Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-11 20:58:22 UTC |
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Update Date | 2023-02-21 17:24:58 UTC |
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HMDB ID | HMDB0035924 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Pyrrole |
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Description | Pyrrole is found in corn. Pyrrole is a flavouring ingredient Pyrrole has very low basicity compared to conventional amines and some other aromatic compounds like pyridine. This decreased basicity is attributed to the delocalization of the lone pair of electrons of the nitrogen atom in the aromatic ring. Pyrrole is a very weak base with a pKaH of about 4. Protonation results in loss of aromaticity, and is, therefore, unfavorable. Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4H4NH. Substituted derivatives are also called pyrroles. For example, C4H4NCH3 is N-methylpyrrole. Porphobilinogen is a trisubstituted pyrrole, which is the biosynthetic precursor to many natural products. The starting materials in the Piloty-Robinson pyrrole synthesis are 2 equivalents of an aldehyde and hydrazine. The product is a pyrrole with specific substituents in the 3 and 4 positions. The aldehyde reacts with the diamine to an intermediate di-imine (R C=N N=C R), which, with added hydrochloric acid, gives ring-closure and loss of ammonia to the pyrrole |
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Structure | InChI=1S/C4H5N/c1-2-4-5-3-1/h1-5H |
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Synonyms | Value | Source |
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1-Aza-2,4-cyclopentadiene | ChEBI | Divinyleneimine | ChEBI | Divinylenimine | ChEBI | Imidole | ChEBI | Monopyrrole | ChEBI | Pyrrol | ChEBI | 1H-Pyrrole | HMDB | 1H-Pyrrole, homopolymer | HMDB | 1H-Pyrrole, potassium salt | HMDB | Azole | HMDB | FEMA 3386 | HMDB | Indole | HMDB | Polypyrrole | HMDB, MeSH | Pyrolle | HMDB | Pyrrhol | HMDB | Pyrroline | HMDB | Pyrrole | ChEBI | Pyrroles | MeSH |
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Chemical Formula | C4H5N |
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Average Molecular Weight | 67.0892 |
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Monoisotopic Molecular Weight | 67.042199165 |
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IUPAC Name | 1H-pyrrole |
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Traditional Name | pyrrole |
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CAS Registry Number | 109-97-7 |
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SMILES | N1C=CC=C1 |
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InChI Identifier | InChI=1S/C4H5N/c1-2-4-5-3-1/h1-5H |
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InChI Key | KAESVJOAVNADME-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Heteroaromatic compounds |
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Sub Class | Not Available |
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Direct Parent | Heteroaromatic compounds |
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Alternative Parents | |
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Substituents | - Heteroaromatic compound
- Pyrrole
- Azacycle
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | |
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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 | Liquid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | -24 °C | Not Available | Boiling Point | 130.00 to 131.00 °C. @ 760.00 mm Hg | The Good Scents Company Information System | Water Solubility | 45 mg/mL at 25 °C | Not Available | LogP | 0.75 | 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 IndicesUnderivatizedDerivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Pyrrole GC-MS (Non-derivatized) - 70eV, Positive | splash10-014i-9000000000-f644c5fdd4d5f9db3117 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Pyrrole GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-00ko-9000000000-8908fc8793c6501dc2d0 | 2015-03-01 | Not Available | 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 - Pyrrole LC-ESI-QFT , positive-QTOF | splash10-014i-9000000000-510c084e3c928fa514ae | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyrrole 10V, Positive-QTOF | splash10-014i-9000000000-150b960a1186c02653f7 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyrrole 20V, Positive-QTOF | splash10-014i-9000000000-3bea04ffb045db51356d | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyrrole 40V, Positive-QTOF | splash10-0uxu-9000000000-bb04398351cbc20c433b | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyrrole 10V, Negative-QTOF | splash10-014i-9000000000-9b747cfdf2fe46d188ee | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyrrole 20V, Negative-QTOF | splash10-014i-9000000000-ac61df56d353d5acb48b | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyrrole 40V, Negative-QTOF | splash10-014i-9000000000-8777c03f1c46a5fcce9d | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyrrole 10V, Negative-QTOF | splash10-014i-9000000000-3f070060c5785123e18c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyrrole 20V, Negative-QTOF | splash10-014i-9000000000-3f070060c5785123e18c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyrrole 40V, Negative-QTOF | splash10-02tc-9000000000-43982034e7a3a595201a | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyrrole 10V, Positive-QTOF | splash10-014i-9000000000-e0673bc7e6a6226fb72e | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyrrole 20V, Positive-QTOF | splash10-014i-9000000000-a3a7192ca6658a081b5b | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Pyrrole 40V, Positive-QTOF | splash10-0f79-9000000000-972ac9fb6e8cbc34f0d3 | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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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 | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Campylobacter jejuni infection | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Clostridium difficile infection | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Ulcerative Colitis | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Ulcerative colitis | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Crohn's disease | | details |
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Associated Disorders and Diseases |
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Disease References | Ulcerative colitis |
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- Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
- De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
| Crohn's disease |
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- De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
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Associated OMIM IDs | |
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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 | FDB014718 |
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KNApSAcK ID | C00018376 |
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Chemspider ID | 7736 |
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KEGG Compound ID | C19907 |
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BioCyc ID | CPD-13300 |
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BiGG ID | Not Available |
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Wikipedia Link | Pyrrole |
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METLIN ID | Not Available |
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PubChem Compound | 8027 |
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PDB ID | Not Available |
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ChEBI ID | 19203 |
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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 | rw1009261 |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Corelli F, Massa S, Stefancich G, Ortenzi G, Strippoli V, Artico M, Simonetti N: [Antibacterial and antifungal agents. IV. Synthesis and antifungal activity of econazole analogs with pyrrole structure]. Farmaco Sci. 1985 May;40(5):315-24. [PubMed:4007154 ]
- Raimondi MV, Cascioferro S, Schillaci D, Petruso S: Synthesis and antimicrobial activity of new bromine-rich pyrrole derivatives related to monodeoxypyoluteorin. Eur J Med Chem. 2006 Dec;41(12):1439-45. Epub 2006 Sep 25. [PubMed:17000033 ]
- Amishiro N, Okamoto A, Murakata C, Tamaoki T, Okabe M, Saito H: Synthesis and antitumor activity of duocarmycin derivatives: modification of segment-A of A-ring pyrrole compounds. J Med Chem. 1999 Jul 29;42(15):2946-60. [PubMed:10425104 ]
- Xia B, Wang T, Fox LM, Wang D: HPLC/MS/MS analysis of 3-carbamyl-4-methylpyrrole analog MNP001, a highly potent antihypertensive agent, in rat plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Jul 1;877(20-21):1867-72. doi: 10.1016/j.jchromb.2009.05.011. Epub 2009 May 15. [PubMed:19487166 ]
- Biava M, Cirilli R, Fares V, Ferretti R, Gallinella B, La Torre F, Poce G, Porretta GC, Supino S, Villani C: HPLC enantioseparation and absolute configuration of novel anti-inflammatory pyrrole derivatives. Chirality. 2008 Jun;20(6):775-80. doi: 10.1002/chir.20518. [PubMed:18200590 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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