(1S,2R,10R,11S,15S)-14-ethylidene-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-5,13-dione

• ChemBase编号: 153785
• 分子式: C21H28O2
• 平均质量: 312.44582
• 单一同位素质量: 312.20893014
• SMILES: C/C=C\1/C(=O)C[C@@H]2[C@@]1(CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)C
• Canonical SMILES: C/C=C\1/C(=O)C[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• InChI: InChI=1S/C21H28O2/c1-4-16-19(23)12-18-15-6-5-13-11-14(22)7-9-20(13,2)17(15)8-10-21(16,18)3/h4,11,15,17-18H,5-10,12H2,1-3H3/t15-,17+,18+,20+,21-/m1/s1
• InChIKey: WDXRGPWQVHZTQJ-NRJJLHBYSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,10R,11S,15S)-14-ethylidene-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,13-dione
• IUPAC传统名: (1S,2R,10R,11S,15S)-14-ethylidene-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,13-dione
• 别名: (17Z)-Pregna-4,17(20)-diene-3,16-dione; 4,17(20)-trans-Pregnadiene-3,16-dione; (Z)-Guggulsterone; (17E)-Pregna-4,17(20)-diene-3,16-dione; (E)-Guggulsterone

登记号

• CAS号: 39025-24-6; 39025-23-5
• MDL号: MFCD01310757; MFCD01310758
• PubChem SID: 162247924; 24278392
• PubChem CID: 6439929

理论计算性质

• Acid pKa: 19.042126
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 4.254959
• LogD (pH = 7.4): 4.254959
• Log P: 4.254959
• 摩尔折射率: 93.6071 cm^3
• 极化性: 36.159924 Å^3
• 极化表面积: 34.14 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: soluble5 mg/mL
• 外观: light yellow powder; white to off-white powder

安全信息

• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 37
• 安全公开号: 36
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥89% (HPLC); ≥95% (HPLC)
• 杂质: ≤5.4% E-form
• Empirical Formula (Hill Notation): C21H28O2

详细说明

Sigma Aldrich - G4923

Biochem/physiol Actions
Naturally occuring bioactive plant sterol isolated from the gum resin of guggul (Commiphora wightii). Antihyperlipidemic. Induces the expression of human CYP3A.1. Guggulsterone potently reverses multi-drug resistance in a number of human cancer cell lines, extending the efficacy of chemotherapy.2

Sigma Aldrich - G5168

Biochem/physiol Actions
(Z)-Guggulsterone is a natural product that lowers cholesterol due to its function as an antagonist ligand for the bile acid receptor. (Z)-Guggulsterone is a nuclear hormone receptor that regulates the transcription of several genes involved in cholesterol metabolism and plays a role in cholesterol level regulation. (Z)-Guggulsterone is also a selective farnesoid X receptor (FXR) modulator.