Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:08:01 UTC |
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Update date | 2019-11-26 03:02:26 UTC |
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Primary ID | FDB008310 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Agmatine |
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Description | Agmatine ((4-aminobutyl)guanidine, NH2-CH2-CH2-CH2-CH2-NH-C(-NH2)(=NH)) is the decarboxylation product of the amino acid arginine and is an intermediate in polyamine biosynthesis. It is a putative neurotransmitter. It is synthesized in the brain, stored in synaptic vesicles, accumulated by uptake, released by membrane depolarization, and inactivated by agmatinase. Agmatine binds to 2-adrenergic receptor and imidazoline binding sites, and blocks NMDA receptors and other cation ligand-gated channels. Agmatine inhibits nitric oxide synthase (NOS), and induces the release of some peptide hormones. Treatment with exogenous agmatine exerts neuroprotective effects in animal models of neurotrauma. -- Wikipedia; Agmatine ((4-aminobutyl)guanidine, NH2-CH2-CH2-CH2-CH2-NH-C(-NH2)(=NH)) is the decarboxylation product of the amino acid arginine and is an intermediate in polyamine biosynthesis. It is discussed as a putative neurotransmitter. It is synthesized in the brain, stored in synaptic vesicles, accumulated by uptake, released by membrane depolarization, and inactivated by agmatinase. Agmatine binds to ?2-adrenergic receptor and imidazoline binding sites, and blocks NMDA receptors and other cation ligand-gated channels. Agmatine inhibits nitric oxide synthase (NOS), and induces the release of some peptide hormones. Agmatine is found in many foods, some of which are fruits, kohlrabi, carob, and burdock. |
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CAS Number | 306-60-5 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C5H14N4 |
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IUPAC name | N-(4-aminobutyl)guanidine |
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InChI Identifier | InChI=1S/C5H14N4/c6-3-1-2-4-9-5(7)8/h1-4,6H2,(H4,7,8,9) |
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InChI Key | QYPPJABKJHAVHS-UHFFFAOYSA-N |
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Isomeric SMILES | NCCCCNC(N)=N |
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Average Molecular Weight | 130.1915 |
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Monoisotopic Molecular Weight | 130.121846468 |
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Classification |
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Description | Belongs to the class of organic compounds known as guanidines. Guanidines are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5. |
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Kingdom | Organic compounds |
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Super Class | Organic nitrogen compounds |
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Class | Organonitrogen compounds |
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Sub Class | Guanidines |
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Direct Parent | Guanidines |
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Alternative Parents | |
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Substituents | - Guanidine
- Carboximidamide
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Primary aliphatic amine
- Imine
- Amine
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | Agmatine, non-derivatized, GC-MS Spectrum | splash10-0002-0900000000-a9f6a71ff1ddda580ea9 | Spectrum | GC-MS | Agmatine, non-derivatized, GC-MS Spectrum | splash10-00di-1910000000-4c97cf5e84d752009d1a | Spectrum | GC-MS | Agmatine, 3 TMS, GC-MS Spectrum | splash10-00di-1910000000-de398de0f062b85c083c | Spectrum | GC-MS | Agmatine, non-derivatized, GC-MS Spectrum | splash10-00di-1910000000-de398de0f062b85c083c | Spectrum | GC-MS | Agmatine, non-derivatized, GC-MS Spectrum | splash10-00di-1910000000-de398de0f062b85c083c | Spectrum | Predicted GC-MS | Agmatine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-008c-9000000000-ba695487db67f42d2617 | Spectrum | Predicted GC-MS | Agmatine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00e9-9700000000-dcb266f2466b6490a487 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00di-9000000000-e4747ffbbb1c0aa02f4e | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00di-9000000000-e97e998997ab8bfcedb5 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-001i-0900000000-4843789c1dd06e41493d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-00di-9200000000-a6b84c1241179a3739f8 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-00di-9000000000-57f390519e8ddbcb80a8 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-00di-9000000000-e38858b8c1a4fb2a6b14 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-00di-9000000000-2e6fd942608b84941a7d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-001i-0900000000-075bad34dbbb7544e053 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-00di-9600000000-368edccb095766335b38 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-001i-0900000000-6599222abf093d406584 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001i-0900000000-4843789c1dd06e41493d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-00di-9200000000-a6b84c1241179a3739f8 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-00di-9000000000-57f390519e8ddbcb80a8 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-00di-9000000000-e38858b8c1a4fb2a6b14 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-00di-9000000000-2e6fd942608b84941a7d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-001i-0900000000-075bad34dbbb7544e053 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00di-9600000000-368edccb095766335b38 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , positive | splash10-0229-9500000000-1c515d08e5bc52668dc4 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03e9-3900000000-21dc8634e0e5c79fc825 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-9300000000-55aa9e9ef7923b67457f | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03dl-9000000000-ec5b24cf1199482a883d | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-002r-9500000000-f8e119f2ba53222591a1 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-9000000000-c4883e27e32ef6874c13 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-2b9c32eb2684272e86a2 | 2015-05-27 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 194 |
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ChEMBL ID | CHEMBL58343 |
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KEGG Compound ID | C00179 |
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Pubchem Compound ID | 199 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17431 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB08838 |
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HMDB ID | HMDB01432 |
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CRC / DFC (Dictionary of Food Compounds) ID | DFV58-L:DFV58-L |
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EAFUS ID | Not Available |
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Dr. Duke ID | AGMATINE |
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BIGG ID | 34153 |
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KNApSAcK ID | C00001400 |
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HET ID | AG2 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Agmatine |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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