Record Information |
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Version | 1.0 |
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Created at | 2006-08-12 21:31:07 UTC |
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Updated at | 2021-06-29 00:47:49 UTC |
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NP-MRD ID | NP0001360 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 4-Guanidinobutanoic acid |
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Description | 4-Guanidinobutanoic acid, also known as gamma-guanidinobutyrate or 4-(carbamimidamido)butanoate, belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. 4-Guanidinobutanoic acid is a normal metabolite present in low concentrations. 4-Guanidinobutanoic acid exists in all eukaryotes, ranging from yeast to humans. Outside of the human body, 4-Guanidinobutanoic acid has been detected, but not quantified in a few different foods, such as apples, french plantains, and loquats. This could make 4-guanidinobutanoic acid a potential biomarker for the consumption of these foods. Patients with hyperargininemia have an arginase deficiency which leads to blockade of the urea cycle in the last step with several clinical symptoms. Owing to the arginase deficiency this patients accumulate arginine which leads eventually to epileptogenic guanidino compounds (PMID 7752905 ). |
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Structure | InChI=1S/C5H11N3O2/c6-5(7)8-3-1-2-4(9)10/h1-3H2,(H,9,10)(H4,6,7,8) |
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Synonyms | Value | Source |
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4-Carbamimidamidobutanoic acid | ChEBI | 4-Guanidinobutanoate | ChEBI | 4-Guanidinobutyric acid | ChEBI | gamma-Guanidinobutyrate | ChEBI | gamma-Guanidinobutyric acid | ChEBI | 4-Carbamimidamidobutanoate | Generator | 4-Guanidinobutyrate | Generator | g-Guanidinobutyrate | Generator | g-Guanidinobutyric acid | Generator | Γ-guanidinobutyrate | Generator | Γ-guanidinobutyric acid | Generator | 4-(Carbamimidamido)butanoate | HMDB | 4-(Carbamimidamido)butanoic acid | HMDB | gamma-Guanidinobutyrate, monosodium salt | HMDB | 4-[(Aminoiminomethyl)amino]butanoate | HMDB | 4-[(Aminoiminomethyl)amino]butanoic acid | HMDB | N-(4-Butanoate)guanidine | HMDB | N-(4-Butanoic acid)guanidine | HMDB | gamma-Guanidinebutyrate | HMDB | gamma-Guanidinebutyric acid | HMDB | Γ-guanidinebutyrate | HMDB | Γ-guanidinebutyric acid | HMDB | 4-Guanidinobutanoic acid | Generator |
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Chemical Formula | C5H11N3O2 |
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Average Mass | 145.1597 Da |
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Monoisotopic Mass | 145.08513 Da |
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IUPAC Name | 4-[(diaminomethylidene)amino]butanoic acid |
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Traditional Name | 4-[(diaminomethylidene)amino]butanoic acid |
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CAS Registry Number | 463-00-3 |
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SMILES | NC(N)=NCCCC(O)=O |
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InChI Identifier | InChI=1S/C5H11N3O2/c6-5(7)8-3-1-2-4(9)10/h1-3H2,(H,9,10)(H4,6,7,8) |
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InChI Key | TUHVEAJXIMEOSA-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Gamma amino acids and derivatives |
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Alternative Parents | |
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Substituents | - Gamma amino acid or derivatives
- Straight chain fatty acid
- Fatty acid
- Fatty acyl
- Guanidine
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carboximidamide
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Carbonyl group
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Mizutani N, Hayakawa C, Ohya Y, Watanabe K, Watanabe Y, Mori A: Guanidino compounds in hyperargininemia. Tohoku J Exp Med. 1987 Nov;153(3):197-205. [PubMed:3433275 ]
- Marescau B, Qureshi IA, De Deyn P, Letarte J, Ryba R, Lowenthal A: Guanidino compounds in plasma, urine and cerebrospinal fluid of hyperargininemic patients during therapy. Clin Chim Acta. 1985 Feb 28;146(1):21-7. [PubMed:3987036 ]
- Gatti R, Gioia MG: Anisoin: a useful pre-chromatographic derivatization fluorogenic reagent for LC analysis of guanidino compounds. J Pharm Biomed Anal. 2006 Sep 11;42(1):11-6. Epub 2006 Feb 3. [PubMed:16460903 ]
- De Deyn PP, Marescau B, Cuykens JJ, Van Gorp L, Lowenthal A, De Potter WP: Guanidino compounds in serum and cerebrospinal fluid of non-dialyzed patients with renal insufficiency. Clin Chim Acta. 1987 Jul 30;167(1):81-8. [PubMed:3665089 ]
- Marescau B, De Deyn PP, Holvoet J, Possemiers I, Nagels G, Saxena V, Mahler C: Guanidino compounds in serum and urine of cirrhotic patients. Metabolism. 1995 May;44(5):584-8. [PubMed:7752905 ]
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