Record Information |
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Version | 2.0 |
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Creation Date | 2009-07-03 22:19:15 UTC |
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Update Date | 2014-12-24 20:25:40 UTC |
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Accession Number | T3D2535 |
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Identification |
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Common Name | Cinobufagin |
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Class | Small Molecule |
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Description | Cinobufagin is a cardiotoxic bufanolide steroid secreted by the Asiatic toad (Bufo gargarizans). (3) |
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Compound Type | - Animal Toxin
- Ester
- Ether
- Frog/Toad Toxin
- Natural Compound
- Organic Compound
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Chemical Structure | |
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Synonyms | Synonym | Cino-bufagin | Cinobufagine |
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Chemical Formula | C26H34O6 |
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Average Molecular Mass | 442.545 g/mol |
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Monoisotopic Mass | 442.236 g/mol |
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CAS Registry Number | 470-37-1 |
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IUPAC Name | 14-hydroxy-7,11-dimethyl-6-(2-oxo-2H-pyran-4-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-5-yl acetate |
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Traditional Name | 14-hydroxy-7,11-dimethyl-6-(2-oxopyran-4-yl)-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadecan-5-yl acetate |
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SMILES | CC(=O)OC1C2OC22C3CCC4CC(O)CCC4(C)C3CCC2(C)C1C1=CC(=O)OC=C1 |
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InChI Identifier | InChI=1S/C26H34O6/c1-14(27)31-22-21(15-8-11-30-20(29)12-15)25(3)10-7-18-19(26(25)23(22)32-26)5-4-16-13-17(28)6-9-24(16,18)2/h8,11-12,16-19,21-23,28H,4-7,9-10,13H2,1-3H3 |
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InChI Key | InChIKey=BNZAGRNEEMGADQ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group. |
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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 esters |
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Direct Parent | Steroid esters |
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Alternative Parents | |
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Substituents | - Steroid ester
- Naphthopyran
- Naphthalene
- Pyranone
- Oxane
- Pyran
- Cyclic alcohol
- Heteroaromatic compound
- Carboxylic acid ester
- Lactone
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Ether
- Oxirane
- Dialkyl ether
- Oxacycle
- Carboxylic acid derivative
- Organooxygen compound
- Alcohol
- Hydrocarbon derivative
- Organic oxygen compound
- Organic oxide
- 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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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available | LogP | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-01po-2809600000-23ac8619fa4e3ed11dec | 2021-09-24 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-03 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-3005900000-c9d4a8ef3d4abaf6ae0d | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0535-4009400000-249ed8ed5dc781480286 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9015000000-48bb1483c4273dc532af | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-052f-5000900000-e5b9dece597ab47ae055 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0536-3007900000-75058b0b45dbd242e38e | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-3009100000-23c8f5b824fa27109547 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004l-0003900000-c10833a5bef940a0387f | 2016-08-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-0209500000-6395a480649d326b5294 | 2016-08-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03yl-4904100000-35d59432fc4064d6d339 | 2016-08-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0009100000-50e6e4f2d31fd935e689 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00or-0019600000-c6497a30fec9972bf7dc | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-022a-2914000000-ff4977984d3e2131065d | 2021-10-12 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Ingestion (1) |
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Mechanism of Toxicity | Cinobufagin blocks the sodium/potassium pump in heart tissue. (3, 4) |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | Cinobufagin is a cardiotoxic bufanolide steroid secreted by the Asiatic toad (Bufo gargarizans). (3) |
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Minimum Risk Level | Not Available |
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Health Effects | Cinobufagin is cardiotoxic. (3) |
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Symptoms | Symptoms include nausea, vomiting, anorexia, diarrhoea, abdominal pain, wild hallucinations, delirium, and severe headache. Depending on the severity the victim may later suffer irregular and slow pulse, tremors, various cerebral disturbances, especially of a visual nature, convulsions, and deadly disturbances of the heart such as heart block, brachycardia, or tachycardia. (3, 4) |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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PubChem Compound ID | 10103 |
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ChEMBL ID | Not Available |
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ChemSpider ID | Not Available |
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KEGG ID | C16931 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | Not Available |
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BioCyc ID | Not Available |
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CTD ID | C002471 |
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Stitch ID | Cinobufagin |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | - Singer TP, Ramsay RR: Mechanism of the neurotoxicity of MPTP. An update. FEBS Lett. 1990 Nov 12;274(1-2):1-8. [2253761 ]
- The Physical and Theoretical Chemistry Laboratory of Oxford University (2007). Material Safety Data Sheet (MSDS) for barium fluoride. [Link]
- Wikipedia. Cinobufagin. Last Updated 23 January 2009. [Link]
- Wikipedia. Digitalis. Last Updated 29 June 2009. [Link]
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Gene Regulation |
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Up-Regulated Genes | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
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Down-Regulated Genes | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
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