(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanoic acid

• ChemBase编号: 1364
• 分子式: C24H40O4
• 平均质量: 392.572
• 单一同位素质量: 392.29265976
• SMILES: O[C@@H]1[C@H]2[C@H]3[C@@]([C@H](CC3)[C@@H](CCC(=O)O)C)(CC[C@@H]2[C@@]2([C@H](C1)C[C@H](O)CC2)C)C
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)C[C@@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=O)O)C)C)O)C
• InChI: InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20+,22+,23+,24-/m1/s1
• InChIKey: RUDATBOHQWOJDD-UZVSRGJWSA-N

名称和登记号

名称

• IUPAC标准名: (4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoic acid; (4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid; (4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-yl]pentanoic acid
• IUPAC传统名: ursodeoxycholic acid
• 商标名: Actigall; Antigall; Arsacol; Cholit-ursan; Delursan; Destolit; Deursil; Dom-ursodiol c; Litursol; Lyeton; PHL-ursodiol c; PMS-ursodiol c; Peptarom; Solutrat; Urso; Ursacol; Urso DS; Urso forte; Ursobilin; Ursochol; Ursodamor; Ursofalk; Ursolvan; Urso 250
• 别名: (3α,5β,7β)-3,7-Dihydroxycholan-24-oic Acid; 17β-(1-Methyl-3-carboxypropyl)etiocholane-3α,7β-diol; 7β-Dihydroxy-5β-cholan-24-oic acid; 3α,7β-Dihydroxy-5β-cholanic Acid; Actigall; Adursal; Arsacol; Cholit-Ursan; Delursan; Desocol; Desol; Destolit; Deursil; Ursodamor; (R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid; URSODESOXYCHOLIC ACID; (3alpha,5beta,7beta)-3,7-dihydroxycholan-24-oic acid; 3,7-Dihydroxycholan-24-oic acid; 3-alpha,7-beta-Dihydroxy-5-beta-cholanoic acid; 3-alpha,7-beta-Dihydroxycholanic acid; 3-alpha,7-beta-Dioxycholanic acid; 3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid; 5beta-Cholan-24-oic acid-3alpha,7beta-diol; 7-beta-Hydroxylithocholic acid; 7beta-Hydroxylithocholic acid; Acide ursodesoxycholique [inn-french]; Acido ursodeossicolico [italian]; Acido ursodeoxicolico [inn-spanish]; Acidum ursodeoxycholicum [inn-latin]; Chenodeoxycholic acid; Iso-ursodeoxycholic acid; UDCS; Ursodesoxycholic acid; Ursodiol; Ursodeoxycholic acid; Ursodeoxycholic acid; UDCA; Ursosan; Ursofalk; Ursodiol; 5 β-Cholan-24-oic acid-3α,7 β-diol; 3α,7 β-Dihydroxy-5 β-cholan-24-oic acid; 7 β-Hydroxylithocholic acid; 3α,7β-Dihydroxy-5β-cholan-24-oic acid; 5β-Cholan-24-oic acid-3α,7β-diol; 7β-Hydroxylithocholic acid; Ursodeoxycholic acid

登记号

• CAS号: 128-13-2
• EC号: 204-879-3
• MDL号: MFCD00003680
• Beilstein号: 3219888
• PubChem SID: 24900651; 160964824; 46508795
• PubChem CID: 31401

理论计算性质

JChem

• Acid pKa: 4.595946
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): 2.7592297
• LogD (pH = 7.4): 0.98345095
• Log P: 3.7133055
• 摩尔折射率: 109.2738 cm^3
• 极化性: 43.768806 Å^3
• 极化表面积: 77.76 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.01
• LOG S: -4.3
• 溶解度: 1.97e-02 g/l

分子性质

理化性质

• 溶解度: 0.02 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; DMSO; ethanol: soluble50 mg/mL, clear; Methanol
• 外观: White Solid
• 熔点: 1978-199°C; 203-204 °C(lit.); 203-205 °C (dec.)
• 比旋光度: [α]20/D +60±2°, c = 2% in ethanol
• 疏水性(logP): 3.00 [RODA,A ET AL. (1990)]

安全信息

• 保存条件: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS编号: FZ2000000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 2
• 危险公开号: R:22
• 安全公开号: S:36/37/39
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥99%; ≥99.0% (T); 99%
• 成盐信息: Free Base
• 简要说明: anionic; anionic detergent
• Empirical Formula (Hill Notation): C24H40O4
• 分类: Genuine Natural Compounds

详细说明

MP Biomedicals - 02158252

Purity: 99%

MP Biomedicals - 05219738

MP Biomedicals Rare Chemical collection

DrugBank - DB01586

• Drug Groups: approved; investigational
• Description: Ursodeoxycholic acid is an epimer of chenodeoxycholic acid (DB06777). It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic. [PubChem]
• Indication: The drug reduces cholesterol absorption and is used to dissolve (cholesterol) gallstones in patients who want an alternative to surgery.
• Pharmacology: Ursodiol (also known as ursodeoxycholic acid) is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. Primary bile acids are produced by the liver and stored in the gall bladder. When secreted into the colon, primary bile acids can be metabolized into secondary bile acids by intestinal bacteria. Primary and secondary bile acids help the body digest fats. Ursodeoxycholic acid helps regulate cholesterol by reducing the rate at which the intestine absorbs cholesterol molecules while breaking up micelles containing cholesterol. Because of this property, ursodeoxycholic acid is used to treat gall stones non-surgically.
• Toxicity: Neither accidental nor intentional overdosing with ursodeoxycholic acid has been reported. Doses of ursodeoxycholic acid in the range of 16-20 mg/kg/day have been tolerated for 6-37 months without symptoms by 7 patients. The LD50 for ursodeoxycholic acid in rats is over 5000 mg/kg given over 7-10 days and over 7500 mg/kg for mice. The most likely manifestation of severe overdose with ursodeoxycholic acid would probably be diarrhea, which should be treated symptomatically.
• Affected Organisms: Humans and other mammals
• Elimination: Only small quantities of ursodiol appear in the systemic circulation and very small amounts are excreted into urine. Eighty percent of lithocholic acid formed in the small bowel is excreted in the feces, but the 20% that is absorbed is sulfated at the 3-hydroxyl group in the liver to relatively insoluble lithocholyl conjugates which are excreted into bile and lost in feces.
• References: Akare S, Jean-Louis S, Chen W, Wood DJ, Powell AA, Martinez JD: Ursodeoxycholic acid modulates histone acetylation and induces differentiation and senescence. Int J Cancer. 2006 Dec 15;119(12):2958-69. [Pubmed] ; Smith T, Befeler AS: High-dose ursodeoxycholic acid for the treatment of primary sclerosing cholangitis. Curr Gastroenterol Rep. 2007 Mar;9(1):54-9. [Pubmed] ; Jackson H, Solaymani-Dodaran M, Card TR, Aithal GP, Logan R, West J: Influence of ursodeoxycholic acid on the mortality and malignancy associated with primary biliary cirrhosis: A population-based cohort study. Hepatology. 2007 Aug 8;46(4):1131-1137. [Pubmed]
• External Links: Wikipedia

Selleck Chemicals - S1643

Research Area: Metabolic Disease
Biological Activity:
Ursodiol reduces cholesterol absorption and is used to dissolve (cholesterol) gallstones. (IC50=0.22 µM) It is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. [1] A hit rate of around 0.4% was observed with a Z’ factor of 0.6 ± 0.2. Two confirmed hits are bile acids, chenodiol and ursodiol with an IC50 of 2.4 and 0.22 µM, respectively. [2]

Sigma Aldrich - U5127

包装
1, 5, 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. U5127.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - U850000

Used as an anticholelithogenic. Epimer with Chenodiol with respect to the hydroxyl group at C7.

参考文献

• Akare S, Jean-Louis S, Chen W, Wood DJ, Powell AA, Martinez JD: Ursodeoxycholic acid modulates histone acetylation and induces differentiation and senescence. Int J Cancer. 2006 Dec 15;119(12):2958-69. Pubmed
• Smith T, Befeler AS: High-dose ursodeoxycholic acid for the treatment of primary sclerosing cholangitis. Curr Gastroenterol Rep. 2007 Mar;9(1):54-9. Pubmed
• Jackson H, Solaymani-Dodaran M, Card TR, Aithal GP, Logan R, West J: Influence of ursodeoxycholic acid on the mortality and malignancy associated with primary biliary cirrhosis: A population-based cohort study. Hepatology. 2007 Aug 8;46(4):1131-1137. Pubmed
• Zhou W et al. J Biomol Screen. 2010 Jun;15(5)
• Tint, G.S., et al.: Gastroenterology, 91, 1007 (1986)
• Poupon, R.E, et al.: N. Engl. J. Med., 324, 1548 (1986)
• MacKenzie, P., et al.: J. Biol. Chem., 283, 36205 (1986)