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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 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 Solubility0.15ALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity96.79 m3·mol-1ChemAxon
Polarizability38.76 Å3ChemAxon
Spectra
Spectra1D NMR2D NMR
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
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000026 (0.000008 - 0.000044) uMAdult (>18 years old)BothNormal
    • Wu AHB. Tietz cli...
details
BloodDetected and Quantified0.00011 (0.000055 - 0.002) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000282 +/- 0.000037 uMElderly (>65 years old)Both
Normal
details
BloodDetected and Quantified0.000263 +/- 0.000014 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00042 +/- 0.00004 uMElderly (>65 years old)Both
Normal
details
SalivaDetected and Quantified<1.00 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.01 (0.006-0.014) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Wu AHB. Tietz cli...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00041 +/- 0.00005 uMAdult (>18 years old)Both
Heart failure
details
BloodDetected and Quantified0.000233 +/- 0.000040 uMAdult (>18 years old)Both
Heart failure
details
Associated Disorders and Diseases
Disease References
Heart failure
  1. 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)Download (PDF)
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

General function:
Involved in monooxygenase activity
Specific function:
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:
CYP11B1
Uniprot ID:
P15538
Molecular weight:
57572.44
Reactions
Deoxycorticosterone + Reduced adrenal ferredoxin + Oxygen → Aldosterone + Oxidized adrenal ferredoxin + Waterdetails
General function:
Involved in oxidoreductase activity
Specific function:
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38
Reactions
11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al + NADP → Aldosterone + NADPH + Hydrogen Iondetails
General function:
Involved in protein serine/threonine kinase activity
Specific function:
Protein kinase that plays an important role in cellular stress response. Activates certain potassium, sodium, and chloride channels, suggesting an involvement in the regulation of processes such as cell survival, neuronal excitability and renal sodium excretion. Sustained high levels and activity may contribute to conditions such as hypertension and diabetic nephropathy. Mediates cell survival signals, phosphorylates and negatively regulates pro-apoptotic FOXO3A. Phosphorylates NEDD4L, which leads to its inactivation and to the subsequent activation of various channels and transporters such as ENaC, KCNA3/Kv1.3 or EAAT1. Isoform 2 exhibited a greater effect on cell plasma membrane expression of ENaC and Na(+) transport than isoform 1
Gene Name:
SGK1
Uniprot ID:
O00141
Molecular weight:
48942.0
References
  1. Cordas E, Naray-Fejes-Toth A, Fejes-Toth G: Subcellular location of serum- and glucocorticoid-induced kinase-1 in renal and mammary epithelial cells. Am J Physiol Cell Physiol. 2007 May;292(5):C1971-81. Epub 2007 Jan 3. Pubmed: 17202226
General function:
Involved in transmembrane receptor protein tyrosine kinase activity
Specific function:
Isoform 2 may act as an antagonist of EGF action
Gene Name:
EGFR
Uniprot ID:
P00533
Molecular weight:
134276.2
References
  1. McEneaney V, Harvey BJ, Thomas W: Aldosterone rapidly activates protein kinase D via a mineralocorticoid receptor/EGFR trans-activation pathway in the M1 kidney CCD cell line. J Steroid Biochem Mol Biol. 2007 Nov-Dec;107(3-5):180-90. Epub 2007 Jun 22. Pubmed: 17681751
General function:
Involved in intracellular signaling pathway
Specific function:
Converts transient diacylglycerol (DAG) signals into prolonged physiological effects, downstream of PKC. Involved in resistance to oxidative stress through activation of NF-kappa-B
Gene Name:
PRKD1
Uniprot ID:
Q15139
Molecular weight:
101703.3
References
  1. McEneaney V, Harvey BJ, Thomas W: Aldosterone regulates rapid trafficking of epithelial sodium channel subunits in renal cortical collecting duct cells via protein kinase D activation. Mol Endocrinol. 2008 Apr;22(4):881-92. Epub 2008 Jan 17. Pubmed: 18202152
General function:
Involved in collagen binding
Specific function:
Anastellin binds fibronectin and induces fibril formation. This fibronectin polymer, named superfibronectin, exhibits enhanced adhesive properties. Both anastellin and superfibronectin inhibit tumor growth, angiogenesis and metastasis. Anastellin activates p38 MAPK and inhibits lysophospholipid signaling
Gene Name:
FN1
Uniprot ID:
P02751
Molecular weight:
262623.1
References
  1. Lai L, Chen J, Hao CM, Lin S, Gu Y: Aldosterone promotes fibronectin production through a Smad2-dependent TGF-beta1 pathway in mesangial cells. Biochem Biophys Res Commun. 2006 Sep 15;348(1):70-5. Epub 2006 Jul 21. Pubmed: 16876110
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
Gene Name:
NPPB
Uniprot ID:
P16860
Molecular weight:
14725.8
General function:
Involved in insulin-like growth factor binding
Specific function:
Major connective tissue mitoattractant secreted by vascular endothelial cells. Promotes proliferation and differentiation of chondrocytes. Mediates heparin- and divalent cation-dependent cell adhesion in many cell types including fibroblasts, myofibroblasts, endothelial and epithelial cells. Enhances fibroblast growth factor-induced DNA synthesis
Gene Name:
CTGF
Uniprot ID:
P29279
Molecular weight:
38091.0
References
  1. Gauer S, Segitz V, Goppelt-Struebe M: Aldosterone induces CTGF in mesangial cells by activation of the glucocorticoid receptor. Nephrol Dial Transplant. 2007 Nov;22(11):3154-9. Epub 2007 Jun 30. Pubmed: 17602195
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for angiotensin II. Mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:
AGTR1
Uniprot ID:
P30556
Molecular weight:
41060.5
References
  1. Yamada M, Kushibiki M, Osanai T, Tomita H, Okumura K: Vasoconstrictor effect of aldosterone via angiotensin II type 1 (AT1) receptor: possible role of AT1 receptor dimerization. Cardiovasc Res. 2008 Jul 1;79(1):169-78. Epub 2008 Mar 7. Pubmed: 18326554
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates target genes. The effect of MC is to increase ion and water transport and thus raise extracellular fluid volume and blood pressure and lower potassium levels
Gene Name:
NR3C2
Uniprot ID:
P08235
Molecular weight:
107066.6
References
  1. White WB: Drospirenone with 17beta-estradiol in the postmenopausal woman with hypertension. Climacteric. 2007 Feb;10 Suppl 1:25-31. Pubmed: 17364595
General function:
Involved in hormone activity
Specific function:
AM and PAMP are potent hypotensive and vasodilatator agents. Numerous actions have been reported most related to the physiologic control of fluid and electrolyte homeostasis. In the kidney, am is diuretic and natriuretic, and both am and pamp inhibit aldosterone secretion by direct adrenal actions. In pituitary gland, both peptides at physiologically relevant doses inhibit basal ACTH secretion. Both peptides appear to act in brain and pituitary gland to facilitate the loss of plasma volume, actions which complement their hypotensive effects in blood vessels
Gene Name:
ADM
Uniprot ID:
P35318
Molecular weight:
20420.2
General function:
Involved in G-protein coupled receptor protein signaling pathway
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
Gene Name:
PTGER4
Uniprot ID:
P35408
Molecular weight:
53118.8
General function:
Involved in monooxygenase activity
Specific function:
Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
Gene Name:
CYP11B2
Uniprot ID:
P19099
Molecular weight:
57559.62
Reactions
18-Hydroxycorticosterone + Reduced adrenal ferredoxin + Oxygen → Aldosterone + Oxidized adrenal ferredoxin + Waterdetails
General function:
Involved in Rab GTPase binding
Specific function:
Rab effector protein involved in melanosome transport. Serves as link between melanosome-bound RAB27A and the motor protein MYO5A
Gene Name:
MLPH
Uniprot ID:
Q9BV36
Molecular weight:
65948.5
References
  1. Martel JA, Michael D, Fejes-Toth G, Naray-Fejes-Toth A: Melanophilin, a novel aldosterone-induced gene in mouse cortical collecting duct cells. Am J Physiol Renal Physiol. 2007 Sep;293(3):F904-13. Epub 2007 Jul 3. Pubmed: 17609287