Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:06:40 UTC |
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Update date | 2019-11-26 03:00:33 UTC |
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Primary ID | FDB005416 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Guanidine |
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Description | Guanidine apparently acts by enhancing the release of acetylcholine following a nerve impulse. It also appears to slow the rates of depolarization and repolarization of muscle cell membranes.; Guanidine is a crystalline compound of strong alkalinity formed by the oxidation of guanine. It is used in the manufacture of plastics and explosives. It is found in urine as a normal product of protein metabolism. The molecule was first synthesized in 1861 by the oxidative degradation of an aromatic natural product, guanine, isolated from Peruvian guano. Despite the provocative simplicity of the molecule, the crystal structure was first described 148 years later.; Guanidine is a polyamine that can function as a strong organic base existing primarily as guanidium ions at physiological pH. With a pKa of 12.5, guanidine is protonated, with a charge of +1 in physiological conditions. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed). Guanidine is a crystalline compound of strong alkalinity formed by the oxidation of guanine. It is used in the manufacture of plastics and explosives. -- Wikipedia; Guanidines are a group of organic compounds sharing a common functional group with the general structure (R1R2N)(R3R4N)C=N-R5. The central bond within this group is that of an imine; the other recognizable motif within this group is an aminal. Examples of guanidines are arginine, triazabicyclodecene and saxitoxin. other derivatives could include guanidine hydroxide, the active ingredient in some non-lye relaxers. Guanidinium salts are well known for their denaturing action on proteins. Guanidinium chloride is one of the most effective denaturants. In 6 M GndHCl all proteins with an ordered structure lose their structure, and most of them become randomly coiled, that is, they do not contain any residual structure. |
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CAS Number | 50-01-1 |
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Structure | |
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Synonyms | Synonym | Source |
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Aminomethanamidine | ChEBI | Gu | ChEBI | Guanidin | ChEBI | H2N-C(=nh)-NH2 | ChEBI | Iminourea | ChEBI | Carbamidine | Kegg | (4-Aminobutyl) guanidine | HMDB | Aminoformamidine | HMDB | Carbamamidine | HMDB | Imidourea | HMDB | Guanidine hydrochloride | HMDB | Guanidine monohydrate | HMDB | Guanidine monohydrochloride | HMDB | Guanidine sulfate | HMDB | Guanidium chloride | HMDB | Chloride, guanidinium | HMDB | Guanidine monohydroiodine | HMDB | Guanidine sulfate (1:1) | HMDB | Guanidine sulfate (2:1) | HMDB | Guanidine sulfite (1:1) | HMDB | Guanidinium | HMDB | Hydrochloride, guanidine | HMDB | Monohydrobromide, guanidine | HMDB | Monohydrochloride, guanidine | HMDB | Phosphate, guanidine | HMDB | Guanidine monohydrobromide | HMDB | Guanidine phosphate | HMDB | Monohydroiodine, guanidine | HMDB | Nitrate, guanidine | HMDB | Chloride, guanidium | HMDB | Guanidine nitrate | HMDB | Guanidinium chloride | HMDB | Monohydrate, guanidine | HMDB | Sulfate, guanidine | HMDB | (NH2)2C=NH | biospider | 1184-68-5 (unspecified sulfate) | biospider | 1763-07-1 (unspecified phosphate) | biospider | 50-01-1 (mono-hydrochloride) | biospider | Bisguanidinium sulfate | biospider | GAI | biospider | GU | biospider | Guanidine, hydrochloride | biospider | Guanidine, sulfate (2:1) | biospider | Guanidinium sulfate | biospider | H2N-C(=NH)-NH2 | biospider | NSC7296 (SULFATE, 2:1) | biospider |
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Predicted Properties | |
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Chemical Formula | CH5N3 |
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IUPAC name | guanidine |
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InChI Identifier | InChI=1S/CH5N3/c2-1(3)4/h(H5,2,3,4) |
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InChI Key | ZRALSGWEFCBTJO-UHFFFAOYSA-N |
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Isomeric SMILES | NC(N)=N |
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Average Molecular Weight | 59.0705 |
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Monoisotopic Molecular Weight | 59.048347175 |
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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
- Imine
- 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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Physiological effect | Health effect: |
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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 | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | 182.3 oC | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | 12.5 | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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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 | Guanidine, 3 TMS, GC-MS Spectrum | splash10-00dj-0920000000-b2c19a9125b059b573fd | Spectrum | GC-MS | Guanidine, non-derivatized, GC-MS Spectrum | splash10-00dj-0920000000-b2c19a9125b059b573fd | Spectrum | Predicted GC-MS | Guanidine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4i-9000000000-6e00e9be1957670e422b | Spectrum | Predicted GC-MS | Guanidine, 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) | splash10-03di-9000000000-4df2949d18a754b6aa19 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0006-9000000000-18b92fabd8878a75412f | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0006-9000000000-6675e99565dbe0735311 | 2012-07-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-9000000000-0bf566c21de369198214 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-9000000000-b4670d41c5cfae856086 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03dl-9000000000-9431377731da436c5aa7 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-9000000000-2280b2044ac4a1f8b7fb | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-9000000000-8278836749ed05b02fb3 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-154d1302bda42480ad7b | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-9000000000-ab782a456c989f06bfc8 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9000000000-36e3aa30c6cc4afb2049 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-36e3aa30c6cc4afb2049 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-9000000000-1c8520c5f7efb1187e43 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9000000000-1c8520c5f7efb1187e43 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-1c8520c5f7efb1187e43 | 2021-09-23 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 3400 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C17349 |
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Pubchem Compound ID | 3520 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 24435 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB00536 |
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HMDB ID | HMDB01842 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | GUANIDINE |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | GAI |
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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 | Guanidine |
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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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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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Anti myasthenic | 52217 | An agent that improves neuromuscular transmission, used to treat myasthenia gravis and other neuromuscular disorders by increasing acetylcholine levels, enhancing muscle strength and reducing fatigue. | DUKE | Convulsant | | An agent that induces convulsions and/or epileptic seizures, acting as a stimulant at low doses. It has no therapeutic applications due to its high risk of causing seizures and excitotoxicity, and is the opposite of an anticonvulsant. | DUKE | Hepatotoxic | 50908 | An agent that causes liver damage or toxicity, disrupting normal liver function. It has no therapeutic applications, but is often a side effect of certain medications, such as acetaminophen overdose, and is a key consideration in medical uses, including monitoring liver function during drug therapy. | DUKE | Hypertensive | | An agent that increases blood pressure, used therapeutically to treat hypotension (low blood pressure) and shock, and medically to manage conditions such as orthostatic hypotension and postural hypotension. | DUKE | Hypoglycemic | 35526 | An agent that lowers blood glucose levels, playing a crucial role in glucose metabolism. Therapeutically, it is used to manage diabetes and insulin resistance, with key medical applications in treating type 1 and 2 diabetes, and preventing diabetic complications. | DUKE | Myostimulant | | An agent that stimulates an increase in the rhythm and amplitude of smooth muscle movement, playing a biological role in enhancing muscle contraction. Therapeutically, it is used to treat gastrointestinal disorders, such as constipation, and other conditions characterized by reduced muscle activity, like urinary retention. | DUKE |
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Enzymes | Name | Gene Name | UniProt ID |
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Arginine decarboxylase | ADC | Q96A70 | Ribonuclease pancreatic | RNASE1 | P07998 | Disks large homolog 4 | DLG4 | P78352 |
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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).
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