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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:41 UTC
Update Date2019-07-23 06:06:45 UTC
HMDB IDHMDB0030569
Secondary Accession Numbers
  • HMDB30569
Metabolite Identification
Common NameSwertiajaponin
DescriptionSwertiajaponin, also known as leucanthoside, 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. Swertiajaponin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Swertiajaponin has been detected, but not quantified in, green vegetables and nuts. This could make swertiajaponin a potential biomarker for the consumption of these foods.
Structure
Data?1563862005
Synonyms
ValueSource
2-(3,4-Dihydroxyphenyl)-6-b-D-glucopyranosyl-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one, 9ciHMDB
6-beta-D-Glucopyranosyl-3',4',5-trihydroxy-7-methoxyflavoneHMDB
Isoorientin 7-methyl etherHMDB
LeucanthosideHMDB
SwertiajaponinMeSH
Chemical FormulaC22H22O11
Average Molecular Weight462.4035
Monoisotopic Molecular Weight462.116211546
IUPAC Name2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
Traditional Name2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
CAS Registry Number6980-25-2
SMILES
COC1=CC2=C(C(=O)C=C(O2)C2=CC(O)=C(O)C=C2)C(O)=C1C1OC(CO)C(O)C(O)C1O
InChI Identifier
InChI=1S/C22H22O11/c1-31-13-6-14-16(11(26)5-12(32-14)8-2-3-9(24)10(25)4-8)19(28)17(13)22-21(30)20(29)18(27)15(7-23)33-22/h2-6,15,18,20-25,27-30H,7H2,1H3
InChI KeyDLVLXOYLQKCAME-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
  • 7-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • Flavone
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Phenolic glycoside
  • Hexose monosaccharide
  • C-glycosyl compound
  • Chromone
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Catechol
  • Alkyl aryl ether
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Oxacycle
  • 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point265 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.14 g/LALOGPS
logP0.51ALOGPS
logP-0.21ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)8.03ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity112.5 m³·mol⁻¹ChemAxon
Polarizability45.59 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0h90-3109600000-afffda626e2b3e04a5fdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-044r-3100069000-878ad4cc91c50f3bba35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0000900000-c0acf7c5ab3196dfbffdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-2302900000-030fac3b1f87a90f3817Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06vj-5269100000-eae9b26f39cb0874510fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0001900000-1c9b54da77b5a8e64a84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01vo-8327900000-b72b199dcabcfb70fcaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9335100000-71afa875f0ab413361faSpectrum
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 IDFDB002457
KNApSAcK IDC00001102
Chemspider ID2794080
KEGG Compound IDC10187
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3556303
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
Swertiajaponin → 6-beta-D-Glucopyranosyl-4',5-dihydroxy-3',7-dimethoxyflavonedetails
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
Swertiajaponin → ({6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-4H-chromen-6-yl]-3,4,5-trihydroxyoxan-2-yl}methoxy)sulfonic aciddetails
Swertiajaponin → {2-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-4H-chromen-6-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}oxidanesulfonic aciddetails
Swertiajaponin → {2-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-4H-chromen-6-yl]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl}oxidanesulfonic aciddetails
Swertiajaponin → {6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4-oxo-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
Swertiajaponin → 6-{[2-(3,4-dihydroxyphenyl)-7-methoxy-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Swertiajaponin → 3,4,5-trihydroxy-6-(2-hydroxy-4-{5-hydroxy-7-methoxy-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-2-yl}phenoxy)oxane-2-carboxylic aciddetails
Swertiajaponin → 3,4,5-trihydroxy-6-(2-hydroxy-5-{5-hydroxy-7-methoxy-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-2-yl}phenoxy)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
Swertiajaponin → (2-hydroxy-5-{5-hydroxy-7-methoxy-4-oxo-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-2-yl}phenyl)oxidanesulfonic aciddetails