| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-12 09:47:55 UTC |
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| Updated at | 2022-09-12 09:47:55 UTC |
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| NP-MRD ID | NP0327320 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | diosmine |
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| Description | Diosmin, 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. diosmine is found in Abies nephrolepis, Citrus limon, Helichrysum arenarium, Hyssopus officinalis, Linaria macroura, Lomelosia caucasica, Meehania urticifolia, Mentha piperita, Mentha spicata, Scutellaria baicalensis and Sechium edule. diosmine was first documented in 2011 (PMID: 21477647). ,However, diosmin products have been used in Europe for over 40 years with no safety issues. |
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| Structure | 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=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 |
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| Synonyms | | Value | Source |
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| 5,7,3'-Trihydroxy-4'-methoxyflavone 7-O-rutinoside | HMDB | | Barosmin | HMDB | | Daflon | HMDB | | Diosmetin 7-O-rutinoside | HMDB | | Diosmetin 7-rutinoside | HMDB | | Diosmetin-7-O-rutinoside | HMDB | | Diosmil | HMDB | | Diosmin, ban, inn | HMDB | | Diosmine | HMDB | | Diosminum | HMDB | | Diovenor | HMDB | | Flebosten | HMDB | | Luteolin 4'-methyl ether 7-rutinoside | HMDB | | Rioven | HMDB | | Salinigricoflavonoloside | HMDB | | Tovene | HMDB | | Ven-detrex | HMDB | | Veno-V | HMDB | | Venosmine | HMDB |
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| Chemical Formula | C28H32O15 |
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| Average Mass | 608.5447 Da |
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| Monoisotopic Mass | 608.17412 Da |
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| 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 |
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| Traditional Name | diosmine |
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| CAS Registry Number | Not Available |
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| 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 |
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| 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 |
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| InChI Key | GZSOSUNBTXMUFQ-UHFFFAOYSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Flavonoids |
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| Sub Class | Flavonoid glycosides |
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| Direct Parent | Flavonoid-7-O-glycosides |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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