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Showing Compound Isolithocholic acid (FDB022201)

Record Information
Version1.0
Creation date2011-09-21 00:10:00 UTC
Update date2015-07-21 06:57:03 UTC
Primary IDFDB022201
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsolithocholic acid
DescriptionA bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic. 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 Number1534-35-6
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(3beta,5beta)-3-Hydroxycholan-24-Oic acidChEBI
3-Epilithocholic acidChEBI
3beta-Hydroxy-5beta-cholan-24-Oic acidChEBI
3beta-Lithocholic acidChEBI
beta-Lithocholanic acidChEBI
beta-Lithocholic acidChEBI
(3b,5b)-3-Hydroxycholan-24-OateGenerator
(3b,5b)-3-Hydroxycholan-24-Oic acidGenerator
(3beta,5beta)-3-Hydroxycholan-24-OateGenerator
(3Β,5β)-3-hydroxycholan-24-OateGenerator
(3Β,5β)-3-hydroxycholan-24-Oic acidGenerator
3-EpilithocholateGenerator
3b-Hydroxy-5b-cholan-24-OateGenerator
3b-Hydroxy-5b-cholan-24-Oic acidGenerator
3beta-Hydroxy-5beta-cholan-24-OateGenerator
3Β-hydroxy-5β-cholan-24-OateGenerator
3Β-hydroxy-5β-cholan-24-Oic acidGenerator
3b-LithocholateGenerator
3b-Lithocholic acidGenerator
3beta-LithocholateGenerator
3Β-lithocholateGenerator
3Β-lithocholic acidGenerator
b-LithocholanateGenerator
b-Lithocholanic acidGenerator
beta-LithocholanateGenerator
Β-lithocholanateGenerator
Β-lithocholanic acidGenerator
b-LithocholateGenerator
b-Lithocholic acidGenerator
beta-LithocholateGenerator
Β-lithocholateGenerator
Β-lithocholic acidGenerator
IsolithocholateGenerator
3b-Hydroxy-5b-cholanateHMDB
3b-Hydroxy-5b-cholanic acidHMDB
3b-Hydroxy-5b-cholanoateHMDB
3b-Hydroxy-5b-cholanoic acidHMDB
5b-Cholanic acid-3b-olHMDB
Acid, isolithocholicHMDB
Acid, lithocholicHMDB
LithocholateHMDB
Lithocholic acidHMDB
3b-Hydroxy-5b-cholan-24-oatehmdb
3b-Hydroxy-5b-cholan-24-oic acidhmdb
3β-hydroxy-5β-cholan-24-OateGenerator
3β-hydroxy-5β-cholan-24-Oic acidGenerator
Isolithocholic acidhmdb
β-lithocholanateGenerator
β-lithocholanic acidGenerator
β-lithocholateGenerator
β-lithocholic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.0005 g/LALOGPS
logP4.38ALOGPS
logP5.02ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)4.79ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.68 m³·mol⁻¹ChemAxon
Polarizability45.89 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC24H40O3
IUPAC name(4R)-4-[(1S,2S,5S,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
InChI IdentifierInChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17+,18+,19-,20+,21+,23+,24-/m1/s1
InChI KeySMEROWZSTRWXGI-WFVDQZAMSA-N
Isomeric SMILES[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](O)CC[C@]12C
Average Molecular Weight376.5726
Monoisotopic Molecular Weight376.297745146
Classification
Description Belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentMonohydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Monohydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
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-MSIsolithocholic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0hft-0109000000-d80c67969566eb069712Spectrum
Predicted GC-MSIsolithocholic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-3214890000-a148637510771fd69f57Spectrum
Predicted GC-MSIsolithocholic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsolithocholic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsolithocholic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsolithocholic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsolithocholic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsolithocholic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0129000000-066ac41ad9941f9e21f42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0249000000-cce770467236fef9c1022021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-001m-9610000000-9bf43cf0de56ef3b91572021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0249000000-319218499f72e4ee3f1f2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0009000000-f631439c42560b6112dc2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bu3-0029000000-77d9dd354e5acfcbb0592016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-1195000000-4e93d1691883a980ad092016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-bc8a31ce5625ab01cbf92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-1009000000-703fb777c311a25b0d152016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-6c71a6df88d4f84121d02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-eccc9e9b8c78169f53132021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0009000000-7777c272612ec6c534f12021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05di-3019000000-e5596a2bcefec4be517a2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0009000000-4fc9c94a2a74d03b596d2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-6579000000-8d70683d9c59bbc7c41e2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-8970000000-50834929c8da38b179bf2021-09-25View Spectrum
NMRNot Available
ChemSpider ID144522
ChEMBL IDCHEMBL270067
KEGG Compound IDC17658
Pubchem Compound ID164853
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00717
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