Showing metabocard for rac-4-Hydroxy-4-O-(beta-D-glucuronide)-all-trans-retinyl acetate (BMDB0096221)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-03-10 17:03:11 UTC
Update Date2020-05-11 20:27:56 UTC
BMDB IDBMDB0096221
Secondary Accession Numbers
  • BMDB96221
Metabolite Identification
Common Namerac-4-Hydroxy-4-O-(beta-D-glucuronide)-all-trans-retinyl acetate
Descriptionrac-4-Hydroxy-4-O-(beta-D-glucuronide)-all-trans-retinyl acetate belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. rac-4-Hydroxy-4-O-(beta-D-glucuronide)-all-trans-retinyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
rac-4-Hydroxy-4-O-(b-D-glucuronide)-all-trans-retinyl acetateGenerator
rac-4-Hydroxy-4-O-(b-D-glucuronide)-all-trans-retinyl acetic acidGenerator
rac-4-Hydroxy-4-O-(beta-D-glucuronide)-all-trans-retinyl acetic acidGenerator
rac-4-Hydroxy-4-O-(β-D-glucuronide)-all-trans-retinyl acetateGenerator
rac-4-Hydroxy-4-O-(β-D-glucuronide)-all-trans-retinyl acetic acidGenerator
Chemical FormulaC28H40O9
Average Molecular Weight520.6118
Monoisotopic Molecular Weight520.267232878
IUPAC Name(2R,3S,4R,5R,6R)-6-{[(1R)-3-[(1E,3E,5E,7E)-9-(acetyloxy)-3,7-dimethylnona-1,3,5,7-tetraen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2R,3S,4R,5R,6R)-6-{[(1R)-3-[(1E,3E,5E,7E)-9-(acetyloxy)-3,7-dimethylnona-1,3,5,7-tetraen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)[C@@H](CCC1(C)C)O[C@@H]1O[C@H]([C@@H](O)[C@@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C28H40O9/c1-16(8-7-9-17(2)13-15-35-19(4)29)10-11-20-18(3)21(12-14-28(20,5)6)36-27-24(32)22(30)23(31)25(37-27)26(33)34/h7-11,13,21-25,27,30-32H,12,14-15H2,1-6H3,(H,33,34)/b9-7+,11-10+,16-8+,17-13+/t21-,22-,23+,24-,25-,27-/m1/s1
InChI KeyLFXATGINAILLFU-BSJULFBXSA-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 skeleton
  • Diterpenoid
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Fatty alcohol ester
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Beta-hydroxy acid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • 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
logP3.3ALOGPS
logP2.45ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.51ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area142.75 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity140.87 m³·mol⁻¹ChemAxon
Polarizability57.56 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, Positivesplash10-0btc-9211630000-b5b9b0d31e744c6ff57bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-052b-8322029000-6c756f3a524ac4e07a48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fft-0229360000-9f88bdfbe6dc3f88c3e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002s-0977100000-7e1fdf354216d8ead095View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-1893000000-f88831fefa093ea292cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05ox-9107470000-d094f9373f14577b1667View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9113100000-ff1de59f60a0942e524bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9124000000-e6ac0f3d130ee151988cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xr-0574910000-45c6ace164794f2ae251View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0291100000-c8f2b2df861b6058acaeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2960000000-9b53dc37e7d2f32e0af2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000120000-2b24dd0bf2b5f08e3623View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-c01bbbf5bed889264ddbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-42b8fec136877de38387View 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 IDHMDB0060141
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB034577
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131769845
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available