(1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

• ChemBase编号: 4257
• 分子式: C27H46O2
• 平均质量: 402.65294
• 单一同位素质量: 402.34978071
• SMILES: C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](CCCC(O)(C)C)C)C)C1)C
• InChI: InChI=1S/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1
• InChIKey: INBGSXNNRGWLJU-ZHHJOTBYSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol; (1S,2R,5S,10S,11S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-ol
• IUPAC传统名: 25-hydroxycholesterol
• 别名: 5-胆甾烯-3β,25-二醇; 25-羟基胆甾醇; (3β)-Cholest-5-ene-3,25-diol; Cholest-5-ene-3β,25-diol; 25-Hydroxy-5-cholestene-3β-ol; 5-Cholesten-3β,25-diol; 25-Hydroxy Cholesterol; (3BETA)-CHOLEST-5-ENE-3,25-DIOL; 5-Cholestene-3β,25-diol; 25-Hydroxycholesterol

登记号

• CAS号: 2140-46-7
• MDL号: MFCD00057815
• Beilstein号: 3161259
• PubChem SID: 160967689; 46506794
• PubChem CID: 65094

理论计算性质

JChem

• Acid pKa: 18.20429
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 5.641774
• LogD (pH = 7.4): 5.641774
• Log P: 5.641774
• 摩尔折射率: 122.4526 cm^3
• 极化性: 48.564686 Å^3
• 极化表面积: 40.46 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 5.95
• LOG S: -6.22
• 溶解度: 2.44e-04 g/l

分子性质

理化性质

• 溶解度: chloroform: soluble50 mg/mL, clear, colorless to slightly yellow

安全信息

• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 20/21/22-36/37/38-48
• 安全公开号: 26-36-45
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Warning
• GHS危险声明: H302-H312-H315-H319-H332-H335-H373
• GHS警示性声明: P261-P280-P305 + P351 + P338

产品相关信息

• 纯度: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C27H46O2

详细说明

DrugBank - DB04705

Drug information: experimental

Sigma Aldrich - 55125

Other Notes
Studies on the regulation mechanism for the synthesis of cholesteryl esters1

Toronto Research Chemicals - H918030

An oxygenated derivative of Cholesterol (C432501); an oxysterol. An inhibitor of human immunodeficiency virus replication in vitro. It induces apoptosis in human monocytic cell lines as well as inducing apoptosis in CEM cells associated with negative reg

参考文献

• Aupeix, K. et al.: Immunobiology, 194, 415 (1995)
• Moog, C. et al.: Antivir. Chem, Chemother., 9, 491 (1995)
• Ayala-Torres, S. et al.: Exp. Cell Res., 246, 193 (1995)