Showing metabocard for 4-Oxo-9-cis-retinoyl-beta-glucuronide (BMDB0096219)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-03-10 17:03:09 UTC
Update Date2020-05-11 20:27:55 UTC
BMDB IDBMDB0096219
Secondary Accession Numbers
  • BMDB96219
Metabolite Identification
Common Name4-Oxo-9-cis-retinoyl-beta-glucuronide
Description4-Oxo-9-cis-retinoyl-beta-glucuronide belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. 4-Oxo-9-cis-retinoyl-beta-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-oxo-9-cis-Retinoyl-b-glucuronideGenerator
4-oxo-9-cis-Retinoyl-β-glucuronideGenerator
Chemical FormulaC26H34O9
Average Molecular Weight490.5428
Monoisotopic Molecular Weight490.220282686
IUPAC Name(2R,3S,4R,5R,6S)-6-{[(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2R,3S,4R,5R,6S)-6-{[(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
C\C(\C=C\C1=C(C)CCC(=O)C1(C)C)=C\C=C\C(\C)=C\C(=O)O[C@@H]1O[C@H]([C@@H](O)[C@@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C26H34O9/c1-14(9-11-17-16(3)10-12-18(27)26(17,4)5)7-6-8-15(2)13-19(28)34-25-22(31)20(29)21(30)23(35-25)24(32)33/h6-9,11,13,20-23,25,29-31H,10,12H2,1-5H3,(H,32,33)/b8-6+,11-9+,14-7-,15-13+/t20-,21+,22-,23-,25-/m1/s1
InChI KeyXEIKLAKHCVSUMR-CAHRZYSUSA-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
  • Cyclohexenone
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Pyran
  • Oxane
  • Hydroxy acid
  • Monosaccharide
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Cyclic ketone
  • Carboxylic acid ester
  • Secondary alcohol
  • Ketone
  • Polyol
  • Carboxylic acid
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Acetal
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.76ALOGPS
logP2.63ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area150.59 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity130.78 m³·mol⁻¹ChemAxon
Polarizability51.36 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, Positivesplash10-0adi-9231400000-f062086043505a587de1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-7492038000-50aa6f79fbde093a1d92View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00r2-0694500000-91987c2043e2552a452eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0891000000-6a3ed9a7d797b6072d2fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gvk-2930000000-9791536a6efa84f501afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0193400000-d1ffe770458ed14d70b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fs-4955200000-e103a6edf04db4033d48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dm-9553000000-817f5bc84a337bc13856View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0351900000-03ecdbb80192ae1778aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0290100000-251862ceb1f90d6faa16View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00p0-1910000000-7cfc19f92754fc0c94fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-d680a79baa48678abf41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0171-1291300000-b72c0e54a1bfedc47fd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bta-4941000000-1513d9b76716e2f19275View 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 IDHMDB0060122
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB034575
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131769834
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available