Record Information |
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Version | 2.0 |
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Created at | 2022-09-03 22:28:07 UTC |
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Updated at | 2022-09-03 22:28:07 UTC |
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NP-MRD ID | NP0183539 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2s)-7-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one |
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Description | Viscumneoside III 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. Viscumneoside III is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2s)-7-{[(2s,3r,4s,5s,6r)-3-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-1-benzopyran-4-one is found in Viscum coloratum. It was first documented in 2011 (PMID: 21922656). Based on a literature review a significant number of articles have been published on viscumneoside III (PMID: 36057450) (PMID: 36057449) (PMID: 36057448) (PMID: 33015841). |
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Structure | COC1=CC(=CC=C1O)[C@@H]1CC(=O)C2=C(O)C=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O[C@@H]3OC[C@](O)(CO)[C@H]3O)C=C2O1 InChI=1S/C27H32O15/c1-37-17-4-11(2-3-13(17)30)16-7-15(32)20-14(31)5-12(6-18(20)40-16)39-25-23(22(34)21(33)19(8-28)41-25)42-26-24(35)27(36,9-29)10-38-26/h2-6,16,19,21-26,28-31,33-36H,7-10H2,1H3/t16-,19+,21+,22-,23+,24-,25+,26-,27+/m0/s1 |
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Synonyms | Value | Source |
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(2S)-5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-beta-D-apiofuranosyl-beta-D-glucopyranoside | ChEBI | Homoeriodictyol-7-O-beta-D-apiosyl-(1->2)-beta-D-glucopyranoside | ChEBI | (2S)-5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-b-D-apiofuranosyl-b-D-glucopyranoside | Generator | (2S)-5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-β-D-apiofuranosyl-β-D-glucopyranoside | Generator | Homoeriodictyol-7-O-b-D-apiosyl-(1->2)-b-D-glucopyranoside | Generator | Homoeriodictyol-7-O-β-D-apiosyl-(1->2)-β-D-glucopyranoside | Generator |
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Chemical Formula | C27H32O15 |
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Average Mass | 596.5380 Da |
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Monoisotopic Mass | 596.17412 Da |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | Not Available |
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SMILES | COC1=CC(=CC=C1O)[C@@H]1CC(=O)C2=C(O)C=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O[C@@H]3OC[C@](O)(CO)[C@H]3O)C=C2O1 |
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InChI Identifier | InChI=1S/C27H32O15/c1-37-17-4-11(2-3-13(17)30)16-7-15(32)20-14(31)5-12(6-18(20)40-16)39-25-23(22(34)21(33)19(8-28)41-25)42-26-24(35)27(36,9-29)10-38-26/h2-6,16,19,21-26,28-31,33-36H,7-10H2,1H3/t16-,19+,21+,22-,23+,24-,25+,26-,27+/m0/s1 |
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InChI Key | BYALYZGUSBVZQP-XJBIVIJWSA-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 |
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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
- 3p-methoxyflavonoid-skeleton
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- Hydroxyflavonoid
- Flavanone
- Flavan
- Phenolic glycoside
- Fatty acyl glycoside of mono- or disaccharide
- Fatty acyl glycoside
- Alkyl glycoside
- O-glycosyl compound
- Glycosyl compound
- Disaccharide
- Chromone
- Methoxyphenol
- Benzopyran
- Chromane
- 1-benzopyran
- Phenoxy compound
- Anisole
- Methoxybenzene
- Aryl alkyl ketone
- Aryl ketone
- Phenol ether
- Phenol
- Alkyl aryl ether
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Oxane
- Benzenoid
- Monocyclic benzene moiety
- Fatty acyl
- Oxolane
- Tertiary alcohol
- Vinylogous acid
- Ketone
- Secondary alcohol
- Oxacycle
- Acetal
- Ether
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organic oxygen compound
- Organooxygen compound
- Primary alcohol
- Aldehyde
- 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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General References | - Micalizzi E, Vaudano AE, Ballerini A, Talami F, Giovannini G, Turchi G, Cioclu MC, Giunta L, Meletti S: Ictal Apnea: a prospective monocentric study in patients with epilepsy. Eur J Neurol. 2022 Sep 3. doi: 10.1111/ene.15547. [PubMed:36057450 ]
- Jiang S, Guo P, Heo HY, Zhang Y, Wu J, Jin Y, Laterra J, Eberhart CG, Lim M, Blakeley JO: Radiomics analysis of amide proton transfer-weighted and structural MR images for treatment response assessment in malignant gliomas. NMR Biomed. 2022 Sep 3:e4824. doi: 10.1002/nbm.4824. [PubMed:36057449 ]
- Agarwal K, Saikia P, Podder I: Metabolic syndrome and Dyslipidemia in xanthelasma palpebrarum and associated risk-factors- a case-control study. J Cosmet Dermatol. 2022 Sep 3. doi: 10.1111/jocd.15353. [PubMed:36057448 ]
- Long X, Kim YG, Pyo YK, Yi R, Zhao X, Park KY: Inhibitory effect of Jangkanghwan (Korean traditional food) on experimental ulcerative colitis in mice. J Food Biochem. 2020 Dec;44(12):e13488. doi: 10.1111/jfbc.13488. Epub 2020 Oct 4. [PubMed:33015841 ]
- Han N, Huang T, Wang YC, Yin J, Kadota S: Flavanone glycosides from viscum coloratum and their inhibitory effects on osteoclast formation. Chem Biodivers. 2011 Sep;8(9):1682-8. doi: 10.1002/cbdv.201000289. [PubMed:21922656 ]
- LOTUS database [Link]
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