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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
11-beta-HydrocortisoneHMDB
11-beta-HydroxycortisoneHMDB
11-HydrocortisoneHMDB
11a-HydroxycorticosteroneHMDB
11alpha-HydroxycorticosteroneHMDB
11b,17,21-TrihydroxyprogesteroneHMDB
11b-HydrocortisoneHMDB
11b-HydroxycortisoneHMDB
11beta,17,21-TrihydroxyprogesteroneHMDB
11beta-HydrocortisoneHMDB
11beta-HydroxycortisoneHMDB
17-HydroxycorticosteroneHMDB
17a-HydroxycorticosteroneHMDB
17alpha-HydroxycorticosteroneHMDB
4-Pregnene-11alpha,21-triol 3,20-dioneHMDB
4-Pregnene-11b,17a,21-triol-3,20-dioneHMDB
ActicortHMDB
Aeroseb HCHMDB
Aeroseb-HCHMDB
Ala-cortHMDB
Ala-scalpHMDB
AlacortHMDB
AlgicirtisHMDB
AlphadermHMDB
AmberinHMDB
AnflamHMDB
Anti-inflammatory hormoneHMDB
AquacortHMDB
Aquanil HCHMDB
Barseb HCHMDB
Basan-cortiHMDB
CaldeCORT sprayHMDB
CetacortHMDB
ChronocortHMDB
Clear aidHMDB
CleitonHMDB
CobadexHMDB
Compound FHMDB
Cor-tar-quinHMDB
Cort-domeHMDB
Cort-quinHMDB
CortanalHMDB
CortenemaHMDB
CortesalHMDB
CorticremeHMDB
CortifanHMDB
CortifoamHMDB
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
EpicortHMDB
Epiderm HHMDB
Esiderm HHMDB
EvacortHMDB
FicortrilHMDB
FiocortrilHMDB
Foille insettiHMDB
GenacortHMDB
gyno-CortisoneHMDB
H-CortHMDB
HCHMDB
Heb cortHMDB
Heb-cortHMDB
HidaloneHMDB
hidro-ColisonaHMDB
HidrocortisonaHMDB
HycortHMDB
HycortolHMDB
HycortoleHMDB
HydracortHMDB
HydrassonHMDB
hydro-AdresonHMDB
hydro-ColisonaHMDB
HydrocortHMDB
HydrocortalHMDB
HydrocorticosteroneHMDB
HydrocortisoneHMDB
Hydrocortisone alcoholHMDB
Hydrocortisone baseHMDB
Hydrocortisone free alcoholHMDB
HydrocortisonumHMDB
HydrocortistabHMDB
HydrocortisylHMDB
HydrocortoneHMDB
HydroskinHMDB
HydroxycortisoneHMDB
HysoneHMDB
HytisoneHMDB
HytoneHMDB
Hytone lotionHMDB
IdrocortisoneHMDB
Incortin-HHMDB
Incortin-hydrogenHMDB
Kendall'S compound FHMDB
Komed HCHMDB
KyypakkausHMDB
Lacticare HCHMDB
Lacticare-HCHMDB
LactisonaHMDB
LubricortHMDB
MaintasoneHMDB
MedicortHMDB
MeusicortHMDB
MildisonHMDB
MillidermHMDB
neo-Cort-domeHMDB
Neosporin-H earHMDB
NutracortHMDB
Nystaform-HCHMDB
OptefHMDB
OtalgineHMDB
Otic-neo-cort-domeHMDB
OtobioticHMDB
OtocortHMDB
Otosone-FHMDB
Pediotic suspensionHMDB
PenecortHMDB
PermicortHMDB
Polcort HHMDB
Preparation H hydrocortisone creamHMDB
PrepcortHMDB
Prestwick_265HMDB
Prevex HCHMDB
ProctocortHMDB
ProctofoamHMDB
ProtocortHMDB
RacetHMDB
RectoidHMDB
Reichstein'S substance mHMDB
Remederm HCHMDB
SanatisonHMDB
Scalpicin capilarHMDB
SchericurHMDB
Scheroson FHMDB
SigmacortHMDB
SignefHMDB
StiefcorcilHMDB
SynacortHMDB
Systral hydrocortHMDB
TarcortinHMDB
TimocortHMDB
TopicortHMDB
Transderma HHMDB
TraumaideHMDB
UnidermHMDB
Vioform-hydrocortisoneHMDB
VoSol HCHMDB
VytoneHMDB
ZenoxoneHMDB
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 DescriptorsNot Available
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity97.4 m3·mol-1ChemAxon
Polarizability39.24 Å3ChemAxon
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-MSsplash10-053r-3967000000-125d928e479016368100View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-03di-3521090000-92c353a6bf125d408dd4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0009000000-862028a83a35574ed4d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01tj-0249000000-f36b2ecd66c42004e163View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-1492000000-120c7b567d593551959fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-cfde4c83b4f9237d6b99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-114u-2019000000-f70fb8347b279a4639b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9075000000-3b98ca796996f423bcadView 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 IDNot Available
HMDB IDHMDB00063
FooDB IDFDB021888
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID35828
BioCyc IDCORTISOL
METLIN ID5124
PDB IDNot Available
Wikipedia LinkCortisol
Chemspider ID571435
ChEBI IDNot Available
PubChem Compound ID657311
Kegg Compound IDC00735
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available