(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanoic acid

• ChemBase编号: 128095
• 分子式: C24H40O3
• 平均质量: 376.5726
• 单一同位素质量: 376.29774514
• SMILES: O=C(O)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2C[C@H](O)CC[C@]12C)C
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)O)C)C)C
• InChI: InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1
• InChIKey: SMEROWZSTRWXGI-HVATVPOCSA-N

名称和登记号

名称

• IUPAC标准名: (4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoic acid
• IUPAC传统名: lithocholic acid
• 别名: 3α-羟基-5β-胆烷酸; 3α-羟基-5β-胆甾烷-24-酸; 5β-胆甾烷-24-酸-3α-醇; 石胆酸; (3α,5β)-3-Hydroxycholan-24-oic Acid; 17β-(1-Methyl-3-carboxypropyl)etiocholan-3α-ol; 3-Hydroxycholan-24-oic Acid; 3α-Hydroxy-5β-cholan-24-oate; 3α-Hydroxy-5β-cholanoic Acid; 3α-Hydroxycholanic Acid; NSC 683770; Lithocholic acid; Lithocholate; Lithocolic acid; 3α-Hydroxy-5β-cholan-24-oic acid; 3α-Hydroxy-5β-cholanic acid; 5β-Cholan-24-oic acid-3α-ol; Lithocholic acid

登记号

• CAS号: 434-13-9
• EC号: 207-099-1
• MDL号: MFCD00003682
• Beilstein号: 3217757
• PubChem SID: 162222409; 24896429
• PubChem CID: 9903
• CHEBI ID: 16325
• CHEMBL: 1478
• Chemspider ID: 9519
• IUPHAR配体索引: 611
• 维基百科标题: Lithocholic_acid

理论计算性质

• Acid pKa: 4.7910433
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 4.2362366
• LogD (pH = 7.4): 2.4612968
• Log P: 5.0220704
• 摩尔折射率: 107.6813 cm^3
• 极化性: 43.144962 Å^3
• 极化表面积: 57.53 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: Ethanol; Methanol
• 外观: White Solid
• 熔点: 183-188 °C; 183-188 °C(lit.); 183-189 °C; 189-191°C
• 比旋光度: [α]20/D +35±1°, c = 1% in ethanol

安全信息

• 保存条件: Refrigerator
• RTECS编号: FZ2275000
• 德国WGK号: 2
• 安全公开号: S22 S24/25
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 相关基因信息: human ... POLA1(5422), TOP2A(7153)rat ... Polb(29240)

产品相关信息

• 纯度: ≥97% (titration); ≥99.0% (TLC)
• 杂质: ~1% deoxycholic acid (TLC)
• Empirical Formula (Hill Notation): C24H40O3

详细说明

Sigma Aldrich - L6250

Biochem/physiol Actions
胆汁酸
包装
10, 25 g in poly bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. L6250.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 62620

Other Notes
One of the major fecal bile acids of humans.; Causes calcium release from the endoplasmic reticulum in rat liver cells1

Toronto Research Chemicals - L469180

A cholic acid derivative as TGR5 modulator. Found in ox bile, human bile, rabbit bile, and in ox and pig gallstones.

参考文献

• Brindle, J., et al.: Nat. Med., 12, 1439 (2002)
• Lindon, J., et al.: Biomarkers, 9, 1 (2002)
• Holmes, E., et al.: Cell, 134, 714 (2002)