| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-04 21:13:26 UTC |
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| Updated at | 2022-09-04 21:13:27 UTC |
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| NP-MRD ID | NP0202077 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (5s)-5-ethenyl-4,5-dihydro-1,3-oxazole-2-thiol |
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| Description | (S)-goitrin belongs to the class of organic compounds known as oxazolidines. Oxazolidines are compounds containing an oxazolidine moiety, which consists of a saturated aliphatic five-member ring with one oxygen atom, one nitrogen, three carbon atoms, and two double bonds (S)-goitrin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (5s)-5-ethenyl-4,5-dihydro-1,3-oxazole-2-thiol is found in Brassica napus, Brassica oleracea, Brassica rapa and Crambe kotschyana. (5s)-5-ethenyl-4,5-dihydro-1,3-oxazole-2-thiol was first documented in 2013 (PMID: 23632915). Based on a literature review a significant number of articles have been published on (S)-goitrin (PMID: 34777891) (PMID: 34543684) (PMID: 32416341) (PMID: 31132308) (PMID: 29886160) (PMID: 33147822). |
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| Structure | InChI=1S/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8)/t4-/m0/s1 |
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| Synonyms | | Value | Source |
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| (-)-5-Vinyl-2-oxazolidinethione | ChEBI | | (5S)-5-Ethenyl-2-oxazolidinethione | ChEBI | | (S)-(-)-Goitrin | ChEBI | | (S)-5-Ethenyl-2-oxazolidinethione | ChEBI | | (S)-5-Vinyloxazolidine-2-thione | ChEBI | | Goitrin | ChEBI | | L-5-Vinyl-2-oxazolidinethione | ChEBI | | L-5-Vinyl-2-thiooxazolidone | ChEBI | | L-Goitrin | ChEBI | | Goitrin, (+-)-isomer | MeSH | | Goitrin, (R)-isomer | MeSH | | 5-Vinyloxazolidin-2-thione | MeSH | | Goitrin, (S)-isomer | MeSH | | 5-Vinyl-2-thiooxazolidone | MeSH | | 5-Vinyloxazolidine-2-thione | MeSH | | Epigoitrin | MeSH |
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| Chemical Formula | C5H7NOS |
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| Average Mass | 129.1800 Da |
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| Monoisotopic Mass | 129.02484 Da |
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| IUPAC Name | (5S)-5-ethenyl-4,5-dihydro-1,3-oxazole-2-thiol |
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| Traditional Name | (5S)-5-ethenyl-4,5-dihydro-1,3-oxazole-2-thiol |
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| CAS Registry Number | Not Available |
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| SMILES | SC1=NC[C@@H](O1)C=C |
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| InChI Identifier | InChI=1S/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8)/t4-/m0/s1 |
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| InChI Key | UZQVYLOFLQICCT-BYPYZUCNSA-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 oxazolidines. Oxazolidines are compounds containing an oxazolidine moiety, which consists of a saturated aliphatic five-member ring with one oxygen atom, one nitrogen, three carbon atoms, and two double bonds. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Azolidines |
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| Sub Class | Oxazolidines |
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| Direct Parent | Oxazolidines |
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| Alternative Parents | |
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| Substituents | - Thiocarbamic acid ester
- Oxazolidine
- Thiocarbamic acid derivative
- Oxacycle
- Azacycle
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic 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 | - Zhang H, Xie W, Liu J, Xiang X, Zhang S, Hu J, Yang J: Systematic Study on a Quantitative Analysis of Multicomponents by Single Marker (QAMS) Method for Simultaneous Determination of Eight Constituents in Pneumonia Mixture by UPLC-MS/MS. J Anal Methods Chem. 2021 Nov 3;2021:8311588. doi: 10.1155/2021/8311588. eCollection 2021. [PubMed:34777891 ]
- Chen J, Zhu Z, Gao T, Chen Y, Yang Q, Fu C, Zhu Y, Wang F, Liao W: Isatidis Radix and Isatidis Folium: A systematic review on ethnopharmacology, phytochemistry and pharmacology. J Ethnopharmacol. 2022 Jan 30;283:114648. doi: 10.1016/j.jep.2021.114648. Epub 2021 Sep 20. [PubMed:34543684 ]
- Xu Y, Li J, Shi Y, Yang L, Wang Z, Han H, Wang R: Stereoselective pharmacokinetic study of epiprogoitrin and progoitrin in rats with UHPLC-MS/MS method. J Pharm Biomed Anal. 2020 Aug 5;187:113356. doi: 10.1016/j.jpba.2020.113356. Epub 2020 May 7. [PubMed:32416341 ]
- Li J, Shi Y, Xu Y, Yang L, Wang Z, Han H, Wang R: Metabolic profiles and pharmacokinetics of goitrin in rats through liquid chromatography combined with electrospray ionization-tandem mass spectrometry. Biomed Chromatogr. 2019 Oct;33(10):e4606. doi: 10.1002/bmc.4606. Epub 2019 Jun 17. [PubMed:31132308 ]
- Agerbirk N, Matthes A, Erthmann PO, Ugolini L, Cinti S, Lazaridi E, Nuzillard JM, Muller C, Bak S, Rollin P, Lazzeri L: Glucosinolate turnover in Brassicales species to an oxazolidin-2-one, formed via the 2-thione and without formation of thioamide. Phytochemistry. 2018 Sep;153:79-93. doi: 10.1016/j.phytochem.2018.05.006. Epub 2018 Jun 7. [PubMed:29886160 ]
- Collett MG, Matthews ZM, Parton KH: Hepatotoxicity of Two Progoitrin-Derived Nitriles in New Zealand White Rabbits. Toxins (Basel). 2020 Nov 2;12(11):695. doi: 10.3390/toxins12110695. [PubMed:33147822 ]
- Tran HTT, Herz C, Ruf P, Stetter R, Lamy E: Human T2R38 Bitter Taste Receptor Expression in Resting and Activated Lymphocytes. Front Immunol. 2018 Dec 11;9:2949. doi: 10.3389/fimmu.2018.02949. eCollection 2018. [PubMed:30619309 ]
- Siebers M, Rohr T, Ventura M, Schutz V, Thies S, Kovacic F, Jaeger KE, Berg M, Dormann P, Schulz M: Disruption of microbial community composition and identification of plant growth promoting microorganisms after exposure of soil to rapeseed-derived glucosinolates. PLoS One. 2018 Jul 3;13(7):e0200160. doi: 10.1371/journal.pone.0200160. eCollection 2018. [PubMed:29969500 ]
- Shi Y, Zheng C, Li J, Yang L, Wang Z, Wang R: Separation and Quantification of Four Main Chiral Glucosinolates in Radix Isatidis and Its Granules Using High-Performance Liquid Chromatography/Diode Array Detector Coupled with Circular Dichroism Detection. Molecules. 2018 May 29;23(6):1305. doi: 10.3390/molecules23061305. [PubMed:29844266 ]
- Nie L, Dai Z, Ma S: Stereospecific Assay of (R)- and (S)-Goitrin in Commercial Formulation of Radix Isatidis by Reversed Phase High-Performance Liquid Chromatography. J Anal Methods Chem. 2017;2017:2810565. doi: 10.1155/2017/2810565. Epub 2017 Aug 15. [PubMed:28894621 ]
- Chen H, Jie C, Tang LP, Meng H, Li XB, Li YB, Chen LX, Yan C, Kurihara H, Li YF, He RR: New insights into the effects and mechanism of a classic traditional Chinese medicinal formula on influenza prevention. Phytomedicine. 2017 Apr 15;27:52-62. doi: 10.1016/j.phymed.2017.02.004. Epub 2017 Feb 14. [PubMed:28314479 ]
- Nie L, Dai Z, Ma S: Improved Chiral Separation of (R,S)-Goitrin by SFC: An Application in Traditional Chinese Medicine. J Anal Methods Chem. 2016;2016:5782942. doi: 10.1155/2016/5782942. Epub 2016 Feb 21. [PubMed:27022502 ]
- Ma LN, Zhang CE, Yan D, Tan MR, Li HB, Zhang LL, Xiong Y, Xiao XH: [Screening bioactive compounds inhibiting influenza virus from isatidis radix by ultrafiltration mass spectrometry]. Zhongguo Zhong Yao Za Zhi. 2014 Mar;39(5):812-6. [PubMed:25204170 ]
- Behrens M, Gunn HC, Ramos PC, Meyerhof W, Wooding SP: Genetic, functional, and phenotypic diversity in TAS2R38-mediated bitter taste perception. Chem Senses. 2013 Jul;38(6):475-84. doi: 10.1093/chemse/bjt016. Epub 2013 Apr 30. [PubMed:23632915 ]
- LOTUS database [Link]
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