Ursocholic acid (CHEM021823)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:13:24 UTC
Update Date2016-11-09 01:17:22 UTC
Accession NumberCHEM021823
Identification
Common NameUrsocholic acid
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3alpha,5beta,7beta,12alpha)-3,7,12-Trihydroxycholan-24-Oic acidChEBI
3alpha,7beta,12alpha-Trihydroxy-5beta-cholan-24-Oic acidChEBI
3alpha,7beta,12alpha-Trihydroxy-5beta-cholanic acidChEBI
7-Epicholic acidChEBI
7beta-Hydroxyisocholic acidKegg
(3a,5b,7b,12a)-3,7,12-Trihydroxycholan-24-OateGenerator
(3a,5b,7b,12a)-3,7,12-Trihydroxycholan-24-Oic acidGenerator
(3alpha,5beta,7beta,12alpha)-3,7,12-Trihydroxycholan-24-OateGenerator
(3Α,5β,7β,12α)-3,7,12-trihydroxycholan-24-OateGenerator
(3Α,5β,7β,12α)-3,7,12-trihydroxycholan-24-Oic acidGenerator
3a,7b,12a-Trihydroxy-5b-cholan-24-OateGenerator
3a,7b,12a-Trihydroxy-5b-cholan-24-Oic acidGenerator
3alpha,7beta,12alpha-Trihydroxy-5beta-cholan-24-OateGenerator
3Α,7β,12α-trihydroxy-5β-cholan-24-OateGenerator
3Α,7β,12α-trihydroxy-5β-cholan-24-Oic acidGenerator
3a,7b,12a-Trihydroxy-5b-cholanateGenerator
3a,7b,12a-Trihydroxy-5b-cholanic acidGenerator
3alpha,7beta,12alpha-Trihydroxy-5beta-cholanateGenerator
3Α,7β,12α-trihydroxy-5β-cholanateGenerator
3Α,7β,12α-trihydroxy-5β-cholanic acidGenerator
7-EpicholateGenerator
7b-HydroxyisocholateGenerator
7b-Hydroxyisocholic acidGenerator
7beta-HydroxyisocholateGenerator
7Β-hydroxyisocholateGenerator
7Β-hydroxyisocholic acidGenerator
UrsocholateGenerator
3a,7b,12a-Trihydroxy-5b-cholanoateHMDB
3a,7b,12a-Trihydroxy-5b-cholanoic acidHMDB
3a,7b,12a-TrihydroxycholanateHMDB
3a,7b,12a-Trihydroxycholanic acidHMDB
3 alpha,7 beta,12 alpha-Trihydroxy-5 beta-cholan-24-Oic acidHMDB
Chemical FormulaC24H40O5
Average Molecular Mass408.571 g/mol
Monoisotopic Mass408.288 g/mol
CAS Registry Number2955-27-3
IUPAC Name(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional Nameursocholic acid
SMILES[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@@H](O)C[C@]2([H])C[C@H](O)CC[C@]12C
InChI IdentifierInChI=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
InChI KeyBHQCQFFYRZLCQQ-UTLSPDKDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Trihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • 7-hydroxysteroid
  • 7-alpha-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.074 g/LALOGPS
logP2.26ALOGPS
logP2.48ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-0.16ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.79 m³·mol⁻¹ChemAxon
Polarizability47.04 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ec-0439000000-abd2a5c162e23ea0d78fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-1100049000-ae391322cbbc458fdb46Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1019800000-4a5ffc11cb3fa93e46cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-7f097ee7b44073c18648Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-07966770f57ff86aa177Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0009100000-915584a506714c470270Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0009000000-f970a088fc3d9cdb8fe6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-017j-3109000000-bb054743c390ef266044Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0008900000-ed202aebd950e99a7852Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-1009300000-db2a4b9107b891a8ef3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9006000000-87df039839010127a1a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-450d1e4d25aae2ed99f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0005900000-630ea179fce67da6f208Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0r09-0019200000-0754019de78fe2be314dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0abc-0009400000-fe4f5c75dd7ef6e8d9ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-059l-3159100000-f0eff49c7e8da5d00c58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9640000000-28284141ad8f72ab8fe1Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000917
FooDB IDFDB022316
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5871
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID109088
ChEBI ID81240
PubChem Compound ID122340
Kegg Compound IDC17644
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Terada, Masaki; Sato, Manabu; Horie, Yoshiaki; Takatsu, Mitsumune; Minami, Junichi. Production of ursocholic acid. Jpn. Kokai Tokkyo Koho (1986), 9 pp.
2. Batta AK, Salen G, Abroon J: Ursocholic acid, a hydrophilic bile acid, fails to improve liver function parameters in primary biliary cirrhosis: comparison with ursodeoxycholic acid. Am J Gastroenterol. 1997 Jun;92(6):1035-7.
3. Lanzini A, Pigozzi G, Facchinetti D, Bettini L, Castellano M, Beschi M, Rossi A, Muiesan G: Effect of chronic ursocholic acid administration on bile lipid composition and bile acid pool size in gallstone patients. Scand J Gastroenterol. 1990 Jul;25(7):711-9.
4. Tint GS, Batta AK, Dayal B, Kovell N, Shefer S, Salen G: Metabolism of ursocholic acid in humans: conversion of ursocholic acid to deoxycholic acid. Hepatology. 1992 Apr;15(4):645-50.
5. Li H, Chen F, Shang Q, Pan L, Shneider BL, Chiang JY, Forman BM, Ananthanarayanan M, Tint GS, Salen G, Xu G: FXR-activating ligands inhibit rabbit ASBT expression via FXR-SHP-FTF cascade. Am J Physiol Gastrointest Liver Physiol. 2005 Jan;288(1):G60-6.
6. Loria P, Carulli N, Medici G, Menozzi D, Salvioli G, Bertolotti M, Montanari M: Effect of ursocholic acid on bile lipid secretion and composition. Gastroenterology. 1986 Apr;90(4):865-74.
7. Nakashima T, Sakamoto Y, Inaba K, Mitsuyoshi H, Ishikawa H, Nakajima Y, Sakai M, Shima T, Kashima K: A paucity of unusual trihydroxy bile acids in the urine of patients with severe liver diseases. Hepatology. 1999 May;29(5):1518-22.
8. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86.
9. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21.
10. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56.
11. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43.
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=10216137
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=12401785
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=1551642
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=1943496
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=2079611
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22198717
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=2396085
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=24076126
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=26718089
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=28751127
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=3660436
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=3715370
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=3949116
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=7676478
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=8500738
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=9177526