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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:35 UTC
Update Date2017-12-07 01:50:32 UTC
HMDB IDHMDB0003128
Secondary Accession Numbers
  • HMDB03128
Metabolite Identification
Common NameCortolone
DescriptionIt is one of the steriod metabolites. It is found in the urine of pregnant (36-40 weeks of gestation) and nonpregnant women and in amniotic fluid from nearly fullterm pregnant women.(PMID: 7419663 ).
Structure
Thumb
Synonyms
ValueSource
20alpha-CortoloneHMDB
5a,17,20a,21-Tetrol-11-oneHMDB
a-CortoloneHMDB
alpha-CortoloneHMDB
CortolonHMDB
Cortolone, (3alpha,5alpha,20S)-isomerMeSH
Cortolone, (3alpha,5beta,20R)-isomerMeSH
Chemical FormulaC21H34O5
Average Molecular Weight366.4917
Monoisotopic Molecular Weight366.240624198
IUPAC Name(1S,2S,5R,7R,10S,11S,14R,15S)-14-[(1S)-1,2-dihydroxyethyl]-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one
Traditional Nameα-cortolone
CAS Registry Number516-42-7
SMILES
[H][C@@]12CC[C@](O)([C@@H](O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C21H34O5/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/h12-15,17-18,22-23,25-26H,3-11H2,1-2H3/t12-,13-,14+,15+,17+,18-,19+,20+,21+/m1/s1
InChI KeyJXCOSKURGJMQSG-AZQJGLEESA-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
  • Pregnane-skeleton
  • 3-hydroxysteroid
  • 11-oxosteroid
  • Oxosteroid
  • 3-alpha-hydroxysteroid
  • 17-hydroxysteroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Primary alcohol
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Role

Industrial application:

Biological role:

  Molecular messenger:

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 Solubility0.72 g/LALOGPS
logP1.26ALOGPS
logP0.88ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)12.99ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity97.44 m³·mol⁻¹ChemAxon
Polarizability40.9 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000j-3319000000-21ccb6077d496d19d89cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-000l-1201139000-f10b8aa6b7295a419813View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0019000000-1920aa591391279e5b03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0129000000-57e86c2dbf01a686c6acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-2292000000-137b0f848fec6a19d4eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-64630d6dbef8f1af9b95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05n1-3039000000-a9418ec033a752ba2efaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052u-5097000000-49285cc5895035763754View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.13 (0.12-0.16) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.13 (0.06-0.16) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.0002 +/- 0.0001 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.19 +/- 0.025 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.0003 +/- 0.00032 umol/mmol creatinineAdult (>18 years old)FemaleStress urinary incontinence details
UrineDetected and Quantified0.17 +/- 0.02 umol/mmol creatinineAdult (>18 years old)Female
Eating disorder
details
UrineDetected and Quantified0.53 +/- 0.079 umol/mmol creatinineAdult (>18 years old)Female
Eating disorder
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 IDFDB023110
KNApSAcK IDNot Available
Chemspider ID141038
KEGG Compound IDC05481
BioCyc IDCORTOLONE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3175
PubChem Compound160499
PDB IDNot Available
ChEBI ID3899
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. McEwen CN, McKay RG, Larsen BS: Analysis of solids, liquids, and biological tissues using solids probe introduction at atmospheric pressure on commercial LC/MS instruments. Anal Chem. 2005 Dec 1;77(23):7826-31. [PubMed:16316194 ]
  2. Kraan GP, Derks HJ, Drayer NM: Quantification of polar glucocorticosteroids in the urine of pregnant and nonpregnant women: a comparison with 6 alpha-hydroxylated metabolites of cortisol in neonatal urine and amniotic fluid. J Clin Endocrinol Metab. 1980 Oct;51(4):754-8. [PubMed:7419663 ]