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Showing Compound 3a,6a,7b-Trihydroxy-5b-cholanoic acid (FDB021983)

Record Information
Version1.0
Creation date2011-09-21 00:06:30 UTC
Update date2015-10-09 22:33:05 UTC
Primary IDFDB021983
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3a,6a,7b-Trihydroxy-5b-cholanoic acid
Description3a,6a,7b-Trihydroxy-5b-cholanoic acid is an unusual trihydroxy bile acid found in the urine of healthy humans, mainly in newborns (PMID 3769218). A 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 Number6830-03-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(3alpha,5beta,6alpha,7beta)-3,6,7-Trihydroxycholan-24-Oic acidChEBI
Omega-mcaChEBI
Omega-muricholic acidKegg
(3a,5b,6a,7b)-3,6,7-Trihydroxycholan-24-OateGenerator
(3a,5b,6a,7b)-3,6,7-Trihydroxycholan-24-Oic acidGenerator
(3alpha,5beta,6alpha,7beta)-3,6,7-Trihydroxycholan-24-OateGenerator
(3Α,5β,6α,7β)-3,6,7-trihydroxycholan-24-OateGenerator
(3Α,5β,6α,7β)-3,6,7-trihydroxycholan-24-Oic acidGenerator
Omega-muricholateGenerator
3a,6a,7b-Trihydroxy-5b-cholanoateGenerator
3a,6a,7b-Trihydroxy-5b-cholan-24-OateHMDB
3a,6a,7b-Trihydroxy-5b-cholan-24-Oic acidHMDB
W-MuricholateHMDB
W-Muricholic acidHMDB
Muricholic acid, (3alpha,5alpha,6alpha,7alpha)-isomerHMDB
Muricholic acid, (3alpha,5beta,6alpha,7alpha)-isomerHMDB
Trihydroxy-5 alpha-cholanoic acidHMDB
3 alpha,6 alpha,7 beta-Trihydroxy-5 beta-cholanoic acidHMDB
alpha-Muricholic acidHMDB
Muricholic acid, (3alpha,5beta,6beta,7beta)-isomerHMDB
3,6,7-Trihydroxy-5-cholanoic acidHMDB
Muricholic acid, sodium saltHMDB
beta-Muricholic acidHMDB
Hyocholic acidHMDB
Muricholic acidHMDB
Muricholic acid, (3alpha,5beta,6alpha,7beta)-isomerHMDB
Muricholic acid, (3alpha,5beta,6beta,7alpha)-isomerHMDB
3a,6a,7b-trihydroxy-5b-Cholan-24-oatehmdb
3a,6a,7b-trihydroxy-5b-Cholan-24-oic acidhmdb
3a,6a,7b-Trihydroxy-5b-cholanoic acidhmdb
omega-Muricholatehmdb
omega-Muricholic acidhmdb
w-Muricholatehmdb
w-Muricholic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.069 g/LALOGPS
logP2.16ALOGPS
logP2.72ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.6ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.56 m³·mol⁻¹ChemAxon
Polarizability47.1 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC24H40O5
IUPAC name(4R)-4-[(1S,2R,5R,7R,8R,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
InChI IdentifierInChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21-,22-,23-,24-/m1/s1
InChI KeyDKPMWHFRUGMUKF-NTPBNISXSA-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@@H](O)[C@H](O)[C@]2([H])C[C@H](O)CC[C@]12C
Average Molecular Weight408.5714
Monoisotopic Molecular Weight408.28757439
Classification
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
  • 6-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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

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-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004l-0329000000-fed34af3d93baa3f7367Spectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-1010029000-e5824ce563bff12a309cSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3a,6a,7b-Trihydroxy-5b-cholanoic acid, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0001900000-d3a03d40e1e660b478562012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-4984300000-003497742d7b2b6ee0042012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-01p7-4920000000-7110ab8e5a56706190512012-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0009100000-aeaf5bcdde74fe1ddf762017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-0009000000-4af1ebd01d1d670d4f422017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003u-2209000000-454d741b691e592d251a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0007900000-e501198616f74730538f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-1009300000-9efc23876fa89e243bc62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9007000000-e5bd870e3f9870c89a142017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0009600000-56beda528763ce5ae6df2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-059j-3449200000-98d256091462f2bbd8822021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052u-4951000000-c203ad5efbf5e653aa092021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0001900000-68e3200734e1d0985f372021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0009800000-a11781ffcf06d8bb288c2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-3009300000-d354f18e540a94d7dfe12021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
ChemSpider ID4446939
ChEMBL IDNot Available
KEGG Compound IDC17727
Pubchem Compound ID5283851
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00364
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
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference