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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:39:26 UTC
Update Date2019-07-23 06:23:46 UTC
HMDB IDHMDB0037411
Secondary Accession Numbers
  • HMDB37411
Metabolite Identification
Common NameLucenin 2,7-O-rhamnoside
DescriptionLucenin 2,7-O-rhamnoside belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Lucenin 2,7-O-rhamnoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Lucenin 2,7-O-rhamnoside has been detected, but not quantified in, a few different foods, such as coffee and coffee products, fats and oils, and tea. This could make lucenin 2,7-O-rhamnoside a potential biomarker for the consumption of these foods.
Structure
Data?1563863026
Synonyms
ValueSource
Lucenin-2,7-O-rhamnosideHMDB
Chemical FormulaC33H40O20
Average Molecular Weight756.6587
Monoisotopic Molecular Weight756.21129372
IUPAC Name2-(3,4-dihydroxyphenyl)-5-hydroxy-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-4-one
Traditional Name2-(3,4-dihydroxyphenyl)-5-hydroxy-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one
CAS Registry Number29432-27-7
SMILES
CC1OC(OC2=C(C3OC(CO)C(O)C(O)C3O)C(O)=C3C(=O)C=C(OC3=C2C2OC(CO)C(O)C(O)C2O)C2=CC(O)=C(O)C=C2)C(O)C(O)C1O
InChI Identifier
InChI=1S/C33H40O20/c1-8-19(39)23(43)28(48)33(49-8)53-30-17(31-26(46)24(44)20(40)14(6-34)51-31)22(42)16-12(38)5-13(9-2-3-10(36)11(37)4-9)50-29(16)18(30)32-27(47)25(45)21(41)15(7-35)52-32/h2-5,8,14-15,19-21,23-28,31-37,39-48H,6-7H2,1H3
InChI KeyJGKAYWDKUOHFBC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-7-o-glycoside
  • Flavonoid c-glycoside
  • Flavonoid-8-c-glycoside
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Chromone
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility28.5 g/LALOGPS
logP-1ALOGPS
logP-4.3ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)7.94ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area346.44 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity171.73 m³·mol⁻¹ChemAxon
Polarizability72.15 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06rf-0100165900-b66b336e778209b84378Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-0200192100-be79da0763eab483f189Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004u-0100792100-ccd3ffeb9a392b0c274cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1100036900-7b8bf832941f73ce2e95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05n3-3200296400-cb18886f3c0b09fc4259Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05rc-4100594000-df8606f3ffe96319f806Spectrum
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 IDFDB016457
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74977634
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 magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
Lucenin 2,7-O-rhamnoside → 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-4-onedetails
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
Lucenin 2,7-O-rhamnoside → ({6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-8-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)sulfonic aciddetails
Lucenin 2,7-O-rhamnoside → ({6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-6-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)sulfonic aciddetails
Lucenin 2,7-O-rhamnoside → {2-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
Lucenin 2,7-O-rhamnoside → {2-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-8-yl]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxidanesulfonic aciddetails
Lucenin 2,7-O-rhamnoside → {6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-8-yl]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
Lucenin 2,7-O-rhamnoside → {2-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
Lucenin 2,7-O-rhamnoside → {2-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-6-yl]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxidanesulfonic aciddetails
Lucenin 2,7-O-rhamnoside → {6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-6-yl]-4,5-dihydroxy-2-(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
Lucenin 2,7-O-rhamnoside → 3,4,5-trihydroxy-6-(2-hydroxy-4-{5-hydroxy-4-oxo-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-2-yl}phenoxy)oxane-2-carboxylic aciddetails
Lucenin 2,7-O-rhamnoside → 3,4,5-trihydroxy-6-(2-hydroxy-5-{5-hydroxy-4-oxo-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-2-yl}phenoxy)oxane-2-carboxylic aciddetails
Lucenin 2,7-O-rhamnoside → 6-{[2-(3,4-dihydroxyphenyl)-4-oxo-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-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
Lucenin 2,7-O-rhamnoside → (2-hydroxy-5-{5-hydroxy-4-oxo-6,8-bis[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-2-yl}phenyl)oxidanesulfonic aciddetails