(1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2-methyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-15-carbaldehyde

• ChemBase ID: 4191
• Molecular Formular: C21H28O5
• Molecular Mass: 360.44402
• Monoisotopic Mass: 360.193674
• SMILES: [C@@H]12CC[C@H](C(=O)CO)[C@]1(C[C@@H]([C@@H]1[C@@]3(C(=CC(=O)CC3)CC[C@@H]21)C)O)C=O
• Canonical SMILES: OCC(=O)[C@H]1CC[C@@H]2[C@]1(C=O)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• 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
• InChIKey: PQSUYGKTWSAVDQ-ZVIOFETBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14S,15R,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-15-carbaldehyde; (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
• IUPAC Traditional name: aldosterone
• Synonyms: 11β,21-Dihydroxy-3,20-dioxo-4-pregnen-18-al; 11β,21-Dihydroxypregn-4-ene-3,18,20-trione; Reichstein X; Aldosterone; (+)-aldosterone; 11beta,21-Dihydroxy-3,20-diketo-4-pregnen-18-al; 11beta,21-Dihydroxy-3,20-diketopregn-4-ene-18-al; 11beta,21-Dihydroxypregn-4-ene-3,18,20-trione; 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; 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; Aldosterone

Database IDs

• CAS Number: 52-39-1
• EC Number: 200-139-9
• MDL Number: MFCD00051136
• Beilstein Number: 3224996
• PubChem SID: 46505770; 160967623; 24891458
• PubChem CID: 5839
• CHEBI ID: 27584
• ATC CODE: H02AA01
• CHEMBL: 273453
• Chemspider ID: 5633
• DrugBank ID: DB04630
• KEGG ID: C01780
• MeSH Name: Aldosterone
• Unique Ingredient Identifier: 4964P6T9RB
• Wikipedia Title: Aldosterone

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.819593
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.0556679
• LogD (pH = 7.4): 1.0556678
• Log P: 1.0556679
• Molar Refractivity: 96.7918 cm^3
• Polarizability: 37.741665 Å^3
• Polar Surface Area: 91.67 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.54
• LOG S: -3.39
• Solubility (Water): 1.48e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.0512 mg/mL at 37 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Hydrophobicity(logP): 1.08 [HANSCH,C ET AL. (1995)]

Safety Information

• RTECS: TU4523000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... SERPINA6(866)rat ... Ar(24208), Nr3c2(25672)

Product Information

• Purity: ≥95% (HPLC); ≥98.5% (UV)
• Empirical Formula (Hill Notation): C21H28O5

DETAILS

DrugBank - DB04630

• Drug 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]
• Pharmacology: 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.
• Affected Organisms: Humans and other mammals
• References: Williams JS, Williams GH: 50th anniversary of aldosterone. J Clin Endocrinol Metab. 2003 Jun;88(6):2364-72. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - A9477

Frequently Asked Questions
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Application
The d-isomer of aldosterone is considered to be the biologically active isomer.
Biochem/physiol Actions
Biologically active aldosterone isomer; a mineralocorticoid produced by the adrenal cortex that induces urinary excretion of K+ and renal reabsorption of Na+.
Other Notes
Exists as an equilibrium mixture of the aldehyde and the hemiacetal.

Sigma Aldrich - 05521

Application
The d-isomer of aldosterone is considered to be the biologically active isomer.
Other Notes
Exists as an equilibrium mixture of the aldehyde and the hemiacetal.
Sales restrictions may apply

REFERENCES

• Williams JS, Williams GH: 50th anniversary of aldosterone. J Clin Endocrinol Metab. 2003 Jun;88(6):2364-72. Pubmed