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Showing Compound Retinoyl beta-glucuronide (FDB023112)

Record Information
Version1.0
Creation date2011-09-21 00:24:52 UTC
Update date2015-07-21 06:57:31 UTC
Primary IDFDB023112
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRetinoyl beta-glucuronide
DescriptionRetinoyl beta-glucuronide is a naturally occurring, biologically active metabolite of vitamin A. Although retinoyl beta-glucuronide is regarded as a detoxification product of retinoic acid, it plays several roles in the functions of vitamin A. It can serve as a source of retinoic acid, and it may be a vehicle for transport of retinoic acid to target tissues. Topically applied retinoyl beta-glucuronide is comparable in efficacy to retinoic acid in the treatment of acne in humans, without the same side effects. Retinoyl beta-glucuronide may or may not be teratogenic, depending on the mode of administration and the species in which it is used. It may be a valuable therapeutic compound for the treatment of skin disorders and certain types of cancers. [HMDB]
CAS Number401-10-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP3.57ALOGPS
logP3.3ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity130.09 m³·mol⁻¹ChemAxon
Polarizability51.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC26H36O8
IUPAC name(2S,3S,4S,5R,6S)-6-{[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI IdentifierInChI=1S/C26H36O8/c1-15(11-12-18-17(3)10-7-13-26(18,4)5)8-6-9-16(2)14-19(27)33-25-22(30)20(28)21(29)23(34-25)24(31)32/h6,8-9,11-12,14,20-23,25,28-30H,7,10,13H2,1-5H3,(H,31,32)/b9-6+,12-11+,15-8+,16-14+/t20-,21-,22+,23-,25+/m0/s1
InChI KeyMTGFYEHKPMOVNE-NEFMKCFNSA-N
Isomeric SMILESO[C@@H]1[C@@H](O)[C@@H](O[C@H](C(O)=O)[C@H]1O)OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
Average Molecular Weight476.5592
Monoisotopic Molecular Weight476.241018128
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 ester
  • Diterpenoid
  • Retinoid skeleton
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Beta-hydroxy acid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Acetal
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSRetinoyl beta-glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9432400000-25dd7257fa97ce57c686Spectrum
Predicted GC-MSRetinoyl beta-glucuronide, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-3051009000-fd7898490f7303f898ccSpectrum
Predicted GC-MSRetinoyl beta-glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ke9-0693400000-31eed182f08fe67861692016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052u-0891000000-ca789901418c22bb04932016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1920000000-e38e08d95bad4a4235512016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1190200000-9141a0351cb4c8689ff42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-3690100000-f02b84b6d3b8cceeb6cf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0535-8590000000-12eae5811075d2fce9f92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-057r-0565900000-0aac4f4c541ab0976b562021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-009f-0923100000-bb8c1ba6dc7f05b15be72021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ac0-2900000000-b37fb8c36dde85ab44882021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0390700000-eddabec40f40511d435f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6s-2391400000-4b33ff2150a642a781362021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0r01-3390000000-158c7d14c4f6713d87da2021-09-25View Spectrum
NMRNot Available
ChemSpider ID4445170
ChEMBL IDNot Available
KEGG Compound IDC11061
Pubchem Compound ID5281877
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03141
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2304843
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGlucuronide
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference