Record Information
Version3.6
Creation Date2008-09-15 17:30:22 UTC
Update Date2013-06-10 17:10:10 UTC
HMDB IDHMDB10340
Secondary Accession NumbersNone
Metabolite Identification
Common NameRetinyl beta-glucuronide
DescriptionRetinyl beta-glucuronide is a natural human metabolite of retinoic 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.
Structure
Thumb
Synonyms
  1. Retinyl b-glucuronide
  2. Retinylglucuronide
Chemical FormulaC26H38O7
Average Molecular Weight462.5757
Monoisotopic Molecular Weight462.26175357
IUPAC Name(2S,3S,4S,5R,6R)-6-{[(2Z,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional IUPAC Name(2S,3S,4S,5R,6R)-6-{[(2Z,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](O)[C@H](OC\C=C(\C)/C=C/C=C(/C)\C=C\C2=C(C)CCCC2(C)C)O[C@H](C(O)=O)[C@H]1O
InChI Identifier
InChI=1S/C26H38O7/c1-16(11-12-19-18(3)10-7-14-26(19,4)5)8-6-9-17(2)13-15-32-25-22(29)20(27)21(28)23(33-25)24(30)31/h6,8-9,11-13,20-23,25,27-29H,7,10,14-15H2,1-5H3,(H,30,31)/b9-6+,12-11+,16-8-,17-13-/t20-,21-,22+,23-,25+/m0/s1
InChI KeyIYHVRAMISWFIRU-GMBUFXMQSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassPrenol Lipids
Sub ClassRetinoids
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Acetal
  • Alkyl Glycoside
  • Beta Hydroxy Acid
  • Carboxylic Acid
  • Cyclohexene
  • Glucuronic Acid Or Derivative
  • Glucuronide
  • Glycosyl Compound
  • Hexose Monosaccharide
  • Isoprene
  • O Glycosyl Compound
  • Oxane
  • Saccharide
  • Secondary Alcohol
  • Sugar Acid
Direct ParentRetinoids
Ontology
StatusDetected and Quantified
Origin
  • Drug metabolite
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Waste products
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.039 g/LALOGPS
logP3.93ALOGPS
logP3.24ChemAxon
logS-4.1ALOGPS
pKa (strongest acidic)3.58ChemAxon
pKa (strongest basic)-3.7ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count7ChemAxon
hydrogen donor count4ChemAxon
polar surface area116.45ChemAxon
rotatable bond count8ChemAxon
refractivity130.2ChemAxon
polarizability51.8ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.0068 +/- 0.004 uMAdult (>18 years old)BothNormal
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00594
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027492
KNApSAcK IDNot Available
Chemspider ID4945190
KEGG Compound IDNot Available
BioCyc IDBeta-D-Glucuronides
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10340
Metagene LinkHMDB10340
METLIN IDNot Available
PubChem Compound6440956
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Gene Name:
UGT2B4
Uniprot ID:
P06133
Gene Name:
UGT1A4
Uniprot ID:
P22310
Gene Name:
UGT2B10
Uniprot ID:
P36537
Gene Name:
UGT2B7
Uniprot ID:
P16662
Gene Name:
UGT2B15
Uniprot ID:
P54855
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Gene Name:
UGT1A1
Uniprot ID:
P22309
Gene Name:
UGT1A9
Uniprot ID:
O60656
Gene Name:
UGT1A8
Uniprot ID:
Q9HAW9
Gene Name:
UGT1A3
Uniprot ID:
P35503
Gene Name:
UGT1A10
Uniprot ID:
Q9HAW8
Gene Name:
UGT2B17
Uniprot ID:
O75795
Gene Name:
UGT1A6
Uniprot ID:
P19224
Gene Name:
UGT1A5
Uniprot ID:
P35504
Gene Name:
UGT2B11
Uniprot ID:
O75310
Gene Name:
UGT1A7
Uniprot ID:
Q9HAW7
Gene Name:
GUSB
Uniprot ID:
P08236
Gene Name:
UGT2A3
Uniprot ID:
Q6UWM9
Gene Name:
UGT1A10
Uniprot ID:
Q5DT02
Gene Name:
UGT1A8
Uniprot ID:
Q5DSZ6