Record Information
Version1.0
Creation date2011-09-21 00:10:09 UTC
Update date2015-10-09 22:29:45 UTC
Primary IDFDB022211
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHyodeoxycholic acid
DescriptionA 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: 11316487, 16037564, 12576301, 11907135) [HMDB]
CAS Number83-49-8
Structure
Thumb
Synonyms
SynonymSource
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
3a,6a-Dihydroxy-5b-cholan-24-oatehmdb
3a,6a-Dihydroxy-5b-cholan-24-oic acidhmdb
Predicted 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
Chemical FormulaC24H40O4
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
InChI IdentifierInChI=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
Isomeric 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
Average Molecular Weight392.572
Monoisotopic Molecular Weight392.292659768
Classification
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

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSHyodeoxycholic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004m-0329000000-58d5a781e1d72501a6fcSpectrum
Predicted GC-MSHyodeoxycholic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-1100290000-3298b2503a68dd31087eSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0006-0009000000-1a7a7cb68338f6eb3692Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-0019000000-7ac011fa76fe71b48725Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-0009000000-77087c5c31c768755c6cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0009000000-581fe3701cfd4409cf1cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0009000000-9218797d27b939f6059aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02vl-1219000000-acd8de6ea11917fdc1bdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-006x-0009000000-f969293bf286459bff3fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-0009000000-c32f7dbb58c16bc8f793Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-a8bee4058c100d760c3cSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID8139282
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID9963687
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00733
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference