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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:05 UTC
Update Date2019-07-23 06:04:20 UTC
HMDB IDHMDB0029548
Secondary Accession Numbers
  • HMDB29548
Metabolite Identification
Common NameDiosmin
DescriptionDiosmin is found in green vegetables. Diosmin is isolated from parsle
Structure
Data?1563861860
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
DescriptionThis compound 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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-7432290000-d70f47a129b3142c35cbJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0900-6331019000-bde6242eed34a2bd808dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0udi-0249000000-bd1d2df9c9ae8a17841fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0090000000-d4179a0eac71cee296c4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0002-0090000000-2d58a9e098baf7884b31JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0001900000-cb8633696196ba8d631aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0001900000-0804b33b8df38a53f208JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0089-0009100000-02518ed6c111bd22a8f2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0089-0009100000-33682b6050606a7b1811JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0249000000-bd1d2df9c9ae8a17841fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udl-0139153000-a5df8b8ace59185711f6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0149100000-745e0883625146afe113JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uei-1598000000-7d042cfcc8d7a6d00ffcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bta-3491236000-47db98d4ee7c0cbbd9d8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2490010000-590296c798c9902cd85cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-1190000000-3e769837d46cbf206b3dJSpectraViewer | MoNA
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 IDFDB000693
KNApSAcK IDC00004362
Chemspider ID4510141
KEGG Compound IDC10039
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5353588
PDB IDNot Available
ChEBI ID1188022
Food Biomarker OntologyNot Available
VMH IDNot Available
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.. .