Basic information
- CAS
52-39-1- Standard SMILES
C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C=O)[C@@H](C(=O)CO)CC[C@@H]12- InChIKey
PQSUYGKTWSAVDQ-ZVIOFETBSA-N- Molecular formula
- C21H28O5
- Average molar mass
- 360.4 g/mol
- Monoisotopic mass
- 360.193674
Overview
Aldosterone is a pregnane-based steroidal hormone produced by the outer-section (zona glomerulosa) of the adrenal cortex in the adrenal gland, and acts on the distal tubules and collecting ducts of the kidney to cause the conservation of sodium, secretion of potassium, increased water retention, and increased blood pressure. The overall effect of aldosterone is to increase reabsorption of ions and water in the kidney. It has a role as a mouse metabolite and a human metabolite. It is a steroid aldehyde, a primary alpha-hydroxy ketone, a mineralocorticoid, a 21-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, a 18-oxo steroid, a 3-oxo-Delta(4) steroid and a C21-steroid hormone. It derives from a hydride of a pregnane.
Names & identifiers
- Preferred name
- Aldosterone
- IUPAC
- (8S,9S,10R,11S,13R,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10-methyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-13-carbaldehyde
- English name
- ALDOSTERONE
- Molecular formula
- C21H28O5
- Molecular weight
- 360.44
Names & synonyms
ALDOSTERONE52-39-1(+)-AldosteroneAldosteronaAldosteronum11beta,21-Dihydroxy-3,20-diketo-4-pregnen-18-al11beta,21-Dihydroxypregn-4-ene-3,18,20-trione(11BETA)-11,21-DIHYDROXY-3,20-DIOXOPREGN-4-EN-18-AL11beta,21-dihydroxy-3,20-dioxopregn-4-en-18-al(8S,9S,10R,11S,13R,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10-methyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-13-carbaldehydeNSC-7385611beta,21-Dihydroxy-3,20-dioxo-4-pregnen-18-al
Show more names
ReichsteinREICHSTEIN XLECTROCORTINALDOSTERONE(RG)Aldosterone-[2,2,4,6,6,17,21,21-2H7]4-PREGNEN-11-BETA, 21-DIOL-3,18,20-TRIONEμ100 97% (CP)ALD ELISA
11beta,21-dihydroxy-3,20-dioxo-pregn-4-ene-18-al4964P6T9RBDTXSID7022419CHEBI:27584NSC73856(8S,9S,10R,11S,13R,14S,17S)-11-hydroxy-17-(2-hydroxyacetyl)-10-methyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta(a)phenanthrene-13-carbaldehydeRefChem:553942DTXCID902419
Database identifiers
- CAS
52-39-1- PubChem CID
- 5839
- DTXSID
DTXSID7022419- ChEMBL
CHEMBL273453- ChEBI
CHEBI:27584- UNII
- 4964P6T9RB
- EC Number
- 200-139-9
- Nikkaji
- J4.130K
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 91.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 682
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Steroids
LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]
LogP
1.08
1.08
Solubility0.0512 mg/mL at 37 °C
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point166.5 °C
Physical DescriptionSolid
Collision Cross Section
188.31 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
181.09 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
202.8 Ų [M+Na]+
Physicochemical properties
- Melting point
- 170 · 170-172°C
- alpha
- 23 · D23 +152.2° (anhydr; c = 2 in acetone); D25 +161° (c = 0.1 in chloroform)
- Boiling point
- 412.46 °C · 412.46°C (rough estimate)
- Density
- 1.28 · 1.28
- refractive index
- 1.612 · 1.6120 (estimate)
- Flash point
- 2 ℃ · 2℃
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
- form
- Crystalline Powder
- pka
- 12.98 · 12.98±0.10(Predicted)
- color
- White
- optical activity
- 14523 · +14523 (c 0.99, acetone)
- Water Solubility
- 51.18 mg/L · 51.18mg/L(37 ºC)
- Merck
- 13 · 13,224
- BRN
- 3224996 · 3224996
- Major Application
- clinical testingclinical testing
- InChIKey
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N
- SMILES
- C[C@]12CCC(=O)C=C1CC[C@H]3[C@@H]4CC[C@H](C(=O)CO)[C@]4(C[C@H](O)[C@H]23)C=O
- CAS DataBase Reference
- 52 · 52-39-1(CAS DataBase Reference)
- NCI Dictionary of Cancer Terms
- aldosterone
- FDA UNII
- 4964 P6T9RB · 4964P6T9RB
- ATC code
- 2 AA01 · H02AA01
- EPA Substance Registry System
- Aldosterone (52-39-1)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 22-24-25
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- TU4523000
- ridadr
- UN 1648 3 / PGII
- hs_code
- 29372900
- risk_code
- 36/37/38-36-20/21/22-11
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- Xi,Xn,F
- safety_code
- 22-24/25-36-26-36/37-16
- Storage Class
- 3 - Flammable liquids
- Hazard statements
- H225-H302+H312+H332-H319
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
- Precautionary statements
- P210-P280-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
H - Systemic hormonal preparations, excl. sex hormones and insulins
QH - Systemic hormonal preparations, excl. sex hormones and insulin
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.
Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm
Metabolite Pathways11-beta-hydroxylase deficiency (CYP11B1)
Uses & manufacturing
General Manufacturing InformationPregn-4-en-18-al, 11,21-dihydroxy-3,20-dioxo-, (11.beta.)-: ACTIVE
Applications
DescriptionAldosterone is a mineralocorticosteroid that takes part in the regulation of electrolytic balance in the organism. Aldosterone lowers excretion of sodium ions from the body, thus increasing their reabsorption and increasing secretion of potassium ions in renal tubules. Being a competitive antagonist of aldosterone, spironlactone blocks aldosterone receptors, thus increasing excretion of sodium, chloride, and corresponding equivalents of water with urine, thus retaining the amount of potassium ions in the organism. Spironolactone is used both individually as well as in combination with thiazides, since it lowers kaliuresis caused by thiazide diuretics.
UsesA labelled adrenocortical steroid which exerts regulatory influence on metabolism of electrolytes and water. Biologically active aldosterone isomer; a mineralocorticoid produced by the adrenal cortex that induces urinary excretion of K+ and renal re
UsesThe d-isomer of aldosterone is considered to be the biologically active isomer.
UsesLabelled Aldosterone. Aldosterone is an adrenocortical steroid which exerts regulatory influence on metabolism of electrolytes and water. Biologically active aldosterone isomer; a mineralocorticoid pr oduced by the adrenal cortex that induces urinary excretion of K+ and renal reabsorptioon of Na+. Exists as an equilibrium mixture of the aldehyde and the hemiacetal.
UsesImatinib intermediate
Useshypnotic, anastethic
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司0731-88532326 13319508186 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
上海康朗生物科技有限公司021-61998208 18217752821 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
江苏艾康生物医药研发有限公司025-58851090 19370895928 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
咸宁深蓝生物医药研发有限公司18171815831 · [email protected]
江苏星科元信息科技有限公司400-605-7200 15335295587 · [email protected]
上海纽雀客生物科技有限公司13916276291 · [email protected]
湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Additional notes
DefinitionChEBI: A pregnane-based steroidal hormone produced by the outer-section (zona glomerulosa) of the adrenal cortex in the adrenal gland, and acts on the distal tubules and collecting ducts of the kidney to cause the conservation of sodium, secretion of potassium, i creased water retention, and increased blood pressure. The overall effect of aldosterone is to increase reabsorption of ions and water in the kidney.
Definitionaldosterone: A hormone producedby the adrenal glands that controlsexcretion of sodium by the kidneysand thereby maintains the balance ofsalt and water in the body fluids.
Related reactions
3 records
Compound notes
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