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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
(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
11beta-HydroxycortisoneHMDB
17alpha-HydroxycorticosteroneHMDB
Anti-inflammatory hormoneHMDB
DihydrocostisoneHMDB
HydrocorticosteroneHMDB
Hydrocortisone acetateHMDB
Hydrocortisone alcoholHMDB
Hydrocortisone baseHMDB
Hydrocortisone butyrateHMDB
Hydrocortisone free alcoholHMDB
Hydrocortisone sodium phosphateHMDB
Hydrocortisone valerateHMDB
HydroxycortisoneHMDB
IdrocortisoneHMDB
Balneol-HCChEMBL, HMDB
CORTRILChEMBL, HMDB, MeSH
CetacortChEMBL, HMDB
Cort-domeChEMBL, HMDB
FlexicortChEMBL, HMDB
Hi-corChEMBL, HMDB
Hydrocortisone in absorbaseChEMBL, HMDB
Nogenic HCChEMBL, HMDB
Aeroseb-HCChEMBL, HMDB
Ala-cortChEMBL, HMDB
Ala-scalpChEMBL, HMDB
PenecortChEMBL, HMDB
TexacortChEMBL, HMDB
H-CortChEMBL, HMDB
HYDROCORTONEChEMBL, HMDB
OphthocortChEMBL, HMDB
Terra-cortrilChEMBL, HMDB
Cor-oticinChEMBL, HMDB
NutracortChEMBL, HMDB
CortifoamChEMBL, HMDB
GlycortChEMBL, HMDB
HC #1ChEMBL, HMDB
HC #4ChEMBL, HMDB
ProctocortChEMBL, HMDB
Anucort-HCChEMBL, HMDB
CortenemaChEMBL, HMDB
DermacortChEMBL, HMDB
Micort-HCChEMBL, HMDB
SynacortChEMBL, HMDB
U-cortChEMBL, HMDB
EldecortChEMBL, HMDB
EpicortChEMBL, HMDB
neo-CortefChEMBL, HMDB
Stie-cortChEMBL, HMDB
Anusol-HCChEMBL, HMDB
Beta-HCChEMBL, HMDB
hydro-RXChEMBL, HMDB
LocoidChEMBL, HMDB
b-HCGenerator, HMDB
β-HCGenerator, HMDB
11-beta-HydrocortisoneHMDB
11-beta-HydroxycortisoneHMDB
11-HydrocortisoneHMDB
11a-HydroxycorticosteroneHMDB
11alpha-HydroxycorticosteroneHMDB
11b,17,21-TrihydroxyprogesteroneHMDB
11b-HydroxycortisoneHMDB
11beta,17,21-TrihydroxyprogesteroneHMDB
17a-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
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
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
HydrocortistabHMDB
HydrocortisylHMDB
HydroskinHMDB
HysoneHMDB
HytisoneHMDB
Hytone lotionHMDB
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, HMDB
Hydrocortisone, (11 alpha)-isomerMeSH, HMDB
Hydrocortisone, (9 beta,10 alpha,11 alpha)-isomerMeSH, HMDB
11 EpicortisolMeSH, HMDB
CortifairMeSH, HMDB
EpicortisolMeSH, HMDB
Chemical FormulaC21H30O5
Average Molecular Weight362.4599
Monoisotopic Molecular Weight362.20932407
IUPAC Name(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
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
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
  • 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
Polarizability39.45 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 3 TMS)splash10-0f7o-3930000000-b7b43b2fc9f20acfd20bSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f7o-3930000000-b7b43b2fc9f20acfd20bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-052f-2910000000-2625335a031486ecb302Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03di-0764390000-da961c85fe1bb83113ddSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-0759000000-b337a46ecfd6de91776bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05fs-3940000000-2bf712a915c3a2c100a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-015a-0189000000-61afe49a8d4a96aae3f9Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00lu-0149000000-b95a11b27f7e7d44dd51Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001l-0019000000-4c4924e6ac472ad52886Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-001j-0259000000-fda4e876e9ef04015946Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0009000000-cc8188e19dbdd6210b77Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-07r1-1985000000-b6d756bd554367393be3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00dj-1930000000-120dc8893cc4709c1f6bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00dm-2910000000-d1f01e1bce5fe0108f40Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05tf-3900000000-4ffd79c22013fe5479b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-054o-4900000000-fdbed869a0cadc21b64bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-002f-7900000000-dac7b2c5b3f8e8b85086Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-016u-7900000000-3a770c3819f82ea45841Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-016r-9800000000-d261cf7141fbf30715f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-056r-0289000000-9a48511b5c3d5fa404e9Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-0759000000-b337a46ecfd6de91776bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-05fs-3940000000-2bf712a915c3a2c100a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-0259000000-4a5fba6c9c5e205dd239Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0019000000-8ad3f8da375dbe757f56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01r2-0249000000-626e28356285f53f3fe6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5i-1591000000-0e29016542b4be9b2b71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-50ebf457069ff74ed883Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-114u-2029000000-385a70405fc241c4d5a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9086000000-3eda615d9551e69f2b4aSpectrum
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 IDHMDB0014879
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHydrocortisone
Chemspider IDNot Available
ChEBI ID17650
PubChem Compound ID5754
Kegg Compound IDC00735
YMDB IDNot Available
ECMDB IDM2MDB005820
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available