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Identification
Name Aldosterone
Accession Number DB04630
Type small molecule
Groups experimental
Description

A hormone secreted by the adrenal cortex that regulates electrolyte and water balance by increasing the renal retention of sodium and the excretion of potassium. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
(+)-aldosterone
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-4-pregnen-18-al
11beta,21-dihydroxy-3,20-dioxo-pregn-4-ene-18-al
11beta,21-dihydroxy-3,20-dioxopregn-4-en-18-al
11beta,21-Dihydroxypregn-4-ene-3,18,20-trione
18-Aldocorticosterone
18-Formyl-11beta,21-dihydroxy-4-pregnene-3,20-dione
18-Oxocorticosterone
Aldocorten
Aldocortene
Aldocortin
Aldosterona [inn-spanish]
Aldosteronum [inn-latin]
D-aldosterone
Electrocortin
Elektrocortin
First Prev Next Last
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories Not Available
CAS number 52-39-1
Weight Average: 360.444
Monoisotopic: 360.193674006
Chemical Formula C21H28O5
InChI Key InChIKey=PQSUYGKTWSAVDQ-ZVIOFETBSA-N
InChI
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
Plain Text
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
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])[C@@]([H])(O)C[C@]12C=O)C(=O)CO
Plain Text
Mass Spec show (12.2 KB)
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Not Available
Pharmacodynamics At the late distal tubule and collecting duct, aldosterone has two main actions: 1) aldosterone acts on mineralocorticoid receptors (MR) on principal cells in the distal tubule of the kidney nephron, increasing the permeability of their apical (luminal) membrane to potassium and sodium and activates their basolateral Na+/K+ pumps, stimulating ATP hydrolysis leading to phosphorylation of the pump and a conformational change in the pump exposes the Na+ ions to the outside. The phosphorylated form of the pump has a low affinity for Na+ ions, hence reabsorbing sodium (Na+) ions and water into the blood, and secreting potassium (K+) ions into the urine; 2) aldosterone stimulates H+ secretion by intercalated cells in the collecting duct, regulating plasma bicarbonate (HCO3−) levels and its acid/base balance; and 3) aldosterone may act on the central nervous system via the posterior pituitary gland to release vasopressin (ADH) which serves to conserve water by direct actions on renal tubular resorption.
Mechanism of action Not Available
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Not Available

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Aldosterone
    		Aldosterone 18-glucuronide Details
    Aldosterone
      		Tetrahydroaldosterone-3-glucuronide Details
      Route of elimination Not Available
      Half life Not Available
      Clearance Not Available
      Toxicity Not Available
      Affected organisms
      • Humans and other mammals
      Pathways Not Available
      Pharmacoeconomics
      Manufacturers Not Available
      Packagers Not Available
      Dosage forms Not Available
      Prices Not Available
      Patents Not Available
      Properties
      State solid
      Experimental Properties
      Property Value Source
      melting point 166.5 °C PhysProp
      water solubility 51.2 mg/L (at 37 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
      logP 1.08 HANSCH,C ET AL. (1995)
      Predicted Properties
      Property Value Source
      water solubility 1.48e-01 g/l ALOGPS
      logP 1.54 ALOGPS
      logP 1.06 ChemAxon
      logS -3.4 ALOGPS
      pKa (strongest acidic) 13.82 ChemAxon
      pKa (strongest basic) -2.9 ChemAxon
      physiological charge 0 ChemAxon
      hydrogen acceptor count 5 ChemAxon
      hydrogen donor count 2 ChemAxon
      polar surface area 91.67 ChemAxon
      rotatable bond count 3 ChemAxon
      refractivity 96.79 ChemAxon
      polarizability 38.87 ChemAxon
      References
      Synthesis Reference Not Available
      General Reference
      1. Williams JS, Williams GH: 50th anniversary of aldosterone. J Clin Endocrinol Metab. 2003 Jun;88(6):2364-72. Pubmed
      External Links
      Resource Link
      KEGG Compound C01780 Link_out
      PubChem Compound 5839 Link_out
      PubChem Substance 46505770 Link_out
      ChemSpider 5633 Link_out
      ChEBI 27584 Link_out
      ChEMBL 27584 Link_out
      Therapeutic Targets Database DAP001344 Link_out
      PharmGKB PA164924487 Link_out
      HET AS4 Link_out
      Wikipedia http://en.wikipedia.org/wiki/Aldosterone Link_out
      ATC Codes
      • H02AA01
      AHFS Codes Not Available
      PDB Entries Not Available
      FDA label Not Available
      MSDS show (68.4 KB)
      Interactions
      Drug Interactions Not Available
      Food Interactions Not Available
      Targets

      1. Mineralocorticoid receptor

      Pharmacological action: unknown

      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

      Organism class: human
      UniProt ID: P08235 Link_out
      Gene: NR3C2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Bruner KL, Derfoul A, Robertson NM, Guerriero G, Fernandes-Alnemri T, Alnemri ES, Litwack G: The unliganded mineralocorticoid receptor is associated with heat shock proteins 70 and 90 and the immunophilin FKBP-52. Recept Signal Transduct. 1997;7(2):85-98. Pubmed
      2. Bunda S, Liu P, Wang Y, Liu K, Hinek A: Aldosterone induces elastin production in cardiac fibroblasts through activation of insulin-like growth factor-I receptors in a mineralocorticoid receptor-independent manner. Am J Pathol. 2007 Sep;171(3):809-19. Pubmed
      3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed
      Enzymes

      1. Cytochrome P450 11B1, mitochondrial

      Actions: substrate

      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

      UniProt ID: P15538 Link_out
      Gene: CYP11B1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

      2. Cytochrome P450 11B2, mitochondrial

      Actions: substrate

      Preferentially catalyzes the conversion of 11- deoxycorticosterone to aldosterone via corticosterone and 18- hydroxycorticosterone

      UniProt ID: P19099 Link_out
      Gene: CYP11B2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

      3. Cytochrome P450 17A1

      Actions: inducer

      Conversion of pregnenolone and progesterone to their 17- alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation and the 17,20-lyase reaction. Involved in sexual development during fetal life and at puberty

      UniProt ID: P05093 Link_out
      Gene: CYP17A1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
      Transporters

      1. Multidrug resistance protein 1

      Actions: substrate, inducer

      Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

      UniProt ID: P08183 Link_out
      Gene: ABCB1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Romiti N, Tramonti G, Chieli E: Influence of different chemicals on MDR-1 P-glycoprotein expression and activity in the HK-2 proximal tubular cell line. Toxicol Appl Pharmacol. 2002 Sep 1;183(2):83-91. Pubmed
      2. Ueda K, Okamura N, Hirai M, Tanigawara Y, Saeki T, Kioka N, Komano T, Hori R: Human P-glycoprotein transports cortisol, aldosterone, and dexamethasone, but not progesterone. J Biol Chem. 1992 Dec 5;267(34):24248-52. Pubmed

      2. Organic cation/carnitine transporter 2

      Actions: inhibitor

      Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also Relative uptake activity ratio of carnitine to TEA is 11.3

      UniProt ID: O76082 Link_out
      Gene: SLC22A5 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. Pubmed

      3. Solute carrier organic anion transporter family member 1A2

      Actions: inhibitor

      Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity)

      UniProt ID: P46721 Link_out
      Gene: SLCO1A2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Kanai N, Lu R, Bao Y, Wolkoff AW, Schuster VL: Transient expression of oatp organic anion transporter in mammalian cells: identification of candidate substrates. Am J Physiol. 1996 Feb;270(2 Pt 2):F319-25. Pubmed
      2. Bossuyt X, Muller M, Hagenbuch B, Meier PJ: Polyspecific drug and steroid clearance by an organic anion transporter of mammalian liver. J Pharmacol Exp Ther. 1996 Mar;276(3):891-6. Pubmed
      Comments
      Drug created on September 11, 2007 11:49 / Updated on February 08, 2013 16:23