Record Information |
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Version | 1.0 |
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Created at | 2021-06-22 17:26:44 UTC |
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Updated at | 2021-08-20 00:00:46 UTC |
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NP-MRD ID | NP0043870 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Esculin |
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Description | Aesculin, also known as esculoside or venoplant, belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. Aesculin 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. Esculin is found in Actinidia chinensis, Afraegle paniculata, Althaea officinalis, Arabidopsis thaliana, Artemisia absinthium, Artemisia jacutica, Artemisia tridentata, Artemisia vulgaris, Cistus creticus, Crataegus monogyna, Cynara cornigera, Fraxinus angustifolia, Fraxinus chinensis, Fraxinus floribunda, Fraxinus insularis, Gundelia tournefortii, Hordeum vulgare, Hydrophyllum tenuipes, Ixeridium laevigatum, Koelpinia linearis, Lithospermum erythrorhizon, Lupinus angustifolius, Manihot esculenta, Morus alba, Myrtus communis, Ocimum tenuiflorum, Olea europaea, Ostericum grosseserratum, Peucedanum japonicum, Phaseolus vulgaris, Rhododendron groenlandicum, Solanum aethiopicum, Taraxacum officinale and Vitis vinifera. It was first documented in 2013 (PMID: 22564167). Based on a literature review a significant number of articles have been published on Aesculin (PMID: 23497098) (PMID: 23499166) (PMID: 34315523) (PMID: 34059101). |
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Structure | OC[C@H]1O[C@@H](OC2=C(O)C=C3OC(=O)C=CC3=C2)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2/t10-,12-,13+,14-,15-/m1/s1 |
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Synonyms | Value | Source |
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6,7-Dihydroxycoumarin 6-glucoside | ChEBI | 6,7-Dihydroxycoumarin-6-O-glucoside | ChEBI | 6-(beta-D-Glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-one | ChEBI | 6-(beta-D-Glucopyranosyloxy)-7-hydroxy-cumarin | ChEBI | 7-Hydroxy-6-glucosyloxy-2H-chromene | ChEBI | Esculetin 6-beta-D-glucoside | ChEBI | Esculetin 6-O-glucoside | ChEBI | Esculoside | ChEBI | 6-(b-D-Glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-one | Generator | 6-(Β-D-glucopyranosyloxy)-7-hydroxy-2H-1-benzopyran-2-one | Generator | 6-(b-D-Glucopyranosyloxy)-7-hydroxy-cumarin | Generator | 6-(Β-D-glucopyranosyloxy)-7-hydroxy-cumarin | Generator | Esculetin 6-b-D-glucoside | Generator | Esculetin 6-β-D-glucoside | Generator | Venoplant | HMDB | (-)-Esculin | HMDB | 6-(beta-D-Glucopyranosyloxy)-7-hydroxycoumarin | HMDB | 6-(Β-D-glucopyranosyloxy)-7-hydroxycoumarin | HMDB | Esculin | HMDB | Esculine | HMDB | Aesculin | ChEBI, MeSH |
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Chemical Formula | C15H16O9 |
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Average Mass | 340.2840 Da |
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Monoisotopic Mass | 340.07943 Da |
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IUPAC Name | 7-hydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one |
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Traditional Name | (-)-esculin |
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CAS Registry Number | Not Available |
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SMILES | OC[C@H]1O[C@@H](OC2=C(O)C=C3OC(=O)C=CC3=C2)[C@H](O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2/t10-,12-,13+,14-,15-/m1/s1 |
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InChI Key | XHCADAYNFIFUHF-TVKJYDDYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | 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 coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Coumarins and derivatives |
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Sub Class | Coumarin glycosides |
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Direct Parent | Coumarin glycosides |
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Alternative Parents | |
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Substituents | - Coumarin o-glycoside
- Coumarin-6-o-glycoside
- Phenolic glycoside
- 7-hydroxycoumarin
- Hydroxycoumarin
- Hexose monosaccharide
- O-glycosyl compound
- Glycosyl compound
- Benzopyran
- 1-benzopyran
- Pyranone
- 1-hydroxy-2-unsubstituted benzenoid
- Pyran
- Monosaccharide
- Oxane
- Benzenoid
- Heteroaromatic compound
- Secondary alcohol
- Lactone
- Acetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Primary alcohol
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | |
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Predicted Properties | |
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General References | - Ohadi R MS, Alvari A, Samim M, Abdin MZ: Plant bio-transformable HMG-CoA reductase gene loaded calcium phosphate nanoparticle: in vitro characterization and stability study. Curr Drug Discov Technol. 2013 Mar;10(1):25-34. doi: 10.2174/1570163811310010005. [PubMed:22564167 ]
- Pandey S, Sree A, Dash SS, Sethi DP: A novel method for screening beta-glucosidase inhibitors. BMC Microbiol. 2013 Mar 8;13:55. doi: 10.1186/1471-2180-13-55. [PubMed:23497098 ]
- Barbic M, Willer EA, Rothenhofer M, Heilmann J, Furst R, Jurgenliemk G: Spirostanol saponins and esculin from Rusci rhizoma reduce the thrombin-induced hyperpermeability of endothelial cells. Phytochemistry. 2013 Jun;90:106-13. doi: 10.1016/j.phytochem.2013.02.004. Epub 2013 Mar 13. [PubMed:23499166 ]
- Lather A, Sharma S, Khatkar A: Aesculin based glucosamine-6-phosphate synthase inhibitors as novel preservatives for food and pharmaceutical products: in-silico studies, antioxidant, antimicrobial and preservative efficacy evaluation. BMC Chem. 2021 Jul 27;15(1):45. doi: 10.1186/s13065-021-00769-8. [PubMed:34315523 ]
- Yu Y, Chen J, Zhang X, Wang Y, Wang S, Zhao L, Wang Y: Identification of anti-inflammatory compounds from Zhongjing formulae by knowledge mining and high-content screening in a zebrafish model of inflammatory bowel diseases. Chin Med. 2021 May 31;16(1):42. doi: 10.1186/s13020-021-00452-z. [PubMed:34059101 ]
- Aleksandra Owczarek, Arkadiusz Kłys, Monika A.Olszewska (2019). Aleksandra Owczarek, Arkadiusz Kłys, Monika A.Olszewska A validated 1H qNMR method for direct and simultaneous quantification of esculin, fraxin and (–)-epicatechin in Hippocastani cortex. Talanta Volume 192, 15 January 2019, Pages 263-269. DOI: 10.1016/j.talanta.2018.09.036. Talanta.
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