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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:55 UTC
Update Date2022-03-07 02:49:16 UTC
HMDB IDHMDB0002513
Secondary Accession Numbers
  • HMDB02513
Metabolite Identification
Common NameLithocholate 3-O-glucuronide
DescriptionAnalysis of sequential bile samples by thin-layer chromatography (TLC) demonstrated that lithocholic acid glucuronide was present in bile throughout the course of the experiments and that its secretion rate paralleled that of total isotope secretion. Initial confirmation of the identity of this metabolite was obtained by the recovery of labeled lithocholic acid after beta-glucuronidase hydrolysis of bile samples. Glucuronates; Lithocholic Acid.
Structure
Data?1582752251
Synonyms
ValueSource
Lithocholic acid 3-O-glucuronideGenerator
Lithocholic acid 3-glucuronideHMDB
Lithocholate 3-O-beta-D-glucuronideHMDB
Lithocholic acid glucuronideHMDB
Chemical FormulaC30H48O9
Average Molecular Weight552.6967
Monoisotopic Molecular Weight552.329833134
IUPAC Name(2S,3S,4S,5R,6R)-6-{[(1S,2S,5S,7R,10R,11S,14R,15R)-14-[(2R)-4-carboxybutan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Namelithocholate 3-O-glucuronide
CAS Registry Number75239-91-7
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](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C30H48O9/c1-15(4-9-22(31)32)19-7-8-20-18-6-5-16-14-17(10-12-29(16,2)21(18)11-13-30(19,20)3)38-28-25(35)23(33)24(34)26(39-28)27(36)37/h15-21,23-26,28,33-35H,4-14H2,1-3H3,(H,31,32)(H,36,37)/t15-,16-,17+,18+,19-,20+,21+,23+,24+,25-,26+,28-,29+,30-/m1/s1
InChI KeyGIQXKAXWRLHLDD-VOJQCDQYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroid glucuronide conjugates
Alternative Parents
Substituents
  • Steroid-glucuronide-skeleton
  • Bile acid, alcohol, or derivatives
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Pyran
  • Hydroxy acid
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP2.72ALOGPS
logP3.57ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)3.45ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.75 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity139.96 m³·mol⁻¹ChemAxon
Polarizability61.69 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-251.12830932474
DeepCCS[M+Na]+225.06430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Lithocholate 3-O-glucuronide[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](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O3923.7Standard polar33892256
Lithocholate 3-O-glucuronide[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](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O4375.3Standard non polar33892256
Lithocholate 3-O-glucuronide[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](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O4480.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lithocholate 3-O-glucuronide,1TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4339.0Semi standard non polar33892256
Lithocholate 3-O-glucuronide,1TMS,isomer #2C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4391.8Semi standard non polar33892256
Lithocholate 3-O-glucuronide,1TMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4398.0Semi standard non polar33892256
Lithocholate 3-O-glucuronide,1TMS,isomer #4C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4395.9Semi standard non polar33892256
Lithocholate 3-O-glucuronide,1TMS,isomer #5C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4342.9Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4282.3Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TMS,isomer #10C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4312.8Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4310.1Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TMS,isomer #3C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4317.1Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TMS,isomer #4C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4305.1Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TMS,isomer #5C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4311.8Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TMS,isomer #6C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4354.8Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TMS,isomer #7C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4359.4Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TMS,isomer #8C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4317.3Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TMS,isomer #9C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4355.4Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4275.5Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TMS,isomer #10C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4328.2Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4283.6Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TMS,isomer #3C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4276.0Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TMS,isomer #4C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4317.8Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TMS,isomer #5C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4319.4Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TMS,isomer #6C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4315.1Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TMS,isomer #7C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4309.8Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TMS,isomer #8C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4316.0Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TMS,isomer #9C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4328.0Semi standard non polar33892256
Lithocholate 3-O-glucuronide,4TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4257.1Semi standard non polar33892256
Lithocholate 3-O-glucuronide,4TMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4255.6Semi standard non polar33892256
Lithocholate 3-O-glucuronide,4TMS,isomer #3C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4279.8Semi standard non polar33892256
Lithocholate 3-O-glucuronide,4TMS,isomer #4C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4271.5Semi standard non polar33892256
Lithocholate 3-O-glucuronide,4TMS,isomer #5C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4263.8Semi standard non polar33892256
Lithocholate 3-O-glucuronide,1TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4603.3Semi standard non polar33892256
Lithocholate 3-O-glucuronide,1TBDMS,isomer #2C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4592.1Semi standard non polar33892256
Lithocholate 3-O-glucuronide,1TBDMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4609.8Semi standard non polar33892256
Lithocholate 3-O-glucuronide,1TBDMS,isomer #4C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4603.5Semi standard non polar33892256
Lithocholate 3-O-glucuronide,1TBDMS,isomer #5C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4591.8Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4752.1Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TBDMS,isomer #10C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4767.9Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TBDMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4761.3Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TBDMS,isomer #3C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4779.4Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TBDMS,isomer #4C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4767.9Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TBDMS,isomer #5C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4754.7Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TBDMS,isomer #6C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4764.7Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TBDMS,isomer #7C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4773.3Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TBDMS,isomer #8C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4767.4Semi standard non polar33892256
Lithocholate 3-O-glucuronide,2TBDMS,isomer #9C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4775.8Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4920.5Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TBDMS,isomer #10C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4953.9Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TBDMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4926.0Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TBDMS,isomer #3C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4932.7Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TBDMS,isomer #4C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4935.5Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TBDMS,isomer #5C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4941.8Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TBDMS,isomer #6C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4945.2Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TBDMS,isomer #7C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O)CC[C@]4(C)[C@H]3CC[C@@]21C4938.1Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TBDMS,isomer #8C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4948.1Semi standard non polar33892256
Lithocholate 3-O-glucuronide,3TBDMS,isomer #9C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4947.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (Non-derivatized) - 70eV, Positivesplash10-002r-6205590000-38694c7925c18dd4ba1c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (2 TMS) - 70eV, Positivesplash10-001i-3406029000-7229a6fee334638895752017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS ("Lithocholate 3-O-glucuronide,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_3_5) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_3_6) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_3_7) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lithocholate 3-O-glucuronide GC-MS (TMS_3_8) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholate 3-O-glucuronide 10V, Positive-QTOFsplash10-0pdr-0009060000-fa8d533035a1529140532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholate 3-O-glucuronide 20V, Positive-QTOFsplash10-056r-0009010000-74247478eda83981ec002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholate 3-O-glucuronide 40V, Positive-QTOFsplash10-016r-0219000000-be750b2c39743b6aa36b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholate 3-O-glucuronide 10V, Negative-QTOFsplash10-0zi0-1206190000-7574484741f16ee01e6a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholate 3-O-glucuronide 20V, Negative-QTOFsplash10-056r-2209120000-c6eb5b3f627f13090a9e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholate 3-O-glucuronide 40V, Negative-QTOFsplash10-0a6r-6109000000-d30e9d34ffefc8d871e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholate 3-O-glucuronide 10V, Negative-QTOFsplash10-0udi-0000090000-f7afaa19600b0cf8248c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholate 3-O-glucuronide 20V, Negative-QTOFsplash10-0ue9-3101290000-0da9a01a36fd677f1f7f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholate 3-O-glucuronide 40V, Negative-QTOFsplash10-0a4i-9103420000-b66fce6cf25d53f02e6f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholate 3-O-glucuronide 10V, Positive-QTOFsplash10-0udr-0000190000-b0bd8da6810e3293385c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholate 3-O-glucuronide 20V, Positive-QTOFsplash10-0a4r-2296230000-2b21fbe8cdc2bfaee1042021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lithocholate 3-O-glucuronide 40V, Positive-QTOFsplash10-0ab9-2934200000-59a123ab0679c6c41b9d2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023020
KNApSAcK IDNot Available
Chemspider ID112415
KEGG Compound IDC03033
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6706
PubChem Compound126511
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Singhal SS, Sharma R, Gupta S, Ahmad H, Zimniak P, Radominska A, Lester R, Awasthi YC: The anionic conjugates of bilirubin and bile acids stimulate ATP hydrolysis by S-(dinitrophenyl)glutathione ATPase of human erythrocyte. FEBS Lett. 1991 Apr 9;281(1-2):255-7. [PubMed:1826661 ]
  2. (). Little JM, Zimniak P, Shattuck KE, Lester R, Radominska A. Metabolism of lithocholic acid in the rat: formation of lithocholic acid 3-O-glucuronide in vivo. J Lipid Res. 1990 Apr;31(4):615-22.. .

Only showing the first 10 proteins. There are 18 proteins in total.

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Molecular weight:
38742.9
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:
UGT2B15
Uniprot ID:
P54855
Molecular weight:
61035.815
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Molecular weight:
60771.605
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT1A3
Uniprot ID:
P35503
Molecular weight:
60337.835
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
Gene Name:
UGT2B17
Uniprot ID:
O75795
Molecular weight:
61094.915

Only showing the first 10 proteins. There are 18 proteins in total.