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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:36 UTC
Update Date2021-09-14 15:39:02 UTC
HMDB IDHMDB0003141
Secondary Accession Numbers
  • HMDB03141
Metabolite Identification
Common NameRetinoyl b-glucuronide
DescriptionRetinoyl beta-glucuronide is a naturally occurring, biologically active metabolite of vitamin A. Although retinoyl beta-glucuronide is regarded as a detoxification product of retinoic acid, it plays several roles in the functions of vitamin A. It can serve as a source of retinoic acid, and it may be a vehicle for transport of retinoic acid to target tissues. Topically applied retinoyl beta-glucuronide is comparable in efficacy to retinoic acid in the treatment of acne in humans, without the same side effects. Retinoyl beta-glucuronide may or may not be teratogenic, depending on the mode of administration and the species in which it is used. It may be a valuable therapeutic compound for the treatment of skin disorders and certain types of cancers.
Structure
Data?1582752264
Synonyms
ValueSource
all-trans-Retinoyl-beta-glucuronideChEBI
Retinoyl glucuronideChEBI
all-trans-Retinoyl-b-glucuronideGenerator
all-trans-Retinoyl-β-glucuronideGenerator
13-cis-RetinoateHMDB
13-cis-Retinoic acidHMDB
13-cis-Retinoic acid acyl beta-D-glucuronideHMDB
13-cis-Retinoic acid acyl beta-delta-glucuronideHMDB
13-cis-Retinoyl glucuronideHMDB
13-cis-Retinoyl-beta-D-glucuronideHMDB
13-cis-Retinoyl-beta-delta-glucuronideHMDB
13-cis-Retinoyl-beta-glucuronideHMDB
9-cis-Retinoyl-beta-D-glucuronideHMDB
9-cis-Retinoyl-beta-delta-glucuronideHMDB
all-trans-Retinoyl-beta-D-glucuronideHMDB
all-trans-Retinoyl-beta-delta-glucuronideHMDB
GlucuronideHMDB
RetinoateHMDB
Retinoic acidHMDB
Retinoic acid beta-D-glucuronideHMDB
Retinoic acid beta-delta-glucuronideHMDB
Retinoyl beta-glucuronideHMDB
Retinoyl-beta-glucuronideHMDB
trans-Retinoyl glucuronideMeSH, HMDB
Chemical FormulaC26H36O8
Average Molecular Weight476.5592
Monoisotopic Molecular Weight476.241018128
IUPAC Name(2S,3S,4S,5R,6S)-6-{[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Nameglucuronide
CAS Registry Number401-10-5
SMILES
O[C@@H]1[C@@H](O)[C@@H](O[C@H](C(O)=O)[C@H]1O)OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
InChI Identifier
InChI=1S/C26H36O8/c1-15(11-12-18-17(3)10-7-13-26(18,4)5)8-6-9-16(2)14-19(27)33-25-22(30)20(28)21(29)23(34-25)24(31)32/h6,8-9,11-12,14,20-23,25,28-30H,7,10,13H2,1-5H3,(H,31,32)/b9-6+,12-11+,15-8+,16-14+/t20-,21-,22+,23-,25+/m0/s1
InChI KeyMTGFYEHKPMOVNE-NEFMKCFNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentDiterpene glycosides
Alternative Parents
Substituents
  • Diterpene glycoside
  • Retinoid ester
  • Diterpenoid
  • Retinoid skeleton
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Beta-hydroxy acid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Acetal
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Process

Naturally occurring process

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 Solubility0.046 g/LALOGPS
logP3.57ALOGPS
logP3.3ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity130.09 m³·mol⁻¹ChemAxon
Polarizability51.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+217.69531661259
DarkChem[M-H]-209.28631661259
DeepCCS[M+H]+218.50730932474
DeepCCS[M-H]-216.61230932474
DeepCCS[M-2H]-249.85230932474
DeepCCS[M+Na]+224.13630932474
AllCCS[M+H]+220.732859911
AllCCS[M+H-H2O]+218.632859911
AllCCS[M+NH4]+222.632859911
AllCCS[M+Na]+223.232859911
AllCCS[M-H]-214.532859911
AllCCS[M+Na-2H]-216.632859911
AllCCS[M+HCOO]-219.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Retinoyl b-glucuronideO[C@@H]1[C@@H](O)[C@@H](O[C@H](C(O)=O)[C@H]1O)OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C5236.0Standard polar33892256
Retinoyl b-glucuronideO[C@@H]1[C@@H](O)[C@@H](O[C@H](C(O)=O)[C@H]1O)OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C3534.3Standard non polar33892256
Retinoyl b-glucuronideO[C@@H]1[C@@H](O)[C@@H](O[C@H](C(O)=O)[C@H]1O)OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C3846.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Retinoyl b-glucuronide,1TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)C(C)(C)CCC13755.3Semi standard non polar33892256
Retinoyl b-glucuronide,1TMS,isomer #2CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)C(C)(C)CCC13766.5Semi standard non polar33892256
Retinoyl b-glucuronide,1TMS,isomer #3CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)C(C)(C)CCC13728.3Semi standard non polar33892256
Retinoyl b-glucuronide,1TMS,isomer #4CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)C(C)(C)CCC13753.6Semi standard non polar33892256
Retinoyl b-glucuronide,2TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)C(C)(C)CCC13701.5Semi standard non polar33892256
Retinoyl b-glucuronide,2TMS,isomer #2CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)C(C)(C)CCC13700.9Semi standard non polar33892256
Retinoyl b-glucuronide,2TMS,isomer #3CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C(C)(C)CCC13704.8Semi standard non polar33892256
Retinoyl b-glucuronide,2TMS,isomer #4CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)C(C)(C)CCC13702.8Semi standard non polar33892256
Retinoyl b-glucuronide,2TMS,isomer #5CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)C(C)(C)CCC13711.0Semi standard non polar33892256
Retinoyl b-glucuronide,2TMS,isomer #6CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)C(C)(C)CCC13701.0Semi standard non polar33892256
Retinoyl b-glucuronide,3TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[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]2O)C(C)(C)CCC13666.9Semi standard non polar33892256
Retinoyl b-glucuronide,3TMS,isomer #2CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C(C)(C)CCC13675.2Semi standard non polar33892256
Retinoyl b-glucuronide,3TMS,isomer #3CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C(C)(C)CCC13691.6Semi standard non polar33892256
Retinoyl b-glucuronide,3TMS,isomer #4CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)C(C)(C)CCC13683.0Semi standard non polar33892256
Retinoyl b-glucuronide,4TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[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]2O[Si](C)(C)C)C(C)(C)CCC13660.4Semi standard non polar33892256
Retinoyl b-glucuronide,1TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C(C)(C)CCC13972.8Semi standard non polar33892256
Retinoyl b-glucuronide,1TBDMS,isomer #2CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC13985.2Semi standard non polar33892256
Retinoyl b-glucuronide,1TBDMS,isomer #3CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)C(C)(C)CCC13963.1Semi standard non polar33892256
Retinoyl b-glucuronide,1TBDMS,isomer #4CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)C(C)(C)CCC13971.5Semi standard non polar33892256
Retinoyl b-glucuronide,2TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[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]2O)C(C)(C)CCC14136.6Semi standard non polar33892256
Retinoyl b-glucuronide,2TBDMS,isomer #2CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[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]2O)C(C)(C)CCC14131.9Semi standard non polar33892256
Retinoyl b-glucuronide,2TBDMS,isomer #3CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC14137.1Semi standard non polar33892256
Retinoyl b-glucuronide,2TBDMS,isomer #4CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC14139.7Semi standard non polar33892256
Retinoyl b-glucuronide,2TBDMS,isomer #5CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC14140.2Semi standard non polar33892256
Retinoyl b-glucuronide,2TBDMS,isomer #6CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[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]2O)C(C)(C)CCC14139.5Semi standard non polar33892256
Retinoyl b-glucuronide,3TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[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]2O)C(C)(C)CCC14278.8Semi standard non polar33892256
Retinoyl b-glucuronide,3TBDMS,isomer #2CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[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]2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC14291.5Semi standard non polar33892256
Retinoyl b-glucuronide,3TBDMS,isomer #3CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[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]2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC14290.9Semi standard non polar33892256
Retinoyl b-glucuronide,3TBDMS,isomer #4CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[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]2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC14313.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Retinoyl b-glucuronide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9432400000-25dd7257fa97ce57c6862017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Retinoyl b-glucuronide GC-MS (3 TMS) - 70eV, Positivesplash10-004i-3051009000-fd7898490f7303f898cc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Retinoyl b-glucuronide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 10V, Positive-QTOFsplash10-0ke9-0693400000-31eed182f08fe67861692016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 20V, Positive-QTOFsplash10-052u-0891000000-ca789901418c22bb04932016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 40V, Positive-QTOFsplash10-000i-1920000000-e38e08d95bad4a4235512016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 10V, Negative-QTOFsplash10-001i-1190200000-9141a0351cb4c8689ff42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 20V, Negative-QTOFsplash10-000t-3690100000-f02b84b6d3b8cceeb6cf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 40V, Negative-QTOFsplash10-0535-8590000000-12eae5811075d2fce9f92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 10V, Positive-QTOFsplash10-057r-0565900000-0aac4f4c541ab0976b562021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 20V, Positive-QTOFsplash10-009f-0923100000-bb8c1ba6dc7f05b15be72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 40V, Positive-QTOFsplash10-0ac0-2900000000-b37fb8c36dde85ab44882021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 10V, Negative-QTOFsplash10-0059-0390700000-eddabec40f40511d435f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 20V, Negative-QTOFsplash10-0a6s-2391400000-4b33ff2150a642a781362021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 40V, Negative-QTOFsplash10-0r01-3390000000-158c7d14c4f6713d87da2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Adipose Tissue
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Pancreas
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0066 +/- 0.0025 uMAdult (>18 years old)BothNormal 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 IDFDB023112
KNApSAcK IDNot Available
Chemspider ID4445170
KEGG Compound IDC11061
BioCyc IDNot Available
BiGG ID2304843
Wikipedia LinkNot Available
METLIN ID2280
PubChem Compound5281877
PDB IDNot Available
ChEBI ID28870
Food Biomarker OntologyNot Available
VMH IDRETNGLC
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yamanaka H, Nakajima M, Katoh M, Kanoh A, Tamura O, Ishibashi H, Yokoi T: Trans-3'-hydroxycotinine O- and N-glucuronidations in human liver microsomes. Drug Metab Dispos. 2005 Jan;33(1):23-30. Epub 2004 Oct 6. [PubMed:15470160 ]
  2. Matsushima S, Maeda K, Kondo C, Hirano M, Sasaki M, Suzuki H, Sugiyama Y: Identification of the hepatic efflux transporters of organic anions using double-transfected Madin-Darby canine kidney II cells expressing human organic anion-transporting polypeptide 1B1 (OATP1B1)/multidrug resistance-associated protein 2, OATP1B1/multidrug resistance 1, and OATP1B1/breast cancer resistance protein. J Pharmacol Exp Ther. 2005 Sep;314(3):1059-67. Epub 2005 May 18. [PubMed:15901800 ]
  3. Kosoglou T, Statkevich P, Johnson-Levonas AO, Paolini JF, Bergman AJ, Alton KB: Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94. [PubMed:15871634 ]
  4. Kochansky CJ, Xia YQ, Wang S, Cato B, Creighton M, Vincent SH, Franklin RB, Reed JR: Species differences in the elimination of a peroxisome proliferator-activated receptor agonist highlighted by oxidative metabolism of its acyl glucuronide. Drug Metab Dispos. 2005 Dec;33(12):1894-904. Epub 2005 Sep 23. [PubMed:16183782 ]
  5. Ghosal A, Yuan Y, Hapangama N, Su AD, Alvarez N, Chowdhury SK, Alton KB, Patrick JE, Zbaida S: Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of 3-hydroxydesloratadine. Biopharm Drug Dispos. 2004 Sep;25(6):243-52. [PubMed:15334623 ]
  6. Brunelle FM, Verbeeck RK: Glucuronidation of diflunisal in liver and kidney microsomes of rat and man. Xenobiotica. 1996 Feb;26(2):123-31. [PubMed:8867997 ]
  7. Niles RM, Cook CP, Meadows GG, Fu YM, McLaughlin JL, Rankin GO: Resveratrol is rapidly metabolized in athymic (nu/nu) mice and does not inhibit human melanoma xenograft tumor growth. J Nutr. 2006 Oct;136(10):2542-6. [PubMed:16988123 ]
  8. Sass JO, Masgrau E, Saurat JH, Nau H: Metabolism of oral 9-cis-retinoic acid in the human. Identification of 9-cis-retinoyl-beta-glucuronide and 9-cis-4-oxo-retinoyl-beta-glucuronide as urinary metabolites. Drug Metab Dispos. 1995 Sep;23(9):887-91. [PubMed:8565776 ]
  9. Calabrese CR, Loadman PM, Lim LS, Bibby MC, Double JA, Brown JE, Lamb JH: In vivo metabolism of the antitumor imidazoacridinone C1311 in the mouse and in vitro comparison with humans. Drug Metab Dispos. 1999 Feb;27(2):240-5. [PubMed:9929509 ]
  10. Sperker B, Murdter TE, Schick M, Eckhardt K, Bosslet K, Kroemer HK: Interindividual variability in expression and activity of human beta-glucuronidase in liver and kidney: consequences for drug metabolism. J Pharmacol Exp Ther. 1997 May;281(2):914-20. [PubMed:9152401 ]
  11. Moss T, Howes D, Williams FM: Percutaneous penetration and dermal metabolism of triclosan (2,4, 4'-trichloro-2'-hydroxydiphenyl ether). Food Chem Toxicol. 2000 Apr;38(4):361-70. [PubMed:10722890 ]
  12. Cunha PD, Lord RS, Johnson ST, Wilker PR, Aster RH, Bougie DW: Immune hemolytic anemia caused by sensitivity to a metabolite of etodolac, a nonsteroidal anti-inflammatory drug. Transfusion. 2000 Jun;40(6):663-8. [PubMed:10864985 ]
  13. Nordin C, Bertilsson L: Active hydroxymetabolites of antidepressants. Emphasis on E-10-hydroxy-nortriptyline. Clin Pharmacokinet. 1995 Jan;28(1):26-40. [PubMed:7712660 ]
  14. Johnson AG, Rigby RJ, Taylor PJ, Jones CE, Allen J, Franzen K, Falk MC, Nicol D: The kinetics of mycophenolic acid and its glucuronide metabolite in adult kidney transplant recipients. Clin Pharmacol Ther. 1999 Nov;66(5):492-500. [PubMed:10579476 ]
  15. Oswald S, Haenisch S, Fricke C, Sudhop T, Remmler C, Giessmann T, Jedlitschky G, Adam U, Dazert E, Warzok R, Wacke W, Cascorbi I, Kroemer HK, Weitschies W, von Bergmann K, Siegmund W: Intestinal expression of P-glycoprotein (ABCB1), multidrug resistance associated protein 2 (ABCC2), and uridine diphosphate-glucuronosyltransferase 1A1 predicts the disposition and modulates the effects of the cholesterol absorption inhibitor ezetimibe in humans. Clin Pharmacol Ther. 2006 Mar;79(3):206-17. Epub 2006 Feb 7. [PubMed:16513445 ]
  16. Kenny JR, Maggs JL, Tettey JN, Harrell AW, Parker SG, Clarke SE, Park BK: Formation and protein binding of the acyl glucuronide of a leukotriene B4 antagonist (SB-209247): relation to species differences in hepatotoxicity. Drug Metab Dispos. 2005 Feb;33(2):271-81. Epub 2004 Nov 2. [PubMed:15523047 ]
  17. Qiao GL, Williams PL, Riviere JE: Percutaneous absorption, biotransformation, and systemic disposition of parathion in vivo in swine. I. Comprehensive pharmacokinetic model. Drug Metab Dispos. 1994 May-Jun;22(3):459-71. [PubMed:8070325 ]
  18. Ethell BT, Riedel J, Englert H, Jantz H, Oekonomopulos R, Burchell B: Glucuronidation of HMR1098 in human microsomes: evidence for the involvement of UGT1A1 in the formation of S-glucuronides. Drug Metab Dispos. 2003 Aug;31(8):1027-34. [PubMed:12867491 ]
  19. Andersen A: Final report on the safety assessment of sodium p-chloro-m-cresol, p-chloro-m-cresol, chlorothymol, mixed cresols, m-cresol, o-cresol, p-cresol, isopropyl cresols, thymol, o-cymen-5-ol, and carvacrol. Int J Toxicol. 2006;25 Suppl 1:29-127. [PubMed:16835130 ]
  20. Sallustio BC, Sabordo L, Evans AM, Nation RL: Hepatic disposition of electrophilic acyl glucuronide conjugates. Curr Drug Metab. 2000 Sep;1(2):163-80. [PubMed:11465081 ]

Only showing the first 10 proteins. There are 22 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
Reactions
all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphatedetails
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
Reactions
all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphatedetails
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
Reactions
all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphatedetails
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:
UGT2B10
Uniprot ID:
P36537
Molecular weight:
60773.485
Reactions
all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphatedetails
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
Reactions
all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphatedetails
References
  1. Gestl SA, Green MD, Shearer DA, Frauenhoffer E, Tephly TR, Weisz J: Expression of UGT2B7, a UDP-glucuronosyltransferase implicated in the metabolism of 4-hydroxyestrone and all-trans retinoic acid, in normal human breast parenchyma and in invasive and in situ breast cancers. Am J Pathol. 2002 Apr;160(4):1467-79. [PubMed:11943730 ]
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
Reactions
all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphatedetails
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
Reactions
all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphatedetails
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
Reactions
all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphatedetails
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
Reactions
all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphatedetails
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:
UGT1A8
Uniprot ID:
Q9HAW9
Molecular weight:
59741.035
Reactions
all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphatedetails

Only showing the first 10 proteins. There are 22 proteins in total.