Record Information |
---|
Version | 1.0 |
---|
Created at | 2021-06-19 21:17:49 UTC |
---|
Updated at | 2021-06-29 23:57:20 UTC |
---|
NP-MRD ID | NP0029756 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | (+) goniothalamin |
---|
Provided By | JEOL Database |
---|
Description | (+) goniothalamin is found in Cryptocarya latifolia, Cryptocarya moschata (Lauraceae), Goniothalamus amuyon, Goniothalamus borneensis, Goniothalamus cardiopetalus, Goniothalamus griffithii, Goniothalamus macrophyllus , Goniothalamus scortechinii and Goniothalamus uvarioides. It was first documented in 2019 (PMID: 31416203). Based on a literature review a significant number of articles have been published on Goniothalamin (PMID: 33665392) (PMID: 33463303) (PMID: 33102840) (PMID: 32810752) (PMID: 32743225) (PMID: 32082432). |
---|
Structure | [H]\C(=C(\[H])[C@]1([H])OC(=O)C([H])=C([H])C1([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] InChI=1S/C13H12O2/c14-13-8-4-7-12(15-13)10-9-11-5-2-1-3-6-11/h1-6,8-10,12H,7H2/b10-9+/t12-/m1/s1 |
---|
Synonyms | Not Available |
---|
Chemical Formula | C13H12O2 |
---|
Average Mass | 200.2370 Da |
---|
Monoisotopic Mass | 200.08373 Da |
---|
IUPAC Name | (6R)-6-[(E)-2-phenylethenyl]-5,6-dihydro-2H-pyran-2-one |
---|
Traditional Name | (6R)-6-[(E)-2-phenylethenyl]-5,6-dihydropyran-2-one |
---|
CAS Registry Number | Not Available |
---|
SMILES | [H]\C(=C(\[H])[C@]1([H])OC(=O)C([H])=C([H])C1([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] |
---|
InChI Identifier | InChI=1S/C13H12O2/c14-13-8-4-7-12(15-13)10-9-11-5-2-1-3-6-11/h1-6,8-10,12H,7H2/b10-9+/t12-/m1/s1 |
---|
InChI Key | RLGHFVLWYYVMQZ-BZYZDCJZSA-N |
---|
Experimental Spectra |
---|
|
| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
---|
|
| Not Available | Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. |
---|
Kingdom | Organic compounds |
---|
Super Class | Benzenoids |
---|
Class | Benzene and substituted derivatives |
---|
Sub Class | Styrenes |
---|
Direct Parent | Styrenes |
---|
Alternative Parents | |
---|
Substituents | - Styrene
- Dihydropyranone
- Pyran
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Lactone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxide
- Organooxygen compound
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Aromatic heteromonocyclic compound
|
---|
Molecular Framework | Aromatic heteromonocyclic 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 | - Sophonnithiprasert T, Aruksakunwong O, Tashiro E, Kondoh Y, Muroi M, Osada H, Imoto M, Watanapokasin R: Corrigendum to "Interaction between goniothalamin and peroxisomal multifunctional enzyme type 2 triggering endoplasmic reticulum stress" [Heliyon 6 (10) (October 2020) e05200]. Heliyon. 2021 Feb 17;7(2):e05907. doi: 10.1016/j.heliyon.2021.e05907. eCollection 2021 Feb. [PubMed:33665392 ]
- Braga CB, Kido LA, Lima EN, Lamas CA, Cagnon VHA, Ornelas C, Pilli RA: Enhancing the Anticancer Activity and Selectivity of Goniothalamin Using pH-Sensitive Acetalated Dextran (Ac-Dex) Nanoparticles: A Promising Platform for Delivery of Natural Compounds. ACS Biomater Sci Eng. 2020 May 11;6(5):2929-2942. doi: 10.1021/acsbiomaterials.0c00057. Epub 2020 Apr 7. [PubMed:33463303 ]
- Sophonnithiprasert T, Aruksakunwong O, Tashiro E, Kondoh Y, Muroi M, Osada H, Imoto M, Watanapokasin R: Interaction between goniothalamin and peroxisomal multifunctional enzyme type 2 triggering endoplasmic reticulum stress. Heliyon. 2020 Oct 15;6(10):e05200. doi: 10.1016/j.heliyon.2020.e05200. eCollection 2020 Oct. [PubMed:33102840 ]
- Xu HW, Jia S, Liu M, Li X, Meng X, Wu X, Yu L, Wang M, Jin CY: A low toxic CRM1 degrader: Synthesis and anti-proliferation on MGC803 and HGC27. Eur J Med Chem. 2020 Nov 15;206:112708. doi: 10.1016/j.ejmech.2020.112708. Epub 2020 Aug 7. [PubMed:32810752 ]
- Pastre JC, Murray PRD, Browne DL, Brancaglion GA, Galaverna RS, Pilli RA, Ley SV: Integrated Batch and Continuous Flow Process for the Synthesis of Goniothalamin. ACS Omega. 2020 Jul 17;5(29):18472-18483. doi: 10.1021/acsomega.0c02390. eCollection 2020 Jul 28. [PubMed:32743225 ]
- Cogswell TJ, Donald CS, Marquez R: Rapid, two-pot procedure for the synthesis of dihydropyridinones; total synthesis of aza-goniothalamin. Beilstein J Org Chem. 2020 Jan 28;16:135-139. doi: 10.3762/bjoc.16.15. eCollection 2020. [PubMed:32082432 ]
- Khaw-On P, Pompimon W, Banjerdpongchai R: Goniothalamin Induces Necroptosis and Anoikis in Human Invasive Breast Cancer MDA-MB-231 Cells. Int J Mol Sci. 2019 Aug 14;20(16). pii: ijms20163953. doi: 10.3390/ijms20163953. [PubMed:31416203 ]
- Delman M, Avci ST, Akcok I, Kanbur T, Erdal E, Cagir A: Antiproliferative activity of (R)-4'-methylklavuzon on hepatocellular carcinoma cells and EpCAM(+)/CD133(+) cancer stem cells via SIRT1 and Exportin-1 (CRM1) inhibition. Eur J Med Chem. 2019 Oct 15;180:224-237. doi: 10.1016/j.ejmech.2019.07.024. Epub 2019 Jul 9. [PubMed:31306909 ]
- Meirelles MA, Braga CB, Ornelas C, Pilli RA: Synthesis of Nitrogen-Containing Goniothalamin Analogues with Higher Cytotoxic Activity and Selectivity against Cancer Cells. ChemMedChem. 2019 Aug 6;14(15):1403-1417. doi: 10.1002/cmdc.201900281. Epub 2019 Jul 24. [PubMed:31260170 ]
- Yuan Q, Sigman MS: Palladium-Catalyzed Enantioselective Alkenylation of Enelactams Using a Relay Heck Strategy. Chemistry. 2019 Aug 14;25(46):10823-10827. doi: 10.1002/chem.201902813. Epub 2019 Jul 26. [PubMed:31216370 ]
- Cavalheiro, A. J., et al. (2000). Cavalheiro, A. J., et al, Phytochemistry 53, 811 (2000). Phytochem..
|
---|