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Record Information
Version2.0
Created at2021-06-22 17:26:30 UTC
Updated at2025-02-11 15:46:47 UTC
NP-MRD IDNP0043865
Natural Product DOIhttps://doi.org/10.57994/1243
Secondary Accession NumbersNone
Natural Product Identification
Common NameDiosmin
DescriptionDiosmin, also known as daflon or neodiosmin, 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. Thus, diosmin is considered to be a flavonoid. Diosmin is found in Abies nephrolepis, Agathosma betulina, Angelica gigas, Asyneuma argutum, Campanula patula, Campanula persicifolia, Citrus glauca, Citrus maxima, Helichrysum arenarium, Hyssopus officinalis, Bryophyllum pinnatum , Meehania urticifolia, Mentha piperita, Mentha spicata, Sechium edule and Toddalia asiatica. Diosmin was first documented in 2015 (PMID: 25620156). Based on a literature review very few articles have been published on Diosmin (PMID: 25821971).
Structure
Thumb
Synonyms
ValueSource
3',5,7-Trihydroxy-4'-methoxyflavone 7-rhamnoglucosideChEBI
3',5,7-Trihydroxy-4'-methoxyflavone-7-rutinosideChEBI
Diosmetin 7-neohesperidosideChEBI
Diosmetin 7-O-rutinosideChEBI
DiosmineChEBI
DiosminumChEBI
NeodiosminChEBI
DaflonKegg
BarosminMeSH
Buchu resinMeSH
Resin, buchuMeSH
VenosmineMeSH
Chemical FormulaC28H32O15
Average Mass608.5447 Da
Monoisotopic Mass608.17412 Da
IUPAC Name5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Namediosmin
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=C(C=C1)C1=CC(=O)C2=C(O)C=C(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)C=C2O1
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/t10-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1
InChI KeyGZSOSUNBTXMUFQ-YFAPSIMESA-N
Experimental Spectra
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 800, C2D6OS, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-14View Spectrum
Species
Species of Origin
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 Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point274.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point926.78 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility407.8 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.140The Good Scents Company Information System
Predicted Properties
PropertyValueSource
logP0.08ALOGPS
logP-0.44ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)7.31ChemAxon
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
Polarizability58.93 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDDB08995
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00004362
Chemspider ID4444932
KEGG Compound IDC10039
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiosmin
METLIN IDNot Available
PubChem Compound5281613
PDB IDNot Available
ChEBI ID4631
Good Scents IDrw1181451
References
General References
  1. Guo P, Yan W, Han Q, Wang C, Zhang Z: Simultaneous quantification of 25 active constituents in the total flavonoids extract from Herba Desmodii Styracifolii by high-performance liquid chromatography with electrospray ionization tandem mass spectrometry. J Sep Sci. 2015 Apr;38(7):1156-63. doi: 10.1002/jssc.201401360. Epub 2015 Feb 27. [PubMed:25620156 ]
  2. Arab HH, Salama SA, Omar HA, Arafa el-SA, Maghrabi IA: Diosmin protects against ethanol-induced gastric injury in rats: novel anti-ulcer actions. PLoS One. 2015 Mar 30;10(3):e0122417. doi: 10.1371/journal.pone.0122417. eCollection 2015. [PubMed:25821971 ]