4-(4-Hydroxyphenyl)-2-butanone O-[2-galloylglucoside] (CHEM032710)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:38:31 UTC
Update Date2016-11-09 01:20:46 UTC
Accession NumberCHEM032710
Identification
Common Name4-(4-Hydroxyphenyl)-2-butanone O-[2-galloylglucoside]
ClassSmall Molecule
DescriptionIsolindleyin is found in garden rhubarb. Isolindleyin is isolated from commercial rhubarb.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4,5-Dihydroxy-6-(hydroxymethyl)-2-[4-(3-oxobutyl)phenoxy]oxan-3-yl 3,4,5-trihydroxybenzoic acidGenerator
Chemical FormulaC23H26O11
Average Molecular Mass478.446 g/mol
Monoisotopic Mass478.148 g/mol
CAS Registry Number87075-18-1
IUPAC Name4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(3-oxobutyl)phenoxy]oxan-3-yl 3,4,5-trihydroxybenzoate
Traditional Name4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(3-oxobutyl)phenoxy]oxan-3-yl 3,4,5-trihydroxybenzoate
SMILESCC(=O)CCC1=CC=C(OC2OC(CO)C(O)C(O)C2OC(=O)C2=CC(O)=C(O)C(O)=C2)C=C1
InChI IdentifierInChI=1S/C23H26O11/c1-11(25)2-3-12-4-6-14(7-5-12)32-23-21(20(30)19(29)17(10-24)33-23)34-22(31)13-8-15(26)18(28)16(27)9-13/h4-9,17,19-21,23-24,26-30H,2-3,10H2,1H3
InChI KeyKHUVRRVIZOSFTI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • Galloyl ester
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • O-glycosyl compound
  • Benzoate ester
  • Benzenetriol
  • Benzoic acid or derivatives
  • Pyrogallol derivative
  • Phenoxy compound
  • Phenol ether
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monosaccharide
  • Monocyclic benzene moiety
  • Oxane
  • Benzenoid
  • Ketone
  • Carboxylic acid ester
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.75 g/LALOGPS
logP1.3ALOGPS
logP1.4ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)8.1ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area183.21 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity115.41 m³·mol⁻¹ChemAxon
Polarizability48 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05i3-9522500000-56f6d6ba93ab54114281Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004i-4710039000-0acca6704535571470d4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02vj-0901400000-9e0a2dde2fdf174fd681Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-6f0ca5458cb34bd9dd2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr2-1900000000-a84e8d4814dea6eed4f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-07fr-0913500000-b7e34eb0f86c0a61323bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-1900000000-53ff2cc93575da5ac93bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07xr-2900000000-718c5f067ee636db7745Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02ta-0759800000-d288d5b5c2802051d7b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ed-0422900000-0a7d67ccf70eeb8ec51cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-4903100000-6a0ada5a83c281f78d2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0102900000-a8cfca541420839c1c42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05r9-2808900000-ac4e230b101147a08002Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016u-3900100000-c528af33c631e5fbe6edSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0039378
FooDB IDFDB018943
Phenol Explorer IDNot Available
KNApSAcK IDC00050945
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID14345583
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM