Human Metabolome Database Version 3.5

Showing metabocard for Aldosterone (HMDB00037)

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 Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 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
  • 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
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
Property Value Source
Water Solubility 0.15 g/L ALOGPS
LogP 1.54 ALOGPS
LogP 1.06 ChemAxon
LogS -3.39 ALOGPS
pKa (strongest acidic) 13.82 ChemAxon
pKa (strongest basic) -2.9 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 91.67 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 96.79 ChemAxon
Polarizability 38.76 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations
  • Blood
  • Saliva
  • Urine
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
Name SMPDB Link KEGG Link
Steroidogenesis SMP00130 map00140 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.000026 (0.000008 - 0.000044) uM Adult (>18 years old) Both Normal
  • Wu AHB. Tiet...
Blood Detected and Quantified
0.00011 (0.000055 - 0.002) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.000282 +/- 0.000037 uM Elderly (>65 years old) Both Comment Normal
Blood Detected and Quantified
0.000263 +/- 0.000014 uM Adult (>18 years old) Both Comment Normal
Blood Detected and Quantified
0.00042 +/- 0.00004 uM Elderly (>65 years old) Both Comment Normal
Saliva Detected and Quantified
<1.00 uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.01 (0.006-0.014) umol/mmol creatinine Adult (>18 years old) Both Normal
  • Wu AHB. Tiet...
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.00041 +/- 0.00005 uM Adult (>18 years old) Both Comment Heart failure
Blood Detected and Quantified 0.000233 +/- 0.000040 uM Adult (>18 years old) Both Comment Heart 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 Link_out
      Associated OMIM IDs None
      DrugBank ID Not Available
      DrugBank Metabolite 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 Link_out
      KEGG Compound ID C01780 Link_out
      BioCyc ID ALDOSTERONE Link_out
      BiGG ID 38397 Link_out
      Wikipedia Link Aldosterone Link_out
      NuGOwiki Link HMDB00037 Link_out
      Metagene Link HMDB00037 Link_out
      METLIN ID 418 Link_out
      PubChem Compound 24758425 Link_out
      PDB ID Not Available
      ChEBI ID 27584 Link_out
      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
      1. Funder JW: The nongenomic actions of aldosterone. Endocr Rev. 2005 May;26(3):313-21. Epub 2005 Apr 6. Pubmed: 15814845 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      5. Lijnen P, Petrov V: Induction of cardiac fibrosis by aldosterone. J Mol Cell Cardiol. 2000 Jun;32(6):865-79. Pubmed: 10888242 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out

      Enzymes
      Name: Cytochrome P450 11B1, mitochondrial
      Reactions:
      Deoxycorticosterone + Reduced adrenal ferredoxin + Oxygen unknown Aldosterone + Oxidized adrenal ferredoxin + Water details
      Gene Name: CYP11B1
      Uniprot ID: P15538 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: 3-oxo-5-beta-steroid 4-dehydrogenase
      Reactions:
      11b,21-Dihydroxy-3,20-oxo-5b-pregnan-18-al + NADP unknown Aldosterone + NADPH + Hydrogen Ion details
      Gene Name: AKR1D1
      Uniprot ID: P51857 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Serine/threonine-protein kinase Sgk1
      Reactions: Not Available
      Gene Name: SGK1
      Uniprot ID: O00141 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Epidermal growth factor receptor
      Reactions: Not Available
      Gene Name: EGFR
      Uniprot ID: P00533 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Serine/threonine-protein kinase D1
      Reactions: Not Available
      Gene Name: PRKD1
      Uniprot ID: Q15139 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Fibronectin
      Reactions: Not Available
      Gene Name: FN1
      Uniprot ID: P02751 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Natriuretic peptides B
      Reactions: Not Available
      Gene Name: NPPB
      Uniprot ID: P16860 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Connective tissue growth factor
      Reactions: Not Available
      Gene Name: CTGF
      Uniprot ID: P29279 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Type-1 angiotensin II receptor
      Reactions: Not Available
      Gene Name: AGTR1
      Uniprot ID: P30556 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Mineralocorticoid receptor
      Reactions: Not Available
      Gene Name: NR3C2
      Uniprot ID: P08235 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: ADM
      Reactions: Not Available
      Gene Name: ADM
      Uniprot ID: P35318 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Prostaglandin E2 receptor EP4 subtype
      Reactions: Not Available
      Gene Name: PTGER4
      Uniprot ID: P35408 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Cytochrome P450 11B2, mitochondrial
      Reactions:
      18-Hydroxycorticosterone + Reduced adrenal ferredoxin + Oxygen unknown Aldosterone + Oxidized adrenal ferredoxin + Water details
      Gene Name: CYP11B2
      Uniprot ID: P19099 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Melanophilin
      Reactions: Not Available
      Gene Name: MLPH
      Uniprot ID: Q9BV36 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA