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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:39:10 UTC
Update Date2019-07-23 06:23:45 UTC
HMDB IDHMDB0037407
Secondary Accession Numbers
  • HMDB37407
Metabolite Identification
Common Name(2R)-6,8-Diglucopyranosyl-4',5,7-trihydroxyflavanone
Description(2R)-6,8-Diglucopyranosyl-4',5,7-trihydroxyflavanone belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Thus, (2R)-6,8-diglucopyranosyl-4',5,7-trihydroxyflavanone is considered to be a flavonoid lipid molecule (2R)-6,8-Diglucopyranosyl-4',5,7-trihydroxyflavanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (2R)-6,8-Diglucopyranosyl-4',5,7-trihydroxyflavanone has been detected, but not quantified in, fruits. This could make (2R)-6,8-diglucopyranosyl-4',5,7-trihydroxyflavanone a potential biomarker for the consumption of these foods.
Structure
Data?1563863025
SynonymsNot Available
Chemical FormulaC27H32O15
Average Molecular Weight596.534
Monoisotopic Molecular Weight596.174120354
IUPAC Name5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-2,3-dihydro-1-benzopyran-4-one
CAS Registry Number81446-26-6
SMILES
OCC1OC(C(O)C(O)C1O)C1=C(O)C2=C(OC(CC2=O)C2=CC=C(O)C=C2)C(C2OC(CO)C(O)C(O)C2O)=C1O
InChI Identifier
InChI=1S/C27H32O15/c28-6-12-17(32)21(36)23(38)26(41-12)15-19(34)14-10(31)5-11(8-1-3-9(30)4-2-8)40-25(14)16(20(15)35)27-24(39)22(37)18(33)13(7-29)42-27/h1-4,11-13,17-18,21-24,26-30,32-39H,5-7H2
InChI KeyKLDARLGFVGIIIL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 8-C-glycosides
Alternative Parents
Substituents
  • Flavonoid-8-c-glycoside
  • Hydroxyflavonoid
  • Flavanone
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Flavan
  • Phenolic glycoside
  • Hexose monosaccharide
  • C-glycosyl compound
  • Chromone
  • Glycosyl compound
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Polyol
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

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
Water Solubility15.3 g/LALOGPS
logP-1.3ALOGPS
logP-2.7ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)7.05ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area267.29 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity137.53 m³·mol⁻¹ChemAxon
Polarizability58.23 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ar9-0000290000-8e0c4992ec5509ecd3f7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0zi9-2300179000-c7791526f1245051388aSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-054t-0229460000-08137595bb1c18fd9ba4Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0909-0295400000-1ed49735da46e5dda657Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0100390000-2b73df47282fdf275259Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ta-0400790000-e7ae84661e616878c0a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004r-0106940000-acb176ba92793ef74819Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000490000-325b84b0097f1b826b3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-3001890000-ebb807ed11bac7e22dd9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bu3-4203950000-3ff891cff2fc72096340Spectrum
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 IDFDB016451
KNApSAcK IDC00006398
Chemspider ID24846344
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14427359
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.. .

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
(2R)-6,8-Diglucopyranosyl-4',5,7-trihydroxyflavanone → ({6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)sulfonic aciddetails
(2R)-6,8-Diglucopyranosyl-4',5,7-trihydroxyflavanone → ({6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-6-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)sulfonic aciddetails
(2R)-6,8-Diglucopyranosyl-4',5,7-trihydroxyflavanone → {2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
(2R)-6,8-Diglucopyranosyl-4',5,7-trihydroxyflavanone → {2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-8-yl]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxidanesulfonic aciddetails
(2R)-6,8-Diglucopyranosyl-4',5,7-trihydroxyflavanone → {6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-8-yl]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
(2R)-6,8-Diglucopyranosyl-4',5,7-trihydroxyflavanone → {6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-6-yl]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
(2R)-6,8-Diglucopyranosyl-4',5,7-trihydroxyflavanone → {2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-6-yl]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxidanesulfonic aciddetails
(2R)-6,8-Diglucopyranosyl-4',5,7-trihydroxyflavanone → {2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
(2R)-6,8-Diglucopyranosyl-4',5,7-trihydroxyflavanone → 3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic aciddetails
(2R)-6,8-Diglucopyranosyl-4',5,7-trihydroxyflavanone → 6-(4-{5,7-dihydroxy-4-oxo-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-2-yl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
(2R)-6,8-Diglucopyranosyl-4',5,7-trihydroxyflavanone → 3,4,5-trihydroxy-6-{[7-hydroxy-2-(4-hydroxyphenyl)-4-oxo-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-5-yl]oxy}oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
(2R)-6,8-Diglucopyranosyl-4',5,7-trihydroxyflavanone → (4-{5,7-dihydroxy-4-oxo-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-1-benzopyran-2-yl}phenyl)oxidanesulfonic aciddetails