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(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid (FDB023001)

Record Information
Version1.0
Creation date2011-09-21 00:23:06 UTC
Update date2015-07-21 06:57:28 UTC
Primary IDFDB023001
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid
Description(3a,5b)-24-oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-b-D-Glucopyranosiduronic acid is a natural human metabolite of Taurolithocholic acid generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. [HMDB]
CAS Number99794-82-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.03 g/LALOGPS
logP0.84ALOGPS
logP0.76ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)-0.98ChemAxon
pKa (Strongest Basic)0.084ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area199.92 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity161.37 m³·mol⁻¹ChemAxon
Polarizability71.24 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC32H53NO11S
IUPAC name(2S,3S,4S,5R,6R)-6-{[(1S,2S,7R,10R,11S,14R,15R)-2,15-dimethyl-14-[(2R)-4-[(2-sulfoethyl)carbamoyl]butan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI IdentifierInChI=1S/C32H53NO11S/c1-17(4-9-24(34)33-14-15-45(40,41)42)21-7-8-22-20-6-5-18-16-19(10-12-31(18,2)23(20)11-13-32(21,22)3)43-30-27(37)25(35)26(36)28(44-30)29(38)39/h17-23,25-28,30,35-37H,4-16H2,1-3H3,(H,33,34)(H,38,39)(H,40,41,42)/t17-,18-,19?,20+,21-,22+,23+,25+,26+,27-,28+,30-,31+,32-/m1/s1
InChI KeyYRKZDONPVFEWNN-CNEWWJQRSA-N
Isomeric SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])CC(CC[C@]4(C)[C@@]3([H])CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)[C@H](C)CCC(=O)NCCS(O)(=O)=O
Average Molecular Weight659.828
Monoisotopic Molecular Weight659.333932233
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
  • Hydroxysteroid
  • 12-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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
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-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0016-7200759000-8ae4eedc2cd5b2b6f0f5Spectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta)-24-Oxo-24-[(2-sulfoethyl)amino]cholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02c6-0400916000-f982046ac3f3f80084f52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05rr-0902700000-36595d1af24418e1c1da2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kdi-4809700000-017e38b18f15f84f97d32017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06si-4200619000-7c03cc7ab81289ecf35c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-5601913000-0a59b8c64361a2d42b952017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0089-8904700000-dab2de6272d12e1df00a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000009000-08821a85d5fa0122a8f82021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5500219000-2122c33229138c79ed292021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300242000-e036fbe265f9a62445cf2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000209000-d580abd8209dffaff2792021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0904-1439703000-294a9446398acf753c522021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rw-5849410000-cf45b26ec2d1d38d85bb2021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53477751
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02429
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
Enzymes
NameGene NameUniProt ID
UDP-glucuronosyltransferase 2B4UGT2B4P06133
UDP-glucuronosyltransferase 1-4UGT1A4P22310
UDP-glucuronosyltransferase 2B7UGT2B7P16662
UDP-glucuronosyltransferase 1-1UGT1A1P22309
UDP-glucuronosyltransferase 1-9UGT1A9O60656
UDP-glucuronosyltransferase 1-6UGT1A6P19224
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference