Showing metabocard for Ursodeoxycholic acid 3-sulfate (BMDB0002642)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:01:04 UTC
Update Date2020-05-11 20:10:19 UTC
BMDB IDBMDB0002642
Secondary Accession Numbers
  • BMDB02642
Metabolite Identification
Common NameUrsodeoxycholic acid 3-sulfate
DescriptionUrsodeoxycholic acid 3-sulfate 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. Ursodeoxycholic acid 3-sulfate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Ursodeoxycholate 3-sulfateGenerator
Ursodeoxycholate 3-sulphateGenerator
Ursodeoxycholic acid 3-sulfuric acidGenerator
Ursodeoxycholic acid 3-sulphuric acidGenerator
(4R)-4-[(1S,2S,5S,9S,10R,11S,14R,15R)-9-Hydroxy-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoateHMDB
(4R)-4-[(1S,2S,5S,9S,10R,11S,14R,15R)-9-Hydroxy-2,15-dimethyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoateHMDB
(4R)-4-[(1S,2S,5S,9S,10R,11S,14R,15R)-9-Hydroxy-2,15-dimethyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acidHMDB
(3a,5b,7b)-7-Hydroxy-3-(sulfooxy)-cholan-24-OateHMDB
(3a,5b,7b)-7-Hydroxy-3-(sulfooxy)-cholan-24-Oic acidHMDB
Ursodeoxycholic acid 3-sulphateHMDB
Chemical FormulaC24H40O7S
Average Molecular Weight472.635
Monoisotopic Molecular Weight472.249474324
IUPAC Name(4R)-4-[(1S,2S,5S,9S,10R,11S,14R,15R)-9-hydroxy-2,15-dimethyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoic acid
Traditional Nameursodeoxycholic acid 3-sulfate
CAS Registry Number68780-73-4
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)CC2C[C@H](CC[C@]12C)OS(O)(=O)=O
InChI Identifier
InChI=1S/C24H40O7S/c1-14(4-7-21(26)27)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(31-32(28,29)30)12-15(23)13-20(22)25/h14-20,22,25H,4-13H2,1-3H3,(H,26,27)(H,28,29,30)/t14-,15?,16+,17-,18+,19+,20+,22+,23+,24-/m1/s1
InChI KeyWHMOBEGYTDWMIG-ROKSHQGPSA-N
Chemical Taxonomy
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
  • Sulfated steroid skeleton
  • Hydroxysteroid
  • 7-hydroxysteroid
  • 7-alpha-hydroxysteroid
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Sulfuric acid monoester
  • Cyclic alcohol
  • Organic sulfuric acid or derivatives
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.49ALOGPS
logP2.32ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)-1.5ChemAxon
pKa (Strongest Basic)-0.54ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.13 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity119.27 m³·mol⁻¹ChemAxon
Polarizability52.6 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0536-0667900000-f5e817c86afceff3bc92View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0udi-3221659000-590f9fc72ad84350b04eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0002900000-abbbbfd5950c6cf2e226View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0009200000-087c5d2f48d7160b5dbcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-1229200000-7f1303ebc6e2d806539eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0001900000-bff4b187cc87bfca1cd0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-2009400000-eab51a83a4551fd439fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5a-9007100000-7432e93f953dc907a065View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0002900000-06cd8122555b78f76406View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1019200000-1a2383b307a87525bad2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1589000000-3a790fd1e8a788615b2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-29034312137a9db3fb88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1000900000-ade2350b3441a8a2d002View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9006400000-0a3dcf516ded28a9a1aaView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen Locations
  • Gallbladder
  • Intestine
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
GallbladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0002642
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023036
KNApSAcK IDNot Available
Chemspider ID13628379
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6728
PubChem Compound21252318
PDB IDNot Available
ChEBI ID89499
References
Synthesis ReferenceBandiera, Tiziano; Albini, Franca Marinone; Albini, Enrico. A convenient procedure for the synthesis of ursodeoxycholic acid sulfated derivatives. Synthetic Communications (1987), 17(9), 1111-17.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available