Record Information |
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Version | 1.0 |
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Created at | 2022-06-29 22:16:48 UTC |
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Updated at | 2022-06-29 22:16:48 UTC |
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NP-MRD ID | NP0141190 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Bufarenogin |
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Description | Bufarenogin belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. Thus, bufarenogin is considered to be a sterol. It was first documented in 2015 (PMID: 26312642). Based on a literature review a significant number of articles have been published on Bufarenogin (PMID: 28712972) (PMID: 35433834) (PMID: 33421322) (PMID: 26615828). |
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Structure | C[C@@]12[C@H](CC[C@]1(O)[C@@H]1CC[C@@H]3C[C@@H](O)CC[C@]3(C)[C@H]1C(=O)[C@H]2O)C1=COC(=O)C=C1 InChI=1S/C24H32O6/c1-22-9-7-15(25)11-14(22)4-5-17-19(22)20(27)21(28)23(2)16(8-10-24(17,23)29)13-3-6-18(26)30-12-13/h3,6,12,14-17,19,21,25,28-29H,4-5,7-11H2,1-2H3/t14-,15+,16-,17-,19-,21-,22+,23+,24+/m1/s1 |
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Synonyms | Not Available |
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Chemical Formula | C24H32O6 |
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Average Mass | 416.5140 Da |
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Monoisotopic Mass | 416.21989 Da |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | Not Available |
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SMILES | C[C@@]12[C@H](CC[C@]1(O)[C@@H]1CC[C@@H]3C[C@@H](O)CC[C@]3(C)[C@H]1C(=O)[C@H]2O)C1=COC(=O)C=C1 |
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InChI Identifier | InChI=1S/C24H32O6/c1-22-9-7-15(25)11-14(22)4-5-17-19(22)20(27)21(28)23(2)16(8-10-24(17,23)29)13-3-6-18(26)30-12-13/h3,6,12,14-17,19,21,25,28-29H,4-5,7-11H2,1-2H3/t14-,15+,16-,17-,19-,21-,22+,23+,24+/m1/s1 |
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InChI Key | SOGONHOGEFLVPE-PUVOGLICSA-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 | Not Available |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Steroid lactones |
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Direct Parent | Bufanolides and derivatives |
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Alternative Parents | |
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Substituents | - Bufanolide-skeleton
- 3-hydroxysteroid
- 12-hydroxysteroid
- 14-hydroxysteroid
- Hydroxysteroid
- 11-oxosteroid
- Oxosteroid
- 3-beta-hydroxysteroid
- Pyranone
- Pyran
- Heteroaromatic compound
- Tertiary alcohol
- Cyclic alcohol
- Secondary alcohol
- Ketone
- Lactone
- Polyol
- Organoheterocyclic compound
- Oxacycle
- Hydrocarbon derivative
- Organic oxygen compound
- Alcohol
- Organic oxide
- Organooxygen compound
- Carbonyl group
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | - Chen L, Mai W, Chen M, Hu J, Zhuo Z, Lei X, Deng L, Liu J, Yao N, Huang M, Peng Y, Ye W, Zhang D: Arenobufagin inhibits prostate cancer epithelial-mesenchymal transition and metastasis by down-regulating beta-catenin. Pharmacol Res. 2017 Sep;123:130-142. doi: 10.1016/j.phrs.2017.07.009. Epub 2017 Jul 14. [PubMed:28712972 ]
- Zhu Y, Zhu Y, Tao S, Liang W, Zhang J, Zhang Y, Xuan Z, Xu J, Peng C, Wu H, Wu D: The Integrated Study on the Chemical Profiling to Explore the Constituents and Mechanism of Traditional Chinese Medicine Preparation Huatuo Jiuxin Pills Based on UPLC-Q-TOF/MS(E) and Network Pharmacology. Front Mol Biosci. 2022 Mar 31;9:818285. doi: 10.3389/fmolb.2022.818285. eCollection 2022. [PubMed:35433834 ]
- Han Q, Zhang C, Zhang Y, Li Y, Wu L, Sun X: Bufarenogin induces intrinsic apoptosis via Bax and ANT cooperation. Pharmacol Res Perspect. 2021 Feb;9(1):e00694. doi: 10.1002/prp2.694. [PubMed:33421322 ]
- Perera Cordova WH, Leitao SG, Cunha-Filho G, Bosch RA, Alonso IP, Pereda-Miranda R, Gervou R, Touza NA, Quintas LE, Noel F: Bufadienolides from parotoid gland secretions of Cuban toad Peltophryne fustiger (Bufonidae): Inhibition of human kidney Na(+)/K(+)-ATPase activity. Toxicon. 2016 Feb;110:27-34. doi: 10.1016/j.toxicon.2015.11.015. Epub 2015 Nov 23. [PubMed:26615828 ]
- Ding J, Wang H: psi-Bufarenogin, a lead compound of anti-cancer drug. Cell Cycle. 2015;14(17):2719-20. doi: 10.1080/15384101.2015.1071139. [PubMed:26312642 ]
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