| Common Name |
Diosmin
| Description |
Diosmin is found in green vegetables. Diosmin is isolated from parsleyDiosmin has been shown to exhibit anti-apoptotic and anti-inflammatory functions (PMID 21477647 , 21477647 ).Diosmin belongs to the family of Flavonoid O-Glycosides. These are compounds containing a carbohydrate moiety which is o-glycosidically linked to one of the flavonoid backbones (2-phenylchromen-4-one, 3-phenylchromen-4-one or 4-phenylcoumarin).
| Structure |
MOLSDFPDBSMILESInChI
Structure for HMDB29548 (Diosmin)
| Synonyms |
| Value |
Source |
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 Formlia |
C28H32O15
| Average Molecliar Weight |
608.5447
| Monoisotopic Molecliar Weight |
608.174120354
| IUPAC Name |
5-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 Name |
diosmine
| CAS Registry Number |
520-27-4
| 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 Key |
GZSOSUNBTXMUFQ-UHFFFAOYSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
anti-apoptotic
anti-inflammatory
| Application |
Nutrient
| Cellliar locations |
Cytoplasm
Extracellliar
| Physical Properties |
| State |
Not Available
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point280 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.14Not Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility1.54 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity142.39 m3·mol-1ChemAxon
Polarizability59.9 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , negativesplash10-0002-0090000000-d4179a0eac71cee296c4View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , negativesplash10-0002-0090000000-2d58a9e098baf7884b31View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-03di-0001900000-cb8633696196ba8d631aView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-03di-0001900000-0804b33b8df38a53f208View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0089-0009100000-02518ed6c111bd22a8f2View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Linear Ion Trap , positivesplash10-0089-0009100000-33682b6050606a7b1811View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – , positivesplash10-0udi-0249000000-bd1d2df9c9ae8a17841fView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-0udl-0139153000-a5df8b8ace59185711f6View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-0udi-0149100000-745e0883625146afe113View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0uei-1598000000-7d042cfcc8d7a6d00ffcView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-0bta-3491236000-47db98d4ee7c0cbbd9d8View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-0002-2490010000-590296c798c9902cd85cView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-000t-1190000000-3e769837d46cbf206b3dView in MoNA
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
232
| FoodDB ID |
FDB000693
| KNApSAcK ID |
C00004362
| Chemspider ID |
4510141
| KEGG Compound ID |
C10039
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB29548
| Metagene Link |
HMDB29548
| METLIN ID |
Not Available
| PubChem Compound |
5353588
| PDB ID |
Not Available
| ChEBI ID |
1188022
Product: Piceatannol
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- 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 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 27165988
