| Record Information |
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| Version | 2.0 |
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| Created at | 2022-04-28 08:23:58 UTC |
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| Updated at | 2022-04-28 08:23:58 UTC |
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| NP-MRD ID | NP0064110 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 7-Deoxonarchinol A |
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| Description | Desoxo-Narchinol A belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 7-Deoxonarchinol A is found in Nardostachys chinensis . 7-Deoxonarchinol A was first documented in 2017 (PMID: 28728067). Based on a literature review a significant number of articles have been published on Desoxo-Narchinol A (PMID: 33220358) (PMID: 29202512) (PMID: 30168019) (PMID: 29221883) (PMID: 33976703) (PMID: 31141964). |
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| Structure | C[C@@H]1CCC=C2C(=O)C=C[C@@H](O)[C@@]12C InChI=1S/C12H16O2/c1-8-4-3-5-9-10(13)6-7-11(14)12(8,9)2/h5-8,11,14H,3-4H2,1-2H3/t8-,11-,12+/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C12H16O2 |
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| Average Mass | 192.2580 Da |
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| Monoisotopic Mass | 192.11503 Da |
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| IUPAC Name | (4R,4aS,5R)-4-hydroxy-4a,5-dimethyl-1,4,4a,5,6,7-hexahydronaphthalen-1-one |
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| Traditional Name | (4R,4aS,5R)-4-hydroxy-4a,5-dimethyl-4,5,6,7-tetrahydronaphthalen-1-one |
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| CAS Registry Number | Not Available |
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| SMILES | C[C@@H]1CCC=C2C(=O)C=C[C@@H](O)[C@@]12C |
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| InChI Identifier | InChI=1S/C12H16O2/c1-8-4-3-5-9-10(13)6-7-11(14)12(8,9)2/h5-8,11,14H,3-4H2,1-2H3/t8-,11-,12+/m1/s1 |
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| InChI Key | YWSIMWUTQXMOSD-FXAINCCUSA-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, 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 | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double 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 | Carbonyl compounds |
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| Direct Parent | Cyclohexenones |
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| Alternative Parents | |
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| Substituents | - Cyclohexenone
- Secondary alcohol
- Organic oxide
- Hydrocarbon derivative
- Alcohol
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic 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 | - Li R, Wang ZM, Wang Y, Dong X, Zhang LH, Wang T, Zhu Y, Gao XM, Wu HH, Xu YT: Antidepressant activities and regulative effects on serotonin transporter of Nardostachys jatamansi DC. J Ethnopharmacol. 2021 Mar 25;268:113601. doi: 10.1016/j.jep.2020.113601. Epub 2020 Nov 18. [PubMed:33220358 ]
- Zhang W, Nan G, Wu HH, Jiang M, Li TX, Wang M, Gao XM, Zhu Y, Song YS, Wang J, Xu YT: A Simple and Rapid UPLC-PDA Method for Quality Control of Nardostachys jatamansi. Planta Med. 2018 May;84(8):536-543. doi: 10.1055/s-0043-123655. Epub 2017 Dec 4. [PubMed:29202512 ]
- Kim KW, Yoon CS, Kim YC, Oh H: Desoxo-narchinol A and Narchinol B Isolated from Nardostachys jatamansi Exert Anti-neuroinflammatory Effects by Up-regulating of Nuclear Transcription Factor Erythroid-2-Related Factor 2/Heme Oxygenase-1 Signaling. Neurotox Res. 2019 Jan;35(1):230-243. doi: 10.1007/s12640-018-9951-x. Epub 2018 Aug 31. [PubMed:30168019 ]
- Yoon CS, Kim KW, Lee SC, Kim YC, Oh H: Anti-neuroinflammatory effects of sesquiterpenoids isolated from Nardostachys jatamansi. Bioorg Med Chem Lett. 2018 Jan 15;28(2):140-144. doi: 10.1016/j.bmcl.2017.11.041. Epub 2017 Nov 24. [PubMed:29221883 ]
- Kim KW, Yoon CS, Park SJ, Bae GS, Kim DG, Kim YC, Oh H: Chemical Analysis of the Ingredients of 20% Aqueous Ethanol Extract of Nardostachys jatamansi through Phytochemical Study and Evaluation of Anti-Neuroinflammatory Component. Evid Based Complement Alternat Med. 2021 Apr 22;2021:5901653. doi: 10.1155/2021/5901653. eCollection 2021. [PubMed:33976703 ]
- Thapa SK, Upadhyay M, Kim TH, Shin S, Park SJ, Shin BS: Liquid Chromatography-Tandem Mass Spectrometry of Desoxo-Narchinol a and Its Pharmacokinetics and Oral Bioavailability in Rats and Mice. Molecules. 2019 May 28;24(11):2037. doi: 10.3390/molecules24112037. [PubMed:31141964 ]
- Le VNH, Zhao Y, Cho CW, Na M, Quan KT, Kim JH, Hwang SY, Kim SW, Kim KT, Kang JS: Pharmacokinetic study comparing pure desoxo-narchinol A and nardosinonediol with extracts from Nardostachys jatamansi. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Dec 1;1102-1103:152-158. doi: 10.1016/j.jchromb.2018.10.003. Epub 2018 Oct 17. [PubMed:30391729 ]
- Le VNH, Khong TQ, Na MK, Kim KT, Kang JS: An optimized HPLC-UV method for quantitatively determining sesquiterpenes in Nardostachyos Radix et Rhizoma. J Pharm Biomed Anal. 2017 Oct 25;145:406-413. doi: 10.1016/j.jpba.2017.06.041. Epub 2017 Jul 8. [PubMed:28728067 ]
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