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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:35 UTC
Update Date2021-09-14 15:40:09 UTC
HMDB IDHMDB0003128
Secondary Accession Numbers
  • HMDB03128
Metabolite Identification
Common NameCortolone
DescriptionCortolone, also known as 20alpha-cortolone, 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. Cortolone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752263
Synonyms
ValueSource
Cortolone, (3alpha,5alpha,20S)-isomerHMDB
Cortolone, (3alpha,5beta,20R)-isomerHMDB
20alpha-CortoloneHMDB
5a,17,20a,21-Tetrol-11-oneHMDB
a-CortoloneHMDB
alpha-CortoloneHMDB
CortolonHMDB
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
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
  • 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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available183.39931661259
DarkChem[M-H]-PredictedNot Available176.49931661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Cortolone,1TMS,#13291.0505https://arxiv.org/abs/1905.12712
Cortolone,1TMS,#23263.8103https://arxiv.org/abs/1905.12712
Cortolone,1TMS,#33265.9998https://arxiv.org/abs/1905.12712
Cortolone,1TMS,#43273.1348https://arxiv.org/abs/1905.12712
Cortolone,1TMS,#53085.8848https://arxiv.org/abs/1905.12712
Cortolone,1TMS,#63148.1794https://arxiv.org/abs/1905.12712
Cortolone,2TMS,#13249.9382https://arxiv.org/abs/1905.12712
Cortolone,2TMS,#23294.4524https://arxiv.org/abs/1905.12712
Cortolone,2TMS,#33307.5554https://arxiv.org/abs/1905.12712
Cortolone,2TMS,#43077.9648https://arxiv.org/abs/1905.12712
Cortolone,2TMS,#53125.591https://arxiv.org/abs/1905.12712
Cortolone,2TMS,#63245.8518https://arxiv.org/abs/1905.12712
Cortolone,2TMS,#73251.793https://arxiv.org/abs/1905.12712
Cortolone,2TMS,#83072.23https://arxiv.org/abs/1905.12712
Cortolone,2TMS,#93102.636https://arxiv.org/abs/1905.12712
Cortolone,2TMS,#103238.7344https://arxiv.org/abs/1905.12712
Cortolone,2TMS,#113063.6492https://arxiv.org/abs/1905.12712
Cortolone,2TMS,#123086.9265https://arxiv.org/abs/1905.12712
Cortolone,2TMS,#133057.6924https://arxiv.org/abs/1905.12712
Cortolone,2TMS,#143097.6455https://arxiv.org/abs/1905.12712
Cortolone,3TMS,#13281.7168https://arxiv.org/abs/1905.12712
Cortolone,3TMS,#23276.818https://arxiv.org/abs/1905.12712
Cortolone,3TMS,#33077.667https://arxiv.org/abs/1905.12712
Cortolone,3TMS,#43073.4426https://arxiv.org/abs/1905.12712
Cortolone,3TMS,#53310.2925https://arxiv.org/abs/1905.12712
Cortolone,3TMS,#63101.1719https://arxiv.org/abs/1905.12712
Cortolone,3TMS,#73128.1494https://arxiv.org/abs/1905.12712
Cortolone,3TMS,#83101.336https://arxiv.org/abs/1905.12712
Cortolone,3TMS,#93112.9795https://arxiv.org/abs/1905.12712
Cortolone,3TMS,#103231.4104https://arxiv.org/abs/1905.12712
Cortolone,3TMS,#113081.9714https://arxiv.org/abs/1905.12712
Cortolone,3TMS,#123067.4812https://arxiv.org/abs/1905.12712
Cortolone,3TMS,#133065.0642https://arxiv.org/abs/1905.12712
Cortolone,3TMS,#143074.8574https://arxiv.org/abs/1905.12712
Cortolone,3TMS,#153044.5388https://arxiv.org/abs/1905.12712
Cortolone,3TMS,#163048.0186https://arxiv.org/abs/1905.12712
Cortolone,4TMS,#13290.6667https://arxiv.org/abs/1905.12712
Cortolone,4TMS,#23125.4482https://arxiv.org/abs/1905.12712
Cortolone,4TMS,#33120.0608https://arxiv.org/abs/1905.12712
Cortolone,4TMS,#43108.316https://arxiv.org/abs/1905.12712
Cortolone,4TMS,#53098.6172https://arxiv.org/abs/1905.12712
Cortolone,4TMS,#63095.3794https://arxiv.org/abs/1905.12712
Cortolone,4TMS,#73141.1213https://arxiv.org/abs/1905.12712
Cortolone,4TMS,#83069.5244https://arxiv.org/abs/1905.12712
Cortolone,4TMS,#93063.912https://arxiv.org/abs/1905.12712
Cortolone,1TBDMS,#13542.4028https://arxiv.org/abs/1905.12712
Cortolone,1TBDMS,#23517.5718https://arxiv.org/abs/1905.12712
Cortolone,1TBDMS,#33532.4673https://arxiv.org/abs/1905.12712
Cortolone,1TBDMS,#43506.6047https://arxiv.org/abs/1905.12712
Cortolone,1TBDMS,#53350.266https://arxiv.org/abs/1905.12712
Cortolone,1TBDMS,#63381.8215https://arxiv.org/abs/1905.12712
Cortolone,2TBDMS,#13764.2578https://arxiv.org/abs/1905.12712
Cortolone,2TBDMS,#23787.614https://arxiv.org/abs/1905.12712
Cortolone,2TBDMS,#33710.0894https://arxiv.org/abs/1905.12712
Cortolone,2TBDMS,#43526.347https://arxiv.org/abs/1905.12712
Cortolone,2TBDMS,#53563.48https://arxiv.org/abs/1905.12712
Cortolone,2TBDMS,#63757.1663https://arxiv.org/abs/1905.12712
Cortolone,2TBDMS,#73705.1504https://arxiv.org/abs/1905.12712
Cortolone,2TBDMS,#83523.9673https://arxiv.org/abs/1905.12712
Cortolone,2TBDMS,#93544.3127https://arxiv.org/abs/1905.12712
Cortolone,2TBDMS,#103715.6135https://arxiv.org/abs/1905.12712
Cortolone,2TBDMS,#113512.6704https://arxiv.org/abs/1905.12712
Cortolone,2TBDMS,#123547.5273https://arxiv.org/abs/1905.12712
Cortolone,2TBDMS,#133513.7952https://arxiv.org/abs/1905.12712
Cortolone,2TBDMS,#143525.7974https://arxiv.org/abs/1905.12712
Cortolone,3TBDMS,#14018.9707https://arxiv.org/abs/1905.12712
Cortolone,3TBDMS,#23964.6824https://arxiv.org/abs/1905.12712
Cortolone,3TBDMS,#33736.8008https://arxiv.org/abs/1905.12712
Cortolone,3TBDMS,#43786.1138https://arxiv.org/abs/1905.12712
Cortolone,3TBDMS,#53976.5508https://arxiv.org/abs/1905.12712
Cortolone,3TBDMS,#63733.137https://arxiv.org/abs/1905.12712
Cortolone,3TBDMS,#73767.983https://arxiv.org/abs/1905.12712
Cortolone,3TBDMS,#83720.14https://arxiv.org/abs/1905.12712
Cortolone,3TBDMS,#93718.4773https://arxiv.org/abs/1905.12712
Cortolone,3TBDMS,#103929.2332https://arxiv.org/abs/1905.12712
Cortolone,3TBDMS,#113719.0386https://arxiv.org/abs/1905.12712
Cortolone,3TBDMS,#123742.1672https://arxiv.org/abs/1905.12712
Cortolone,3TBDMS,#133731.8616https://arxiv.org/abs/1905.12712
Cortolone,3TBDMS,#143700.6738https://arxiv.org/abs/1905.12712
Cortolone,3TBDMS,#153714.5503https://arxiv.org/abs/1905.12712
Cortolone,3TBDMS,#163714.7595https://arxiv.org/abs/1905.12712
Cortolone,4TBDMS,#14202.825https://arxiv.org/abs/1905.12712
Cortolone,4TBDMS,#23940.2742https://arxiv.org/abs/1905.12712
Cortolone,4TBDMS,#33997.2368https://arxiv.org/abs/1905.12712
Cortolone,4TBDMS,#43941.1885https://arxiv.org/abs/1905.12712
Cortolone,4TBDMS,#53935.014https://arxiv.org/abs/1905.12712
Cortolone,4TBDMS,#63940.1475https://arxiv.org/abs/1905.12712
Cortolone,4TBDMS,#73939.216https://arxiv.org/abs/1905.12712
Cortolone,4TBDMS,#83924.4412https://arxiv.org/abs/1905.12712
Cortolone,4TBDMS,#93916.846https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000j-3319000000-21ccb6077d496d19d89c2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-000l-1201139000-f10b8aa6b7295a4198132017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0019000000-1920aa591391279e5b032016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001j-0129000000-57e86c2dbf01a686c6ac2016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-2292000000-137b0f848fec6a19d4ee2016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-64630d6dbef8f1af9b952016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05n1-3039000000-a9418ec033a752ba2efa2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052u-5097000000-49285cc58950357637542016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-44285e972a9370f0bcdc2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-0009000000-0aa7cbf55342fd38a9de2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gbi-0049000000-0525ab10e5951e6696fb2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00l2-0009000000-a50c09cee301f58e3db52021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0901000000-7b1d26399016cdb46c422021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-8950000000-93ba12c45160faa96c072021-09-06View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
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 ]