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Record Information
Version3.6
Creation Date2006-05-22 15:12:39 UTC
Update Date2016-02-11 01:06:06 UTC
HMDB IDHMDB03180
Secondary Accession NumbersNone
Metabolite Identification
Common NameCortol
DescriptionInvolved in C21-Steroid hormone metabolism.
Structure
Thumb
Synonyms
ValueSource
20alpha-CortolHMDB
3alpha,11beta,17,20alpha,21-PentahydroxypregnaneHMDB
5beta-Pregnane-3alpha,11beta,17,20,21-pentolHMDB
alpha-CortolHMDB
Chemical FormulaC21H36O5
Average Molecular Weight368.5075
Monoisotopic Molecular Weight368.256274262
IUPAC Name(1S,2S,5R,7R,10S,11S,14R,15S,17S)-14-[(1S)-1,2-dihydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14,17-triol
Traditional Namecortol
CAS Registry Number516-38-1
SMILES
[H][C@@]12CC[C@](O)([C@@H](O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C21H36O5/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/h12-18,22-26H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,17+,18-,19+,20+,21+/m1/s1
InChI KeyInChIKey=FFPUNPBUZDTHJI-XPOJVAQCSA-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
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • Pregnane-skeleton
  • 17-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • 3-hydroxysteroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.05 mg/mLALOGPS
logP1.43ALOGPS
logP0.5ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)12.99ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area101.15 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity98.37 m3·mol-1ChemAxon
Polarizability41.55 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.23 +/- 0.16 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.047 (0.038-0.065) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.035 (0.026-0.046) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.039 +/- 0.0065 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified48E-5 +/- 2.9E-6 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.039 +/- 0.0078 umol/mmol creatinineAdult (>18 years old)Female
Eating disorder
details
UrineDetected and Quantified0.072 +/- 0.015 umol/mmol creatinineAdult (>18 years old)Female
Eating disorder
details
UrineDetected and Quantified0.0001 +/- 0.0001 umol/mmol creatinineAdult (>18 years old)FemaleStress urinary incontinence details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023120
KNApSAcK IDNot Available
Chemspider ID216069
KEGG Compound IDC05482
BioCyc IDCORTOL
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03180
Metagene LinkHMDB03180
METLIN ID3174
PubChem Compound246873
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Poor V, Biro I, Bufa A, Gati A, Fenyvesi I, Juricskay S, Tenyi T, Kilar F: Urinary steroids in young women with eating disorders. J Biochem Biophys Methods. 2004 Oct 29;61(1-2):199-205. [15560936 ]
  2. Setchell KD, Shackleton CH: The in vivo metabolism of cortisol and corticosterone by the macaque monkey (Macaca fascicularis). Acta Endocrinol (Copenh). 1975 Jan;78(1):91-109. [1172896 ]