Record Information |
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Version | 2.0 |
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Created at | 2022-09-12 11:24:31 UTC |
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Updated at | 2022-09-12 11:24:32 UTC |
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NP-MRD ID | NP0328173 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 5,8-dihydroxy-2-[(1r)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3h-naphthalen-2-yl acetate |
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Description | Shikonin acetate belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). 5,8-dihydroxy-2-[(1r)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3h-naphthalen-2-yl acetate is found in Arnebia decumbens. It was first documented in 2016 (PMID: 27278171). Based on a literature review a significant number of articles have been published on shikonin acetate (PMID: 34271983) (PMID: 32984979) (PMID: 30092983) (PMID: 28211616). |
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Structure | CC(C)=CC[C@@H](O)C1(CC(=O)C2=C(O)C=CC(O)=C2C1=O)OC(C)=O InChI=1S/C18H20O7/c1-9(2)4-7-14(23)18(25-10(3)19)8-13(22)15-11(20)5-6-12(21)16(15)17(18)24/h4-6,14,20-21,23H,7-8H2,1-3H3/t14-,18?/m1/s1 |
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Synonyms | Value | Source |
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Shikonin acetic acid | Generator |
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Chemical Formula | C18H20O7 |
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Average Mass | 348.3510 Da |
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Monoisotopic Mass | 348.12090 Da |
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IUPAC Name | 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-1,2,3,4-tetrahydronaphthalen-2-yl acetate |
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Traditional Name | 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dioxo-3H-naphthalen-2-yl acetate |
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CAS Registry Number | Not Available |
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SMILES | CC(C)=CC[C@@H](O)C1(CC(=O)C2=C(O)C=CC(O)=C2C1=O)OC(C)=O |
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InChI Identifier | InChI=1S/C18H20O7/c1-9(2)4-7-14(23)18(25-10(3)19)8-13(22)15-11(20)5-6-12(21)16(15)17(18)24/h4-6,14,20-21,23H,7-8H2,1-3H3/t14-,18?/m1/s1 |
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InChI Key | MNGVKFABFGGTBC-IKJXHCRLSA-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 naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Naphthalenes |
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Sub Class | Naphthoquinones |
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Direct Parent | Naphthoquinones |
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Alternative Parents | |
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Substituents | - Naphthoquinone
- Tetralin
- Aryl alkyl ketone
- Aryl ketone
- Quinone
- 1-hydroxy-2-unsubstituted benzenoid
- Alpha-acyloxy ketone
- Vinylogous acid
- Secondary alcohol
- Ketone
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic homopolycyclic 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 | - Arampatzis AS, Kontogiannopoulos KN, Theodoridis K, Aggelidou E, Rat A, Willems A, Tsivintzelis I, Papageorgiou VP, Kritis A, Assimopoulou AN: Electrospun wound dressings containing bioactive natural products: physico-chemical characterization and biological assessment. Biomater Res. 2021 Jul 16;25(1):23. doi: 10.1186/s40824-021-00223-9. [PubMed:34271983 ]
- Wu Q, Er-Bu A, Liang X, Luan S, He C, Yin L, Yin Z, Zou Y, Li L, Song X: Determination of the main naphthoquinones in Onosma hookeri Clarke. var. longiforum Duthie and its optimization of the ultrasound-assisted extraction using response surface methodology. J Food Sci. 2021 Feb;86(2):357-365. doi: 10.1111/1750-3841.15460. Epub 2020 Sep 27. [PubMed:32984979 ]
- Khoshnevisan K, Maleki H, Samadian H, Shahsavari S, Sarrafzadeh MH, Larijani B, Dorkoosh FA, Haghpanah V, Khorramizadeh MR: Cellulose acetate electrospun nanofibers for drug delivery systems: Applications and recent advances. Carbohydr Polym. 2018 Oct 15;198:131-141. doi: 10.1016/j.carbpol.2018.06.072. Epub 2018 Jun 18. [PubMed:30092983 ]
- Qiu HY, Wang F, Wang X, Sun WX, Qi JL, Pang YJ, Yang RW, Lu GH, Wang XM, Yang YH: Design, Synthesis, and Biological Evaluation of Chalcone-Containing Shikonin Derivatives as Inhibitors of Tubulin Polymerization. ChemMedChem. 2017 Mar 7;12(5):399-406. doi: 10.1002/cmdc.201700001. Epub 2017 Feb 17. [PubMed:28211616 ]
- Katoch P, Rana S, Kumar D, Kumar S, Bhushan S: Concurrent NP-HPTLC Determination of Shikonin and beta,beta-Dimethylacryl Shikonin in Arnebia benthamii. J Chromatogr Sci. 2016 Sep;54(8):1421-7. doi: 10.1093/chromsci/bmw096. Epub 2016 Jun 8. [PubMed:27278171 ]
- LOTUS database [Link]
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