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Showing Compound Sulfolithocholic acid (FDB022312)

Record Information
Version1.0
Creation date2011-09-21 00:11:57 UTC
Update date2015-10-09 22:30:52 UTC
Primary IDFDB022312
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSulfolithocholic 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 Number34669-57-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
SulfolithocholateGenerator
SulpholithocholateGenerator
Sulpholithocholic acidGenerator
(4R)-4-[(1S,2S,5R,10R,11S,14R,15R)-2,15-Dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoateHMDB
(4R)-4-[(1S,2S,5R,10R,11S,14R,15R)-2,15-Dimethyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoateHMDB
(4R)-4-[(1S,2S,5R,10R,11S,14R,15R)-2,15-Dimethyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acidHMDB
(3a-alpha,5-beta)-3-(sulfooxy)-Cholan-24-oatehmdb
(3a-alpha,5-beta)-3-(sulfooxy)-Cholan-24-oic acidhmdb
3a-Sulfate-5b-cholan-24-oatehmdb
3a-Sulfate-5b-cholan-24-oic acidhmdb
Lithocholic acid 3-alpha-sulfatehmdb
Lithocholic acid 3-alpha-sulphateHMDB
Lithocholic acid 3-O-sulfatehmdb
Lithocholic acid 3-O-sulphateHMDB
Lithocholic acid 3-sulfatehmdb
Lithocholic acid 3-sulphateHMDB
Lithocholic acid 3a-sulfatehmdb
Lithocholic acid 3a-sulphateHMDB
Sulfolithocholic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.00052 g/LALOGPS
logP1.39ALOGPS
logP5.08ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)-1.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity117.67 m³·mol⁻¹ChemAxon
Polarizability51.26 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC24H40O6S
IUPAC name(4R)-4-[(1S,2S,5R,10R,11S,14R,15R)-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
InChI IdentifierInChI=1S/C24H40O6S/c1-15(4-9-22(25)26)19-7-8-20-18-6-5-16-14-17(30-31(27,28)29)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21H,4-14H2,1-3H3,(H,25,26)(H,27,28,29)/t15-,16?,17-,18+,19-,20+,21+,23+,24-/m1/s1
InChI KeyAXDXVEYHEODSPN-YPLGJCPNSA-N
Isomeric SMILES[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](CC[C@]12C)OS(O)(=O)=O
Average Molecular Weight456.636
Monoisotopic Molecular Weight456.254559702
Classification
Description Belongs to the class of organic compounds known as bile acids, alcohols and derivatives. These are organic compounds containing an alcohol or acid derivative of cholic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentBile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Bile acid, alcohol, or derivatives
  • Sulfated steroid skeleton
  • Sulfuric acid monoester
  • Sulfate-ester
  • Alkyl sulfate
  • Sulfuric acid ester
  • Organic sulfuric acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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-MSSulfolithocholic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-057l-0229800000-ff3e444dad7e1b360459Spectrum
Predicted GC-MSSulfolithocholic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03k9-3215690000-b14d9ba0d2e22d0fac76Spectrum
Predicted GC-MSSulfolithocholic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSulfolithocholic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSulfolithocholic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSulfolithocholic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0003900000-45985ba677e49ad3783c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bt9-0019100000-5d9cbda8c60a2dc8a7242016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01wn-1195200000-7cb7e68c25434da3bc7c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0002900000-b2a37041a37ebaa49afb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-2009300000-ecff746129e597d768bd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9007000000-d1e8fe2d2625c0cb51292016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-60e87f56a547dd8dd9ce2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1000900000-0c13f66f5774e8dbcce32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9004200000-63456d901c6542b0de142021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0003900000-9db7d620eecb7837bdf32021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5i-1297100000-c5c099d5d80e5500ff092021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-2985000000-c0e22e97b9340e821e3c2021-09-25View 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 ID8429048
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID10253562
Pubchem Substance IDNot Available
ChEBI ID35421
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00907
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