Isodeoxycholic acid (CHEM022845)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:56:23 UTC
Update Date2016-11-09 01:17:35 UTC
Accession NumberCHEM022845
Identification
Common NameIsodeoxycholic acid
ClassSmall Molecule
DescriptionIsodeoxycholic acid is a human fecal bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 3667743, 11316487, 16037564, 12576301, 11907135).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
7alpha,12alpha-Dihydroxy-5beta-cholanic acidKegg
7alpha,12alpha-Dihydroxycholanoic acidKegg
7a,12a-Dihydroxy-5b-cholanateGenerator
7a,12a-Dihydroxy-5b-cholanic acidGenerator
7alpha,12alpha-Dihydroxy-5beta-cholanateGenerator
7Α,12α-dihydroxy-5β-cholanateGenerator
7Α,12α-dihydroxy-5β-cholanic acidGenerator
7a,12a-DihydroxycholanoateGenerator
7a,12a-Dihydroxycholanoic acidGenerator
7alpha,12alpha-DihydroxycholanoateGenerator
7Α,12α-dihydroxycholanoateGenerator
7Α,12α-dihydroxycholanoic acidGenerator
IsodeoxycholateGenerator
3-Deoxycholic acidHMDB
7a,12a-Dihydroxy-5b-cholan-24-OateHMDB
7a,12a-Dihydroxy-5b-cholan-24-Oic acidHMDB
7a,12a-Dihydroxy-5b-cholanoateHMDB
7a,12a-Dihydroxy-5b-cholanoic acidHMDB
7alpha,12alpha-Dihydroxy-5beta-cholan-24-OateHMDB
7alpha,12alpha-Dihydroxy-5beta-cholan-24-Oic acidHMDB
Isodeoxycholic acidKEGG
(4R)-4-[(1S,2S,7S,9R,10R,11S,14R,15R,16S)-9,16-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoateGenerator, HMDB
Chemical FormulaC24H40O4
Average Molecular Mass392.572 g/mol
Monoisotopic Mass392.293 g/mol
CAS Registry Number566-17-6
IUPAC Name(4R)-4-[(1S,2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])CCCC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O
InChI IdentifierInChI=1S/C24H40O4/c1-14(7-10-21(27)28)16-8-9-17-22-18(13-20(26)24(16,17)3)23(2)11-5-4-6-15(23)12-19(22)25/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
InChI KeyZHCAAZIHTDCFJX-QLEQUTGBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Dihydroxy bile acid, alcohol, or derivatives
  • 12-hydroxysteroid
  • Hydroxysteroid
  • 7-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Solubility0.025 g/LALOGPS
logP3.16ALOGPS
logP3.87ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-0.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.12 m³·mol⁻¹ChemAxon
Polarizability46.11 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, Positivesplash10-01r2-1349000000-c20944bdb515b39b1d8bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-1110190000-4fbd3514c97db8f97c4dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0009000000-875537fa9339c3a3bbecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-1009000000-20a7c31d6177cdac7eccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02vj-7009000000-e32583ec8a96a2d6796dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-a7e668c25bb4e322f429Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-1009000000-af1365631dc58c1b7979Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-33d068d8853add57effaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-e572c29938091d5ba610Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05bf-5297000000-e9bd316f7bfb3538706aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-9530000000-343097ad815cfbd487e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-7eba834115ee2c679208Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0009000000-03834bc03b5a1c28e5f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1039000000-b5eba12dd80348c13a4dSpectrum
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 IDHMDB0002536
FooDB IDFDB023024
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID144358
ChEBI ID81256
PubChem Compound ID164672
Kegg Compound IDC17661
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Grand, R.; Reichstein, T. Bile acids and related compounds. XXXIII. Derivatives of cholic acid. Helvetica Chimica Acta (1945), 28 344-9.
2. Ikawa S, Miyake M, Mura T, Ikeguchi M: High-performance liquid chromatographic-fluorescence determination of human faecal bile acids. J Chromatogr. 1987 Jul 29;400:149-61.
3. 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.
4. 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.
5. 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.
6. 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.