Record Information |
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Version | 1.0 |
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Created at | 2022-05-11 16:23:11 UTC |
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Updated at | 2022-05-11 16:23:11 UTC |
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NP-MRD ID | NP0086521 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 1H-Imidazole-4(5)-propanoic acid |
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Description | Imidazolepropionic acid, also known as deaminohistidine or 4-imidazolylpropionate, belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring. Imidazolepropionic acid is a very strong basic compound (based on its pKa). Imidazolepropionic acid exists in all living organisms, ranging from bacteria to humans. 1H-Imidazole-4(5)-propanoic acid is found in Coprinopsis atramentaria. It was first documented in 1962 (PMID: 13987921). A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 3 has been replaced by an imidazol-4-yl group (PMID: 32033212) (PMID: 6021220) (PMID: 6136484) (PMID: 23078170) (PMID: 2547218). |
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Structure | InChI=1S/C6H8N2O2/c9-6(10)2-1-5-3-7-4-8-5/h3-4H,1-2H2,(H,7,8)(H,9,10) |
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Synonyms | Value | Source |
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1H-Imidazole-4-propanoic acid | ChEBI | 3-(1H-Imidazol-4-yl)propionic acid | ChEBI | 3-(Imidazol-4-yl)propanoic acid | ChEBI | 3-(Imidazol-4-yl)propionic acid | ChEBI | 4-Imidazolylpropanoic acid | ChEBI | 4-Imidazolylpropionic acid | ChEBI | Deaminohistidine | ChEBI | Imidazolylpropionic acid | ChEBI | 3-(1H-Imidazol-4-yl)propanoate | Kegg | 1H-Imidazole-4-propanoate | Generator | 3-(1H-Imidazol-4-yl)propionate | Generator | 3-(Imidazol-4-yl)propanoate | Generator | 3-(Imidazol-4-yl)propionate | Generator | 4-Imidazolylpropanoate | Generator | 4-Imidazolylpropionate | Generator | Imidazolylpropionate | Generator | 3-(1H-Imidazol-4-yl)propanoic acid | Generator | Imidazolepropionate | Generator | Dihydrourocanate | HMDB | 3-(1H-Imidazol-4-yl)-propionate | HMDB | 3-(1H-Imidazol-4-yl)-propionic acid | HMDB | 5-Imidazolepropionate | HMDB | 5-Imidazolepropionic acid | HMDB | Deamino-histidine | HMDB | URO | HMDB | Imidazole propionate | HMDB | 1H-Imidazole-4(5)-propanoate | HMDB | 1H-Imidazole-4-propionic acid | HMDB | 3-(1H-4-Imidazolyl)propanoic acid | HMDB | 3-(1H-4-Imidazolyl)propionic acid | HMDB | 3-(4-Imidazolyl)propanoic acid | HMDB | 3-(4-Imidazolyl)propionic acid | HMDB | 3-(Imidazol-4(5)-yl)propanoic acid | HMDB | 3-(Imidazol-4(5)-yl)propionic acid | HMDB | 5-(2-Carboxyethyl) imidazole | HMDB | Dihydrourocanic acid | HMDB | Dihydrourocanoic acid | HMDB | Imidazole-4(5)-propanoic acid | HMDB | Imidazole-4(5)-propionic acid | HMDB | Imidazole-4-propanoic acid | HMDB | Imidazole-4-propionic acid | HMDB | Imidazolylpropanoic acid | HMDB | beta-(5-Imidazolyl)propanoic acid | HMDB | beta-(5-Imidazolyl)propionic acid | HMDB | beta-Imidazolyl-4(5)-propanoic acid | HMDB | beta-Imidazolyl-4(5)-propionic acid | HMDB | Β-(5-imidazolyl)propanoic acid | HMDB | Β-(5-imidazolyl)propionic acid | HMDB | Β-imidazolyl-4(5)-propanoic acid | HMDB | Β-imidazolyl-4(5)-propionic acid | HMDB |
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Chemical Formula | C6H8N2O2 |
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Average Mass | 140.1399 Da |
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Monoisotopic Mass | 140.05858 Da |
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IUPAC Name | 3-(1H-imidazol-5-yl)propanoic acid |
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Traditional Name | 5-imidazolepropionic acid |
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CAS Registry Number | Not Available |
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SMILES | OC(=O)CCC1=CNC=N1 |
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InChI Identifier | InChI=1S/C6H8N2O2/c9-6(10)2-1-5-3-7-4-8-5/h3-4H,1-2H2,(H,7,8)(H,9,10) |
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InChI Key | ZCKYOWGFRHAZIQ-UHFFFAOYSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| 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 imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Azoles |
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Sub Class | Imidazoles |
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Direct Parent | Imidazolyl carboxylic acids and derivatives |
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Alternative Parents | |
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Substituents | - Imidazolyl carboxylic acid derivative
- Heteroaromatic compound
- Azacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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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 | - Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
- Block WD, Westhoff MH, Steele BF: Histidine metabolism in the human adult: histidine blood tolerance, and the effect of continued free L-histidine ingestion on the concentration of imidazole compounds in blood and urine. J Nutr. 1967 Feb;91(2):189-94. doi: 10.1093/jn/91.2.189. [PubMed:6021220 ]
- Antener I, Verwilghen AM, Van Geert C, Mauron J: Biochemical study of malnutrition. Part VI: Histidine and its metabolites. Int J Vitam Nutr Res. 1983;53(2):199-209. [PubMed:6136484 ]
- SEN NP, McGEER PL, PAUL RM: Imidazolepropionic acid as a urinary metabolite of L-histidine. Biochem Biophys Res Commun. 1962 Oct 17;9:257-61. doi: 10.1016/0006-291x(62)90069-4. [PubMed:13987921 ]
- Bogachev AV, Bertsova YV, Bloch DA, Verkhovsky MI: Urocanate reductase: identification of a novel anaerobic respiratory pathway in Shewanella oneidensis MR-1. Mol Microbiol. 2012 Dec;86(6):1452-63. doi: 10.1111/mmi.12067. Epub 2012 Nov 1. [PubMed:23078170 ]
- Norval M, Simpson TJ, Bardshiri E, Howie SE: Urocanic acid analogues and the suppression of the delayed type hypersensitivity response to Herpes simplex virus. Photochem Photobiol. 1989 May;49(5):633-9. doi: 10.1111/j.1751-1097.1989.tb08435.x. [PubMed:2547218 ]
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