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Record Information
Version1.0
Creation Date2016-09-30 22:18:48 UTC
Update Date2020-03-18 18:12:34 UTC
BMDB IDBMDB0000037
Secondary Accession Numbers
  • BMDB00037
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
(+)-AldosteroneChEBI
(11beta)-11,21-Dihydroxy-3,20-dioxopregn-4-en-18-alChEBI
11beta,21-Dihydroxy-3,20-dioxo-4-pregnen-18-alChEBI
(11b)-11,21-Dihydroxy-3,20-dioxopregn-4-en-18-alGenerator
(11Β)-11,21-dihydroxy-3,20-dioxopregn-4-en-18-alGenerator
11b,21-Dihydroxy-3,20-dioxo-4-pregnen-18-alGenerator
11Β,21-dihydroxy-3,20-dioxo-4-pregnen-18-alGenerator
Aldosterone, (+-)-isomerHMDB
Aldosterone, (11 beta,17 alpha)-isomerHMDB
11beta,21-Dihydroxy-3,20-diketo-4-pregnen-18-alHMDB
11beta,21-Dihydroxy-3,20-diketopregn-4-ene-18-alHMDB
11beta,21-Dihydroxypregn-4-ene-3,18,20-trioneHMDB
11Β,21-dihydroxy-3,20-diketo-4-pregnen-18-alHMDB
11Β,21-dihydroxy-3,20-diketopregn-4-ene-18-alHMDB
11Β,21-dihydroxypregn-4-ene-3,18,20-trioneHMDB
18-Formyl-11beta,21-dihydroxy-4-pregnene-3,20-dioneHMDB
18-Formyl-11β,21-dihydroxy-4-pregnene-3,20-dioneHMDB
18-OxocorticosteroneHMDB
AldosteroneHMDB
Chemical FormulaC21H28O5
Average Molecular Weight360.444
Monoisotopic Molecular Weight360.193674006
IUPAC Name(1S,2R,10S,11S,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(1S,2R,10S,11S,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
[H][C@@]12CC[C@H](C(=O)CO)[C@]1(C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C)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+/m0/s1
InChI KeyPQSUYGKTWSAVDQ-ZVIOFETBSA-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 Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point166.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0512 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
Polarizability38.82 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-06si-0694000000-60e1d35ad11d153b5152View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0596-2961000000-38453356e63a34116d1eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0596-2961000000-38453356e63a34116d1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0019000000-2c34b91dc8d5030ac25bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01tc-0219000000-9e4b8f664dbb988d46f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0540-4594000000-185caf2f40c5027fdb0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-ba327369eee699ad5a21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-1019000000-f6f3606b25ff21806842View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbc-8096000000-deeb08e544bed8419dd5View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Milk
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Cardiovascular System
  • Fibroblasts
  • Intestine
  • Kidney
  • Lung
  • Muscle
  • Nerve Cells
  • Pancreas
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Testes
  • Thyroid Gland
Pathways
NameSMPDB LinkKEGG Link
Angiotensin MetabolismSMP0119379Not Available
Kidney FunctionSMP0119376Not Available
SteroidogenesisSMP0087238Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04630
Phenol Explorer Compound IDNot Available
FooDB IDFDB021883
KNApSAcK IDNot Available
Chemspider ID5633
KEGG Compound IDC01780
BioCyc IDALDOSTERONE
BiGG IDNot Available
Wikipedia LinkAldosterone
METLIN IDNot Available
PubChem Compound5839
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)Not Available
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 ]

Enzymes

General function:
Involved in prostaglandin E receptor activity
Specific function:
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. Has a relaxing effect on smooth muscle. May play an important role in regulating renal hemodynamics, intestinal epithelial transport, adrenal aldosterone secretion, and uterine function (By similarity).
Gene Name:
PTGER4
Uniprot ID:
Q8MJ08
Molecular weight:
53298.0
General function:
Involved in hormone activity
Specific function:
Cardiac hormone which may function as a paracrine antifibrotic factor in the heart. Also plays a key role in cardiovascular homeostasis through natriuresis, diuresis, vasorelaxation, and inhibition of renin and aldosterone secretion. Specifically binds and stimulates the cGMP production of the NPR1 receptor. Binds the clearance receptor NPR3 (By similarity).
Gene Name:
NPPB
Uniprot ID:
P13204
Molecular weight:
14113.0