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Record Information
Version3.6
Creation Date2012-09-11 20:58:22 UTC
Update Date2016-02-11 02:44:04 UTC
HMDB IDHMDB35924
Secondary Accession NumbersNone
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. Pyrrole has been shown to exhibit anti-fungal, anti-microbial, anti-tumor, anti-hypertensive and anti-inflammatory functions (PMID 4007154 , 17000033 , 10425104 , 19487166 , 18200590 ). Pyrrole belongs to the family of Pyrroles. These are compounds containing a pyrrole ring, which is a five-member aromatic heterocycle with one nitrogen atom and four carbon atoms.
Structure
Thumb
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
PyrolleHMDB
PyrrholHMDB
PyrrolineHMDB
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 KeyInChIKey=KAESVJOAVNADME-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as heteroaromatic compounds. These 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
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Food
Biofunction
  • Nutrient
  • anti-fungal
  • anti-hypertensive
  • anti-inflammatory
  • anti-microbial
  • anti-tumor
Application
  • Flavoring Agent
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-24 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility45 mg/mL at 25 °CNot Available
LogP0.75Not Available
Predicted Properties
PropertyValueSource
Water Solubility445.0 mg/mLALOGPS
logP0.76ALOGPS
logP1.05ChemAxon
logS0.82ALOGPS
pKa (Strongest Acidic)18ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area15.79 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity20.82 m3·mol-1ChemAxon
Polarizability7.17 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9000000000-150b960a1186c02653f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9000000000-3bea04ffb045db51356dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxu-9000000000-bb04398351cbc20c433bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-9b747cfdf2fe46d188eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-ac61df56d353d5acb48bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-8777c03f1c46a5fcce9dView in MoNA
MSMass Spectrum (Electron Ionization)splash10-00ko-9000000000-8908fc8793c6501dc2d0View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Feces
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB014718
KNApSAcK IDNot Available
Chemspider ID7736
KEGG Compound IDC19907
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPyrrole
NuGOwiki LinkHMDB35924
Metagene LinkHMDB35924
METLIN IDNot Available
PubChem Compound8027
PDB IDNot Available
ChEBI ID19203
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. [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. [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. [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. [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. [18200590 ]
  6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.