| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-08 23:59:26 UTC |
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| Updated at | 2022-09-08 23:59:26 UTC |
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| NP-MRD ID | NP0276042 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | methyl (4s,5r,6s)-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[2-(3,4,5-trihydroxybenzoyloxy)ethyl]-5,6-dihydro-4h-pyran-3-carboxylate |
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| Description | Cornuside belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. methyl (4s,5r,6s)-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[2-(3,4,5-trihydroxybenzoyloxy)ethyl]-5,6-dihydro-4h-pyran-3-carboxylate is found in Cornus officinalis. methyl (4s,5r,6s)-5-ethenyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[2-(3,4,5-trihydroxybenzoyloxy)ethyl]-5,6-dihydro-4h-pyran-3-carboxylate was first documented in 2022 (PMID: 35897876). Based on a literature review a small amount of articles have been published on Cornuside (PMID: 35745012) (PMID: 35956355) (PMID: 35748214) (PMID: 35684087). |
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| Structure | COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](C=C)[C@@H]1CCOC(=O)C1=CC(O)=C(O)C(O)=C1 InChI=1S/C24H30O14/c1-3-11-12(4-5-35-21(32)10-6-14(26)17(28)15(27)7-10)13(22(33)34-2)9-36-23(11)38-24-20(31)19(30)18(29)16(8-25)37-24/h3,6-7,9,11-12,16,18-20,23-31H,1,4-5,8H2,2H3/t11-,12+,16-,18-,19+,20-,23+,24+/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C24H30O14 |
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| Average Mass | 542.4900 Da |
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| Monoisotopic Mass | 542.16356 Da |
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| IUPAC Name | methyl (2S,3R,4S)-3-ethenyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[2-(3,4,5-trihydroxybenzoyloxy)ethyl]-3,4-dihydro-2H-pyran-5-carboxylate |
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| Traditional Name | methyl (4S,5R,6S)-5-ethenyl-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[2-(3,4,5-trihydroxybenzoyloxy)ethyl]-5,6-dihydro-4H-pyran-3-carboxylate |
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| CAS Registry Number | Not Available |
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| SMILES | COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](C=C)[C@@H]1CCOC(=O)C1=CC(O)=C(O)C(O)=C1 |
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| InChI Identifier | InChI=1S/C24H30O14/c1-3-11-12(4-5-35-21(32)10-6-14(26)17(28)15(27)7-10)13(22(33)34-2)9-36-23(11)38-24-20(31)19(30)18(29)16(8-25)37-24/h3,6-7,9,11-12,16,18-20,23-31H,1,4-5,8H2,2H3/t11-,12+,16-,18-,19+,20-,23+,24+/m1/s1 |
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| InChI Key | SMTKSCGLXONVGL-UPIRYGIPSA-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 terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Terpene glycosides |
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| Direct Parent | Terpene glycosides |
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| Alternative Parents | |
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| Substituents | - Terpene glycoside
- Galloyl ester
- Gallic acid or derivatives
- P-hydroxybenzoic acid alkyl ester
- M-hydroxybenzoic acid ester
- P-hydroxybenzoic acid ester
- O-glycosyl compound
- Secoiridoid-skeleton
- Glycosyl compound
- Monoterpenoid
- Aromatic monoterpenoid
- Monocyclic monoterpenoid
- Benzoate ester
- Pyrogallol derivative
- Benzenetriol
- Benzoic acid or derivatives
- Benzoyl
- 1-hydroxy-4-unsubstituted benzenoid
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- Sugar acid
- Monocyclic benzene moiety
- Dicarboxylic acid or derivatives
- Benzenoid
- Monosaccharide
- Oxane
- Methyl ester
- Vinylogous ester
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Secondary alcohol
- Carboxylic acid ester
- Carboxylic acid derivative
- Organoheterocyclic compound
- Oxacycle
- Polyol
- Acetal
- Alcohol
- Primary alcohol
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organic oxygen compound
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic 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 | - Luo G, Lin J, Cheng W, Liu Z, Yu T, Yang B: UHPLC-Q-Orbitrap-MS-Based Metabolomics Reveals Chemical Variations of Two Types of Rhizomes of Polygonatum sibiricum. Molecules. 2022 Jul 22;27(15):4685. doi: 10.3390/molecules27154685. [PubMed:35897876 ]
- Seo CS, Lee MY: Simultaneous Determination of Fourteen Marker Compounds in the Traditional Herbal Prescription, Geumgwesingihwan, Using Ultra-Performance Liquid Chromatography-Tandem Mass Spectrometry. Molecules. 2022 Jun 17;27(12):3890. doi: 10.3390/molecules27123890. [PubMed:35745012 ]
- Shi JZ, Zheng XM, Zhou YF, Yun LY, Luo DM, Hao JJ, Liu PF, Zhang WK, Xu JK, Yan Y, Xie XM, He YY, Pang XB: Cornuside Is a Potential Agent against Alzheimer's Disease via Orchestration of Reactive Astrocytes. Nutrients. 2022 Aug 3;14(15):3179. doi: 10.3390/nu14153179. [PubMed:35956355 ]
- Kim C, Kim N, Bae JS: Anti-Inflammatory and Anti-oxidant Functions of Cornuside by Regulating NF-[Formula: see text]B, STAT-1, and Nrf2-HO-1 Pathways. Am J Chin Med. 2022;50(5):1349-1360. doi: 10.1142/S0192415X22500574. Epub 2022 Jun 23. [PubMed:35748214 ]
- Oledzka A, Cichocka K, Wolinski K, Melzig MF, Czerwinska ME: Potentially Bio-Accessible Metabolites from an Extract of Cornus mas Fruit after Gastrointestinal Digestion In Vitro and Gut Microbiota Ex Vivo Treatment. Nutrients. 2022 May 30;14(11):2287. doi: 10.3390/nu14112287. [PubMed:35684087 ]
- LOTUS database [Link]
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