| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:07:47 -0700 |
| HMDB ID |
HMDB00037 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Aldosterone |
| Description |
Aldosterone 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (+)-Aldosterone
- (11b)-11,21-dihydroxy-3,20-dioxo-pregn-4-en-18-al
- (11beta)-11,21-dihydroxy-3,20-dioxo-Pregn-4-en-18-al
- 11,21-Dihydroxy-3,20-dioxopregn-4-en-18-al
- 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
- 11b,21-Dihydroxy-3,20-dioxo-pregn-4-en-18-al
- 11beta,21-Dihydroxy-3,20-diketo-4-pregnen-18-al
- 11beta,21-Dihydroxy-3,20-diketopregn-4-ene-18-al
- 11beta,21-Dihydroxy-3,20-dioxo-pregn-4-en-18-al
- 11beta,21-Dihydroxypregn-4-ene-3,18,20-trione
- 18-Formyl-11beta,21-dihydroxy-4-pregnene-3,20-dione
- 18-Oxocorticosterone
- Aldocorten
- Aldocortene
- Aldocortin
- Aldosterone
- Aldosteronum
- D-Aldosterone
- delta-Aldosterone
- Electrocortin
- Elektrocortin
- Reichstein X
|
| Chemical Formula |
C21H28O5 |
| Average Molecular Weight |
360.444 |
| Monoisotopic Molecular Weight |
360.193674006 |
| 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 Number |
52-39-1 |
| 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 Key |
PQSUYGKTWSAVDQ-SRPWZAMTSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Steroids and Steroid Derivatives |
| Sub Class |
Gluco/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 Parent |
Gluco/mineralocorticoids, Progestogins and Derivatives |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| 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 |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
166.5 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
0.0512 mg/mL at 37 °C |
Not Available |
| LogP |
1.08 |
HANSCH,C ET AL. (1995) |
|
| Predicted Properties |
|
| Spectra |
|---|
|
|
| Biological Properties |
|---|
| Cellular Locations |
- Cytoplasm
- Extracellular
- Membrane
- Mitochondria
|
| Biofluid Locations |
|
| Tissue Location |
- Muscle
- Skeletal Muscle
- Fibroblasts
- Intestine
- Pancreas
- Placenta
- Testes
- Kidney
- Thyroid Gland
- Adrenal Gland
- Adipose Tissue
- Adrenal Cortex
- Adrenal Medulla
- Cardiovascular System
- Lung
- Nerve Cells
- Platelet
|
| Pathways |
|
| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.000026 (0.000008 - 0.000044) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.00011 (0.000055 - 0.002) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
0.000282 +/- 0.000037 uM |
Elderly (>65 years old) |
Both |
Normal |
In plasma from subjects older than 55 years...
|
| Blood |
Detected and Quantified |
|
0.000263 +/- 0.000014 uM |
Adult (>18 years old) |
Both |
Normal |
In plasma from subjects less than 30 yo after...
|
| Blood |
Detected and Quantified |
|
0.00042 +/- 0.00004 uM |
Elderly (>65 years old) |
Both |
Normal |
In plasma after 8 days of low-salt intake
|
| Saliva |
Detected and Quantified |
|
<1.00 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.01 (0.006-0.014) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.00041 +/- 0.00005 uM |
Adult (>18 years old) |
Both |
Heart failure |
In plasma after 8 days of low-salt intake
|
| Blood |
Detected and Quantified |
|
0.000233 +/- 0.000040 uM |
Adult (>18 years old) |
Both |
Heart failure |
In plasma after 8 days of normal-salt intake
|
|
| 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 IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB021883 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
24774738 |
| KEGG Compound ID |
C01780 |
| BioCyc ID |
ALDOSTERONE |
| BiGG ID |
38397 |
| Wikipedia Link |
Aldosterone |
| NuGOwiki Link |
HMDB00037 |
| Metagene Link |
HMDB00037 |
| METLIN ID |
418 |
| PubChem Compound |
24758425 |
| PDB ID |
Not Available |
| ChEBI ID |
27584 |
| References |
|---|
| Synthesis Reference |
Bear, 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 |
- Funder JW: The nongenomic actions of aldosterone. Endocr Rev. 2005 May;26(3):313-21. Epub 2005 Apr 6.
Pubmed: 15814845
- 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
- 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
- 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
- Lijnen P, Petrov V: Induction of cardiac fibrosis by aldosterone. J Mol Cell Cardiol. 2000 Jun;32(6):865-79.
Pubmed: 10888242
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Touger L, Joseph M, Hasan KS: Hypertension in a patient with aldosterone deficiency. Endocr Pract. 2005 Mar-Apr;11(2):104-7.
Pubmed: 15901525
- 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
- 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
- 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
- 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
- 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
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