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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 20:58:22 UTC
Update Date2022-03-07 02:54:42 UTC
HMDB IDHMDB0035924
Secondary Accession Numbers
  • HMDB35924
Metabolite Identification
Common NamePyrrole
DescriptionPyrrole 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
Structure
Data?1563862794
Synonyms
ValueSource
1-Aza-2,4-cyclopentadieneChEBI
DivinyleneimineChEBI
DivinylenimineChEBI
ImidoleChEBI
MonopyrroleChEBI
PyrrolChEBI
1H-PyrroleHMDB
1H-Pyrrole, homopolymerHMDB
1H-Pyrrole, potassium saltHMDB
AzoleHMDB
FEMA 3386HMDB
IndoleHMDB
PolypyrroleHMDB, MeSH
PyrolleHMDB
PyrrholHMDB
PyrrolineHMDB
PyrroleChEBI
PyrrolesMeSH
Chemical FormulaC4H5N
Average Molecular Weight67.0892
Monoisotopic Molecular Weight67.042199165
IUPAC Name1H-pyrrole
Traditional Namepyrrole
CAS Registry Number109-97-7
SMILES
N1C=CC=C1
InChI Identifier
InChI=1S/C4H5N/c1-2-4-5-3-1/h1-5H
InChI KeyKAESVJOAVNADME-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassHeteroaromatic compounds
Sub ClassNot Available
Direct ParentHeteroaromatic compounds
Alternative Parents
Substituents
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-24 °CNot Available
Boiling Point130.00 to 131.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility45 mg/mL at 25 °CNot Available
LogP0.75Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility445 g/LALOGPS
logP0.76ALOGPS
logP1.05ChemAxon
logS0.82ALOGPS
pKa (Strongest Acidic)18ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area15.79 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity20.82 m³·mol⁻¹ChemAxon
Polarizability7.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+107.62631661259
DarkChem[M-H]-103.26831661259
DeepCCS[M+H]+117.8130932474
DeepCCS[M-H]-115.59730932474
DeepCCS[M-2H]-151.4230932474
DeepCCS[M+Na]+125.95230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PyrroleN1C=CC=C11503.3Standard polar33892256
PyrroleN1C=CC=C1703.2Standard non polar33892256
PyrroleN1C=CC=C1743.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pyrrole,1TMS,isomer #1C[Si](C)(C)N1C=CC=C1909.7Semi standard non polar33892256
Pyrrole,1TMS,isomer #1C[Si](C)(C)N1C=CC=C1984.4Standard non polar33892256
Pyrrole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=CC=C11150.1Semi standard non polar33892256
Pyrrole,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C=CC=C11152.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pyrrole GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-9000000000-f644c5fdd4d5f9db31172017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pyrrole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00ko-9000000000-8908fc8793c6501dc2d02015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Pyrrole LC-ESI-QFT , positive-QTOFsplash10-014i-9000000000-510c084e3c928fa514ae2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole 10V, Positive-QTOFsplash10-014i-9000000000-150b960a1186c02653f72015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole 20V, Positive-QTOFsplash10-014i-9000000000-3bea04ffb045db51356d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole 40V, Positive-QTOFsplash10-0uxu-9000000000-bb04398351cbc20c433b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole 10V, Negative-QTOFsplash10-014i-9000000000-9b747cfdf2fe46d188ee2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole 20V, Negative-QTOFsplash10-014i-9000000000-ac61df56d353d5acb48b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole 40V, Negative-QTOFsplash10-014i-9000000000-8777c03f1c46a5fcce9d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole 10V, Negative-QTOFsplash10-014i-9000000000-3f070060c5785123e18c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole 20V, Negative-QTOFsplash10-014i-9000000000-3f070060c5785123e18c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole 40V, Negative-QTOFsplash10-02tc-9000000000-43982034e7a3a595201a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole 10V, Positive-QTOFsplash10-014i-9000000000-e0673bc7e6a6226fb72e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole 20V, Positive-QTOFsplash10-014i-9000000000-a3a7192ca6658a081b5b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pyrrole 40V, Positive-QTOFsplash10-0f79-9000000000-972ac9fb6e8cbc34f0d32021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease
details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. 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 ]
  2. 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
  1. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014718
KNApSAcK IDC00018376
Chemspider ID7736
KEGG Compound IDC19907
BioCyc IDCPD-13300
BiGG IDNot Available
Wikipedia LinkPyrrole
METLIN IDNot Available
PubChem Compound8027
PDB IDNot Available
ChEBI ID19203
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1009261
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .