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Ursocholic acid (Standard)

CAT: 0804-HY-113212RSize: 1 EachDry Ice: NoHazardous: No
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Description
Ursocholic acid (Standard) is the analytical standard of Ursocholic acid. This product is intended for research and analytical applications. Ursocholic acid, a bile acid present in mammalian bile, is converted to deoxycholic acid (UDC) by the mouse intestinal flora. Ursocholic acid acts as a gallstone dissolving agent in the liver through anti-apoptosis, anti-inflammatory, immunomodulatory, bile regulation, and coordinated changes in mitochondrial integrity and cell signaling, Ursocholic acid also has favorable effects on bones in patients with chronic cholestasis[1][2][3][4][5].
CAS Number
2955-27-3
UNSPSC
12352211
Target
Apoptosis; Endogenous Metabolite; Reference Standards
Related Pathways
Apoptosis; Metabolic Enzyme/Protease; Others
Field of Research
Metabolic Disease; Inflammation/Immunology
Smiles
C[C@H](CCC(O)=O)[C@H]1CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C
Molecular Formula
C24H40O5
Molecular Weight
408.57
References & Citations
[1]MacDonald IA, et al. Formation of ursodeoxycholic acid from chenodeoxycholic acid by a 7 beta-hydroxysteroid dehydrogenase-elaborating Eubacterium aerofaciens strain cocultured with 7 alpha-hydroxysteroid dehydrogenase-elaborating organisms. Appl Environ Microbiol. 1982 Nov;44 (5) :1187-95.|[2]Lee HI, et al. Ursodeoxycholic acid, an inhibitor of hepatocyte nuclear factor 1α, did not increase the systemic exposure of pitavastatin. Int J Clin Pharmacol Ther. 2014 Nov;52 (11) :981-5.|[3]Ikegami, et al. Ursodeoxycholic acid: mechanism of action and novel clinical applications. Hepatology Research 38.2 (2008) : 123-131.|[4]Kim, et al. Ursodeoxycholic acid attenuates 5‑fluorouracil‑induced mucositis in a rat model. Oncology letters 16.2 (2018) : 2585-2590.|[5]Dubreuil, et al. Ursodeoxycholic acid increases differentiation and mineralization and neutralizes the damaging effects of bilirubin on osteoblastic cells. Liver international 33.7 (2013) : 1029-1038.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Ursocholic acid

Ursocholic acid is a bile acid that is 5beta-cholan-24-oic acid bearing three hydroxy substituents at positions 3alpha, 7beta and 12alpha. It has a role as an EC 1.1.1.159 (7alpha-hydroxysteroid dehydrogenase) inhibitor and a human urinary metabolite. It is a C24-steroid, a trihydroxy-5beta-cholanic acid, a bile acid, a 7beta-hydroxy steroid, a 3alpha-hydroxy steroid and a 12alpha-hydroxy steroid. It is a conjugate acid of an ursocholate.

CAS Number2955-27-3
PubChem CID122340
IUPAC Name(4R)-4-[(3R,5S,7S,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
Molecular FormulaC24H40O5
Molecular Weight408.6
XLogP3.6
Topological Polar Surface Area98
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Heavy Atom Count29
Formal Charge0
Complexity637
SMILES
C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2[C@H](C[C@H]4[C@@]3(CC[C@H](C4)O)C)O)O)C
InChI
InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19+,20+,22+,23+,24-/m1/s1
InChIKey
BHQCQFFYRZLCQQ-UTLSPDKDSA-N
Chemical Structure
2D Structure
2D structure of Ursocholic acid
CAS: 2955-27-3
CID: 122340
Formula: C24H40O5
MW: 408.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight408.6
XLogP33.6
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Exact Mass408.28757437
Monoisotopic Mass408.28757437
Topological Polar Surface Area98 Ų
Heavy Atom Count29
Formal Charge0
Complexity637
Isotope Atom Count0
Defined Atom Stereocenter Count11
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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