Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:47 UTC
HMDB IDHMDB00037
Secondary Accession NumbersNone
Metabolite Identification
Common NameAldosterone
DescriptionAldosterone is a steroid hormone produced by the adrenal cortex in the adrenal gland to regulate sodium and potassium balance in the blood. Specifically it regulates electrolyte and water balance by increasing the renal retention of sodium and the excretion of potassium. It is synthesized from cholesterol by aldosterone synthase, which is absent in other sections of the adrenal gland. It is the sole endogenous member of the class of mineralocorticoids. Aldosterone increases the permeability of the apical (luminal) membrane of the kidney's collecting ducts to potassium and sodium and activates their basolateral Na+/K+ pumps, stimulating ATP hydrolysis, reabsorbing sodium (Na+) ions and water into the blood, and excreting potassium (K+) ions into the urine.
Structure
Thumb
Synonyms
  1. (+)-Aldosterone
  2. (11b)-11,21-dihydroxy-3,20-dioxo-pregn-4-en-18-al
  3. (11beta)-11,21-dihydroxy-3,20-dioxo-Pregn-4-en-18-al
  4. 11,21-Dihydroxy-3,20-dioxopregn-4-en-18-al
  5. 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-carbaldehyde
  6. 11b,21-Dihydroxy-3,20-dioxo-pregn-4-en-18-al
  7. 11beta,21-Dihydroxy-3,20-diketo-4-pregnen-18-al
  8. 11beta,21-Dihydroxy-3,20-diketopregn-4-ene-18-al
  9. 11beta,21-Dihydroxy-3,20-dioxo-pregn-4-en-18-al
  10. 11beta,21-Dihydroxypregn-4-ene-3,18,20-trione
  11. 18-Formyl-11beta,21-dihydroxy-4-pregnene-3,20-dione
  12. 18-Oxocorticosterone
  13. Aldocorten
  14. Aldocortene
  15. Aldocortin
  16. Aldosterone
  17. Aldosteronum
  18. D-Aldosterone
  19. delta-Aldosterone
  20. Electrocortin
  21. Elektrocortin
  22. Reichstein X
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 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
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
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassGluco/mineralocorticoids, Progestogins and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
Substituents
  • 11 Hydroxy Steroid
  • 20 Keto Steroid
  • 3 Keto Steroid
  • Aldehyde
  • Alpha Ketoaldehyde
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Decaline
  • Ketone
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentGluco/mineralocorticoids, Progestogins and Derivatives
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
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
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
water solubility0.15 g/LALOGPS
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 area91.67ChemAxon
rotatable bond count3ChemAxon
refractivity96.79ChemAxon
polarizability38.76ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations
  • Blood
  • Saliva
  • Urine
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
SteroidogenesisSMP00130map00140
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.000026 (0.000008 - 0.000044) uMAdult (>18 years old)BothNormal
  • Wu AHB. Tiet...
BloodDetected and Quantified0.00011 (0.000055 - 0.002) uMAdult (>18 years old)BothNormal
BloodDetected and Quantified0.000282 +/- 0.000037 uMElderly (>65 years old)BothCommentNormal
BloodDetected and Quantified0.000263 +/- 0.000014 uMAdult (>18 years old)BothCommentNormal
BloodDetected and Quantified0.00042 +/- 0.00004 uMElderly (>65 years old)BothCommentNormal
SalivaDetected and Quantified<1.00 uMAdult (>18 years old)BothNormal
UrineDetected and Quantified0.01 (0.006-0.014) umol/mmol creatinineAdult (>18 years old)BothNormal
  • Wu AHB. Tiet...
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.00041 +/- 0.00005 uMAdult (>18 years old)BothCommentHeart failure
BloodDetected and Quantified0.000233 +/- 0.000040 uMAdult (>18 years old)BothCommentHeart failure
Associated Disorders and Diseases
Disease References
Heart failure
  • Ferreira A, Bettencourt P, Pestana M, Correia F, Serrao P, Martins L, Cerqueira-Gomes M, Soares-Da-Silva P: Heart failure, aging, and renal synthesis of dopamine. Am J Kidney Dis. 2001 Sep;38(3):502-9. Pubmed: 11532681
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021883
KNApSAcK IDNot Available
Chemspider ID24774738
KEGG Compound IDC01780
BioCyc IDALDOSTERONE
BiGG ID38397
Wikipedia LinkAldosterone
NuGOwiki LinkHMDB00037
Metagene LinkHMDB00037
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)Not Available
General References
  1. Funder JW: The nongenomic actions of aldosterone. Endocr Rev. 2005 May;26(3):313-21. Epub 2005 Apr 6. Pubmed: 15814845
  2. Shima H, Kawanaka H, Yabumoto Y, Okamoto E, Ikoma F: A case of 17 alpha-hydroxylase deficiency with chromosomal karyotype 46,XY and high plasma aldosterone concentration. Int Urol Nephrol. 1991;23(6):611-8. Pubmed: 1769794
  3. Rosendahl W, Konig M, Haack D, Vecsei P, Lewicka S: [Variability of corticosterone methyl oxidase (type II) deficiency. Presentation of three case reports] Klin Padiatr. 1993 May-Jun;205(3):180-4. Pubmed: 8350592
  4. Christ M, Zange J, Janson CP, Muller K, Kuklinski P, Schmidt BM, Tillmann HC, Gerzer R, Wehling M: Hypoxia modulates rapid effects of aldosterone on oxidative metabolism in human calf muscle. J Endocrinol Invest. 2001 Sep;24(8):587-97. Pubmed: 11686541
  5. Lijnen P, Petrov V: Induction of cardiac fibrosis by aldosterone. J Mol Cell Cardiol. 2000 Jun;32(6):865-79. Pubmed: 10888242
  6. du Cheyron D, Lesage A, Daubin C, Ramakers M, Charbonneau P: Hyperreninemic hypoaldosteronism: a possible etiological factor of septic shock-induced acute renal failure. Intensive Care Med. 2003 Oct;29(10):1703-9. Epub 2003 Aug 28. Pubmed: 14551679
  7. Laskowska M, Leszczynska-Gorzelak B, Laskowska K, Oleszczuk J: Evaluation of the renin-angiotensin-aldosterone system in pregnancy complicated by preeclampsia with and without intrauterine growth retardation. Ann Univ Mariae Curie Sklodowska [Med]. 2004;59(2):451-6. Pubmed: 16146128
  8. Few JD, Chaudry S, James VH: The direct determination of aldosterone in human saliva. J Steroid Biochem. 1984 Jul;21(1):87-92. Pubmed: 6748658
  9. Cicoira M, Zanolla L, Franceschini L, Rossi A, Golia G, Zeni P, Caruso B, Zardini P: Relation of aldosterone "escape" despite angiotensin-converting enzyme inhibitor administration to impaired exercise capacity in chronic congestive heart failure secondary to ischemic or idiopathic dilated cardiomyopathy. Am J Cardiol. 2002 Feb 15;89(4):403-7. Pubmed: 11835920
  10. Goodfriend TL, Kelley DE, Goodpaster BH, Winters SJ: Visceral obesity and insulin resistance are associated with plasma aldosterone levels in women. Obes Res. 1999 Jul;7(4):355-62. Pubmed: 10440591
  11. Lewicka S, Vecsei P, Bige K, Fisher T, Winter J, Abdelhamid S, Heinrich U, Bokkenheuser VD: Urinary excretion of aldosterone metabolite Kelly-M1 in patients with adrenal dysfunction. J Steroid Biochem. 1988 Mar;29(3):333-9. Pubmed: 3258645
  12. Heindl S, Holzschneider J, Hinz A, Sayk F, Fehm HL, Dodt C: Acute effects of aldosterone on the autonomic nervous system and the baroreflex function in healthy humans. J Neuroendocrinol. 2006 Feb;18(2):115-21. Pubmed: 16420280
  13. Engeli S, Bohnke J, Gorzelniak K, Janke J, Schling P, Bader M, Luft FC, Sharma AM: Weight loss and the renin-angiotensin-aldosterone system. Hypertension. 2005 Mar;45(3):356-62. Epub 2005 Jan 3. Pubmed: 15630041
  14. Velazquez H, Perazella MA, Wright FS, Ellison DH: Renal mechanism of trimethoprim-induced hyperkalemia. Ann Intern Med. 1993 Aug 15;119(4):296-301. Pubmed: 8328738
  15. Touger L, Joseph M, Hasan KS: Hypertension in a patient with aldosterone deficiency. Endocr Pract. 2005 Mar-Apr;11(2):104-7. Pubmed: 15901525
  16. Summa V, Camargo SM, Bauch C, Zecevic M, Verrey F: Isoform specificity of human Na(+), K(+)-ATPase localization and aldosterone regulation in mouse kidney cells. J Physiol. 2004 Mar 1;555(Pt 2):355-64. Epub 2003 Dec 23. Pubmed: 14694143
  17. Fox CS, Larson MG, Hwang SJ, Leip EP, Rifai N, Levy D, Benjamin EJ, Murabito JM, Meigs JB, Vasan RS: Cross-sectional relations of serum aldosterone and urine sodium excretion to urinary albumin excretion in a community-based sample. Kidney Int. 2006 Jun;69(11):2064-9. Pubmed: 16572107
  18. Badalian SS, Mikhailov AV: [Characteristics of the renin-aldosterone system of the fetoplacental complex in fetal erythroblastosis] Akush Ginekol (Mosk). 1990 May;(5):55-8. Pubmed: 2118736
  19. Tanemoto M, Abe T, Obara N, Abe M, Satoh F, Ito S: Successful treatment of severe hypertension with the combination of angiotensin converting enzyme inhibitor and angiotensin II receptor blocker. Hypertens Res. 2003 Oct;26(10):863-8. Pubmed: 14621191
  20. Pitt B, Stier CT Jr, Rajagopalan S: Mineralocorticoid receptor blockade: new insights into the mechanism of action in patients with cardiovascular disease. J Renin Angiotensin Aldosterone Syst. 2003 Sep;4(3):164-8. Pubmed: 14608520

Enzymes

Gene Name:
CYP11B1
Uniprot ID:
P15538
Reactions
Deoxycorticosterone + Reduced adrenal ferredoxin + Oxygen unknown Aldosterone + Oxidized adrenal ferredoxin + Waterdetails
Gene Name:
AKR1D1
Uniprot ID:
P51857
Reactions
11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al + NADP unknown Aldosterone + NADPH + Hydrogen Iondetails
Gene Name:
EGFR
Uniprot ID:
P00533
Gene Name:
PRKD1
Uniprot ID:
Q15139
Gene Name:
FN1
Uniprot ID:
P02751
Gene Name:
NPPB
Uniprot ID:
P16860
Gene Name:
CTGF
Uniprot ID:
P29279
Gene Name:
AGTR1
Uniprot ID:
P30556
Gene Name:
NR3C2
Uniprot ID:
P08235
11. ADM
Gene Name:
ADM
Uniprot ID:
P35318
Gene Name:
PTGER4
Uniprot ID:
P35408
Gene Name:
CYP11B2
Uniprot ID:
P19099
Reactions
18-Hydroxycorticosterone + Reduced adrenal ferredoxin + Oxygen unknown Aldosterone + Oxidized adrenal ferredoxin + Waterdetails
Gene Name:
MLPH
Uniprot ID:
Q9BV36