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Record Information
Version1.0
Creation Date2016-09-30 22:18:48 UTC
Update Date2019-02-05 20:35:43 UTC
MCDB ID BMDB00037
Secondary Accession NumbersNone
Metabolite Identification
Common NameAldosterone
DescriptionAldosterone, also known as aldocorten or delta-aldosterone, 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. Aldosterone exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Aldosterone exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
Synonyms
ValueSource
(+)-AldosteroneHMDB
(11b)-11,21-Dihydroxy-3,20-dioxo-pregn-4-en-18-alHMDB
(11beta)-11,21-Dihydroxy-3,20-dioxo-pregn-4-en-18-alHMDB
11,21-Dihydroxy-3,20-dioxopregn-4-en-18-alHMDB
11-Hydroxy-17-(2-hydroxyacetyl)-10-methyl-3-oxo-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-13-carbaldehydeHMDB
11b,21-Dihydroxy-3,20-dioxo-pregn-4-en-18-alHMDB
11beta,21-Dihydroxy-3,20-diketo-4-pregnen-18-alHMDB
11beta,21-Dihydroxy-3,20-diketopregn-4-ene-18-alHMDB
11beta,21-Dihydroxy-3,20-dioxo-pregn-4-en-18-alHMDB
11beta,21-Dihydroxypregn-4-ene-3,18,20-trioneHMDB
18-Formyl-11beta,21-dihydroxy-4-pregnene-3,20-dioneHMDB
18-OxocorticosteroneHMDB
AldocortenHMDB
AldocorteneHMDB
AldocortinHMDB
AldosteronumHMDB
D-AldosteroneHMDB
delta-AldosteroneHMDB
ElectrocortinHMDB
ElektrocortinHMDB
Reichstein XHMDB
Chemical FormulaC21H28O5
Average Molecular Weight360.444
Monoisotopic Molecular Weight360.193674006
IUPAC Name(2R,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-15-carbaldehyde
Traditional Name(2R,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-15-carbaldehyde
CAS Registry Number52-39-1
SMILES
C[C@]12CCC(=O)C=C1CCC1C3CC[C@H](C(=O)CO)[C@]3(C[C@H](O)C21)C=O
InChI Identifier
InChI=1S/C21H28O5/c1-20-7-6-13(24)8-12(20)2-3-14-15-4-5-16(18(26)10-22)21(15,11-23)9-17(25)19(14)20/h8,11,14-17,19,22,25H,2-7,9-10H2,1H3/t14?,15?,16-,17+,19?,20+,21-/m1/s1
InChI KeyPQSUYGKTWSAVDQ-SRPWZAMTSA-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
  • 18-oxosteroid
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Aldehyde
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point166.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.051 mg/mL at 37 °CNot Available
LogP1.08HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP1.54ALOGPS
logP1.06ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)13.82ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity96.79 m³·mol⁻¹ChemAxon
Polarizability38.77 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fac-1819000000-0b50da8505c74770718eJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0553-1610900000-d3811f7824c7bb3be5f9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0009000000-eaba9dd7aea85d496f50JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01tc-0219000000-7247d6fc103cd84f62faJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0540-4494000000-f1432f7c464b86003cd4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-e56c87d6074fb6487b17JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-1019000000-bfed6380c146561bfa02JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9085000000-f708fe69e1df3e835b6fJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000037
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021883
KNApSAcK IDNot Available
Chemspider ID24774738
KEGG Compound IDC01780
BioCyc IDNot Available
BiGG ID38397
Wikipedia LinkAldosterone
METLIN ID418
PubChem Compound24758425
PDB IDNot Available
ChEBI ID27584
References
Synthesis ReferenceBear, Brian R.; Parnes, Jason S.; Shea, Kenneth J. Progress toward the Total Synthesis of (+)-Aldosterone: Synthesis of the A-D Rings. Organic Letters (2003), 5(10), 1613-1616.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]