(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编号: 4191
• 分子式: C21H28O5
• 平均质量: 360.44402
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: aldosterone
• 别名: 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

登记号

• CAS号: 52-39-1
• EC号: 200-139-9
• MDL号: MFCD00051136
• Beilstein号: 3224996
• PubChem SID: 160967623; 24891458; 46505770
• PubChem CID: 5839
• CHEBI ID: 27584
• ATC码: H02AA01
• CHEMBL: 273453
• Chemspider ID: 5633
• DrugBank ID: DB04630
• KEGG ID: C01780
• 医学主题词(MeSH): Aldosterone
• 美国药典/FDA物质标识码: 4964P6T9RB
• 维基百科标题: Aldosterone

理论计算性质

JChem

• Acid pKa: 13.819593
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 1.0556679
• LogD (pH = 7.4): 1.0556678
• Log P: 1.0556679
• 摩尔折射率: 96.7918 cm^3
• 极化性: 37.741665 Å^3
• 极化表面积: 91.67 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.54
• LOG S: -3.39
• 溶解度: 1.48e-01 g/l

分子性质

理化性质

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

安全信息

• RTECS编号: TU4523000
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... SERPINA6(866)rat ... Ar(24208), Nr3c2(25672)

产品相关信息

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

详细说明

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
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

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

参考文献

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