Record Information |
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Version | 1.0 |
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Created at | 2022-06-29 21:43:31 UTC |
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Updated at | 2022-06-29 21:43:31 UTC |
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NP-MRD ID | NP0140621 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Forsythoside A |
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Description | Forsythoside A, also known as forsythiaside, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Forsythoside A is found in Calceolaria plectranthifolia, Digitalis purpurea, Forsythia europaea, Forsythia koreana, Forsythia suspensa, Forsythia viridissima, Globularia alypum, Veronica stricta, Penstemon linarioides, Rehmannia glutinosa and Syringa vulgaris. It was first documented in 2022 (PMID: 35850836). Based on a literature review a significant number of articles have been published on Forsythoside A (PMID: 35733131) (PMID: 35637849) (PMID: 35537260) (PMID: 35533916). |
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Structure | C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OCCC3=CC(O)=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O InChI=1S/C29H36O15/c1-13-22(35)23(36)25(38)29(42-13)41-12-20-27(44-21(34)7-4-14-2-5-16(30)18(32)10-14)24(37)26(39)28(43-20)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27+,28+,29+/m0/s1 |
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Synonyms | Value | Source |
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Forsythiaside | MeSH |
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Chemical Formula | C29H36O15 |
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Average Mass | 624.5920 Da |
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Monoisotopic Mass | 624.20542 Da |
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IUPAC Name | (2R,3S,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-2-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-3-yl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate |
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Traditional Name | forsythiaside |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OCCC3=CC(O)=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C29H36O15/c1-13-22(35)23(36)25(38)29(42-13)41-12-20-27(44-21(34)7-4-14-2-5-16(30)18(32)10-14)24(37)26(39)28(43-20)40-9-8-15-3-6-17(31)19(33)11-15/h2-7,10-11,13,20,22-33,35-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27+,28+,29+/m0/s1 |
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InChI Key | DTOUWTJYUCZJQD-UJERWXFOSA-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 coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Cinnamic acids and derivatives |
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Sub Class | Hydroxycinnamic acids and derivatives |
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Direct Parent | Coumaric acids and derivatives |
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Alternative Parents | |
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Substituents | - Coumaric acid or derivatives
- Cinnamic acid ester
- Disaccharide
- Glycosyl compound
- O-glycosyl compound
- Tyrosol derivative
- Catechol
- Styrene
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Fatty acid ester
- Phenol
- Fatty acyl
- Benzenoid
- Monocyclic benzene moiety
- Oxane
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Secondary alcohol
- Carboxylic acid ester
- Oxacycle
- Polyol
- Organoheterocyclic compound
- Carboxylic acid derivative
- Acetal
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Carbonyl group
- Alcohol
- Organic oxygen compound
- Organic oxide
- Organooxygen compound
- 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 | - Liu Y, Luo J, Gu YZ, Luo Y, Tan T, Liao ZG, Yang M: [Comparative analysis of powder and piece decocting processes of Yinqiao Powder based on determination of multiple primary components]. Zhongguo Zhong Yao Za Zhi. 2022 Jul;47(14):3788-3797. doi: 10.19540/j.cnki.cjcmm.20210913.302. [PubMed:35850836 ]
- Zheng X, Chen Z, Shi S, Yan H, Zhou J, Jiang L, Wang H, Hou G, Jiang Z: Forsythiaside A improves Influenza A virus infection through TLR7 signaling pathway in the lungs of mice. BMC Complement Med Ther. 2022 Jun 22;22(1):164. doi: 10.1186/s12906-022-03644-8. [PubMed:35733131 ]
- Bibi S, Khan MS, El-Kafrawy SA, Alandijany TA, El-Daly MM, Yousafi Q, Fatima D, Faizo AA, Bajrai LH, Azhar EI: Virtual screening and molecular dynamics simulation analysis of Forsythoside A as a plant-derived inhibitor of SARS-CoV-2 3CLpro. Saudi Pharm J. 2022 Jul;30(7):979-1002. doi: 10.1016/j.jsps.2022.05.003. Epub 2022 May 25. [PubMed:35637849 ]
- Zhang J, Xu X, Li L, Li H, Gao L, Yuan X, Du H, Guan Y, Zang H: Multi critical quality attributes monitoring of Chinese oral liquid extraction process with a spectral sensor fusion strategy. Spectrochim Acta A Mol Biomol Spectrosc. 2022 Oct 5;278:121317. doi: 10.1016/j.saa.2022.121317. Epub 2022 May 2. [PubMed:35537260 ]
- Liu C, Zhen D, Du H, Gong G, Wu Y, Ma Q, Quan ZS: Synergistic anti-inflammatory effects of peimine, peiminine, and forsythoside a combination on LPS-induced acute lung injury by inhibition of the IL-17-NF-kappaB/MAPK pathway activation. J Ethnopharmacol. 2022 Sep 15;295:115343. doi: 10.1016/j.jep.2022.115343. Epub 2022 May 6. [PubMed:35533916 ]
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