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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:00 UTC
Update Date2019-07-23 06:06:30 UTC
HMDB IDHMDB0030470
Secondary Accession Numbers
  • HMDB30470
Metabolite Identification
Common NameLindleyin
DescriptionLindleyin 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. Lindleyin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Lindleyin has been detected, but not quantified in, garden rhubarbs and green vegetables. This could make lindleyin a potential biomarker for the consumption of these foods.
Structure
Data?1563861990
Synonyms
ValueSource
{3,4,5-trihydroxy-6-[4-(3-oxobutyl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoic acidGenerator
Chemical FormulaC23H26O11
Average Molecular Weight478.4459
Monoisotopic Molecular Weight478.147511674
IUPAC Name{3,4,5-trihydroxy-6-[4-(3-oxobutyl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate
Traditional Name{3,4,5-trihydroxy-6-[4-(3-oxobutyl)phenoxy]oxan-2-yl}methyl 3,4,5-trihydroxybenzoate
CAS Registry Number59282-56-3
SMILES
CC(=O)CCC1=CC=C(OC2OC(COC(=O)C3=CC(O)=C(O)C(O)=C3)C(O)C(O)C2O)C=C1
InChI Identifier
InChI=1S/C23H26O11/c1-11(24)2-3-12-4-6-14(7-5-12)33-23-21(30)20(29)19(28)17(34-23)10-32-22(31)13-8-15(25)18(27)16(26)9-13/h4-9,17,19-21,23,25-30H,2-3,10H2,1H3
InChI KeyBJYRNIFAMMOVGW-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
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Benzenoid
  • Ketone
  • Carboxylic acid ester
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point210 - 211 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.58 g/LALOGPS
logP1.22ALOGPS
logP1.4ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)8.11ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area183.21 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity115.41 m³·mol⁻¹ChemAxon
Polarizability47.23 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-5892600000-be7ce827b18bccbc8d96Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-016u-6257009000-d4f8d8339038a125bf0aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02vj-0901400000-62ea819d7f47c3076d6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-e9c0bbbfb642215744a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr2-0900000000-4d20dbebf42c4b2293e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02di-0910400000-19f8b96590416e190bdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-0900000000-9fef125fa190409af411Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0900-2900000000-d4a63883c3702595e95aSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002339
KNApSAcK IDC00037422
Chemspider ID26502074
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14345581
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .