Record Information |
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Version | 2.0 |
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Creation Date | 2014-08-29 05:04:53 UTC |
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Update Date | 2014-12-24 20:26:38 UTC |
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Accession Number | T3D4084 |
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Identification |
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Common Name | Veratramine |
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Class | Small Molecule |
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Description | Veratramine is a hypotensive alkaloid isolated from the rhizomes of Veratrum. |
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Compound Type | - Amine
- Natural Compound
- Organic Compound
- Plant Toxin
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Chemical Structure | |
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Synonyms | Synonym | (3beta,23beta)-14,15,16,17-Tetradehydroveratraman-3,23-diol |
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Chemical Formula | C27H39NO2 |
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Average Molecular Mass | 409.604 g/mol |
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Monoisotopic Mass | 409.298 g/mol |
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CAS Registry Number | 60-70-8 |
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IUPAC Name | (2S,3R,5S)-2-[(1S)-1-[(1S,2R,5S,10R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-7,11(16),12,14-tetraen-14-yl]ethyl]-5-methylpiperidin-3-ol |
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Traditional Name | veratramine |
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SMILES | [H][C@](C)(C1=C(C)C2=C(C=C1)[C@]1([H])CC=C3C[C@@]([H])(O)CC[C@]3(C)[C@@]1([H])C2)[C@]1([H])NC[C@@]([H])(C)C[C@@]1([H])O |
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InChI Identifier | InChI=1S/C27H39NO2/c1-15-11-25(30)26(28-14-15)17(3)20-7-8-21-22-6-5-18-12-19(29)9-10-27(18,4)24(22)13-23(21)16(20)2/h5,7-8,15,17,19,22,24-26,28-30H,6,9-14H2,1-4H3/t15-,17-,19-,22-,24-,25+,26-,27-/m0/s1 |
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InChI Key | InChIKey=MALFODICFSIXPO-KFKQDBFTSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as fluorenes. Fluorenes are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Fluorenes |
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Sub Class | Not Available |
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Direct Parent | Fluorenes |
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Alternative Parents | |
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Substituents | - Fluorene
- Indane
- Aralkylamine
- Piperidine
- Cyclic alcohol
- 1,2-aminoalcohol
- Secondary alcohol
- Secondary aliphatic amine
- Azacycle
- Organoheterocyclic compound
- Secondary amine
- Organonitrogen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Organic nitrogen compound
- Organic oxygen compound
- Organooxygen compound
- Alcohol
- Amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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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 LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0009200000-ec5dca7319fd20180492 | 2016-06-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00dl-1009000000-6e277f23d48e4caef089 | 2016-06-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-2397000000-9702c3c9564aafaa8684 | 2016-06-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0004900000-386171edb4cefa097aca | 2016-08-04 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-052f-5219500000-844961e46c4ea9d3d354 | 2016-08-04 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03dm-9201000000-d82d38207055f9bd6729 | 2016-08-04 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Veratramine produces a characteristic excitatory action on the central nervous system, producing both tremor and a characteristic "struggling" behavior. This behavioral excitation is accompanied by changes in serotonin content in hypothalamus. The central serotonin agonist methysergide in doses of 5--15 mg per kg produces a dose-dependent inhibition of veratramine's action, while parachlorophenylalanine has no effect. (1) |
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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 | Veratramine is a hypotensive alkaloid isolated from the rhizomes of Veratrum. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Normal Concentrations |
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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 | 6070 |
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ChEMBL ID | CHEMBL464724 |
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ChemSpider ID | 5845 |
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KEGG ID | C10829 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | CHEBI:9951 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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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 | - Izumi K, Butterworth RF, Tunnicliff G, Gonce M, Barbeau A: Possible serotonin-agonist action of veratramine. Brain Res Bull. 1978 May-Jun;3(3):237-10. [213177 ]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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