(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 ID: 1364
• Molecular Formular: C24H40O4
• Molecular Mass: 392.572
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: ursodeoxycholic acid
• Brand Name: 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
• Synonyms: (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

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.595946
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.7592297
• LogD (pH = 7.4): 0.98345095
• Log P: 3.7133055
• Molar Refractivity: 109.2738 cm^3
• Polarizability: 43.768806 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.01
• LOG S: -4.3
• Solubility (Water): 1.97e-02 g/l

PROPERTIES

Physical Property

• Solubility: 0.02 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; DMSO; ethanol: soluble50 mg/mL, clear; Methanol
• Apperance: White Solid
• Melting Point: 1978-199°C; 203-204 °C(lit.); 203-205 °C (dec.)
• Optical Rotation: [α]20/D +60±2°, c = 2% in ethanol
• Hydrophobicity(logP): 3.00 [RODA,A ET AL. (1990)]

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: FZ2000000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: R:22
• Safety Statements: S:36/37/39
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99%; ≥99.0% (T); 99%
• Salt Data: Free Base
• Description: anionic; anionic detergent
• Empirical Formula (Hill Notation): C24H40O4
• Classification: Genuine Natural Compounds

DETAILS

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.

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
• 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)