Record Information |
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Version | 1.0 |
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Created at | 2022-09-02 02:38:30 UTC |
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Updated at | 2022-09-02 02:38:30 UTC |
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NP-MRD ID | NP0147105 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2s,3r,4r,5s,6s)-2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-3-yl]oxy}-5-hydroxy-6-methyl-3-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl acetate |
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Description | Sagittatoside C 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. (2s,3r,4r,5s,6s)-2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-3-yl]oxy}-5-hydroxy-6-methyl-3-{[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl acetate is found in Epimedium diphyllum, Epimedium grandiflorum and Epimedium sagittatum. It was first documented in 2019 (PMID: 30941194). Based on a literature review a significant number of articles have been published on Sagittatoside C (PMID: 35283431) (PMID: 33049236) (PMID: 30554645) (PMID: 30470129). |
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Structure | COC1=CC=C(C=C1)C1=C(O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](OC(C)=O)[C@H]2OC2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=O)C2=C(O)C=C(O)C(CC=C(C)C)=C2O1 InChI=1S/C35H42O16/c1-14(2)6-11-19-20(38)12-21(39)23-26(42)32(29(49-30(19)23)17-7-9-18(45-5)10-8-17)50-35-33(31(47-16(4)37)24(40)15(3)46-35)51-34-28(44)27(43)25(41)22(13-36)48-34/h6-10,12,15,22,24-25,27-28,31,33-36,38-41,43-44H,11,13H2,1-5H3/t15-,22+,24-,25+,27-,28+,31+,33+,34?,35-/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C35H42O16 |
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Average Mass | 718.7050 Da |
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Monoisotopic Mass | 718.24729 Da |
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IUPAC Name | (2S,3R,4R,5S,6S)-2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-3-yl]oxy}-5-hydroxy-6-methyl-3-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl acetate |
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Traditional Name | (2S,3R,4R,5S,6S)-2-{[5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxochromen-3-yl]oxy}-5-hydroxy-6-methyl-3-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-4-yl acetate |
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CAS Registry Number | Not Available |
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SMILES | COC1=CC=C(C=C1)C1=C(O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](OC(C)=O)[C@H]2OC2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=O)C2=C(O)C=C(O)C(CC=C(C)C)=C2O1 |
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InChI Identifier | InChI=1S/C35H42O16/c1-14(2)6-11-19-20(38)12-21(39)23-26(42)32(29(49-30(19)23)17-7-9-18(45-5)10-8-17)50-35-33(31(47-16(4)37)24(40)15(3)46-35)51-34-28(44)27(43)25(41)22(13-36)48-34/h6-10,12,15,22,24-25,27-28,31,33-36,38-41,43-44H,11,13H2,1-5H3/t15-,22+,24-,25+,27-,28+,31+,33+,34?,35-/m0/s1 |
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InChI Key | QGVUYZAEBBWPRU-WRWOQAAESA-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
- 8-prenylated flavone
- 4p-methoxyflavonoid-skeleton
- Hydroxyflavonoid
- Flavone
- 7-hydroxyflavonoid
- 5-hydroxyflavonoid
- O-glycosyl compound
- Glycosyl compound
- Disaccharide
- Chromone
- 1-benzopyran
- Benzopyran
- Phenoxy compound
- Methoxybenzene
- Phenol ether
- Anisole
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- Alkyl aryl ether
- Benzenoid
- Pyran
- Oxane
- Monocyclic benzene moiety
- Heteroaromatic compound
- Vinylogous acid
- Secondary alcohol
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Monocarboxylic acid or derivatives
- Ether
- Carboxylic acid derivative
- Acetal
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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 | - Wang Z, Liu C, Yu H, Wu B, Huai B, Zhuang Z, Sun C, Xu L, Jin F: Icaritin Preparation from Icariin by a Special Epimedium Flavonoid-Glycosidase from Aspergillus sp.y848 Strain. J Microbiol Biotechnol. 2022 Apr 28;32(4):437-446. doi: 10.4014/jmb.2112.12036. [PubMed:35283431 ]
- Shen Y, Wang M, Zhou J, Chen Y, Wu M, Yang Z, Yang C, Xia G, Tam JP, Zhou C, Yang H, Jia X: Construction of Fe(3)O(4)@alpha-glucosidase magnetic nanoparticles for ligand fishing of alpha-glucosidase inhibitors from a natural tonic Epimedii Folium. Int J Biol Macromol. 2020 Dec 15;165(Pt A):1361-1372. doi: 10.1016/j.ijbiomac.2020.10.018. Epub 2020 Oct 10. [PubMed:33049236 ]
- Zhong R, Chen Y, Ling J, Xia Z, Zhan Y, Sun E, Shi Z, Feng L, Jia X, Song J, Wei Y: The Toxicity and Metabolism Properties of Herba Epimedii Flavonoids on Laval and Adult Zebrafish. Evid Based Complement Alternat Med. 2019 Mar 3;2019:3745051. doi: 10.1155/2019/3745051. eCollection 2019. [PubMed:30941194 ]
- Shen Y, Wang M, Chen Y, Xu L, Lu Y, Zhou Y, Tam JP, Han F, Yang H, Jia X: Convenient preparation of sagittatoside B, a rare bioactive secondary flavonol glycoside, by recyclable and integrated biphase enzymatic hydrolysis. Enzyme Microb Technol. 2019 Feb;121:51-58. doi: 10.1016/j.enzmictec.2018.12.002. Epub 2018 Dec 3. [PubMed:30554645 ]
- Shen Y, Lu Y, Gao J, Zhu Y, Wang M, Jing S, Xu L, Yang H, Jia X: Efficient preparation of rare Sagittatoside A from epimedin A, by recyclable aqueous organic two-phase enzymatic hydrolysis. Nat Prod Res. 2019 Nov;33(21):3095-3102. doi: 10.1080/14786419.2018.1519820. Epub 2018 Nov 23. [PubMed:30470129 ]
- LOTUS database [Link]
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