Home > Compound List > Compound details
52-39-1 molecular structure
click picture or here to close

(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 and InChIs

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

Cite this record

CBID:4191 http://www.chembase.cn/molecule-4191.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(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
(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
CAS Number
52-39-1
EC Number
200-139-9
MDL Number
MFCD00051136
Beilstein Number
3224996
PubChem SID
160967623
24891458
46505770
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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.819593  H Acceptors
H Donor LogD (pH = 5.5) 1.0556679 
LogD (pH = 7.4) 1.0556678  Log P 1.0556679 
Molar Refractivity 96.7918 cm3 Polarizability 37.741665 Å3
Polar Surface Area 91.67 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.54  LOG S -3.39 
Solubility (Water) 1.48e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.0512 mg/mL at 37 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] expand Show data source
Hydrophobicity(logP)
1.08 [HANSCH,C ET AL. (1995)] expand Show data source
RTECS
TU4523000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Gene Information
human ... SERPINA6(866)rat ... Ar(24208), Nr3c2(25672) expand Show data source
Purity
≥95% (HPLC) expand Show data source
≥98.5% (UV) expand Show data source
Empirical Formula (Hill Notation)
C21H28O5 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
DrugBank - DB04630 external link
Item Information
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 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
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 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Williams JS, Williams GH: 50th anniversary of aldosterone. J Clin Endocrinol Metab. 2003 Jun;88(6):2364-72. Pubmed
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle