(1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one

• ChemBase编号: 2567
• 分子式: C19H30O2
• 平均质量: 290.4403
• 单一同位素质量: 290.2245802
• SMILES: C1C[C@@H](O)C[C@H]2CC[C@@H]3[C@@H]([C@@]12C)CC[C@]1([C@H]3CCC1=O)C
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C)C
• InChI: InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18+,19+/m1/s1
• InChIKey: QGXBDMJGAMFCBF-BNSUEQOYSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one; (1S,2S,5R,7R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-one
• IUPAC传统名: α-etiocholanolone
• 别名: 本胆烷-3α-醇-17-酮; 苯胆烷醇酮; 还原尿睾酮 溶液; 3α-羟基-5β-雄甾烷-17-酮; 5β-雄酮; 还原尿睾酮; 还原胆烷醇酮; (3α,5β)-3-Hydroxyandrostan-17-one; 3α-Etiocholanolone; 3α-Hydroxy-5β-androstane-17-one; 5-Isoandrosterone; 5β-Androstan-3α-ol-17-one; 5β-Androstane-3α-ol-17-one; Aetiocholanolone; Etiocholanolone; NSC 50908; α-Etiocholanolone; 5β-Androsterone; Etiocholan-3α-ol-17-one; Etiocholanone solution; ETIOCHOLAN-3α-01-17-ONE; Aetiocholanolone; Etiocholan-3α-ol-17-one; 3α-Hydroxy-5β-androstan-17-one; 5β-Androsterone; Etiocholanone

登记号

• CAS号: 53-42-9
• EC号: 200-835-2
• MDL号: MFCD00064133
• Beilstein号: 2217625
• PubChem SID: 46507911; 160966017; 24894603
• PubChem CID: 5880

理论计算性质

JChem

• 可自由旋转的化学键: 0
• 里宾斯基五规则: true
• Acid pKa: 18.296396
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 3.7672846
• LogD (pH = 7.4): 3.7672846
• Log P: 3.7672846
• 摩尔折射率: 83.8089 cm^3
• 极化性: 33.49998 Å^3
• 极化表面积: 37.3 Å^2

ALOGPS 2.1

• 溶解度: 6.34e-03 g/l
• Log P: 3.71
• LOG S: -4.66

分子性质

理化性质

• 闪点: 2 °C; 35.6 °F

安全信息

• 欧盟危险性物质标志: 易燃性(Flammable) (F); 有害性(Harmful) (Xn)
• 德国WGK号: 2; 3
• 危险公开号: 11-20/21/22-36
• 安全公开号: 16-36/37
• GHS危险品标识: GHS02; GHS07
• GHS警示词: Danger
• GHS危险声明: H225-H302-H312-H319-H332
• GHS警示性声明: P210-P280-P305 + P351 + P338
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 毒品管制信息: regulated under CDSA - not available from Sigma-Aldrich Canada
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... SERPINA6(866)rat ... Gabra1(29705), Gabra2(29706), Gabrg2(29709)

产品相关信息

• 纯度: 98%
• 浓度: 100 ng/μL in acetonitrile
• 级别: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C19H30O2

详细说明

MP Biomedicals - 05203853

MP Biomedicals Rare Chemical collection

DrugBank - DB02854

• Drug Groups: experimental
• Description: The 5-beta-reduced isomer of androsterone. Etiocholanolone is a major metabolite of testosterone and androstenedione in many mammalian species including humans. It is excreted in the urine. [PubChem]

Sigma Aldrich - E5126

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. E5126.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 32833

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - A637630

5β-Androsterone is a metabolite of Testosterone (T155000). β-Androsterone is a stereoisomer of Androsterone (A637535). 5β-Androsterone showed a weak estrogenic action.

参考文献

• Park, J., et al.: J. Anal. Toxicol., 14, 66 (1990)
• Palonek, E., et al.: J. Steroid Mol. Biol., 55, 121 (1990)
• Aguilera, R., et al.: Clin. Chem. 47, 292 (1990)
• Flenker, U., et al.: Steroids, 73, 408 (1990)