Record Information |
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Version | 1.0 |
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Created at | 2022-09-01 21:58:32 UTC |
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Updated at | 2022-09-01 21:58:32 UTC |
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NP-MRD ID | NP0143263 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2s,3r,4s,5s)-2-{[(2r,3r,4s,5r,6s)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4,5-dihydroxyoxan-3-yl acetate |
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Description | Kaempferol 3-[2'''-acetyl-alpha-l-arabinopyranosyl-(1->6)-galactoside] belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Thus, kaempferol 3-[2'''-acetyl-alpha-L-arabinopyranosyl-(1->6)-galactoside] is considered to be a flavonoid. (2s,3r,4s,5s)-2-{[(2r,3r,4s,5r,6s)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4,5-dihydroxyoxan-3-yl acetate is found in Trillium tschonoskii. It was first documented in 2016 (PMID: 27561783). Based on a literature review a significant number of articles have been published on Kaempferol 3-[2'''-acetyl-alpha-l-arabinopyranosyl-(1->6)-galactoside] (PMID: 35357710) (PMID: 31991676) (PMID: 30678336) (PMID: 28554386). |
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Structure | CC(=O)O[C@@H]1[C@@H](O)[C@@H](O)CO[C@H]1OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@H]1O InChI=1S/C28H30O16/c1-10(29)41-26-19(34)15(33)8-39-28(26)40-9-17-20(35)22(37)23(38)27(43-17)44-25-21(36)18-14(32)6-13(31)7-16(18)42-24(25)11-2-4-12(30)5-3-11/h2-7,15,17,19-20,22-23,26-28,30-35,37-38H,8-9H2,1H3/t15-,17+,19-,20-,22-,23+,26+,27-,28-/m0/s1 |
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Synonyms | Value | Source |
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Kaempferol 3-[2'''-acetyl-a-L-arabinopyranosyl-(1->6)-galactoside] | Generator | Kaempferol 3-[2'''-acetyl-α-L-arabinopyranosyl-(1->6)-galactoside] | Generator |
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Chemical Formula | C28H30O16 |
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Average Mass | 622.5320 Da |
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Monoisotopic Mass | 622.15338 Da |
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IUPAC Name | (2S,3R,4S,5S)-2-{[(2R,3R,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4,5-dihydroxyoxan-3-yl acetate |
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Traditional Name | (2S,3R,4S,5S)-2-{[(2R,3R,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-4,5-dihydroxyoxan-3-yl acetate |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)O[C@@H]1[C@@H](O)[C@@H](O)CO[C@H]1OC[C@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C28H30O16/c1-10(29)41-26-19(34)15(33)8-39-28(26)40-9-17-20(35)22(37)23(38)27(43-17)44-25-21(36)18-14(32)6-13(31)7-16(18)42-24(25)11-2-4-12(30)5-3-11/h2-7,15,17,19-20,22-23,26-28,30-35,37-38H,8-9H2,1H3/t15-,17+,19-,20-,22-,23+,26+,27-,28-/m0/s1 |
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InChI Key | DQRYUGWCHIIJRX-QHGCNJJSSA-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-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-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-3-O-glycosides |
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Alternative Parents | |
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Substituents | - Flavonoid-3-o-glycoside
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Flavone
- Hydroxyflavonoid
- Glycosyl compound
- Disaccharide
- O-glycosyl compound
- Chromone
- Benzopyran
- 1-benzopyran
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Pyran
- Oxane
- Vinylogous acid
- Heteroaromatic compound
- Secondary alcohol
- Carboxylic acid ester
- Acetal
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Polyol
- Monocarboxylic acid or derivatives
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Organic oxygen compound
- Alcohol
- Organooxygen compound
- 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 | - Xie L, Guo Y, Ren C, Cao Y, Li J, Lin J, Grierson D, Zhao X, Zhang B, Sun C, Chen K, Li X: Unravelling the consecutive glycosylation and methylation of flavonols in peach in response to UV-B irradiation. Plant Cell Environ. 2022 Jul;45(7):2158-2175. doi: 10.1111/pce.14323. Epub 2022 Apr 13. [PubMed:35357710 ]
- Soib HH, Ismail HF, Husin F, Abu Bakar MH, Yaakob H, Sarmidi MR: Bioassay-Guided Different Extraction Techniques of Carica papaya (Linn.) Leaves on In Vitro Wound-Healing Activities. Molecules. 2020 Jan 24;25(3):517. doi: 10.3390/molecules25030517. [PubMed:31991676 ]
- Lu Y, He Y, Zhu S, Zhong X, Chen D, Liu Z: New Acylglycosides Flavones from Fuzhuan Brick Tea and Simulation Analysis of Their Bioactive Effects. Int J Mol Sci. 2019 Jan 24;20(3):494. doi: 10.3390/ijms20030494. [PubMed:30678336 ]
- Han S, Hanh Nguyen TT, Hur J, Kim NM, Kim SB, Hwang KH, Moon YH, Kang C, Chung B, Kim YM, Kim TS, Park JS, Kim D: Synthesis and characterization of novel astragalin galactosides using beta-galactosidase from Bacillus circulans. Enzyme Microb Technol. 2017 Aug;103:59-67. doi: 10.1016/j.enzmictec.2017.05.003. Epub 2017 May 12. [PubMed:28554386 ]
- Rojas Rodas F, Di S, Murai Y, Iwashina T, Sugawara S, Mori T, Nakabayashi R, Yonekura-Sakakibara K, Saito K, Takahashi R: Cloning and characterization of soybean gene Fg1 encoding flavonol 3-O-glucoside/galactoside (1-->6) glucosyltransferase. Plant Mol Biol. 2016 Nov;92(4-5):445-456. doi: 10.1007/s11103-016-0523-2. Epub 2016 Aug 25. [PubMed:27561783 ]
- LOTUS database [Link]
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