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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:32:44 UTC
Update Date2019-07-23 06:21:11 UTC
HMDB IDHMDB0036408
Secondary Accession Numbers
  • HMDB36408
Metabolite Identification
Common NameFranguloside
DescriptionFranguloside, also known as frangulin a, belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Franguloside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Franguloside has been detected, but not quantified in, green vegetables. This could make franguloside a potential biomarker for the consumption of these foods.
Structure
Data?1563862871
Synonyms
ValueSource
Frangulin aHMDB
Frangulin a (8ci)HMDB
Chemical FormulaC21H20O9
Average Molecular Weight416.3781
Monoisotopic Molecular Weight416.110732238
IUPAC Name1,8-dihydroxy-3-methyl-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-9,10-dihydroanthracene-9,10-dione
Traditional Name1,8-dihydroxy-3-methyl-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]anthracene-9,10-dione
CAS Registry Number521-62-0
SMILES
CC1OC(OC2=CC3=C(C(O)=C2)C(=O)C2=C(C=C(C)C=C2O)C3=O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C21H20O9/c1-7-3-10-14(12(22)4-7)18(26)15-11(17(10)25)5-9(6-13(15)23)30-21-20(28)19(27)16(24)8(2)29-21/h3-6,8,16,19-24,27-28H,1-2H3
InChI KeyDTTVUKLWJFJOHO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthraquinones
Direct ParentAnthraquinones
Alternative Parents
Substituents
  • 9,10-anthraquinone
  • Anthraquinone
  • Phenolic glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Ketone
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point228 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.8 g/LALOGPS
logP1.33ALOGPS
logP2.6ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)9.06ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.75 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity102.74 m³·mol⁻¹ChemAxon
Polarizability41.38 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0072-9215000000-ea6d63c3b6272319dd1bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-6720119000-442c6dd845e504917c42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-0194400000-9687641ab8c41c3d957eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0290000000-fd57c335ab4cbae536dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-3590000000-e6dcb25b0e5fa25b1e23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2074900000-20f90e590e352c8491d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1091000000-7245294f45a793dc731cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3390000000-386ae4b5902acf035d14Spectrum
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
FoodDB IDFDB015288
KNApSAcK IDC00002824
Chemspider ID308991
KEGG Compound IDC10346
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound348160
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.. .