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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:05 UTC
Update Date2020-02-26 21:43:54 UTC
HMDB IDHMDB0029548
Secondary Accession Numbers
  • HMDB29548
Metabolite Identification
Common NameDiosmin
DescriptionDiosmin, also known as barosmin or daflon, 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. This leads to a reduction in the release of inflammatory mediators, principally oxygen free radicals and prostaglandins (PGE2, PGF2a). Diosmin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Diosmin is found, on average, in the highest concentration within a few different foods, such as hyssops, peppermints, and lemons. Diosmin has also been detected, but not quantified in, several different foods, such as green vegetables, mandarin orange (clementine, tangerine), rosemaries, spearmints, and sweet oranges. This could make diosmin a potential biomarker for the consumption of these foods. The enhanced version of diosmin, Vasculera, is sold as a medical food product. Furthermore, diosmin with hesperidine decreases the diameter of lymphatic capillaries and the intralymphatic pressure. It is also speculated that diosmin might have potential in the treatment of neurodegenerative diseases, such as Alzheimer's disease, and its anti-inflammatory and anti-apoptotic activity has been demonstrated in neuronal cells, in vitro. It is an oral phlebotropic drug used in the treatment of venous disease, i.e., chronic venous insufficiency (CVI) including spider and varicose veins, leg swelling (edema), stasis dermatitis and venous ulcers. ,however, diosmin products have been used in Europe for over 40 years with no safety issues.
Structure
Data?1582753434
Synonyms
ValueSource
5,7,3'-Trihydroxy-4'-methoxyflavone 7-O-rutinosideHMDB
BarosminHMDB
DaflonHMDB
Diosmetin 7-O-rutinosideHMDB
Diosmetin 7-rutinosideHMDB
Diosmetin-7-O-rutinosideHMDB
DiosmilHMDB
Diosmin, ban, innHMDB
DiosmineHMDB
DiosminumHMDB
DiovenorHMDB
FlebostenHMDB
Luteolin 4'-methyl ether 7-rutinosideHMDB
RiovenHMDB
SalinigricoflavonolosideHMDB
ToveneHMDB
Ven-detrexHMDB
Veno-VHMDB
VenosmineHMDB
Chemical FormulaC28H32O15
Average Molecular Weight608.5447
Monoisotopic Molecular Weight608.174120354
IUPAC Name5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-4H-chromen-4-one
Traditional Namediosmine
CAS Registry Number520-27-4
SMILES
COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O1)C=C(OC1OC(COC3OC(C)C(O)C(O)C3O)C(O)C(O)C1O)C=C2O
InChI Identifier
InChI=1S/C28H32O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-8,10,19,21-30,32-37H,9H2,1-2H3
InChI KeyGZSOSUNBTXMUFQ-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
  • 4p-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • Chromone
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Phenol
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Oxane
  • Pyran
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point280 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.14Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.54 g/LALOGPS
logP0.08ALOGPS
logP-0.44ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)8.48ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area234.29 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity142.39 m³·mol⁻¹ChemAxon
Polarizability59.9 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-7432290000-d70f47a129b3142c35cbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0900-6331019000-bde6242eed34a2bd808dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-0249000000-bd1d2df9c9ae8a17841fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0090000000-d4179a0eac71cee296c4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0090000000-2d58a9e098baf7884b31Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0001900000-cb8633696196ba8d631aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0001900000-0804b33b8df38a53f208Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0089-0009100000-02518ed6c111bd22a8f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0089-0009100000-33682b6050606a7b1811Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0249000000-bd1d2df9c9ae8a17841fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udl-0139153000-a5df8b8ace59185711f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0149100000-745e0883625146afe113Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uei-1598000000-7d042cfcc8d7a6d00ffcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bta-3491236000-47db98d4ee7c0cbbd9d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2490010000-590296c798c9902cd85cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-1190000000-3e769837d46cbf206b3dSpectrum
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 IDFDB000693
KNApSAcK IDC00004362
Chemspider ID4510141
KEGG Compound IDC10039
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiosmin
METLIN IDNot Available
PubChem Compound5353588
PDB IDNot Available
ChEBI ID1188022
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Dholakiya SL, Benzeroual KE: Protective effect of diosmin on LPS-induced apoptosis in PC12 cells and inhibition of TNF-alpha expression. Toxicol In Vitro. 2011 Aug;25(5):1039-44. doi: 10.1016/j.tiv.2011.04.003. Epub 2011 Apr 6. [PubMed:21477647 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .