| Record Information |
|---|
| Version | 2.0 |
|---|
| Created at | 2022-09-10 00:40:42 UTC |
|---|
| Updated at | 2022-09-10 00:40:42 UTC |
|---|
| NP-MRD ID | NP0292921 |
|---|
| Secondary Accession Numbers | None |
|---|
| Natural Product Identification |
|---|
| Common Name | zenone |
|---|
| Description | Cis-Zearalenone belongs to the class of organic compounds known as zearalenones. These are macrolides which contains a fourteen-member lactone fused to 1,3-dihydroxybenzene. zenone is found in Fusarium culmorum. zenone was first documented in 2012 (PMID: 23157684). Based on a literature review a small amount of articles have been published on cis-Zearalenone (PMID: 26335359) (PMID: 25254638) (PMID: 22412694). |
|---|
| Structure | C[C@H]1CCCC(=O)CCC\C=C/C2=CC(O)=CC(O)=C2C(=O)O1 InChI=1S/C18H22O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h3,7,10-12,20-21H,2,4-6,8-9H2,1H3/b7-3-/t12-/m0/s1 |
|---|
| Synonyms | Not Available |
|---|
| Chemical Formula | C18H22O5 |
|---|
| Average Mass | 318.3690 Da |
|---|
| Monoisotopic Mass | 318.14672 Da |
|---|
| IUPAC Name | (3S)-14,16-dihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecine-1,7-dione |
|---|
| Traditional Name | (-)-zearalenone |
|---|
| CAS Registry Number | Not Available |
|---|
| SMILES | C[C@H]1CCCC(=O)CCC\C=C/C2=CC(O)=CC(O)=C2C(=O)O1 |
|---|
| InChI Identifier | InChI=1S/C18H22O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h3,7,10-12,20-21H,2,4-6,8-9H2,1H3/b7-3-/t12-/m0/s1 |
|---|
| InChI Key | MBMQEIFVQACCCH-MIBUCLJRSA-N |
|---|
| Experimental Spectra |
|---|
|
| Not Available | | Predicted Spectra |
|---|
|
| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
|---|
| 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 |
|---|
|
| Not Available | | Species |
|---|
| Species of Origin | |
|---|
| Chemical Taxonomy |
|---|
| Description | Belongs to the class of organic compounds known as zearalenones. These are macrolides which contains a fourteen-member lactone fused to 1,3-dihydroxybenzene. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Phenylpropanoids and polyketides |
|---|
| Class | Macrolides and analogues |
|---|
| Sub Class | Zearalenones |
|---|
| Direct Parent | Zearalenones |
|---|
| Alternative Parents | |
|---|
| Substituents | - Zearalenone-skeleton
- Dihydroxybenzoic acid
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Vinylogous acid
- Carboxylic acid ester
- Ketone
- Lactone
- Cyclic ketone
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Organic oxide
- Organooxygen compound
- Carbonyl group
- Organic oxygen compound
- Hydrocarbon derivative
- Aromatic heteropolycyclic compound
|
|---|
| Molecular Framework | Aromatic heteropolycyclic compounds |
|---|
| External Descriptors | Not Available |
|---|
| Physical Properties |
|---|
| State | Not Available |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
|
|---|
| Predicted Properties | |
|---|
| General References | - Drzymala SS, Binder J, Brodehl A, Penkert M, Rosowski M, Garbe LA, Koch M: Estrogenicity of novel phase I and phase II metabolites of zearalenone and cis-zearalenone. Toxicon. 2015 Oct;105:10-2. doi: 10.1016/j.toxicon.2015.08.027. Epub 2015 Sep 1. [PubMed:26335359 ]
- Drzymala SS, Herrmann AJ, Maul R, Pfeifer D, Garbe LA, Koch M: In vitro phase I metabolism of cis-zearalenone. Chem Res Toxicol. 2014 Nov 17;27(11):1972-8. doi: 10.1021/tx500312g. Epub 2014 Oct 15. [PubMed:25254638 ]
- Koppen R, Riedel J, Proske M, Drzymala S, Rasenko T, Durmaz V, Weber M, Koch M: Photochemical trans-/cis-isomerization and quantitation of zearalenone in edible oils. J Agric Food Chem. 2012 Nov 28;60(47):11733-40. doi: 10.1021/jf3037775. Epub 2012 Nov 19. [PubMed:23157684 ]
- Koppen R, Riedel J, Emmerling F, Koch M: (3S,11Z)-14,16-Dihy-droxy-3-methyl-3,4,5,6,9,10-hexa-hydro-1H-2-benz-oxacyclo-tetra-decine-1,7(8H)-dione (cis-zearalenone): a redetermination. Acta Crystallogr Sect E Struct Rep Online. 2012 Mar 1;68(Pt 3):o832. doi: 10.1107/S1600536812002735. Epub 2012 Feb 24. [PubMed:22412694 ]
- LOTUS database [Link]
|
|---|