(1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase编号: 105424
• 分子式: C21H30O3
• 平均质量: 330.4611
• 单一同位素质量: 330.21949482
• SMILES: C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@@H]2C(=O)CO
• Canonical SMILES: OCC(=O)[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• InChI: InChI=1S/C21H30O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1
• InChIKey: ZESRJSPZRDMNHY-YFWFAHHUSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one; (1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
• IUPAC传统名: 11-deoxycorticosterone; Doc; (1S,2R,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• 别名: ‘Reichstein Q’; 21-Hydroxy-4-pregnene-3,20-dione; 4-Pregnen-21-ol-3,20-dione; Kendall’s desoxy compound B; 21-Hydroxyprogesterone; 11-DESOXYCORTICOSTERONE; 11-Desoxycorticosterone; Deoxycorticosterone; Cortexone; Deoxycortone; Desoxycortone; DOC; 11-Deoxycorticosterone; 11-Deoxycorticosterone; 21-Hydroxyprogesterone; δ^4-Pregnen-21-ol-3,20-dione; Reichstein's Substance Q; DEOXYCORTICOSTERONE; NSC 11319-d8; 4-Pregnene-21-ol-3,20-dione-d8; 11-Deoxy Corticosterone-d8; Desoxycorticosterone; NSC 11319; 4-Pregnene-21-ol-3,20-dione; 11-Deoxy Corticosterone; 21-Hydroxypregn-4-ene-3,20-dione-d8; 11-Deoxycorticosterone-d8; 11-Dehydroxy-corticosterone-d8; 11-Desoxycorticosterone-d8; 21-Hydroxy-3,20-dioxopregn-4-ene-d8; 21-Hydroxy-4-pregnane-3,20-dione-d8; 21-Hydroxyprogesterone-d8; Cortexone-d8; DOC-d8; Deoxycortone-d8; Desoxycorticosterone-d8; Desoxycortone-d8; 21-Hydroxypregn-4-ene-3,20-dione; 11-Dehydroxy-corticosterone; 21-Hydroxy-3,20-dioxopregn-4-ene; 21-Hydroxy-4-pregnane-3,20-dione; Corthormon; Cortexon;Corticormon; Decortene; Kendall's desoxy compound B; Ocriten; Ormosurrenol; Desoxycortone

登记号

• CAS号: 55487-63-3; 64-85-7
• EC号: 200-596-4
• MDL号: MFCD00003661
• Beilstein号: 2062123
• PubChem SID: 162093607; 24894056
• PubChem CID: 6166
• CHEBI ID: 16973
• ATC码: H02AA03
• CHEMBL: 1498
• Chemspider ID: 5932
• 美国药典/FDA物质标识码: 40GP35YQ49
• 维基百科标题: 11-Deoxycorticosterone

理论计算性质

• Acid pKa: 13.864724
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 3.3313563
• LogD (pH = 7.4): 3.3313563
• Log P: 3.3313563
• 摩尔折射率: 94.4075 cm^3
• 极化性: 37.013763 Å^3
• 极化表面积: 54.37 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; Ethyl Acetate
• 外观: White Solid; White to Off-White Solid
• 熔点: 132-134°C; 137-139°C

安全信息

• 保存条件: Refrigerator; Room Temperature (15-30°C)
• RTECS编号: HG0350000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 40-48; R:22
• 安全公开号: 22-24/25; S:36/37/39
• GHS危险品标识: GHS08
• GHS警示词: Warning
• GHS危险声明: H351-H373
• GHS警示性声明: P281
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 相关基因信息: human ... SERPINA6(866)
• 生物活性机理: ACTH secretion inhibitor; Gluconeogenesis promoter; Glycogen deposition inhibitor

产品相关信息

• 纯度: ≥97% (HPLC)
• 生物来源: Obt. by incubation of 9b,10a-pregn-4-ene-3,20-dione with Curvularia spp.
• 应用领域: Mineralocorticoid

详细说明

MP Biomedicals - 02190185

Crystalline

MP Biomedicals - 05203891

MP Biomedicals Rare Chemical collection

Sigma Aldrich - D6875

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D6875.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - D232590

A mineralocorticoid that occurs in adrenal cortex. It acts as a precursor to Aldosterone (A514700).

Toronto Research Chemicals - D232592

Labelled Deoxycorticosterone. A mineralocorticoid that occurs in adrenal cortex. It acts as a precursor to Aldosterone (A514700).

参考文献

• Bohl, C., et al.: J. Med.Chem., 47, 3765 (2004)
• Smith, J., et al.: Steroids, 73, 1160 (2004)
• Bohl, C., et al.: J. Med.Chem., 47, 3765 (2004)
• Smith, J., et al.: Steroids, 73, 1160 (2004)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 583C; 602C, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1054B, (ir)
• Reichstein, T. et al., Helv. Chim. Acta, 1937, 20, 1164; 1938, 21, 1197, (isol)
• Schindler, W. et al., Helv. Chim. Acta, 1941, 24, 371, (synth)
• Zaffaroni, A. et al., Experientia, 1955, 11, 219, (synth)
• U.S. Pat., 1966, 3 254 098; CA, 65, 8999, (synth)
• Grostic, M.F. et al., J.O.C., 1968, 33, 1740, (ms)
• van der Sijde, D. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1969, 88, 1437, (synth)
• Schambelan, M. et al., J. Clin. Endocrinol. Metab., 1972, 34, 695, (metab)
• Dideberg, O. et al., Acta Cryst. B, 1973, 29, 103, (cryst struct)
• Gonzalez, M.D. et al., Org. Magn. Reson., 1984, 22, 586, (cmr)
• Numazawa, M. et al., J.O.C., 1985, 50, 81, (synth)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6984, (synonyms)
• Kirk, D.N. et al., J.C.S. Perkin 2, 1990, 1567, (pmr)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 727
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DAQ600; DAQ800