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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:39:30 UTC
Update Date2022-03-07 02:55:19 UTC
HMDB IDHMDB0037412
Secondary Accession Numbers
  • HMDB37412
Metabolite Identification
Common Name3,6-Diglucopyranosyl-4',5,7-trihydroxyflavone
Description3,6-Diglucopyranosyl-4',5,7-trihydroxyflavone belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. 3,6-Diglucopyranosyl-4',5,7-trihydroxyflavone has been detected, but not quantified in, citrus. This could make 3,6-diglucopyranosyl-4',5,7-trihydroxyflavone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3,6-Diglucopyranosyl-4',5,7-trihydroxyflavone.
Structure
Data?1563863026
Synonyms
ValueSource
3,6-Di-b-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneHMDB
3,6-Di-C-glucosylapigeninHMDB
3,6-DiglucopyranosylapigeninHMDB
3,6-DiglucosylapigeninHMDB
Chemical FormulaC27H30O15
Average Molecular Weight594.5181
Monoisotopic Molecular Weight594.15847029
IUPAC Name5,7-dihydroxy-2-(4-hydroxyphenyl)-3,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
Traditional Name5,7-dihydroxy-2-(4-hydroxyphenyl)-3,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
CAS Registry Number90456-55-6
SMILES
OCC1OC(C(O)C(O)C1O)C1=C(O)C2=C(OC(C3=CC=C(O)C=C3)=C(C3OC(CO)C(O)C(O)C3O)C2=O)C=C1O
InChI Identifier
InChI=1S/C27H30O15/c28-6-12-17(32)21(36)23(38)26(41-12)14-10(31)5-11-15(19(14)34)20(35)16(25(40-11)8-1-3-9(30)4-2-8)27-24(39)22(37)18(33)13(7-29)42-27/h1-5,12-13,17-18,21-24,26-34,36-39H,6-7H2
InChI KeyLXJLIJWTKFLSRJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid C-glycosides
Alternative Parents
Substituents
  • Flavonoid c-glycoside
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • Chromone
  • C-glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Oxane
  • Benzenoid
  • Monosaccharide
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Primary alcohol
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
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 IDFDB016458
KNApSAcK IDC00006232
Chemspider ID35014416
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74977439
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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
3,6-Diglucopyranosyl-4',5,7-trihydroxyflavone → ({6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-3-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)sulfonic aciddetails
3,6-Diglucopyranosyl-4',5,7-trihydroxyflavone → ({6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-6-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)sulfonic aciddetails
3,6-Diglucopyranosyl-4',5,7-trihydroxyflavone → {2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-3-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
3,6-Diglucopyranosyl-4',5,7-trihydroxyflavone → {2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-3-yl]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxidanesulfonic aciddetails
3,6-Diglucopyranosyl-4',5,7-trihydroxyflavone → {6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-3-yl]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
3,6-Diglucopyranosyl-4',5,7-trihydroxyflavone → {6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-6-yl]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
3,6-Diglucopyranosyl-4',5,7-trihydroxyflavone → {2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-6-yl]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxidanesulfonic aciddetails
3,6-Diglucopyranosyl-4',5,7-trihydroxyflavone → {2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-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
3,6-Diglucopyranosyl-4',5,7-trihydroxyflavone → 3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-7-yl]oxy}oxane-2-carboxylic aciddetails
3,6-Diglucopyranosyl-4',5,7-trihydroxyflavone → 6-(4-{5,7-dihydroxy-4-oxo-3,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-2-yl}phenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3,6-Diglucopyranosyl-4',5,7-trihydroxyflavone → 3,4,5-trihydroxy-6-{[7-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-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
3,6-Diglucopyranosyl-4',5,7-trihydroxyflavone → (4-{5,7-dihydroxy-4-oxo-3,6-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-2-yl}phenyl)oxidanesulfonic aciddetails