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Showing Compound Taurochenodeoxycholate-7-sulfate (FDB023016)

Record Information
Version1.0
Creation date2011-09-21 00:23:18 UTC
Update date2015-07-21 06:57:28 UTC
Primary IDFDB023016
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTaurochenodeoxycholate-7-sulfate
DescriptionTaurochenodeoxycholate-7-sulfate is a sulfated bile acid. Under normal circumstances, bile acid sulfation is a minor pathway. However in the presence of cholestasis, the fraction of the bile acid pool which is sulfated increases. Sulfation of bile acids increases the aqueous solubility of the amphipathic compounds and results in more efficient renal clearance as well as in decreased reabsorption from the intestinal lumen. 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 Number66874-12-2
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP-0.61ALOGPS
logP-0.18ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)-1.2ChemAxon
pKa (Strongest Basic)0.13ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area167.3 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity140.67 m³·mol⁻¹ChemAxon
Polarizability61.86 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H45NO9S2
IUPAC name2-[(4R)-4-[(1S,2S,5R,7S,9R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyl-9-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid
InChI IdentifierInChI=1S/C26H45NO9S2/c1-16(4-7-23(29)27-12-13-37(30,31)32)19-5-6-20-24-21(9-11-26(19,20)3)25(2)10-8-18(28)14-17(25)15-22(24)36-38(33,34)35/h16-22,24,28H,4-15H2,1-3H3,(H,27,29)(H,30,31,32)(H,33,34,35)/t16-,17+,18-,19-,20+,21+,22-,24+,25+,26-/m1/s1
InChI KeyWTKQKSAFONWCMW-BJLOMENOSA-N
Isomeric SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)OS(O)(=O)=O)[C@H](C)CCC(=O)NCCS(O)(=O)=O
Average Molecular Weight579.767
Monoisotopic Molecular Weight579.253573423
Classification
Description Belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTaurinated bile acids and derivatives
Alternative Parents
Substituents
  • Taurinated bile acid
  • Hydroxy bile acid, alcohol, or derivatives
  • Monohydroxy bile acid, alcohol, or derivatives
  • Sulfated steroid skeleton
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Alkyl sulfate
  • Fatty acyl
  • Sulfuric acid ester
  • Fatty amide
  • Sulfate-ester
  • Sulfuric acid monoester
  • N-acyl-amine
  • Alkanesulfonic acid
  • Cyclic alcohol
  • Sulfonyl
  • Organic sulfuric acid or derivatives
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organosulfonic acid
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Organic oxide
  • Organosulfur compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTaurochenodeoxycholate-7-sulfate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ir0-0111490000-c5d125fc31dddead1b34Spectrum
Predicted GC-MSTaurochenodeoxycholate-7-sulfate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-4111229000-3d024bd929698d60002fSpectrum
Predicted GC-MSTaurochenodeoxycholate-7-sulfate, "Taurochenodeoxycholate-7-sulfate,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTaurochenodeoxycholate-7-sulfate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTaurochenodeoxycholate-7-sulfate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTaurochenodeoxycholate-7-sulfate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTaurochenodeoxycholate-7-sulfate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTaurochenodeoxycholate-7-sulfate, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTaurochenodeoxycholate-7-sulfate, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTaurochenodeoxycholate-7-sulfate, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0400790000-22a57b24b98e38cf6e012017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06w9-1902810000-057a4b14380262b29d572017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-5905310000-78a229274535fac0c4f32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000390000-f77169c49f0f60e9ab2f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-2200920000-fb72eddde9880d0804bb2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0089-9402100000-62b74344c0bf631ebfbb2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000390000-e50614f3a63cfee3a2582021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1201940000-70bac8b02903f54f9d172021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000w-9735400000-7c2260cc5b1a1bbe85f22021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000090000-a9fb7801669e515fe4ad2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1000090000-088387fb9420a01a1d212021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9100040000-9565ad793a9435a2f62d2021-09-24View Spectrum
NMRNot Available
ChemSpider ID24850142
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID20842013
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02498
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
Processing...
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