Showing metabocard for Retinyl beta-glucuronide (BMDB0010340)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-10-03 18:04:41 UTC
Update Date2020-05-11 20:25:11 UTC
BMDB IDBMDB0010340
Secondary Accession Numbers
  • BMDB10340
Metabolite Identification
Common NameRetinyl beta-glucuronide
DescriptionRetinyl beta-glucuronide belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. Retinyl beta-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Retinyl b-glucuronideGenerator
Retinyl β-glucuronideGenerator
RetinylglucuronideHMDB
(2S,3S,4S,5R,6R)-6-{[(2Z,4E,6Z)-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-carboxylateHMDB
Retinyl beta-glucuronideMeSH
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 Nameretinyl β-glucuronide
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
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
  • Diterpenoid
  • Retinoid skeleton
  • Fatty acyl glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Alkyl glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Fatty acyl
  • Pyran
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • 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
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 Area116.45 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity130.2 m³·mol⁻¹ChemAxon
Polarizability51.8 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9417500000-fb337d0040baffcd1d91View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03di-5162039000-e99f016f764d9c5bd86eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p2-0361900000-9580eec2fb7747637d3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-1971200000-6c240334f3dd3bdd4286View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002r-4920100000-cc19503557a0b71cd9feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-2331900000-f032e18ef6357a405038View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004v-4931300000-975bb93eab639e62fb7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-9430000000-c64c697b73c4d7f182faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-0100900000-99edc85ce251eb4e8660View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06vr-9652300000-2e1a8e4b74afa81bac68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-5390000000-4e0597f224f6fb6d1fa2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0942600000-9d9399245f1cc0c0a078View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00rb-1921100000-4b9eeada09794cc68398View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0101-2910000000-636d65a3f001924dcb1dView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0010340
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027492
KNApSAcK IDNot Available
Chemspider ID4945190
KEGG Compound IDNot Available
BioCyc IDBeta-D-Glucuronides
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6440956
PDB IDNot Available
ChEBI ID88739
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available