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Showing Compound rac-4-Hydroxy-4-O-(beta-D-glucuronide)-all-trans-retinyl acetate (FDB034577)

Record Information
Version1.0
Creation date2019-08-07 19:37:38 UTC
Update date2025-11-19 03:04:16 UTC
Primary IDFDB034577
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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).
CAS NumberNot Available
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
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
Predicted Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC28H40O9
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
InChI IdentifierInChI=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
Isomeric SMILESCC(=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
Average Molecular Weight520.6118
Monoisotopic Molecular Weight520.267232878
Classification
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSrac-4-Hydroxy-4-O-(beta-D-glucuronide)-all-trans-retinyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0btc-9211630000-b5b9b0d31e744c6ff57bSpectrum
Predicted GC-MSrac-4-Hydroxy-4-O-(beta-D-glucuronide)-all-trans-retinyl acetate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052b-8322029000-6c756f3a524ac4e07a48Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fft-0229360000-9f88bdfbe6dc3f88c3e32017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002s-0977100000-7e1fdf354216d8ead0952017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-1893000000-f88831fefa093ea292cb2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05ox-9107470000-d094f9373f14577b16672017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9113100000-ff1de59f60a0942e524b2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9124000000-e6ac0f3d130ee151988c2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03xr-0574910000-45c6ace164794f2ae2512021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0291100000-c8f2b2df861b6058acae2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2960000000-9b53dc37e7d2f32e0af22021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000120000-2b24dd0bf2b5f08e36232021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-42b8fec136877de383872021-10-12View Spectrum
NMRNot Available
ChemSpider ID30778553
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB0060141
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference