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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:06 UTC
HMDB IDHMDB0000733
Secondary Accession Numbers
  • HMDB00733
Metabolite Identification
Common NameHyodeoxycholic acid
DescriptionHyodeoxycholic acid is a bile acid. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the 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: 11316487 , 16037564 , 12576301 , 11907135 ).
Structure
Data?1582752152
Synonyms
ValueSource
HyodeoxycholateGenerator
3a,6a-Dihydroxy-5b-cholan-24-OateHMDB
3a,6a-Dihydroxy-5b-cholan-24-Oic acidHMDB
3a,6a-Dihydroxy-5b-cholanateHMDB
3a,6a-Dihydroxy-5b-cholanic acidHMDB
3a,6a-Dihydroxy-5b-cholanoateHMDB
3a,6a-Dihydroxy-5b-cholanoic acidHMDB
6a-HydroxylithocholateHMDB
6a-Hydroxylithocholic acidHMDB
7-DeoxyhyocholateHMDB
7-Deoxyhyocholic acidHMDB
a-HyodeoxycholateHMDB
a-Hyodeoxycholic acidHMDB
alpha-HyodeoxycholateHMDB
alpha-Hyodeoxycholic acidHMDB
HyodesoxycholateHMDB
Hyodesoxycholic acidHMDB
IodeoxycholateHMDB
Iodeoxycholic acidHMDB
3,6-Dihydroxy-5alpha-cholanoic acidHMDB
NaHDC compoundHMDB
Hyodeoxycholic acid, (3alpha,5beta,6beta)-isomerHMDB
Hyodeoxycholic acid, (3alpha,6beta)-isomerHMDB
Hyodeoxycholic acid, sodium saltHMDB
Murideoxycholic acidHMDB
Sodium hyodeoxycholateHMDB
(4R)-4-[(1S,2R,5R,8S,10S,11S,14R,15R)-5,8-Dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoateHMDB
Hyodeoxycholic acidMeSH
Chemical FormulaC24H40O4
Average Molecular Weight392.572
Monoisotopic Molecular Weight392.292659768
IUPAC Name(4R)-4-[(1S,2R,5R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2R,5R,8S,10S,11S,14R,15R)-5,8-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
CAS Registry Number83-49-8
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@H](O)C2C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17-,18+,19+,20?,21+,23-,24-/m1/s1
InChI KeyDGABKXLVXPYZII-CDONHWFASA-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
  • 3-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 6-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point198.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.06 mg/mLNot Available
LogP3.08RODA,A ET AL. (1990)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP2.98ALOGPS
logP3.71ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.79ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.27 m³·mol⁻¹ChemAxon
Polarizability46.69 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+193.73131661259
DarkChem[M-H]-185.70331661259
AllCCS[M+H]+201.15732859911
AllCCS[M-H]-198.89232859911
DeepCCS[M-2H]-236.05730932474
DeepCCS[M+Na]+210.74730932474
AllCCS[M+H]+201.232859911
AllCCS[M+H-H2O]+199.032859911
AllCCS[M+NH4]+203.132859911
AllCCS[M+Na]+203.732859911
AllCCS[M-H]-198.932859911
AllCCS[M+Na-2H]-200.232859911
AllCCS[M+HCOO]-201.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Hyodeoxycholic acid[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@H](O)C2C[C@H](O)CC[C@]12C3499.6Standard polar33892256
Hyodeoxycholic acid[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@H](O)C2C[C@H](O)CC[C@]12C3310.2Standard non polar33892256
Hyodeoxycholic acid[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@H](O)C2C[C@H](O)CC[C@]12C3503.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hyodeoxycholic acid,1TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](O)C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3344.3Semi standard non polar33892256
Hyodeoxycholic acid,1TMS,isomer #2C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3362.1Semi standard non polar33892256
Hyodeoxycholic acid,1TMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C[C@H](O)C4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3408.0Semi standard non polar33892256
Hyodeoxycholic acid,2TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3277.4Semi standard non polar33892256
Hyodeoxycholic acid,2TMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](O)C4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3328.0Semi standard non polar33892256
Hyodeoxycholic acid,2TMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3331.1Semi standard non polar33892256
Hyodeoxycholic acid,3TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C)C4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3286.8Semi standard non polar33892256
Hyodeoxycholic acid,1TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](O)C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3606.4Semi standard non polar33892256
Hyodeoxycholic acid,1TBDMS,isomer #2C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C(C)(C)C)C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3562.7Semi standard non polar33892256
Hyodeoxycholic acid,1TBDMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C[C@H](O)C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3622.4Semi standard non polar33892256
Hyodeoxycholic acid,2TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C(C)(C)C)C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3745.2Semi standard non polar33892256
Hyodeoxycholic acid,2TBDMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](O)C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3808.9Semi standard non polar33892256
Hyodeoxycholic acid,2TBDMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C(C)(C)C)C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3764.9Semi standard non polar33892256
Hyodeoxycholic acid,3TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3C[C@H](O[Si](C)(C)C(C)(C)C)C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3944.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-004m-0329000000-58d5a781e1d72501a6fc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (3 TMS) - 70eV, Positivesplash10-0006-1100290000-3298b2503a68dd31087e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hyodeoxycholic acid GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Hyodeoxycholic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-0006-0009000000-1a7a7cb68338f6eb36922012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hyodeoxycholic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-0006-0019000000-7ac011fa76fe71b487252012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hyodeoxycholic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0006-0009000000-77087c5c31c768755c6c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hyodeoxycholic acid 35V, Positive-QTOFsplash10-0002-5910000000-e85c0f620f0f33eda3832021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hyodeoxycholic acid 35V, Positive-QTOFsplash10-0002-2900000000-60e4234bfb052d4919452021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hyodeoxycholic acid 20V, Positive-QTOFsplash10-0006-2219000000-5b9c1050cbb76dafa7452021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hyodeoxycholic acid 20V, Positive-QTOFsplash10-0006-2219000000-be669783febc610d32a72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hyodeoxycholic acid 40V, Negative-QTOFsplash10-0006-0009000000-ba6aa3d13b20ed0d0c092021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hyodeoxycholic acid 30V, Negative-QTOFsplash10-0006-0009000000-34256fe4b0144e1f191b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hyodeoxycholic acid 20V, Positive-QTOFsplash10-0006-2219000000-815553fc5ecb67a781b42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hyodeoxycholic acid 30V, Negative-QTOFsplash10-0006-0009000000-8753654f95e1512222932021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hyodeoxycholic acid 40V, Negative-QTOFsplash10-0006-0009000000-30ddec6babbef6e84fde2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyodeoxycholic acid 10V, Positive-QTOFsplash10-056r-0009000000-581fe3701cfd4409cf1c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyodeoxycholic acid 20V, Positive-QTOFsplash10-056r-0009000000-9218797d27b939f6059a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyodeoxycholic acid 40V, Positive-QTOFsplash10-02vl-1219000000-acd8de6ea11917fdc1bd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyodeoxycholic acid 10V, Negative-QTOFsplash10-006x-0009000000-f969293bf286459bff3f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyodeoxycholic acid 20V, Negative-QTOFsplash10-00dl-0009000000-c32f7dbb58c16bc8f7932017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyodeoxycholic acid 40V, Negative-QTOFsplash10-0a4l-9006000000-a8bee4058c100d760c3c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyodeoxycholic acid 10V, Positive-QTOFsplash10-054o-0009000000-79e7c3afd290f34646cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyodeoxycholic acid 20V, Positive-QTOFsplash10-0a4i-3159000000-20e08d1a7b218eb91ebd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyodeoxycholic acid 40V, Positive-QTOFsplash10-0a4j-9681000000-7db68edc57414ccf438e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyodeoxycholic acid 10V, Negative-QTOFsplash10-0006-0009000000-7eba834115ee2c6792082021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyodeoxycholic acid 20V, Negative-QTOFsplash10-006x-0009000000-375fefa884fafe6b05bd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hyodeoxycholic acid 40V, Negative-QTOFsplash10-000g-2009000000-f58a3057b3e321a1006c2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Gall Bladder
  • Intestine
  • Kidney
  • Liver
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.1 (0.0-0.2) uMAdult (>18 years old)Both
Biliary cirrhosis
details
UrineDetected and Quantified0.0056 (0.0-0.011) umol/mmol creatinineAdult (>18 years old)Both
Biliary cirrhosis
details
Associated Disorders and Diseases
Disease References
Primary biliary cirrhosis
  1. Batta AK, Arora R, Salen G, Tint GS, Eskreis D, Katz S: Characterization of serum and urinary bile acids in patients with primary biliary cirrhosis by gas-liquid chromatography-mass spectrometry: effect of ursodeoxycholic acid treatment. J Lipid Res. 1989 Dec;30(12):1953-62. [PubMed:2621422 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022211
KNApSAcK IDNot Available
Chemspider ID8139282
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHyodeoxycholic acid
METLIN ID5701
PubChem Compound9963687
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceEyssen, H. J.; De Pauw, G.; Van Eldere, J. Formation of hyodeoxycholic acid from muricholic acid and hyocholic acid by an unidentified Gram-positive rod termed HDCA-1 isolated from rat intestinal microflora. Applied and Environmental Microbiology (1999),
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Radominska A, Comer KA, Zimniak P, Falany J, Iscan M, Falany CN: Human liver steroid sulphotransferase sulphates bile acids. Biochem J. 1990 Dec 15;272(3):597-604. [PubMed:2268288 ]
  2. Pillot T, Ouzzine M, Fournel-Gigleux S, Lafaurie C, Radominska A, Burchell B, Siest G, Magdalou J: Glucuronidation of hyodeoxycholic acid in human liver. Evidence for a selective role of UDP-glucuronosyltransferase 2B4. J Biol Chem. 1993 Dec 5;268(34):25636-42. [PubMed:8244999 ]
  3. Fournel-Gigleux S, Sutherland L, Sabolovic N, Burchell B, Siest G: Stable expression of two human UDP-glucuronosyltransferase cDNAs in V79 cell cultures. Mol Pharmacol. 1991 Feb;39(2):177-83. [PubMed:1847492 ]
  4. Summerfield JA, Billing BH, Shackleton CH: Identification of bile acids in the serum and urine in cholestasis. Evidence for 6alpha-hydroxylation of bile acids in man. Biochem J. 1976 Feb 15;154(2):507-16. [PubMed:938463 ]
  5. Marschall HU, Matern H, Egestad B, Matern S, Sjovall S: 6 alpha-glucuronidation of hyodeoxycholic acid by human liver, kidney and small bowel microsomes. Biochim Biophys Acta. 1987 Sep 25;921(2):392-7. [PubMed:2820501 ]
  6. 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. [PubMed:11316487 ]
  7. 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. [PubMed:16037564 ]
  8. 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. [PubMed:12576301 ]
  9. 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. [PubMed:11907135 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
Reactions
Lithocholic acid + NADPH + Oxygen → Hyodeoxycholic acid + NADP + Waterdetails
General function:
Involved in binding
Specific function:
Ileal protein which stimulates gastric acid and pepsinogen secretion. Seems to be able to bind to bile salts and bilirubins. Isoform 2 is essential for the survival of colon cancer cells to bile acid-induced apoptosis
Gene Name:
FABP6
Uniprot ID:
P51161
Molecular weight:
14371.2
References
  1. Kurz M, Brachvogel V, Matter H, Stengelin S, Thuring H, Kramer W: Insights into the bile acid transportation system: the human ileal lipid-binding protein-cholyltaurine complex and its comparison with homologous structures. Proteins. 2003 Feb 1;50(2):312-28. [PubMed:12486725 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
Gene Name:
SLCO1B3
Uniprot ID:
Q9NPD5
Molecular weight:
77402.2
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular weight:
76448.0
References
  1. Michalski C, Cui Y, Nies AT, Nuessler AK, Neuhaus P, Zanger UM, Klein K, Eichelbaum M, Keppler D, Konig J: A naturally occurring mutation in the SLC21A6 gene causing impaired membrane localization of the hepatocyte uptake transporter. J Biol Chem. 2002 Nov 8;277(45):43058-63. Epub 2002 Aug 23. [PubMed:12196548 ]
General function:
Involved in ATP binding
Specific function:
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:
ABCC3
Uniprot ID:
O15438
Molecular weight:
169341.1
General function:
Involved in ATP binding
Specific function:
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:
ABCB11
Uniprot ID:
O95342
Molecular weight:
146405.8
General function:
Involved in bile acid:sodium symporter activity
Specific function:
Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism
Gene Name:
SLC10A2
Uniprot ID:
Q12908
Molecular weight:
37697.4
References
  1. Kramer W, Girbig F, Glombik H, Corsiero D, Stengelin S, Weyland C: Identification of a ligand-binding site in the Na+/bile acid cotransporting protein from rabbit ileum. J Biol Chem. 2001 Sep 21;276(38):36020-7. Epub 2001 Jul 10. [PubMed:11447228 ]
General function:
Involved in bile acid:sodium symporter activity
Specific function:
The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
Gene Name:
SLC10A1
Uniprot ID:
Q14973
Molecular weight:
38118.64
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:
SLCO1A2
Uniprot ID:
P46721
Molecular weight:
74144.1
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate
Gene Name:
SLCO4A1
Uniprot ID:
Q96BD0
Molecular weight:
77192.5