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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:05 UTC
HMDB IDHMDB0000708
Secondary Accession Numbers
  • HMDB00708
Metabolite Identification
Common NameGlycoursodeoxycholic acid
DescriptionGlycoursodeoxycholic acid is an acyl glycine and a bile acid-glycine conjugate. It is a secondary bile acid produced by the action of enzymes existing in the microbial flora of the colonic environment. In hepatocytes, both primary and secondary bile acids undergo amino acid conjugation at the C-24 carboxylic acid on the side chain, and almost all bile acids in the bile duct therefore exist in a glycine conjugated form (PMID: 16949895 ). Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the 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 ).
Structure
Data?1582752150
Synonyms
ValueSource
3alpha,7beta-Dihydroxy-5beta-cholanoylglycineChEBI
Glycine ursodeoxycholic acidChEBI
Glycylursodeoxycholic acidChEBI
GUDCAChEBI
N-(3alpha,7beta-Dihydroxy-5beta-cholan-24-oyl)glycineChEBI
N-[(3alpha,5beta,7beta)-3,7-Dihydroxy-24-oxocholan-24-yl]glycineChEBI
UrsodeoxycholylglycineChEBI
3a,7b-Dihydroxy-5b-cholanoylglycineGenerator
3Α,7β-dihydroxy-5β-cholanoylglycineGenerator
Glycine ursodeoxycholateGenerator
GlycylursodeoxycholateGenerator
N-(3a,7b-Dihydroxy-5b-cholan-24-oyl)glycineGenerator
N-(3Α,7β-dihydroxy-5β-cholan-24-oyl)glycineGenerator
N-[(3a,5b,7b)-3,7-Dihydroxy-24-oxocholan-24-yl]glycineGenerator
N-[(3Α,5β,7β)-3,7-dihydroxy-24-oxocholan-24-yl]glycineGenerator
GlycoursodeoxycholateGenerator
(3beta,5beta,7beta)-3,7-Dihydroxycholan-24-oic acidHMDB
(3β,5β,7β)-3,7-Dihydroxycholan-24-oic acidHMDB
3beta,7beta-Dihydroxy-5beta-cholan-24-oic acidHMDB
3beta,7beta-Dihydroxy-5beta-cholanic acidHMDB
3beta,7beta-Dihydroxy-5beta-cholanoic acidHMDB
3beta-Ursodeoxycholic acidHMDB
3β,7β-Dihydroxy-5β-cholan-24-oic acidHMDB
3β,7β-Dihydroxy-5β-cholanic acidHMDB
3β,7β-Dihydroxy-5β-cholanoic acidHMDB
3β-Ursodeoxycholic acidHMDB
Isoursodeoxycholic acidHMDB
Chemical FormulaC26H43NO5
Average Molecular Weight449.6233
Monoisotopic Molecular Weight449.314123491
IUPAC Name2-[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid
Traditional Name[(4R)-4-[(1S,2S,5R,7S,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]acetic acid
CAS Registry Number64480-66-6
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCC(O)=O
InChI Identifier
InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21+,24+,25+,26-/m1/s1
InChI KeyGHCZAUBVMUEKKP-XROMFQGDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentGlycinated bile acids and derivatives
Alternative Parents
Substituents
  • Glycinated bile acid
  • Dihydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 7-hydroxysteroid
  • 7-alpha-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Fatty amide
  • Fatty acyl
  • N-acyl-amine
  • Cyclic alcohol
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organooxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organonitrogen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0014 mg/mLNot Available
LogP2.02RODA,A ET AL. (1990)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0079 g/LALOGPS
logP2.4ALOGPS
logP2.61ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-0.49ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity122.08 m³·mol⁻¹ChemAxon
Polarizability52.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+211.97732859911
AllCCS[M-H]-205.32532859911
DeepCCS[M-2H]-249.11430932474
DeepCCS[M+Na]+223.13130932474
AllCCS[M+H]+212.032859911
AllCCS[M+H-H2O]+210.332859911
AllCCS[M+NH4]+213.532859911
AllCCS[M+Na]+214.032859911
AllCCS[M-H]-205.332859911
AllCCS[M+Na-2H]-207.332859911
AllCCS[M+HCOO]-209.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Glycoursodeoxycholic acid[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCC(O)=O4052.7Standard polar33892256
Glycoursodeoxycholic acid[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCC(O)=O3655.0Standard non polar33892256
Glycoursodeoxycholic acid[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCC(=O)NCC(O)=O4162.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glycoursodeoxycholic acid,1TMS,isomer #1C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3828.5Semi standard non polar33892256
Glycoursodeoxycholic acid,1TMS,isomer #2C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3919.4Semi standard non polar33892256
Glycoursodeoxycholic acid,1TMS,isomer #3C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3893.9Semi standard non polar33892256
Glycoursodeoxycholic acid,1TMS,isomer #4C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3918.1Semi standard non polar33892256
Glycoursodeoxycholic acid,2TMS,isomer #1C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3795.4Semi standard non polar33892256
Glycoursodeoxycholic acid,2TMS,isomer #2C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3790.7Semi standard non polar33892256
Glycoursodeoxycholic acid,2TMS,isomer #3C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3762.0Semi standard non polar33892256
Glycoursodeoxycholic acid,2TMS,isomer #4C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3870.1Semi standard non polar33892256
Glycoursodeoxycholic acid,2TMS,isomer #5C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3877.7Semi standard non polar33892256
Glycoursodeoxycholic acid,2TMS,isomer #6C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3864.1Semi standard non polar33892256
Glycoursodeoxycholic acid,3TMS,isomer #1C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3761.4Semi standard non polar33892256
Glycoursodeoxycholic acid,3TMS,isomer #2C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3710.9Semi standard non polar33892256
Glycoursodeoxycholic acid,3TMS,isomer #3C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3727.2Semi standard non polar33892256
Glycoursodeoxycholic acid,3TMS,isomer #4C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3806.6Semi standard non polar33892256
Glycoursodeoxycholic acid,4TMS,isomer #1C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3717.1Semi standard non polar33892256
Glycoursodeoxycholic acid,4TMS,isomer #1C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3799.2Standard non polar33892256
Glycoursodeoxycholic acid,4TMS,isomer #1C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C)C[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4109.9Standard polar33892256
Glycoursodeoxycholic acid,1TBDMS,isomer #1C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4040.4Semi standard non polar33892256
Glycoursodeoxycholic acid,1TBDMS,isomer #2C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4132.1Semi standard non polar33892256
Glycoursodeoxycholic acid,1TBDMS,isomer #3C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4148.0Semi standard non polar33892256
Glycoursodeoxycholic acid,1TBDMS,isomer #4C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4148.1Semi standard non polar33892256
Glycoursodeoxycholic acid,2TBDMS,isomer #1C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4228.5Semi standard non polar33892256
Glycoursodeoxycholic acid,2TBDMS,isomer #2C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4211.3Semi standard non polar33892256
Glycoursodeoxycholic acid,2TBDMS,isomer #3C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4208.8Semi standard non polar33892256
Glycoursodeoxycholic acid,2TBDMS,isomer #4C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4312.0Semi standard non polar33892256
Glycoursodeoxycholic acid,2TBDMS,isomer #5C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4326.7Semi standard non polar33892256
Glycoursodeoxycholic acid,2TBDMS,isomer #6C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4321.3Semi standard non polar33892256
Glycoursodeoxycholic acid,3TBDMS,isomer #1C[C@H](CCC(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4390.9Semi standard non polar33892256
Glycoursodeoxycholic acid,3TBDMS,isomer #2C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C4368.1Semi standard non polar33892256
Glycoursodeoxycholic acid,3TBDMS,isomer #3C[C@H](CCC(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4385.6Semi standard non polar33892256
Glycoursodeoxycholic acid,3TBDMS,isomer #4C[C@H](CCC(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3[C@@H](O)C[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C4485.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0560-0224900000-2103b0ed015d6247c6992017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (3 TMS) - 70eV, Positivesplash10-0uk9-5010149000-89aeea919821513ec3682017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycoursodeoxycholic acid GC-MS (TBDMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycoursodeoxycholic acid 10V, Positive-QTOFsplash10-00e9-7001900000-5c674a4196bbe59213952016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycoursodeoxycholic acid 20V, Positive-QTOFsplash10-00di-9002100000-4253862988128e5343db2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycoursodeoxycholic acid 40V, Positive-QTOFsplash10-00di-9001000000-8c0e27e07cce4587ddaa2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycoursodeoxycholic acid 10V, Negative-QTOFsplash10-0002-0001900000-1e432b0f0b5728b038db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycoursodeoxycholic acid 20V, Negative-QTOFsplash10-008a-3104900000-5e705b527c1bedaf73b82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycoursodeoxycholic acid 40V, Negative-QTOFsplash10-00dl-9101000000-bfc254147e11f3a6e4d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycoursodeoxycholic acid 10V, Positive-QTOFsplash10-0ue9-0001900000-28796894c0d6a18a38602021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycoursodeoxycholic acid 20V, Positive-QTOFsplash10-0rni-3119300000-db3285a6df8081cc87712021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycoursodeoxycholic acid 40V, Positive-QTOFsplash10-0ar1-9240000000-c34a9d68066faf1ca11d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycoursodeoxycholic acid 10V, Negative-QTOFsplash10-0002-0000900000-fef3697e38cd672c8bac2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycoursodeoxycholic acid 20V, Negative-QTOFsplash10-0002-0001900000-dc11416231d9e9c5f55b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycoursodeoxycholic acid 40V, Negative-QTOFsplash10-00dj-9003400000-72e57065d02a7d2198b22021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Gall Bladder
  • Intestine
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.1(0-0.4) uMInfant (0-1 year old)Both
Normal
details
BloodDetected and Quantified0.19 (0.10-0.70) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified2.39 +/- 2.1 nmol/g dry fecesNot SpecifiedNot Specified
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNot Available details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.1(0-0.5) uMInfant (0-1 year old)Both
Severe acute malnutrition
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022194
KNApSAcK IDNot Available
Chemspider ID19973534
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5676
PubChem Compound12310288
PDB IDNot Available
ChEBI ID89929
Food Biomarker OntologyNot Available
VMH IDHC02196
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKanazawa, Teiichi; Shimazaki, Akio; Sato, Tetsuo; Hoshino, Toshio. Synthesis of ursodeoxycholic acid and its conjugated bile acid. Proc. Japan Acad. (1954), 30 391-2.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Marschall HU, Griffiths WJ, Zhang J, Wietholtz H, Matern H, Matern S, Sjovall J: Positions of conjugation of bile acids with glucose and N-acetylglucosamine in vitro. J Lipid Res. 1994 Sep;35(9):1599-610. [PubMed:7806974 ]
  2. Igimi H, Carey MC: pH-Solubility relations of chenodeoxycholic and ursodeoxycholic acids: physical-chemical basis for dissimilar solution and membrane phenomena. J Lipid Res. 1980 Jan;21(1):72-90. [PubMed:7354256 ]
  3. Goto T, Myint KT, Sato K, Wada O, Kakiyama G, Iida T, Hishinuma T, Mano N, Goto J: LC/ESI-tandem mass spectrometric determination of bile acid 3-sulfates in human urine 3beta-Sulfooxy-12alpha-hydroxy-5beta-cholanoic acid is an abundant nonamidated sulfate. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Feb 1;846(1-2):69-77. Epub 2006 Sep 1. [PubMed:16949895 ]
  4. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [PubMed:11316487 ]
  5. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [PubMed:16037564 ]
  6. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [PubMed:12576301 ]
  7. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]

Enzymes

General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:
GLYATL1
Uniprot ID:
Q969I3
Molecular weight:
35100.895
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:
GLYATL2
Uniprot ID:
Q8WU03
Molecular weight:
34277.055
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Acyltransferase which transfers the acyl group to the N- terminus of glycine
Gene Name:
GLYATL3
Uniprot ID:
Q5SZD4
Molecular weight:
32703.3