Record Information |
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Version | 1.0 |
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Created at | 2023-07-17 20:07:15 UTC |
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Updated at | 2024-04-19 09:49:33 UTC |
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NP-MRD ID | NP0331726 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Hydroxytyrosol-1-O-β-glucoside |
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Description | 2-(3,4-Dihydroxyphenyl)-ethyl-O-beta-D-glucopyranoside, also known as dopaol beta-D-glucoside or hydroxytyrosol glucoside, belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. 2-(3,4-Dihydroxyphenyl)-ethyl-O-beta-D-glucopyranoside 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. It was first documented in 2004 (PMID: 15706916). Based on a literature review a significant number of articles have been published on 2-(3,4-dihydroxyphenyl)-ethyl-O-beta-D-glucopyranoside (PMID: 21261296) (PMID: 20575386) (PMID: 34352331) (PMID: 24199567) (PMID: 16722374) (PMID: 15133218). |
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Structure | OC[C@H]1O[C@@H](OCCC2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O InChI=1S/C14H20O8/c15-6-10-11(18)12(19)13(20)14(22-10)21-4-3-7-1-2-8(16)9(17)5-7/h1-2,5,10-20H,3-4,6H2/t10-,11-,12+,13-,14-/m1/s1 |
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Synonyms | Value | Source |
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Dopaol beta-D-glucoside | ChEBI | Hydroxytyrosol glucoside | ChEBI | Dopaol b-D-glucoside | Generator | Dopaol β-D-glucoside | Generator | 2-(3,4-Dihydroxyphenyl)-ethyl-O-b-D-glucopyranoside | Generator | 2-(3,4-Dihydroxyphenyl)-ethyl-O-β-D-glucopyranoside | Generator |
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Chemical Formula | C14H20O8 |
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Average Mass | 316.3060 Da |
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Monoisotopic Mass | 316.11582 Da |
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IUPAC Name | (2R,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol |
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Traditional Name | (2R,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol |
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CAS Registry Number | Not Available |
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SMILES | OC[C@H]1O[C@@H](OCCC2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C14H20O8/c15-6-10-11(18)12(19)13(20)14(22-10)21-4-3-7-1-2-8(16)9(17)5-7/h1-2,5,10-20H,3-4,6H2/t10-,11-,12+,13-,14-/m1/s1 |
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InChI Key | PQQITYGQJLPDFC-RKQHYHRCSA-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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HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | yupingfu424@163.com | Not Available | Not Available | 2023-07-17 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | yupingfu424@163.com | Not Available | Not Available | 2023-07-17 | View Spectrum | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | yupingfu424@163.com | Not Available | Not Available | 2023-07-17 | View Spectrum | 1D NMR | [1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | yupingfu424@163.com | Not Available | Not Available | 2023-07-17 | View Spectrum | 1D NMR | [13C, ] NMR Spectrum (2D, 151 MHz, CD3OD, experimental) | yupingfu424@163.com | Not Available | Not Available | 2023-07-17 | View Spectrum | 1D NMR | [1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | yupingfu424@163.com | Not Available | Not Available | 2023-07-17 | View Spectrum |
| 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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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 | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | O-glycosyl compounds |
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Alternative Parents | |
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Substituents | - Hexose monosaccharide
- O-glycosyl compound
- Tyrosol derivative
- Catechol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Monosaccharide
- Oxane
- Secondary alcohol
- Acetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Alcohol
- Primary alcohol
- Hydrocarbon derivative
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic 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 | 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 | - Yang JH, Kondratyuk TP, Jermihov KC, Marler LE, Qiu X, Choi Y, Cao H, Yu R, Sturdy M, Huang R, Liu Y, Wang LQ, Mesecar AD, van Breemen RB, Pezzuto JM, Fong HH, Chen YG, Zhang HJ: Bioactive compounds from the fern Lepisorus contortus. J Nat Prod. 2011 Feb 25;74(2):129-36. doi: 10.1021/np100373f. Epub 2011 Jan 24. [PubMed:21261296 ]
- Huang X, Yin Z, Ye W, Shen W: [Chemical constituents from fruits of Ligustrum lucidum]. Zhongguo Zhong Yao Za Zhi. 2010 Apr;35(7):861-4. doi: 10.4268/cjcmm20100712. [PubMed:20575386 ]
- Maciag D, Dobrowolska E, Sharafan M, Ekiert H, Tomczyk M, Szopa A: Akebia quinata and Akebia trifoliata - a review of phytochemical composition, ethnopharmacological approaches and biological studies. J Ethnopharmacol. 2021 Nov 15;280:114486. doi: 10.1016/j.jep.2021.114486. Epub 2021 Aug 2. [PubMed:34352331 ]
- Liu SK, Que S, Cheng W, Zhang QY, Liang H: [Chemical constituents from whole plants of Carduus acanthoides]. Zhongguo Zhong Yao Za Zhi. 2013 Jul;38(14):2334-7. [PubMed:24199567 ]
- Shang XY, Li C, Zhang CZ, Yang YC, Shi JG: [Non-alkaloid constituents from a Tibetan medicine Meconopsis quintuplinervia]. Zhongguo Zhong Yao Za Zhi. 2006 Mar;31(6):468-71. [PubMed:16722374 ]
- Wang H, Ye WC, Xiong F, Zhao SX: [Phenylethanoid glycosides from root of Picrorhiza scrophulariiflora]. Zhongguo Zhong Yao Za Zhi. 2004 Jun;29(6):531-4. [PubMed:15706916 ]
- Wang H, Sun Y, Ye WC, Xiong F, Wu JJ, Yang CH, Zhao SX: Antioxidative phenylethanoid and phenolic glycosides from Picrorhiza scrophulariiflora. Chem Pharm Bull (Tokyo). 2004 May;52(5):615-7. doi: 10.1248/cpb.52.615. [PubMed:15133218 ]
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