDB
Incortin-HHMDB
Incortin-hydrogenHMDB
Komed HCHMDB
KyypakkausHMDB
Lacticare HCHMDB
Lacticare-HCHMDB
LactisonaHMDB
LubricortHMDB
MaintasoneHMDB
MedicortHMDB
MeusicortHMDB
MildisonHMDB
MillidermHMDB
neo-Cort-domeHMDB
Neosporin-H earHMDB
Nystaform-HCHMDB
OptefHMDB
OtalgineHMDB
Otic-neo-cort-domeHMDB
OtobioticHMDB
OtocortHMDB
Otosone-FHMDB
Pediotic suspensionHMDB
PermicortHMDB
Polcort HHMDB
Preparation H hydrocortisone creamHMDB
PrepcortHMDB
Prestwick_265HMDB
Prevex HCHMDB
ProctofoamHMDB
ProtocortHMDB
RacetHMDB
RectoidHMDB
Remederm HCHMDB
SanatisonHMDB
Scalpicin capilarHMDB
SchericurHMDB
Scheroson FHMDB
SigmacortHMDB
SignefHMDB
StiefcorcilHMDB
Systral hydrocortHMDB
TarcortinHMDB
TimocortHMDB
TopicortHMDB
Transderma HHMDB
TraumaideHMDB
UnidermHMDB
Vioform-hydrocortisoneHMDB
VoSol HCHMDB
VytoneHMDB
ZenoxoneHMDB
11-EpicortisolMeSH
Hydrocortisone, (11 alpha)-isomerMeSH
Hydrocortisone, (9 beta,10 alpha,11 alpha)-isomerMeSH
11 EpicortisolMeSH
CortifairMeSH
EpicortisolMeSH
Hydrocortisone acetateHMDB
Hydrocortisone butyrateHMDB
Hydrocortisone sodium phosphateHMDB
Hydrocortisone valerateHMDB
Chemical FormulaC21H30O5
Average Molecular Weight362.4599
Monoisotopic Molecular Weight362.20932407
IUPAC Name(1S,2R,10S,11S,14S,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name17α-hydroxycorticosterone
CAS Registry Number50-23-7
SMILES
[H][C@@]12CC[C@@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C21H30O5/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/h9,14-16,18,22,24,26H,3-8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21+/m0/s1
InChI KeyJYGXADMDTFJGBT-CZFMHFDVSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 20-oxosteroid
  • Pregnane-skeleton
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • 17-hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Cyclic ketone
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.79ALOGPS
logP1.28ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)12.58ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity97.4 m³·mol⁻¹ChemAxon
Polarizability39.24 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 3 TMS)splash10-0f7o-3930000000-b7b43b2fc9f20acfd20bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f7o-3930000000-b7b43b2fc9f20acfd20bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052f-2910000000-2625335a031486ecb302View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03di-0764390000-da961c85fe1bb83113ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-0759000000-b337a46ecfd6de91776bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05fs-3940000000-2bf712a915c3a2c100a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-015a-0189000000-61afe49a8d4a96aae3f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00lu-0149000000-b95a11b27f7e7d44dd51View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001l-0019000000-4c4924e6ac472ad52886View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-001j-0259000000-fda4e876e9ef04015946View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0009000000-cc8188e19dbdd6210b77View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-07r1-1985000000-b6d756bd554367393be3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00dj-1930000000-120dc8893cc4709c1f6bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00dm-2910000000-d1f01e1bce5fe0108f40View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05tf-3900000000-4ffd79c22013fe5479b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-054o-4900000000-fdbed869a0cadc21b64bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-002f-7900000000-dac7b2c5b3f8e8b85086View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-016u-7900000000-3a770c3819f82ea45841View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-016r-9800000000-d261cf7141fbf30715f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-056r-0289000000-9a48511b5c3d5fa404e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0759000000-b337a46ecfd6de91776bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-05fs-3940000000-2bf712a915c3a2c100a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0019000000-8ad3f8da375dbe757f56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01r2-0249000000-626e28356285f53f3fe6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5i-1591000000-0e29016542b4be9b2b71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-50ebf457069ff74ed883View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-114u-2029000000-385a70405fc241c4d5a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9086000000-3eda615d9551e69f2b4aView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Plasma
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
PlasmaDetected and Quantified0.877 +/- 0.0248-0.877+/-0.052 uMNot AvailablePorcine details
PlasmaDetected and Quantified0.930 +/- 0.0359-0.99+/-0.028 uMNot AvailablePorcine details
PlasmaDetected and Quantified1.167 +/- 0.0193-1.67+/-0.028 uMNot AvailablePorcine details
DrugBank IDDB00741
HMDB IDHMDB0000063
FooDB IDFDB021888
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID35828
BioCyc IDCORTISOL
METLIN ID5124
PDB IDNot Available
Wikipedia LinkHydrocortisone
Chemspider ID5551
ChEBI ID17650
PubChem Compound ID5754
Kegg Compound IDC00735
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available