Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 17:54:16 UTC |
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Update Date | 2023-02-21 17:23:13 UTC |
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HMDB ID | HMDB0033188 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole |
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Description | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole, also known as tryptophan pyrolysis product 2 or 1-methyl-3-amino-5H-pyrido(4,3-b)indole, belongs to the class of organic compounds known as gamma carbolines. These are polycyclic aromatic compounds containing a gamma-carbazole(5H-pyrido[4,3-b]indole) moiety, with a structure characterized by the presence of pyridine fused to the pyrrole ring of an indole. Based on a literature review a significant number of articles have been published on 3-Amino-1-methyl-5H-pyrido[4,3-b]indole. |
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Structure | CC1=NC(N)=CC2=C1C1=CC=CC=C1N2 InChI=1S/C12H11N3/c1-7-12-8-4-2-3-5-9(8)15-10(12)6-11(13)14-7/h2-6,15H,1H3,(H2,13,14) |
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Synonyms | Value | Source |
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Tryptophan pyrolysis product 2 | MeSH | 1-Methyl-3-amino-5H-pyrido(4,3-b)indole | MeSH | 3-Amino-1-methyl-5H-pyrido(4,3-b)indole | MeSH | Tryptophan pyrolysate | MeSH | Tryptophan pyrolysis product II | MeSH | 1-Methyl-5H-pyrido(4,3-b)indol-3-amine | HMDB | 1-Methyl-5H-pyrido[3,4-b]indol-1-amine, 9ci | HMDB | 1-Methyl-5H-pyrido[4,3-b]indol-3-amine | HMDB | 1-Methyl-9H-pyrido(4,3-b)indol-3-amine | HMDB | 3-amino-1-Methyl-gamma-carboline | HMDB | RP-P-2 | HMDB | TRP-2 | HMDB | TRP-P-2 | HMDB | TRP-P2 | HMDB | Tryptophan P2 | HMDB | Tryptophan-P-2 | HMDB | Trytophan pyrolysate 2 | HMDB | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole | KEGG |
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Chemical Formula | C12H11N3 |
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Average Molecular Weight | 197.2358 |
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Monoisotopic Molecular Weight | 197.095297367 |
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IUPAC Name | 1-methyl-5H-pyrido[4,3-b]indol-3-amine |
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Traditional Name | 1-methyl-5H-pyrido[4,3-b]indol-3-amine |
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CAS Registry Number | 62450-07-1 |
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SMILES | CC1=NC(N)=CC2=C1C1=CC=CC=C1N2 |
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InChI Identifier | InChI=1S/C12H11N3/c1-7-12-8-4-2-3-5-9(8)15-10(12)6-11(13)14-7/h2-6,15H,1H3,(H2,13,14) |
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InChI Key | LKKMLIBUAXYLOY-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as gamma carbolines. These are polycyclic aromatic compounds containing a gamma-carbazole(5H-pyrido[4,3-b]indole) moiety, with a structure characterized by the presence of pyridine fused to the pyrrole ring of an indole. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Indoles and derivatives |
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Sub Class | Pyridoindoles |
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Direct Parent | Gamma carbolines |
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Alternative Parents | |
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Substituents | - Gamma-carboline
- Indole
- Pyrrolopyridine
- Aminopyridine
- Methylpyridine
- Imidolactam
- Benzenoid
- Pyridine
- Heteroaromatic compound
- Pyrrole
- Azacycle
- Hydrocarbon derivative
- Primary amine
- Organonitrogen compound
- Amine
- Organic nitrogen compound
- Organopnictogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 242 - 247 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 32.86 mg/L @ 25 °C (est) | The Good Scents Company Information System | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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3-Amino-1-methyl-5H-pyrido[4,3-b]indole,1TMS,isomer #1 | CC1=NC(N[Si](C)(C)C)=CC2=C1C1=CC=CC=C1[NH]2 | 2466.1 | Semi standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,1TMS,isomer #1 | CC1=NC(N[Si](C)(C)C)=CC2=C1C1=CC=CC=C1[NH]2 | 2218.6 | Standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,1TMS,isomer #2 | CC1=NC(N)=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C | 2403.1 | Semi standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,1TMS,isomer #2 | CC1=NC(N)=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C | 2185.7 | Standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,2TMS,isomer #1 | CC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=CC2=C1C1=CC=CC=C1[NH]2 | 2475.8 | Semi standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,2TMS,isomer #1 | CC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=CC2=C1C1=CC=CC=C1[NH]2 | 2284.3 | Standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,2TMS,isomer #2 | CC1=NC(N[Si](C)(C)C)=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C | 2402.5 | Semi standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,2TMS,isomer #2 | CC1=NC(N[Si](C)(C)C)=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C | 2232.9 | Standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,3TMS,isomer #1 | CC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C | 2449.6 | Semi standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,3TMS,isomer #1 | CC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C | 2305.9 | Standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,1TBDMS,isomer #1 | CC1=NC(N[Si](C)(C)C(C)(C)C)=CC2=C1C1=CC=CC=C1[NH]2 | 2686.4 | Semi standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,1TBDMS,isomer #1 | CC1=NC(N[Si](C)(C)C(C)(C)C)=CC2=C1C1=CC=CC=C1[NH]2 | 2375.0 | Standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,1TBDMS,isomer #2 | CC1=NC(N)=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C | 2621.4 | Semi standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,1TBDMS,isomer #2 | CC1=NC(N)=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C | 2382.5 | Standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,2TBDMS,isomer #1 | CC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC2=C1C1=CC=CC=C1[NH]2 | 2883.6 | Semi standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,2TBDMS,isomer #1 | CC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC2=C1C1=CC=CC=C1[NH]2 | 2674.6 | Standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,2TBDMS,isomer #2 | CC1=NC(N[Si](C)(C)C(C)(C)C)=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C | 2768.0 | Semi standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,2TBDMS,isomer #2 | CC1=NC(N[Si](C)(C)C(C)(C)C)=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C | 2621.2 | Standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,3TBDMS,isomer #1 | CC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C | 2944.0 | Semi standard non polar | 33892256 | 3-Amino-1-methyl-5H-pyrido[4,3-b]indole,3TBDMS,isomer #1 | CC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C | 2895.2 | Standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - 3-Amino-1-methyl-5H-pyrido[4,3-b]indole EI-B (Non-derivatized) | splash10-0002-3900000000-8ba44f186f86b672eda5 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 3-Amino-1-methyl-5H-pyrido[4,3-b]indole EI-B (Non-derivatized) | splash10-0002-3900000000-8ba44f186f86b672eda5 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Amino-1-methyl-5H-pyrido[4,3-b]indole GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-0900000000-c023c3277c709a0628fa | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Amino-1-methyl-5H-pyrido[4,3-b]indole GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Amino-1-methyl-5H-pyrido[4,3-b]indole 10V, Positive-QTOF | splash10-0002-0900000000-8c1ba829e5497870011b | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Amino-1-methyl-5H-pyrido[4,3-b]indole 20V, Positive-QTOF | splash10-0002-0900000000-c01ed14fcd7efcce22aa | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Amino-1-methyl-5H-pyrido[4,3-b]indole 40V, Positive-QTOF | splash10-0kai-0900000000-b076010a26f7e599a957 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Amino-1-methyl-5H-pyrido[4,3-b]indole 10V, Negative-QTOF | splash10-0002-1900000000-d9e6c66d929e6e00785a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Amino-1-methyl-5H-pyrido[4,3-b]indole 20V, Negative-QTOF | splash10-0002-0900000000-861d27c1dfaaea2b88b7 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Amino-1-methyl-5H-pyrido[4,3-b]indole 40V, Negative-QTOF | splash10-0006-6900000000-f58db98e4dc8860c9a3e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Amino-1-methyl-5H-pyrido[4,3-b]indole 10V, Negative-QTOF | splash10-0002-0900000000-081eee6e904048150332 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Amino-1-methyl-5H-pyrido[4,3-b]indole 20V, Negative-QTOF | splash10-0002-0900000000-081eee6e904048150332 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Amino-1-methyl-5H-pyrido[4,3-b]indole 40V, Negative-QTOF | splash10-0ufr-3900000000-3a50971a0a6deaaace9b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Amino-1-methyl-5H-pyrido[4,3-b]indole 10V, Positive-QTOF | splash10-0002-0900000000-732fba02eb75c1e91307 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Amino-1-methyl-5H-pyrido[4,3-b]indole 20V, Positive-QTOF | splash10-0002-0900000000-732fba02eb75c1e91307 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Amino-1-methyl-5H-pyrido[4,3-b]indole 40V, Positive-QTOF | splash10-055e-0900000000-3f16a34eea3f165ca9cc | 2021-09-22 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Abnormal Concentrations |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB011200 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 4447540 |
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KEGG Compound ID | C14416 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 5284476 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1379881 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Schindl R, Fritsch R, Jardin I, Frischauf I, Kahr H, Muik M, Riedl MC, Groschner K, Romanin C: Canonical transient receptor potential (TRPC) 1 acts as a negative regulator for vanilloid TRPV6-mediated Ca2+ influx. J Biol Chem. 2012 Oct 12;287(42):35612-20. doi: 10.1074/jbc.M112.400952. Epub 2012 Aug 29. [PubMed:22932896 ]
- Sammels E, Devogelaere B, Mekahli D, Bultynck G, Missiaen L, Parys JB, De Smedt H: Unraveling the role of polycystin-2/inositol 1,4,5-trisphosphate receptor interaction in Ca signaling. Commun Integr Biol. 2010 Nov;3(6):530-2. doi: 10.4161/cib.3.6.12751. Epub 2010 Nov 1. [PubMed:21331231 ]
- Zhu J, Yu Y, Ulbrich MH, Li MH, Isacoff EY, Honig B, Yang J: Structural model of the TRPP2/PKD1 C-terminal coiled-coil complex produced by a combined computational and experimental approach. Proc Natl Acad Sci U S A. 2011 Jun 21;108(25):10133-8. doi: 10.1073/pnas.1017669108. Epub 2011 Jun 3. [PubMed:21642537 ]
- Du J, Wong WY, Sun L, Huang Y, Yao X: Protein kinase G inhibits flow-induced Ca2+ entry into collecting duct cells. J Am Soc Nephrol. 2012 Jul;23(7):1172-80. doi: 10.1681/ASN.2011100972. Epub 2012 Apr 19. [PubMed:22518003 ]
- Cantero Mdel R, Cantiello HF: Effect of lithium on the electrical properties of polycystin-2 (TRPP2). Eur Biophys J. 2011 Sep;40(9):1029-42. doi: 10.1007/s00249-011-0715-2. Epub 2011 Jun 16. [PubMed:21678023 ]
- Hofherr A, Kottgen M: TRPP channels and polycystins. Adv Exp Med Biol. 2011;704:287-313. doi: 10.1007/978-94-007-0265-3_16. [PubMed:21290302 ]
- Feng S, Rodat-Despoix L, Delmas P, Ong AC: A single amino acid residue constitutes the third dimerization domain essential for the assembly and function of the tetrameric polycystin-2 (TRPP2) channel. J Biol Chem. 2011 May 27;286(21):18994-9000. doi: 10.1074/jbc.M110.192286. Epub 2011 Apr 7. [PubMed:21474446 ]
- Kottgen M, Hofherr A, Li W, Chu K, Cook S, Montell C, Watnick T: Drosophila sperm swim backwards in the female reproductive tract and are activated via TRPP2 ion channels. PLoS One. 2011;6(5):e20031. doi: 10.1371/journal.pone.0020031. Epub 2011 May 20. [PubMed:21625494 ]
- Gilliam JC, Wensel TG: TRP channel gene expression in the mouse retina. Vision Res. 2011 Dec 8;51(23-24):2440-52. doi: 10.1016/j.visres.2011.10.009. Epub 2011 Oct 20. [PubMed:22037305 ]
- Berrout J, Jin M, O'Neil RG: Critical role of TRPP2 and TRPC1 channels in stretch-induced injury of blood-brain barrier endothelial cells. Brain Res. 2012 Feb 3;1436:1-12. doi: 10.1016/j.brainres.2011.11.044. Epub 2011 Dec 1. [PubMed:22192412 ]
- Hoffmeister H, Babinger K, Gurster S, Cedzich A, Meese C, Schadendorf K, Osten L, de Vries U, Rascle A, Witzgall R: Polycystin-2 takes different routes to the somatic and ciliary plasma membrane. J Cell Biol. 2011 Feb 21;192(4):631-45. doi: 10.1083/jcb.201007050. Epub 2011 Feb 14. [PubMed:21321097 ]
- Dong HW, Davis JC, Ding S, Nai Q, Zhou FM, Ennis M: Expression of transient receptor potential (TRP) channel mRNAs in the mouse olfactory bulb. Neurosci Lett. 2012 Aug 22;524(1):49-54. doi: 10.1016/j.neulet.2012.07.013. Epub 2012 Jul 20. [PubMed:22820212 ]
- Spirli C, Locatelli L, Fiorotto R, Morell CM, Fabris L, Pozzan T, Strazzabosco M: Altered store operated calcium entry increases cyclic 3',5'-adenosine monophosphate production and extracellular signal-regulated kinases 1 and 2 phosphorylation in polycystin-2-defective cholangiocytes. Hepatology. 2012 Mar;55(3):856-68. doi: 10.1002/hep.24723. [PubMed:21987453 ]
- Holzer P: Transient receptor potential (TRP) channels as drug targets for diseases of the digestive system. Pharmacol Ther. 2011 Jul;131(1):142-70. doi: 10.1016/j.pharmthera.2011.03.006. Epub 2011 Mar 21. [PubMed:21420431 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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