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 17:53:57 UTC |
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Update Date | 2023-02-21 17:23:08 UTC |
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HMDB ID | HMDB0033141 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 2-Amino-a-carboline |
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Description | 2-Amino-a-carboline, also known as a-alpha-C or a-a-C, belongs to the class of organic compounds known as alpha carbolines. These are organic compounds containing a pyrido[2,3-b]indole core (which is a pyridine fused to an indole). Based on a literature review a significant number of articles have been published on 2-Amino-a-carboline. |
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Structure | NC1=NC2=C(C=C1)C1=CC=CC=C1N2 InChI=1S/C11H9N3/c12-10-6-5-8-7-3-1-2-4-9(7)13-11(8)14-10/h1-6H,(H3,12,13,14) |
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Synonyms | Value | Source |
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2-Amino-alpha-carboline | Kegg | a-alpha-C | Kegg | 2-Amino-α-carboline | Generator | a-a-C | Generator | a-Α-C | Generator | 2-Amino-9H-pyrido(2,3-b)indole | MeSH | 2-Amino-9H-pyrido(2,3-b)indole, D-labeled | MeSH | 1H-pyrido(2,3-b)indol-2-Amine | HMDB | 2-amino-9H-pyrido[2,3-b]Indole | HMDB | 3-amino-3-Carboline (obsol.) | HMDB | 9H-pyrido[2,3-b]indol-2-Amine | HMDB | amino-alpha-Carboline | HMDB | Glob-P-2 | HMDB | 2-Amino-a-carboline | Generator |
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Chemical Formula | C11H9N3 |
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Average Molecular Weight | 183.2093 |
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Monoisotopic Molecular Weight | 183.079647303 |
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IUPAC Name | 9H-pyrido[2,3-b]indol-2-amine |
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Traditional Name | 2-amino-9H-pyrido[2,3-b]indole |
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CAS Registry Number | 26148-68-5 |
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SMILES | NC1=NC2=C(C=C1)C1=CC=CC=C1N2 |
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InChI Identifier | InChI=1S/C11H9N3/c12-10-6-5-8-7-3-1-2-4-9(7)13-11(8)14-10/h1-6H,(H3,12,13,14) |
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InChI Key | FJTNLJLPLJDTRM-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as alpha carbolines. These are organic compounds containing a pyrido[2,3-b]indole core (which is a pyridine fused to 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 | Alpha carbolines |
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Alternative Parents | |
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Substituents | - Alpha-carboline
- Pyrrolopyridine
- Indole
- Imidolactam
- Benzenoid
- Pyridine
- Heteroaromatic compound
- Pyrrole
- Azacycle
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen 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 | Not Available |
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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 | 202 - 203 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | 2.60 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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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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2-Amino-a-carboline,1TMS,isomer #1 | C[Si](C)(C)NC1=CC=C2C(=N1)[NH]C1=CC=CC=C12 | 2304.4 | Semi standard non polar | 33892256 | 2-Amino-a-carboline,1TMS,isomer #1 | C[Si](C)(C)NC1=CC=C2C(=N1)[NH]C1=CC=CC=C12 | 2161.3 | Standard non polar | 33892256 | 2-Amino-a-carboline,1TMS,isomer #2 | C[Si](C)(C)N1C2=CC=CC=C2C2=CC=C(N)N=C21 | 2266.4 | Semi standard non polar | 33892256 | 2-Amino-a-carboline,1TMS,isomer #2 | C[Si](C)(C)N1C2=CC=CC=C2C2=CC=C(N)N=C21 | 2120.3 | Standard non polar | 33892256 | 2-Amino-a-carboline,2TMS,isomer #1 | C[Si](C)(C)N(C1=CC=C2C(=N1)[NH]C1=CC=CC=C12)[Si](C)(C)C | 2333.7 | Semi standard non polar | 33892256 | 2-Amino-a-carboline,2TMS,isomer #1 | C[Si](C)(C)N(C1=CC=C2C(=N1)[NH]C1=CC=CC=C12)[Si](C)(C)C | 2284.2 | Standard non polar | 33892256 | 2-Amino-a-carboline,2TMS,isomer #2 | C[Si](C)(C)NC1=CC=C2C3=CC=CC=C3N([Si](C)(C)C)C2=N1 | 2288.5 | Semi standard non polar | 33892256 | 2-Amino-a-carboline,2TMS,isomer #2 | C[Si](C)(C)NC1=CC=C2C3=CC=CC=C3N([Si](C)(C)C)C2=N1 | 2194.9 | Standard non polar | 33892256 | 2-Amino-a-carboline,3TMS,isomer #1 | C[Si](C)(C)N(C1=CC=C2C3=CC=CC=C3N([Si](C)(C)C)C2=N1)[Si](C)(C)C | 2297.9 | Semi standard non polar | 33892256 | 2-Amino-a-carboline,3TMS,isomer #1 | C[Si](C)(C)N(C1=CC=C2C3=CC=CC=C3N([Si](C)(C)C)C2=N1)[Si](C)(C)C | 2289.0 | Standard non polar | 33892256 | 2-Amino-a-carboline,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C2C(=N1)[NH]C1=CC=CC=C12 | 2536.6 | Semi standard non polar | 33892256 | 2-Amino-a-carboline,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=CC=C2C(=N1)[NH]C1=CC=CC=C12 | 2325.0 | Standard non polar | 33892256 | 2-Amino-a-carboline,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C2=CC=CC=C2C2=CC=C(N)N=C21 | 2472.2 | Semi standard non polar | 33892256 | 2-Amino-a-carboline,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N1C2=CC=CC=C2C2=CC=C(N)N=C21 | 2316.7 | Standard non polar | 33892256 | 2-Amino-a-carboline,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=CC=C2C(=N1)[NH]C1=CC=CC=C12)[Si](C)(C)C(C)(C)C | 2746.6 | Semi standard non polar | 33892256 | 2-Amino-a-carboline,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=CC=C2C(=N1)[NH]C1=CC=CC=C12)[Si](C)(C)C(C)(C)C | 2697.6 | Standard non polar | 33892256 | 2-Amino-a-carboline,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC1=CC=C2C3=CC=CC=C3N([Si](C)(C)C(C)(C)C)C2=N1 | 2689.5 | Semi standard non polar | 33892256 | 2-Amino-a-carboline,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NC1=CC=C2C3=CC=CC=C3N([Si](C)(C)C(C)(C)C)C2=N1 | 2602.6 | Standard non polar | 33892256 | 2-Amino-a-carboline,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=CC=C2C3=CC=CC=C3N([Si](C)(C)C(C)(C)C)C2=N1)[Si](C)(C)C(C)(C)C | 2867.3 | Semi standard non polar | 33892256 | 2-Amino-a-carboline,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N(C1=CC=C2C3=CC=CC=C3N([Si](C)(C)C(C)(C)C)C2=N1)[Si](C)(C)C(C)(C)C | 2909.0 | 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 - 2-Amino-a-carboline EI-B (Non-derivatized) | splash10-001i-6900000000-f274c4663b258cba600d | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2-Amino-a-carboline EI-B (Non-derivatized) | splash10-001i-6900000000-f274c4663b258cba600d | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Amino-a-carboline GC-MS (Non-derivatized) - 70eV, Positive | splash10-053r-0900000000-5c4ec40046c4c105b132 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Amino-a-carboline GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Amino-a-carboline 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Amino-a-carboline APCI-ITFT , negative-QTOF | splash10-0006-0900000000-3bdfae9d7010d49fc99a | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Amino-a-carboline ESI-ITFT , positive-QTOF | splash10-001i-0900000000-f6e28bb7831900d6ad8d | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Amino-a-carboline APCI-ITFT , positive-QTOF | splash10-00lr-0900000000-d7ca8cf399170a1846e1 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Amino-a-carboline 10V, Positive-QTOF | splash10-001i-0900000000-8f80b0ded52944ffe17e | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Amino-a-carboline 20V, Positive-QTOF | splash10-001i-0900000000-8456e1d36c9bed2d70be | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Amino-a-carboline 40V, Positive-QTOF | splash10-0006-0900000000-f70e6be8fbd6b9147b5a | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Amino-a-carboline 30V, Positive-QTOF | splash10-014l-0900000000-27f6450790ed85c55c52 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Amino-a-carboline 50V, Positive-QTOF | splash10-0006-0900000000-d3676e137577c5a0c8fb | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 2-Amino-a-carboline 35V, Positive-QTOF | splash10-001i-0900000000-f6e28bb7831900d6ad8d | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Amino-a-carboline 10V, Positive-QTOF | splash10-001i-0900000000-40420b8554fb9b744f9a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Amino-a-carboline 20V, Positive-QTOF | splash10-001i-0900000000-3a936d103eb70483c5bf | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Amino-a-carboline 40V, Positive-QTOF | splash10-014i-0900000000-abe05524e994f27c1662 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Amino-a-carboline 10V, Negative-QTOF | splash10-001i-0900000000-39da2723de9d6114edd8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Amino-a-carboline 20V, Negative-QTOF | splash10-001i-0900000000-fb27400b5d7940df7bfe | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Amino-a-carboline 40V, Negative-QTOF | splash10-067i-1900000000-e2bd4f7e390fcf75eed8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Amino-a-carboline 10V, Negative-QTOF | splash10-001i-0900000000-5ed329ab18240e3f7699 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Amino-a-carboline 20V, Negative-QTOF | splash10-001i-0900000000-5ed329ab18240e3f7699 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Amino-a-carboline 40V, Negative-QTOF | splash10-0f6x-0900000000-f789de2c65d991670b1b | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Amino-a-carboline 10V, Positive-QTOF | splash10-001i-0900000000-93c20d3cb3e863c5d375 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Amino-a-carboline 20V, Positive-QTOF | splash10-001i-0900000000-93c20d3cb3e863c5d375 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Amino-a-carboline 40V, Positive-QTOF | splash10-000x-0900000000-c78317e6ffd98846784f | 2021-09-24 | 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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| Not Available |
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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 | FDB011142 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 56541 |
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KEGG Compound ID | C19186 |
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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 | 62805 |
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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 | Not Available |
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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 | - Melo A, Viegas O, Petisca C, Pinho O, Ferreira IM: Effect of beer/red wine marinades on the formation of heterocyclic aromatic amines in pan-fried beef. J Agric Food Chem. 2008 Nov 26;56(22):10625-32. doi: 10.1021/jf801837s. [PubMed:18950185 ]
- Bessette EE, Yasa I, Dunbar D, Wilkens LR, Le Marchand L, Turesky RJ: Biomonitoring of carcinogenic heterocyclic aromatic amines in hair: a validation study. Chem Res Toxicol. 2009 Aug;22(8):1454-63. doi: 10.1021/tx900155f. [PubMed:19588936 ]
- De Andres F, Zougagh M, Castaneda G, Rios A: Simultaneous determination of six non-polar heterocyclic amines in meat samples by supercritical fluid extraction-capillary electrophoresis under fluorimetric detection. Electrophoresis. 2010 Jul;31(13):2165-73. doi: 10.1002/elps.201000080. [PubMed:20593391 ]
- Bessette EE, Goodenough AK, Langouet S, Yasa I, Kozekov ID, Spivack SD, Turesky RJ: Screening for DNA adducts by data-dependent constant neutral loss-triple stage mass spectrometry with a linear quadrupole ion trap mass spectrometer. Anal Chem. 2009 Jan 15;81(2):809-19. doi: 10.1021/ac802096p. [PubMed:19086795 ]
- Stidl R, Sontag G, Koller V, Knasmuller S: Binding of heterocyclic aromatic amines by lactic acid bacteria: results of a comprehensive screening trial. Mol Nutr Food Res. 2008 Mar;52(3):322-9. doi: 10.1002/mnfr.200700034. [PubMed:18320573 ]
- Turesky RJ, Bendaly J, Yasa I, Doll MA, Hein DW: The impact of NAT2 acetylator genotype on mutagenesis and DNA adducts from 2-amino-9H-pyrido[2,3-b]indole. Chem Res Toxicol. 2009 Apr;22(4):726-33. doi: 10.1021/tx800473w. [PubMed:19243127 ]
- Bessette EE, Spivack SD, Goodenough AK, Wang T, Pinto S, Kadlubar FF, Turesky RJ: Identification of carcinogen DNA adducts in human saliva by linear quadrupole ion trap/multistage tandem mass spectrometry. Chem Res Toxicol. 2010 Jul 19;23(7):1234-44. doi: 10.1021/tx100098f. [PubMed:20443584 ]
- Calbiani F, Careri M, Elviri L, Mangia A, Zagnoni I: Validation of an ion-pair liquid chromatography-electrospray-tandem mass spectrometry method for the determination of heterocyclic aromatic amines in meat-based infant foods. Food Addit Contam. 2007 Aug;24(8):833-41. [PubMed:17613070 ]
- Costa M, Viegas O, Melo A, Petisca C, Pinho O, Ferreira IM: Heterocyclic aromatic amine formation in barbecued sardines (Sardina pilchardus) and Atlantic salmon (Salmo salar). J Agric Food Chem. 2009 Apr 22;57(8):3173-9. doi: 10.1021/jf8035808. [PubMed:19265446 ]
- Back YM, Lee JH, Shin HS, Lee KG: Analysis of heterocyclic amines and beta-carbolines by liquid chromatography-mass spectrometry in cooked meats commonly consumed in Korea. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2009 Mar;26(3):298-305. doi: 10.1080/02652030802526834. [PubMed:19680902 ]
- Turesky RJ, Yuan JM, Wang R, Peterson S, Yu MC: Tobacco smoking and urinary levels of 2-amino-9H-pyrido[2,3-b]indole in men of Shanghai, China. Cancer Epidemiol Biomarkers Prev. 2007 Aug;16(8):1554-60. [PubMed:17684128 ]
- Lopez-Mendez C, Bermudez-Fajardo A, Ioannides C, Oviedo-Orta E: Effect of 2-amino-9H-pyrido[2,3-b]indole (AalphaC), a carcinogenic heterocyclic amine present in food, on atherosclerotic plaque development in apoE deficient mice. Toxicol Lett. 2009 Mar 10;185(2):73-8. doi: 10.1016/j.toxlet.2008.11.014. Epub 2008 Dec 3. [PubMed:19103270 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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